The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds

THE SHULGIN INDEX
FIRST EDITION
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Transform
PRJE S S
TRANSFORM PRESS
BERKELEY, CA, USA
THE
SHULGIN INDEX
VOLUME ONE
Psychedelic Phenethylamines
and Related Compounds
ALEXANDER T. SHULGIN
TANIA MANNING
PAUL F. DALEY
FIRST EDITION
Published by
TRANSFO RM PRESS
BERKELEY, CA, USA

2011
Title: The Shulgin Index Vol I
Psychedelic Phenethylamines and Related Compounds
Alexander T. Shulgin
Tania Manning
and Paul F. Daley
Copyright © 2011
All Rights Reserved.

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Acknowledgments
Without the devotion and encouragement of many individuals, this volume could not
have sprung to life. First we would like to acknowledge the careful and thoughtful
assistance of our reviewers, Nicholas V. Cozzi, Ph.D. (Department of Pharmacology,
University of Wisconsin School of Medicine and Public Health, Madison, WI), Simon
D. Brandt, Ph.D. (School of Pharmacy & Biomolecular Sciences, Liverpool John Moores
University, Liverpool, UK), Steve Ripple, M.D., and Tom Seeger, Ph.D.
Jon Singer (Resident Researcher, T he Joss Research Institute), Earth and Fire Erowid,
and Jon Hanna of Erowid Center, Jonathan Tay lor, and J. Duberman, provided in
valuable commentary and proofreading of the main text, and particularly helped
in retrieval of source material for the Bibliography. Jacob Nasim, Chelsea Donovan,
Douglas H. Crawford (Xochipili Design & Production), and Bob Jesse were especially
diligent in manuscript checking and assembly of the Alphabetical Index. Keeper Trout
helped draw chemical structures to prepare IUPAC names, Andrea Lange assisted
with file tracking and cleanup, Jen Zariat provided graphical design, and Jen Dely th
(www.ninthwavepublishing.com) provided layout assistance in development of the
Mass Spectrometry Appendix, and worked closely with Wendy Tucker, the Manager
of Transform Press, in numerous aspects during the final assembly of this book. We
are particularly grateful to have had the opportunity to work with Wendy during the
final stages of completion of this work; her expertise, ey e for detail, and great attitude
made this massive project more enjoyable than we could have possibly anticipated.
All of their efforts have helped make this a readable, and hopefully more useful work,
and are greatly appreciated.
We also want to recognize the lengthy and productive association Dr. Shulgin has had
with Dr. Neal L. Benowitz and the rest of the staff of the Clinical Pharmacology and
Experimental T herapeutics Division of the University of California at San Francisco,
who provided extensive instrumentation access and many other research resources
essential to this work.
John Gilmore, Ashawna Hailey, and Betsy Gordon provided much needed support
throughout this project, and without their help this book would not have been pro
duced.
Finally, we are grateful to our families, Ann Shulgin, Greg Manning, Jason Tucker, and
Nancy for their unending patience, love and support.
Vll
TABLE OF CONTENTS
Acknowledgments . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . vii
Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xi
Main Entry Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1
Tables . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 317
CAS Registry Numbers Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 363
Appendix A - Additional Notes on IUPAC Nomenclature . . . . . . . . . . 423
Appendix B - State Law on the Web . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 429
Appendix C - Mass Spectra . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 434
B ibliography . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 521
Alphab etical Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 665
ix
INTRODUCTION
Our objective in presenting this volume was to produce an encyclopedia about a particular
group of psychedelic drugs, the phenethylamines. Phenethylamines are drugs with
profound mind-altering properties that we find both fascinating and rewarding. It is our
conviction that the varied potency, duration, and character of these many compounds
should be explored further, so that they may be rated as to efficacy and safety, and
become practical tools in the work of medical professionals and lay therapists, as well
as in the hands of spiritual guides and seekers. Their potential is great, but with great
benefit, there also may be great risks. In order to lay a solid foundation based on known
biochemistry, pharmacology, and toxicology, we have explored the available literature on
chemical, medical, and legal aspects of the known psychedelics, and attempted to present
that information so that future practitioners have a concise source of information to guide
further work.
What are the Psychedelics?

From the earliest moments of human evolution our ancestors were dependent on plant life
for food and shelter. In the search for food sources, early humans encountered toxic plants
that produced poisonings, but also some that profoundly altered their perceptions. While
the advantage these plants gained by manufacturing chemicals that alter mammalian
nervous systems still remains a mystery, there is no doubt that the experiences produced
by consumption of psychoactive plants were dramatic, and were likely perceived by early
humans as visits to the spirit world. These profound incidents no doubt contributed to
development of a healthy respect for the power of these plants, and undoubtedly led to
the beginnings of mythology and religion. Interest in psychoactive plants and their effects
persisted through the centuries, and eventually gave rise to psychopharmacology as we
know it today.
The plant-sourced psychoactive materials known to western science at the opening of the
nineteenth century were relatively few in number, but comprised humanity's most an
cient, yet still widely used drugs. Some relieved pain (opium, cannabis), or provided se
dation (valerian, kava) . Some provided stimulation (coffee, tea, ephedra, coca, tobacco).
When science revealed the structure of their active components, there quickly followed
the synthesis of new compounds with related, or even entirely new activity, derived from
these structures. The number of new psychoactive materials useful for many applications
is ever increasing, thanks to the development of an international pharmaceutical establish
ment of enormous size and sophistication.
Within the realm of psychoactive drugs lies an even more unusual neighborhood that is
in 1956, the word psychedelic is derived from the Greek words 'ljluxfi (psyche, "soul" or
the subject of this volume, the group of compounds known as the psychedelics. Coined
"mind") and 011A.wctK6 (delein, "to manifest" ), or 011A.00v (deloun, "to reveal, or make evi
dent"), hence "mind manifesting" (Osmond, 1957; Stafford, 1992; Wikipedia, 2010). These
drugs, at doses where somatic disturbance is absent or minimal, produce profound expe
riential and emotional transformations. The psychological effects have been described as
xi
Introduction
resembling dreams, with colorful visual images, altered perceptions of time and space,
changes in body image and sensations, and intense mood changes ranging from euphoria
to sadness to wonder and delight. For many years this class of compounds has been typi
fied by three well-known materials that produce these effects: mescaline, psilocybin, and
LSD. The first of these is known chemically as a phenethylamine, and its closest relatives
are the focus of this book.
At a major meeting in 1957 that addressed the burgeoning interest in the mechanism of
action of LSD in producing these states, researcher Humphry Osmond said, "Psychotomi
metic agents are substances that produce changes in thought, perception, mood and some
times posture, occurring alone or in concert, without causing either major disturbances
of the autonomic nervous system or addictive craving, and although, with overdosage,
disorientation, memory disturbance, stupor, and even narcosis may occur, these reactions
are not characteristic" (Osmond, 1957) . In PIHKAL, Alexander Shulgin described psyche
delics as "physically non-addictive compounds which temporarily alter the state of one's
consciousness" (Shulgin and Shulgin, 1991). Noted addiction specialist (and former Drug
Czar under the administration of President Richard Nixon) Jerome H. Jaffe (1990) offered:
"The feature that distinguishes the psychedelic agents from other classes of drugs is their
capacity reliably to induce states of altered perception, thought, and feeling that are not
experienced otherwise except in dreams or at times of religious exaltation." Many in the
public might not be familiar with older medically derived terms such as psychotomimetic
(resembling psychosis) . "Hallucinogen" could also be thought to also apply to chemicals
(e.g. : tropane alkaloids such as scopolamine and atropine) that produce complete separa
tion from consensual reality, producing frank delirium. Psychosis and delirium are en
tirely unlike the experiences catalyzed by true psychedelics. Similarly, more specialized
terms like "empathogen" and "entactogen" (coined respectively by Ralph Metzner in 1983,
and David Nichols in 1986; Metzner and Adamson, 1988; Nichols, 1986b) to describe the
uniquely emotional effects of some of the methylenedioxy amphetamines and related com
pounds might be unfamiliar; we will attempt to point out lines of evidence that support
the identification of these latter compounds as a separate, though related class, and how
their patterns of use have diverged from the other psychedelics. We have chosen to inclu
sively use the term "psychedelic" in this book for both the classic psychedelics and the
entactogen class, because we feel this term has the greatest potential to identify our subject
matter to the widest audience.
Aims and Scope

Modern research into the nature of psychedelics commenced in the late nineteenth cen
tury with Arthur Carl Wilhelm Heffter 's pioneering studies of the alkaloids in peyote
(Lophophora williamsii (Lemaire) Coulter; Heffter, 1 894, 1896, 1 898), followed in the first
decades of the twentieth century by the elucidation of the structure of mescaline through
synthesis (Spath, 1919). In this period amphetamine was first synthesized, based on the
structure of ephedrine, which had been determined in Japan by Nagayoshi Nagai (Schul
tes and von Reis, 1995) . New discoveries of synthetic psychedelics were postponed until
the spectacular discovery of the psychoactive effects of LSD by Albert Hofmann in 1943
(Hofmann, 1983) . The extraordinary potency and character of this compound captured the
attention of the scientific community, and with the near-coincident discovery of serotonin
in 1949, paved the way for an explosion of research in the psychopharmacology of con
sciousness (Nichols, 2004).
xii The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

Introduction
Psychedelic drugs were initially perceived as interesting, if somewhat obscure, tools for
exploration of altered psychological states. Research aimed at discovering the structural
characteristics of molecules that create the psychedelic "effect" proliferated in many
academic and commercial laboratories. Early work in psychiatric circles showed great
potential for treatment of deeply refractory conditions, including alcoholism (Kurland et
al., 1967, 1971; Yensen and Dryer, 2007), and the pain and existential anxiety produced by
terminal cancer (Kast, 1962; Kast and Collins, 1964; Fisher, 1970) . But a shift was in the wind.
By the late 1950s, members of the cognoscenti in the United States and Europe became
aware of the potential for deeply meaningful experiences under the influence of LSD and
mescaline. This news was supplanted by the discovery by the amateur ethnomycologist R.
Gordon Wasson and his wife Valentina of the shamanic use of psychedelic mushrooms in
Mexico, which debuted to the world in the pages of Life Magazine on May 1 3, 1957, in the
article entitled "Seeking the Magic Mushroom." The stage was set for an upheaval no one
predicted.
By the early 1960s, popular interest in then-legal psychedelic drugs spread quickly from
universities and psychologists' offices to the general public. The youth of North America
and Europe quickly embraced the concept of expanding consciousness through experi
mentation with psychedelics, and these drugs became a rite of passage for a generation.
The political establishment of the United States, already reeling from popular rejection of
the deteriorating state of the war in Vietnam, reacted vigorously, and on October 24, 1968,
the assembled United States Senate and House of Representatives declared LSD an illegal
substance, through an amendment of the Food, Drug, and Cosmetic Act (U.S. Congress,
1968). Several other psychedelics were designated Schedule I drugs (the most restrictive
classification, along with cannabis and heroin), with the passage of the Controlled Sub
stances Act (CSA) in 1970. With the declaration that the major known psychedelic drugs
had high abuse potential, unknown safety (even if used under medical supervision), and
no accepted medical use, funding for research quickly evaporated, and the scientific study
of psychedelics in the United States, with a very few exceptions, virtually disappeared.
Walsh (1 982) aptly summarized the situation: "There have probably been few areas in psy
chology that have been subject to as much misinformation and sensationalistic reporting
by the media as psychedelic experiences. While preliminary clinical research suggested
that they might have considerable research and clinical potential, the popular press preoc
cupied itself almost entirely with sensationalistic accounts of dangers. This media treat
ment soon resulted in the cessation of almost all research and a bias at many levels of
society toward the dissemination of only negative reports."
Limited, but important human research took place in Europe in this period, exemplified
by the pioneering application of LSD to psychotherapy (Grof, 1976) . With human experi
mentation curtailed in the U.S., research shifted to the underlying mechanisms of action
of the psychedelics, probed with animal models, reactions of isolated tissues and cells,
and more recently, with cloned receptors (Glennon et al., 1979; Glennon and Young, 1982,
1984b; Nichols, 2004; Nichols and Nichols, 2008) . A concensus was built that attributes the
effects of the psychedelics to agonist (activating or stimulating) activity at serotonin recep
tors, particularly the 5-HT2A receptor. Recent work suggests the character of different psy
chedelic drugs may be modulated by responses at a variety of non-serotonergic receptor
targets as well (Ray, 2010). Exciting new applications of brain imaging to the psychedelic
state have been developed, and are continuing in Switzerland (Vollenweider et al., 1997) .
xiii
Introduction
Forty years have passed, and again it seems a change can be felt. A small group of psy
chologists and psychiatrists has sought and gained approval to administer psychedelics to
patients seeking resolution of obsessive-compulsive disorder (Moreno and Delgado, 1997;
Moreno et al., 2006), post-traumatic stress disorder (Mithoefer et al., 201 0), and the anxiety
accompanying terminal stages of cancer (Grob, 2007; Gasser, 2007) . New technologies that
permit non-invasive probing of brain activity have been brought to the question of how,
and in what parts of the neural apparatus, do the effects of psychedelics seem to manifest
themselves (Vollenweider et al., 1997; Gamma et al., 2001; Carter et al., 2005, 2007) . In an
even more intriguing study, medically normal volunteers who had no previous experience
with psychedelic drugs were given psilocybin. These volunteers reported spiritual and
mystical experiences ranked "among the top five experiences of a lifetime, on a par with
the birth of a child or the loss of a parent," (Snyder, 2006) that also produced long-lasting
betterment, detectable both by examination of the subjects, but also by their family mem
bers and colleagues (Griffiths et al., 2006, 2008) . These studies, growing in number, illus
trate clearly that in a serious context, with adequate preparation, the psychedelic state may
indeed produce substantial improvement to the human medical and psychological condi
tion. The stage would seem to be set for a sober re-evaluation of the psychedelic drugs.
In this contemporary work the drugs chosen were limited to MOMA, psilocybin, and very
recently, LSD. Yet, prior to the enactment of the CSA and subsequent collapse of formal
research, several hundred psychedelic phenethylamines, amphetamines, tryptamines, and
ergot alkaloid derivatives were discovered, and at least initially characterized (Shulgin
and Shulgin, 1991, 1997) . The research that gave rise to these substances is the topic of this
book.
We have stepped away from attempts to describe the psychological effects of these mate
rials, and discussion of their potential for application, feeling that this territory has been
extensively explored elsewhere. Instead, we have chosen to focus review on the available
chemical, biochemical and pharmacological literature; as we have heavily relied on the
Chemical Abstracts Service (CAS) and on-line databases, owing to their limitations, we may
have omitted coverage of some specialized literature not represented in those sources. We
acknowledge that, apart from a few cases, we have not addressed the literature of com
putational structure-activity analysis, as our expertise does not extend into this domain,
though we recognize the growing importance of this approach to drug design.
How to use this Book

We have organized this review of the technical literature on psychedelic phenethylamines
around chemical structure relationships, and have used several mechanisms to aid
information retrieval. One hundred and twenty-six compounds were selected as
prototypes, which we treat in short chapters called the main entries. Many of the entry
compounds have known psychedelic activity; others are included for comparison with
known psychedelic compounds, or for their structural proximity to compounds of known
activity. The extent of existing literature on specific compounds was also used as a guide
for selection of compounds warranting a complete entry. Structurally related compounds
with less coverage in the literature are included in Homologue and Analogue tables in
most of the main entries. Each of the entries includes:
1 . Names - Main entry compounds are identified by a preferred code name and an
International Union of Pure and Applied Chemistry (IUPAC) name, along with
additional common names and alternative codes encountered in the chemical,
xiv The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

Introduction
pharmacological, toxicological, and forensic literature. Code numbers applied by

the National Cancer Institute Chemical Chemotherapy National Service Center
(NSC) and the U.S. Army Edgewood Arsenal (EA), and some numbers applied by
pharmaceutical companies are also included. A chemical structure accompanies
each main entry.
2. Registry Numbers - Registry numbers from the CAS are included for the freebases,
salts, chiral forms (where applicable), and isotopically labeled versions.
Compounds scheduled in the Controlled Substances Act (Federal Register, 2007)
include their Drug Enforcement Agency Controlled Substances administrative
Code Numbers, which we refer to, for simplicity, as DEA numbers.
3. Synthesis and Chemistry - Brief sketches of synthetic routes are presented
chronologically, along with reports of resolution methods for optical isomers,
or stereospecific syntheses. The sketches are followed by the empirical formula,
exact mass and molecular weight, predicted mass spectral ratios associated with
molecular ions, a calculated elemental analyses (of the freebase compounds), and a
table of melting and boiling points. These physical data are followed by discussion
of analytical methods.
4. Positional Isomer, Homologue, and Analogue Tables - The Controlled Substances
Act identifies several psychedelic compounds as Schedule I controlled substances.
The definition includes "any of its salts, isomers, and salts of isomers whenever
the existence of such salts, isomers, and salts of isomers is possible within the
specific chemical designation (for purposes of this paragraph only, the term
'isomer' includes the optical, position and geometric isomers)." Accordingly, for
these entries, we include a Positional Isomers table, identifying rearrangements
of ring substituents that render the derivative compounds Schedule I under this
definition.
In addition, most entries include tables of Homologues and Analogues. These are
compounds closely related in structure to each of their main entry compounds,
but they have received less literature attention. They are identified primarily by
compound codes, with substituent locations illustrated in the tables; relevant
citations are provided. IUPAC names for compounds appearing in Homologue
and Analogue tables are provided in the Alphabetical Index. Additional notes
regarding substituent numbering schemes emerging from the IUPAC system are
presented in Appendix A
5. Biochemistry - Main entry compounds' biochemical coverage includes known
metabolic fate in animals and other biological systems, effects on isolated tissues,
organs and organelles, and interactions with purified enzymes, transporters, and
receptors.
6. Pharmacology - The pharmacology section reviews effects at the whole-organism
level, with an emphasis on physiological responses, behavioral studies, and
toxicology (from experimental animal studies, and based on emergency room
and autopsy reports in the medical literature). Reliable reports of doses required
for human psychedelic activity, and duration of effects are included; note that
many compounds that may have full psychedelic effects, but were only taken to
threshold levels during exploratory tests, are also reported on, with the dose that
produced threshold effects provided. Duration of effect in these circumstances are
generally difficult to discern or are unknown.
xv
Introduction
7. Legal Status - The formal scheduling status of all main entry compounds was
determined in United States federal law (Federal Register, 2007), and by
examination of statutes in the fifty states, and the District of Columbia. State and
District laws were found at web sites maintained by justice and health departments;
the addresses of the sites referred to are presented in Appendix B; these resource
addresses (universal resource locators, URLs) were accurate in late 2008, but may
change in time.
The main entries are accompanied by a set of reference tables that support rapid compound
identification and location in the entries. Table 1 summarizes functional group abbrevia
tions found in chemical codes (see discussion below), followed by ten structural reference
tables that show substituent locations, identification codes, and the entry location for infor
mation on each compound. The structure tables are followed by two tables that give Chemi
cal Abstracts Service (CAS) registry numbers for all main entry compounds, salts, isomers,
and labeled versions, as well as homologues and analogues. Note that many compounds
have multiple CAS numbers; CAS numbers were selected for homologues and analogues
on the basis of the largest number of reports linked to the given number. The CAS tables
were sorted both alphabetically by code name, and numerically by the CAS number.
Appendices present additional information not covered elsewhere, including the table of
URLs used to assess legal status, and an extensive set of mass spectra from the Shulgin
collection (Appendix C).
The Bibliography and Alphabetical Index complete the present volume. Every effort has
been made to ensure accuracy in these sections, but we realize that an encyclopedia is never
truly complete, and is always in need of revision, correction and updating. In keeping with
the stated goals of this work, we welcome communication from our readers that can help
us ferret out inaccuracies, and we urge you to contribute to that ongoing conversation at
www.transformpress.com.
Notes on Nomenclature
General Structure of Phenethylamines and Amphetamines
Despite efforts to the contrary, scientific literature is often bedeviled by inconsistent or

contradictory nomenclature, contributing to misunderstanding and errors. We address the
problem of identifying the psychedelic drugs by reporting names from three naming sys
tems: IUPAC nomenclature, common names, and acronymic code names. Each of the main
entry compounds, Positional Isomers (for scheduled compounds), their Homologues and
Analogues, and the compounds included in the mass spectral appendix, are identified by
a preferred acronym code and their IUPAC names (IUPAC names for Positional Isomers,
Homologues and Analogues are found in the Alphabetical Index) . Common names from
both scientific literature and colloquial use are listed for main entry compounds (some
Homologue and Analogue table notes may include additional common names). Addi
tional abbreviated code names, and codes applied by medical and defense department
laboratories (e.g. : National Cancer Institute NSC codes, an Edgewood Arsenal, or EA code
numbers) are included for main entry compounds where available. A brief introduction to
the chemical structure of the psychedelic phenethylamines may aid the understanding of
these naming systems.
xvi The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

Introduction
Phenethylamine Amphetamine
,-------,
A(lpha)-m(ethyl)-ph(en)
Phenyl Ethyl Amine
et(hyl)-amine
H
V
I
N
'H
IUPACNames:
2-phenylethanamine 1-phenylpropan-2-amine
Figure 1 . General structure and nomenclature of

phenethylamines and amphetamines.
IUPACName:
N-methyl-1-(2,4,5-trimethoxyphenyl)propan-2-amine
CommonName:
N-methyl-2,4,5-trimethoxyamphetamine
CodeName:
N-Me-TMA-2
Figure 2. Ring-numbering and compound name examples.
mCPP r NH
Y�
a , N-Me-FEA
(' o yy
H
"
N
L!I I
Cl
l-(furan-2-yl)-N -methylpropan-2-amine 1-(3-chlorophenyl)piperazine
Figure 3. Examples of a furylethylamine and a phenylpiperazine,

compounds related to phenethylamines, also covered in this volume.
xvii
Introduction
The phenethylamines and amphetamines generally contain a six-carbon, unsaturated

(benzene) ring, or phenyl group, attached to an alkane side-chain of two or more car
bons, to which an amino nitrogen is attached. In the phenethylamines, the side-chain is
two carbons in length; for the amphetamines the side-chain has three carbons. In both
cases the amine nitrogen is two carbons from the ring (Figure 1 ) . An example showing the
ring-numbering and compound naming conventions is given in Figure 2. Other structures
we address include furylethylamines and substituted phenyl- and benzylpiperazines, as
shown in Figure 3.
The IUPAC nomenclature system assumes one unambiguous name should be assigned to
any compound; conventions of the method and precedence rules of the IUPAC system are
promulgated both online and in print (IUPAC, 1993; Leigh et al., 1998; Hellwinkel, 2001 ),
which should be consulted for details. In this system, for the phenethylamines, the par
ent structure is ethanamine; the amine is assumed to be on the number one carbon of the
ethane side-chain (and is not enumerated in the IUPAC name); the phenyl ring is located
on the number two carbon of the chain. For amphetamines, the side-chains have three
carbons; the amine resides at the number two carbon, and the phenyl group on carbon
one. Other functional groups can substitute for hydrogens on the aromatic ring, the carbon
chain, or on the amino nitrogen.
The common names, trivial names, and colloquial names reported here reflect usage in
the chemical as well as medical and forensic literature, and are subject to less stringent
conventions. Common names often reflect underlying structure (as in the derivation of
"amphetamine" from a(lpha)-m(ethyl)-ph(en)-et(hyl)-amine); some reflect natural sources
(mescaline), and homologues subsequently derived from them (escaline, proscaline, etc.).
Compound code names (MOMA, DOM, etc.) are often generated by the originating chemist
for shorthand reference, and as such are at once acronymic and mnemonic. They were
historically not present in much of the primary medicinal chemistry literature, although
they are appearing more commonly in recent years.
Code names are, however, quite generally encountered in the pharmacology and toxicol
ogy journals, so some introduction is in order. Code names are usually abbreviations de
rived from underlying structures and functional groups, such as MDA for 3,4-m(ethylene)
d(ioxy)a(mphetamine) . These code names may also reflect relationships with other materi
als, or historical connections, such as the production of a series of homologues. In these
situations a root code may be followed by a simple series number; the suffix numbering
of the two-carbon chain thioether (2C-T) series (2C-T-2, 2C-T-21, etc.) is an example. Code
names have sometimes been chosen that seem to have little connection with their struc
tures. These relationships may emerge on further examination; a general description may
guide interpretation.
Phenethylamines are abbreviated PEA, with substituents noted as prefixes. Thus,

3,4-dimethoxyphenethylamine becomes 3,4-DMPEA. "A" is the root abbreviation for
many amphetamines, generating codes such as 2,5-DMA for 2,5-dimethoxyamphetamine,
and PMA for para-methoxyamphetamine (or 4-methoxyamphetamine) . Abbreviations
of functional groups are combined with root letters to form codes. Those used in this
book are given in Table 1, which presents them in the preferred sorting order applied to
Homologue, Analogue, and structure tables (see discussion below) . Numerical prefixes for
xviii The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

Introduction
codes generally indicate substituent positions around the phenyl ring, where the "one"
position is assumed to be the location of the side-chain. Structures illustrated in this book
show the ring "one" position at the upper right, with clockwise numbering of the ring
carbons.
Code suffixes can indicate chain modifications, such as the addition of ketone oxygens
at the f3 carbon (-f3k) . Simple numerical suffixes denote specific substituent patterns, in
increasing order depending on the sum of substituent locations. Patterns closely related to
naturally occurring prototypes such as 3,4-dimethoxy- or 3,4,5-trimethoxyphenethylamine
have precedence in this usage, and do not take a suffix:
Number of
Substituents Positions Code Common Name
1 2- 2-MA 2-Methoxyamphetamine
2 2,3- DMA-2 2,3-Dimethoxyamphetamine

2,4- DMA-3 2,4-Dimethoxyamphetamine
3,4- OMA 3,4-Dimethoxyamphetamine
3 3,4,5- TMA 3,4,5-Trimethoxyamphetamine

2,4,5- TMA-2 2,4,5-Trimethoxyamphetamine
4 2,3,4,5- TeMA 2,3,4,5-Tetramethoxyamphetamine

2,3,4,6- TeMA-2 2,3,4,6-Tetramethoxyamphetamine
2,3,5,6- TeMA-3 2,3,5,6-Tetramethoxyamphetamine
5 2,3,4,5,6- PeMA Pentamethoxyamphetamine
This system must change when two of the substituents cannot be separated, as with the
ring-methoxylated compounds related to MMDA, that contain a methylendioxy group
attached to the phenyl ring:
�
MeO- -{OCH}- Code Common Name
3- 4,5- MMDA 3-Methoxy-4,5-methylenedioxyamphetamine

2- 4,5- MMDA-2 2-Methoxy-4,5-methy lenedioxyamphetamine
2- 3,4- MMDA-3a 2-Methoxy-3,4-methylenedioxyamphetamine
4- 2,3- MMDA-3b 4-Methoxy-2,3-methylenedioxyamphetamine
5- 2,3- MMDA-4 5-Methoxy-2,3-methylenedioxyamphetamine
6- 2,3- MMDA-5 6-Methoxy-2,3-methylenedioxyamphetamine
xix
Introduction
The TMA series is of particular historical interest. TMA itself (3,4,5-trimethoxyamphet

amine) was the first synthetic psychedelic (Hey, 1947), and had roughly twice the potency
of its model compound, mescaline. In the early 1960s Shulgin synthesized the balance of
the positional TMA isomers, and discovered that while some were inactive (TMA-3), oth
ers had notable potency and character, exemplified by TMA-2. This compound possesses
the 2,4,5- substitution pattern found in many psychedelically active phenethylamines and
amphetamines. This structure further increased potency to approximately twenty times
that of mescaline (Shulgin et al., 1969) . Shulgin further modified the ring functions by
substitution of methyl groups for methoxy, giving rise to codes that refer to the removal of
oxygen (Des-Oxy); this resulted in the DO series of substituted amphetamines, exempli
fied by DOM, DOET, DOB, and DOI. All of these are active psychedelics in the low mil
ligram range, are quite long in duration of effect, and have been extensively studied with
in vitro systems, animals, and in humans.
Although the first chemically defined psychedelic was the phenethylamine mescaline, the
first synthetics in this class were amphetamines, with three-carbon side-chains. Other early
modifications in this class included chain lengthening at the a-carbon, and following ear
lier conventions, these became known both by the length of that addition (e.g.: phenyl-
2-aminobutanes are often referred to as a-ethylphenethylamines), or by their total chain
length, so 2,5-dimethoxy-4-methyl-a-ethylphenethylamine is also known by the code 4C
DOM (indicating a four-carbon side-chain), and by the trivial name ARIADNE. The latter
name, again, reflects a research program; this is discussed further in entry #7.
Many psychedelic phenethylamines were first discovered after their amphetamine coun
terparts were already known, and their code names indicate their shorter alkyl chains. For
example, 2C-B (2,5-dimethoxy-4-bromo-phenethylamine) is the two-carbon homologue of
DOB (2,5-dimethoxy-4-bromoamphetamine) . The position of the hyphen in these codes
can also cause some confusion:
Code Structure Reference

2C-T Two-carbon chain (2C), connected to a sulfur atom
-(thio, for 2,5-dimethoxy-4-methylthiophenethylamine)
2-CT CT is chlorotryptamine; 2 is the ring position

(2-chlorotryptamine)
2-CM 2-Chloromescaline
HO-T Hydroxytryptamine
HOT N-Hydroxyphenethylamine thio ethers (e.g.: HOT-2,

N-hydroxy-2,5-dimethoxy-4-ethylthiophenethylamine)
Some side-chain variants move the amino function away from the ring with an additional
methylene; these homo-derivatives (e.g.: homo-MDA, homo-MDMA) have received
comparatively little attention, although there are reports of their appearance as street
drugs in Asia (Matsumoto et al., 2006).
xx The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

Introduction
Sorting Conventions
The entry Homologue and Analogue tables, Positional Isomer tables, and the main struc
tural reference tables (Tables 2 through 1 0) assist location of compound information based
on structure. The tables are subdivided by number of substituent groups; as mentioned
above, Table 1 shows root structure and functional group abbreviations used throughout
the tables, in the order given priority for sorting substituents. Compounds are first sorted
alphabetically by their base code abbreviation (code without prefixes - ASB, BOB, CCPA,
etc) . Codes may contain various modifiers, such as N-Me-[code] meaning N-methyl, or
j3, j3,N-Me-[code] meaning j3,j3,N-trimethyl. These do not affect the primary alphabetical
prefixes (a, j3) denote substituent location on side-chain carbons (See Figure l); the 'ljJ (Greek
sorting; their individual preference level (Table 1) affects secondary placement. Greek letter
"psi") refers to a 2,6-dimethoxy arrangement, instead of the parent 2,5-dimethoxy pattern,

as in 'ljJ-DOM, 'ljJ-2C-T and 'ljJ-4C-T-4. Compounds with codes denoting chain length modi
fications (e.g. : homo-PEA) receive separate treatment in the structure tables (Table 10).
Some compounds that, logically, one would assume to have been made, might not actually
have been synthesized. These are only included in this book if they would be considered
positional isomers of Schedule I controlled substances. In these cases a Positional Isomers
table precedes the Homologue and Analogue tables of the affected entry.
xxi
"How long will this last, this delicious feeling of
being alive, of having penetrated the veil which
hides beauty and the wonders of celestial vistas?
It doesn't matter, as there can be nothing but
gratitude for even a glimpse of what exists
for those who can become open to it. "
- Alexander Shulgin
Pihkal: A Chemical Love Story
MAIN ENTRY COMPOUNDS
AEM / AL
#1. AEM
1 -(3,4,5-Trimethoxyphenyl)butan-2-amine
a-Ethyl-1 -(3,4,5-trimethoxyphenyl)ethylamine
2-Amino-1-(3,4,5-trimethoxyphenyl)butane
1 -(3,4,5-Trimethoxybenzyl)propylamine
a-Ethylmescaline
Registry Numbers
HCI salt
CAS #
[40393-68-8]
Freebase [17097-73-3]
Synthesis and Chemistry

From 3,4,5-trimethoxybenzaldehyde (with nitropropane) to 1 -(3,4,5-trimethoxyphenyl)-2-
nitrobutene; (with LAH) to AEM (Shulgin, 1963) .
Fragmentation patterns of some fifty-five phenethylamines were determined by a variety

of mass spectrometry techniques (Kolliker and Oehme, 2004) .
Exact Mass: 239.1521

Molecular Weight: 239.31
Elemental Analysis: C, 65.25; H, 8.84; N , 5.85; 0 , 20.06

m / z: 239.1521 (100.0% ), 240. 1555 (14. 1 % )
HCI salt °C
°C
m.p. 192-193 (Shulgin, 1963)
Picrate m.p. 177-181 (Shulgin, 1963)
Homologues
A number of higher a-homologues of AEM have been synthesized, but not yet assayed in
humans. These are listed in # 1 1 7.
Pharmacology
Correlation was assessed between human activity and mouse behavioral responses (Come
and Pickering, 1967) . Human potency was studied, as influenced by changes in substitu
tion patterns (Shulgin et al., 1969). Studies were made of injection into the rat optic nerve
and the cat sciatic nerve (Paulson and McClure, 1973) .
Threshold activity in humans at 220 mg; duration unknown (Shulgin, 1963; Shulgin and
Shulgin, 1 991).
Legal Status
AEM is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
�
#2. AL
2-(4-(Allyloxy)-3,5-dimethoxyphenyl)ethanamine
H3CO NH2
4-Allyloxy-3,5-dimethoxyphenethylamine - -------�
I
3,5-Dimethoxy-4-(2-propenyloxy)-
H2C� :::::...
phenethylamine
0
-----·-·· -------
OCH3
Main Entry Compounds

AL / ALEPH
Registry Numbers
CAS # CAS # CAS #
HCl salt [39201-76-8] PtC16 salt [39697-36-4] Freebase [39201-75-7]
Bisulfate [54110-94-0] Sulfate [39477-28-6]

From 4-allyloxy-3,5-dimethoxybenzaldehyde (with nitromethane) to 1 -(4-allyloxy-3,5-
dimethoxyphenyl)-2-nitroethene; (with Zn) to AL (Leminger, 1972b) .
From homosyringonitrile (with ally! iodide, base) t o 3,5-dimethoxy-4-allylphenylaceto

nitrile; (with LAH) to AL (Shulgin and Shulgin, 1991).
Exact Mass: 237. 1365

m / z: 237. 1365 (100.0%), 238.1398 (14. 1 % )
Elemental Analysis: C , 65.80; H , 8.07; N , 5.90; 0 , 20.23
HCI, H2S04 and H2PtCl6 salts were prepared (Leminger, 1972b); their melting points
were not given in Chemical Abstracts.
Pharmacology
This drug has been researched in an extensive QSAR study (Beuerle et al., 1997) .
Orally active in humans at 20-35 mg; duration 8-12 hours (Shulgin and Shulgin, 1 99 1 ) .
Legal Status
AL is not a scheduled compound under federal drug law, or under District of Columbia or
any state laws.
#3. ALEPH
1 -(2,5-Dimethoxy-4-(methylthio)phenyl)propan-2-amine
2,5-Dimethoxy-4-methylthioamphetamine
3C-T
DMMTA
DOT
p-DOT
PARA-DOT
Registry Numbers
CAS #
HCI salt [61638-08-2]
Freebase [61638-07-1]
R-Isomer [64813-14-5]

From 2,5-dimethoxy-4-methylthiobenzaldehyde (with nitroethane, acetic acid, and
ammonium acetate) to 2-(2,5-dimethoxy-4-methylthiophenyl)-1-methyl-1 -nitroethene;
(with LAH) to ALEPH (Nichols and Shulgin, 1976; Jacob et al., 1977; Shulgin and Nichols,
1978) .
Synthesis of sulforide and sulfoxide oxidation products of ALEPH was described (Rezende
et al., 2002) . LC resolution was described, with four chiral reagents (Miller et al., 1984) .
2 The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

ALEPH
Exact Mass: 241 . 1136

Molecular Weight: 241 .35
m / z: 241 . 1136 (100.0% ), 242.1170 (13.0% ), 243.1094 (4.5% )
Elemental Analysis: C, 59.72; H, 7.93; N, 5.80; 0, 13.26; S, 13.29
HCI salt m.p. 204-205 °C (Nichols and Shulgin, 1976) (IPA / Etp)
Freebase m.p. 91-93 °C (Nichols and Shulgin, 1976) (hexane)
Homologues and Analogues

2- 4- 5- 6- a- N- Name CAS # Ref
MeO Meo MeS -- Me -- m-DOT [79440-52-1] (1-5)
MeO Me MeS -- Me -- 5-TOM [ 207740-45-2] (6-8)
MeO MeS MeO -- Me -- ALEPH (this entry) (9)
MeO MeS -- MeO Me -- 1jl-ALEPH [914221-14-0] (10)
MeO MeS Meo -- Me Me N-Me-ALEPH [849919-88-6] (9)
MeO Mes MeO -- Et -- 4C-T [ 69501-21-9] (11-14)
MeO MeS MeO -- Et Me N-Me-4C-T [849919-91-1] (9)
MeO MeS02 MeO -- Me -- ALEPH sulfone [146724-75-6] (15)
-
MeO EtS - MeO Me -- 1jl-ALEPH-2 [914221-16-2] (10)
MeO EtS MeO -- Me Me N-Me-ALEPH-2 [849919-89-7] (9)
MeO EtS MeO -- Et -- 4C-T-2 [849919-79-5] (6)
MeO EtS MeO -- Et Me N-Me-4C-T-2 [849919-92-2] (9)
MeO PrS MeO -- Me Me N-Me-ALEPH-7 [849919-90-0] (9)
MeO PrS MeO -- Et -- 4C-T-7 [849919-80-8] (9)
-
Meo PrS MeO - Et Me N-Me-4C-T-7 [849919-93-3] (9)
MeO BuS MeO -- Me -- ALEPH-19 [849919-75-1 ] (9)
Meo AmS MeO -- Me -- ALEPH-S-amyl [849919-76-2] (9)
MeO PhS MeO -- Me -- ALEPH-6 [952006-44-9] (16)
MeO PhEtS MeO -- Me -- ALEPH-S-PhEt [849919-78-4] (9)
MeS MeO MeO -- Me -- o-DOT [79440-51-0] (1-4)
MeS Me MeO -- Me -- 2-TOM [84910-90-7] (6, 1 7)
MeS Me MeS -- Me -- BIS-TOM [756225-27-2] (6,7)
(1) Among a series of amphetamines studied for correlation between 5-HT2 receptor affinity, charge
complex stability, rabbit hyperthermia, human activity (Domelsmith et al., 1981).
(2) Synthesis and bioassay for hyperthermia in the rabbit (Jacob et al., 1977).
(3) Among a large number of methoxylated amphetamine analogues, for which the rabbit hyper
thermia response paralleled human potency as psychedelics (Anderson et al., 1978b).
(4) Threshold oral activity in humans, 25 mg; duration unknown (cf: META-DOT, ORTHO-DOT;
Shulgin and Shulgin, 1991).
(5) Threshold oral activity in humans, 35 mg; duration unknown (Shulgin and Shulgin, 1991).
(6) Synthesis, human pharmacology described (Jacob and Shulgin, 1983).
(7) Serotonin receptor affinities determined in isolated rat fundus preparation, but only partially
generalized for the training drug in rats that discriminated 5-MeO-DMT from saline (Glennon et
al., 1981a).
Main Entry Compounds 3

ALEPH
(8) Orally active in humans at 30-50 mg; duration 6-1 0 hours (Shulgin and Shulgin, 1991).
(9) Compounds were synthesized and assayed for their ability to inhibit MAOA and MAOB. Most
were active against MAOA; none were very active against MAOB. (Gallardo-Godoy et al., 2005).
(10) Not in the scientific literature, but listed in 2008 catalogs of the Ambinter Stock Screening
Collection, and the ChemPacific Pharmaceutical Product List.
(11) Has been studied in cat behavior (Standridge et al., 1980).
( 12) A possible active metabolite of 4C-D (Partyka et al., 1978). Several compounds synthesized and
assayed as MAOA and MAOB inhibitors. Most were active against MAOA; none were very
active against MAOB (Gallardo-Godoy et al., 2005).
(13) Patented for increasing mental alertness in geriatric patients (Partyka et al., 1978).
(14) Synthesis (Standridge et al., 1980).
(15) A study on the biotransformation products of TMA, MEM, MPM, and ALEPH by Cunning
hamella echinulata (Foster et al., 1992).
( 16) Synthesis described; orally active in humans at 40 mg (Shulgin and Shulgin, 1991).
(17) Orally active in humans at 60-100 mg; duration 8-10 hours (Shulgin and Shulgin, 1991).
Biochemistry
Four psychedelic amphetamines were incubated with the filamentous fungus Cunning
hamella echinulata: TMA-2 and MEM were poorly metabolized. MPM was acetylated and
0-dealkylated, and ALEPH was oxidized to the sulfoxide (Foster et al., 1992) .
Several compounds were synthesized and assayed for their ability to inhibit MAOA and
MAOB. Most were active against MAOA; none were appreciably active against MAOB
(Gallardo-Godoy et al., 2005) . The electron withdrawing or donating nature of the 4-posi
tion substituent was correlated with the human potency of the compound (Neuvonen et
al., 2006).
Pharmacology
The relationship between partition coefficients, steric bulk, and in vitro activity was used to
predict potency in humans (Nichols et al., 1977) . ALEPH (as opposed to the positional iso
mers a-DOT and m-DOT) had significant activity in the rabbit hyperthermia assay (Jacob
et al., 1977) . In a series of psychoactive compounds, those with greater potency had lower
ionization potential as measured by photoelectron spectroscopy (Domelsmith and Houk,
1 978) . A series of amphetamines were studied for correlation between 5-HT2 receptor affin
ity, charge complex stability, rabbit hyperthermia, human activity (Anderson et al., 1978b;
Domelsmith et al., 1 981 ) .
Discriminative properties o f TMA, MEM, and ALEPH were determined i n rats trained to
discriminate amphetamine from saline (Corrigall et al., 1992a) . This drug has been exam
ined extensively in QSAR studies (Clare, 1998; Beuerle et al., 1997) .
Orally active in humans at 5-1 5 mg; duration 6-8 hours (Shulgin and Nichols, 1978; Shulgin
and Shulgin, 1 991).
Legal Status
ALEPH is not a scheduled compound under federal drug law, or under District of Colum
bia or any state laws.

ALEPH-2
XJC:f
#4. ALEPH-2
1-( 4-(E thylthio )-2,5-dimethoxyphenyl)propan-2-amine
N H2
�-----
2,5-Dimethoxy-4-ethylthioamphetamine
H3CO
Registry Numbers
� ::::::....
I CH3
CAS #
H3C S OCH3
HCI salt [178485-02-4] CAS #
Freebase [185562-00-9] R-Isomer freebase [255732-51-5]

From 2,5-dimethoxy-4-ethylthiobenzaldehyde (with nitroethane, acetic acid, and ammoni
um acetate) to 2-(2,5-dimethoxy-4-ethyl-thiophenyl)-1 -methyl-1-nitropropene; (with LAH)
to ALEPH-2 (Shulgin and Shulgin, 1 991 ) .
The synthesis o f the sulforide and sulfoxide oxidation products o f ALEPH-2 was described
(Rezende et al., 2002).

m / z: 255. 1293 (100.0%), 256. 1327 (14. 1 % ), 257. 1251 (4.5% )
Elemental Analysis: C, 61. 14; H, 8.29; N, 5.48; 0, 12.53; S, 12.56
HCI salt m.p. 128-130 °C (Shulgin and Shulgin, 1991) (IPA / Etp)
Biochemistry
The octanol-water partition coefficient was found to serve as a predictor of human psyche
delic potency (Nichols et al., 1 977), and molecular connectivity analysis gave excellent cor
relation to serotonin agonist activity in a large number of phenethylamines and amphet
amines (Kier and Glennon, 1978a). ALEPH-2 was a suspected anxiolytic and psychedelic
phenylisopropylamine derivative, and shown to be a 5-HT2a and 5-HT2c receptor agonist
(Acuna-Castillo et al., 2000) .
The MAO-inhibiting properties of ALEPH-2 were evaluated (Scorza et al., 1997) . Several
compounds were synthesized and assayed for their ability to inhibit MAOA and MAOB.
Most were active against MAOA; none were very active against MAOB (Gallardo-Godoy
et al., 2005).
The electron withdrawing or donating nature of the 4-position substituent is correlated

with the human potency of the compound (Neuvonen et al., 2006).
Pharmacology
Behavioral effects of ALEPH-2 were studied in rats and mice (Scorza et al., 1 996). The puta
tive anxiolytic effects were studied in rodents. In rats, there were symptoms of serotonergic
syndrome and a decrease of motor activity. In mice, there was hypothermia (Reyes-Parada
et al., 1996) . A review of animal tests for evaluating the effects of compounds (including
ALEPH-2) on anxiety was presented (Graeff et al., 1998) .
Orally active in humans at 4-8 mg; duration 8-16 hours (Shulgin and Shulgin, 1991).
Legal Status
ALEPH-2 is not a scheduled compound under federal drug law, or under District of Co
lumbia or any state laws.

ALEPH-4 / ALEPH-7
#5. ALEPH-4
1-(4-(Isopropylthio )-2,5-dimethoxyphenyl)propan-2-amine
2,5-Dimethoxy-4-(i)-propylthioamphetamine
Registry Numbers
CAS #
HCl salt [849919-77-3]
Freebase [ 123643-26-5]
R-Isomer [255732-52-6]

From 2,5-dimethoxy-4-isopropylthiobenzaldehyde (with nitroethane, acetic acid, and am
monium acetate) to 1-( 2,5-dimethoxy-4-isopropylthiophenyl)-2-nitropropene; (with LAH)
to ALEPH-4 (Shulgin and Shulgin, 1991).

m / z: 269.1449 (100.0% ), 270. 1483 (15.1 % ), 271 . 1407 (4.5% ), 271 .1517 ( 1 . 1 % )
Elemental Analysis: C , 62.42; H , 8.61; N , 5.20; 0, 11.88; S , 11 .90
HCl salt m.p. 146-147 °C (Shulgin and Shulgin, 1991) (IPA)
Biochemistry
Sulfur-substituted a-alkyl phenethylamines are selective and reversible MAOA inhibitors;
several compounds were synthesized and assayed for their ability to inhibit MAOA and
MAOB. Most were active against MAOA; none were appreciably active against MAOB
(Gallardo-Godoy et al., 2005).
Pharmacology
This drug was evaluated in extensive QSAR studies (Clare, 1998; Beuerle et al., 1 997) . The
electron withdrawing or donating nature of the 4-position substituent is correlated with
the human potency of the compound (Neuvonen et al., 2006).
Orally active in humans at 7-12 mg; duration 12-20 hours (Shulgin and Shulgin, 199 1 ) .
Legal Status
ALEPH-4 is not a scheduled compound under federal drug law, or under District of Co
#6. ALEPH-7
1-(2,5-Dimethoxy-4-(propylthio )phenyl)propan-2-amine
2,5-Dimethoxy-4-propylthioamphetamine
Registry Numbers
CAS #
HCl salt [849919-74-0]
Freebase [207740-16-7]

From 2,5-dimethoxy-4-propylthiobenzaldehyde (with nitroethane, acetic acid, and
ammonium acetate) to 1-(2,5-dimethoxy-4-propylthiophenyl)-2-nitropropene; (with LAH)
to ALEPH-7 (Shulgin and Shulgin, 1991).

ALEPH-7 / ARIADNE

m / z: 269.1449 (100.0%), 270. 1483 (15. 1 % ), 271 . 1407 (4.5% ), 271 . 1517 ( 1 . 1 % )
Elemental Analysis: C , 62.42; H , 8.61; N , 5.20; 0 , 11 .88; S , 11 .90
HCl salt 135-142 °C (Gallardo et al., 2005)
Biochemistry
Sulfur-substituted a-alkyl phenethylamines as selective and reversible MAOA inhibitors:
biological activities (Gallardo-Godoy et al., 2005).
Pharmacology
This drug has been evaluated in extensive QSAR studies (Clare, 1 998; Beuerle et al., 1997).
Orally active in humans at 4-7 mg; duration 1 5-30 hours (Shulgin and Shulgin, 1 991 ) .
Legal Status
ALEPH-7 is not a scheduled compound under federal drug law, or under District of
Columbia or any state laws.
# 7. ARIADNE
1 -(2,5-Dimethoxy-4-methylphenyl)butan-2-amine
4C-DOM
2,5-Dimethoxy-4-methyl-a-ethylphenethylamine
2-Amino-1 -(2,5-dimethoxy-4-methylphenyl)-butane
Dimoxamine (R-isomer freebase)
BL-3912 (racemate HCl salt)
BL-3912A (R-isomer HCl salt)
NSC-292248 (R-isomer HCl salt)
Registry Numbers
CAS #
HCl salt [54690-19-6]
Freebase [52842-58-7]
R-(-)-Isomer HCl salt [52663-86-2]
S-( +)-Isomer HCl salt [5291 8-31-7]
R-(-)-Isomer 2-chlorotartranilide salt [52842-60-1] CAS #
S-( +)-Isomer 2-chlorotartranilide salt [54713-06-3] R-(-)-Isomer freebase [52842-59-8]
S-( +)-Isomer 2-nitrotartranilide salt [52881-89-7] S-(+)-Isomer freebase [52881-88-6]

From 2,5-dimethoxytoluene (with N-methylformanilide, POC13 ) to 2,5-dimethoxy-4-
methylbenzaldehyde; (with nitropropane) to 1-(2,5-dimethoxy-4-methylphenyl)-2-nitro-1-
butene; (with LAH) to 4C-DOM (Standridge et al., 1976) .
C 1 3H2 N02 Exact Mass: 223. 1572

1
m / z: 223. 1572 (100.0% ), 224.1606 (14. 1 % )
HCl salt m.p. 232.5-234.5 °C (Standridge et al., 1976)(IPA)

ARIADNE

4- Name CAS # Ref
-- 4C-H [722550-58-5] (1 3)
-
Me ARIADNE (this entry)

Et 4C-E [72667-79-9] (1,4)
Pr 4C-P [72667-81 -3] (1,4)
iPr 4C-iP [72667-80-2] (1,4)
Bu 4C-BU [72667-82-4] (1,4)
(1) Effects studied on cat behavior (Standridge et al., 1980).
(3) The fragmentation patterns of some fifty-five phenethylamines were determined by a variety of
mass spectrometry techniques (Ki:illiker and Oehme, 2004).
(4) Synthesis (Standridge et al., 1980) .
The optical isomers were synthesized (Standridge et al., 1976). ARIADNE was identified as
a new designer drug in Canada by NMR (Dawson and Neville 1989).
History
4C-DOM was originally called ARIADNE, being the first of the series of the ten possible
homologues of DOM. The concept of replacing each of the ten different hydrogens with
a methyl group produced a series of compounds called "the 10 classic ladies," and each
would receive a notable woman's name. ARIADNE was the first (Shulgin and Shulgin,
1991). It was developed commercially by the Bristol-Myers Company to increase mental
alertness in geriatric patients, and was patented in Germany, France, and the United States
(Shulgin, 1974a, 1974b, 1977a). Its commercial name, Dimoxamine, does not have a classic
female ring to it.
Biochemistry
4C-DOM, a weak serotonin agonist, increased the efflux of labeled serotonin into the rat
brain ventricle (Kantak et al., 1 978) .
Pharmacology
Studies were made of ARIADNE injection into the rat optic nerve and the cat sciatic nerve
(Paulson and McClure, 1 973) . R-DOM and R-4C-DOM were compared with amphetamine
in the dog (Buyniski et al., 1974), and the rat (Tilson et al., 1977a, 1977b). R-DOM and R-4C
DOM are partial agonists of serotonin receptors in non-innervated vascular smooth muscle
(sheep umbilical arteries; Dyer, 1976) .
R-4C-DOM was compared t o S-amphetamine i n rat avoidance behavior (Tilson e t al.,

1977a, 1977b). The decreased frequency of rat limb flicks correlated well with the drop off
in potency of several 2,5-dimethoxy compounds: DOM, R-DOB, and 2,5-DMA were the
most effective, S-DOB and DOET were weaker, and 4C-DOM was almost without activity
(Rusterholz et al., 1977) . 4C-DOM substituted completely for LSD in a rat two-lever dis
crimination test (Winter, 1980) . About a dozen psychedelics were compared to stimulants
in rats trained in a conditioned avoidance study (Davis and Hatoum, 1987) . The replace
ment of the a-methyl group with an a-ethyl group eliminated the psychedelic action, but
maintained the MDMA-generalized stimulus responses in rats (DOM and 4C-M, a-MT
[a-methyltryptamine] and a-ET [a-ethyltryptamine]; Glennon, 1 993) .

ARIADNE / ASB
Amphetamine, and, to a greater extent, several psychedelics (PMA, MDA, DOM, DOB,
and 4C-DOM), protected rats from electroshock-induced seizure (Davis et al., 1982) .
I n normal human subjects, R-4C-DOM orally a t 25-50 m g increased mental alertness and
feelings of well-being. At 1 00 mg / day, the symptoms of Parkinson's disease went into re
mission. With psychotic patients there was a consistent relief of manic depression at doses
of 50-1 00 mg (Shulgin, 1977a; Partyka et al., 1978) .
A single human oral ingestion of 270 mg produced a change of state of consciousness but
evoked no psychedelic effects (Winter, 1980).
Legal Status
ARIADNE is not a scheduled compound under federal drug law, or under District of
# 8. ASB
2-(3,4-Diethoxy-5-methoxyphenyl)ethanamine
�------�
3,4-Diethoxy-5-methoxyphenethylamine
Asymbescaline
Registry Numbers
CAS # CAS #
HCl salt [90132-30-2] Freebase [63918-08-1]

From 3,4-diethoxy-5-methoxybenzaldehyde (with nitromethane) to 1 -(3,4-diethoxy-5-
methoxy)-2-nitroethene; (with LAH) to ASB (Jacob and Shulgin, 1984) .
From 5-bromobourbonal (with Etl) t o 3-bromo-4,5-diethoxybenzaldehyde; (with butyl

borate) to 3,4-diethoxy-5-hydroxybenzaldehyde; (with methyl iodide) to 3,4-diethoxy-5-
methoxybenzaldehyde; (with nitromethane) to 1-(3,4-diethoxy-5-methoxyphenyl)-2-nitro
ethene; (with LAH) to ASB (Shulgin and Shulgin, 1991).

m / z: 239. 1521 (100.0% ), 240. 1555 (14. 1 % )
Elemental Analysis: C , 65.25; H , 8.84; N , 5.85; 0, 20.06
HCl salt m.p. 142-143 °C (Shulgin and Shulgin, 1991)
Biochemistry
Effects on alkaline phosphatase activity and pyruvate utilization in rat brain homogenates
(Clark et al., 1956)
Pharmacology
ASB produced experimental catatonia in cats (Noteboom, 1934); the action of mescaline,
escaline, and ASB was observed on frogs, cats, and dogs (Grace, 1934) .
This drug was evaluated i n extensive QSAR studies (Clare, 1998; Beuerle e t al., 1997) .
Reported to be orally active in humans at 120-140 mg (Jacob and Shulgin, 1 984), and at
200-280 mg; duration 10-15 hours (Shulgin and Shulgin, 1991).

BDB
Legal Status
ASB is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
# 9. BDB
1-(Benzo [d] [l,3]dioxol-5-yl)butan-2-amine
1-(3,4-Methylenedioxyphenyl)-2-butanamine
2-Amino-1-(1,3-benzodioxo-5-yl)butane
2-Amino-1-(3,4-methylenedioxyphenyl)butane
a-Ethyl-3,4-methylenedioxyphenethylamine
a-Ethyl-1,3-benzodioxole-5-ethanamine
MDP-2-B
J
NSC 1 72188
Registry Numbers
CAS # CAS # CAS #
HCl salt [42542-07-4] R-Isomer HCl salt [103882-47-9] S-( +)-Isomer [103882-52-6]
Freebase [107447-03-0] S-Isomer HCI salt [103882-48-0] R-(-)-Isomer [103882-51-5]

From piperonal (with the Grignard of propyl bromide, dilute HCl, saturated aque
ous ammonium chloride) to 1-(3,4-methylenedioxyphenyl)-2-butanol; (with KHS04 ) to
1 -(3,4-methylenedioxyphenyl)-1 -butene; (with hydrogen peroxide) to 1 -(3,4-methylene
dioxyphenyl)-2-butanone; (with sodium cyanoborohydride, ammonium acetate) to BDB
(Nichols et al., 1986a; Shulgin and Shulgin, 1991).

m / z: 193.1103 (100.0% ), 194.1136 (12.0 % )
Elemental Analysis: C , 68.37; H, 7.82; N , 7.25; 0 , 16.56
HCI salt m.p. 159-161 °C (Nichols et al., 1986a) (EtOH / Etp)

MDMA and BDB can be distinguished by careful analysis of their LC retention time,
though mass spectra are very similar (Noggle et al., 1991c) . Several a-ethyl phenethyl
amines were synthesized and analytically compared with their amphetamine coun
terparts (Clark et al., 1996a) . Eight structurally related methylenedioxy drugs were
distinguished by reversed-phase chromatographic analysis (DeRuiter et al., 1998c) .
Synthesis and spectral characterization has been accomplished for MBDB, BDB, GEA,
and N-Me-a-Et-GEA (Kanamori et al. 1999); FTIR spectral analysis has been report
ed (Praisler et al., 2000). MDMA was distinguished from several structurally related
compounds in human urine, including BDB (Chung et al., 2001). Enantiomeric anal
ysis of MBDB and its metabolite BDB was developed for rat urine (Nagai et al., 2002).
Synthesis and GC / MS spectral discrimination of the 2,3- and 3,4-isomers was reported
(Borth et al., 2000). A plasma screening and quantitative GC / MS analysis was reported
(Peters et al., 2003). Analysis by non-polar GC, and MS comparison to MDMA was report
ed (Aalberg et al., 2004); fragmentation patterns of some fifty-five phenethylamines were
determined by a variety of mass spectrometry techniques (Kolliker and Oehme, 2004) .

BOB
Analysis by LC-ESI-MS-MS and comparison to MOMA has been performed (Pihlainen et
ropropionamide (Liu, 2005). MOMA and nine isomers were identified by GC I MS (Aalberg
al., 2005); BDB could be distinguished from MOMA by GC / MS analysis of the pentafluo
et al., 2000, 2004) and by LC-ESI-MS-MS (Pihlainen et al., 2005).
BDB identification by neural network, and by neural networks coupled with principal
component analysis, was applied to IR spectra (Gosav et al., 2005) . Synthesis, and analysis
of MBDB and its analogues by IR and NMR, GC / MS and LC reported (Sanuki et al., 2006).
Analytical procedures were developed for the drug analysis of hair samples (Junker et al.,
2001; Van Den Berg et al., 2002).
A reproducible, simple, and small-scale method was developed for detecting the reuptake
and release of monoamines (dopamine, serotonin, and norepinephrine) using rat brain
synaptosomes (Nagai et al., 2007) .

3- I 4- Name CAS # Ref
-OCO- BDB (this entry)
-OCFp- F 2-BDB [914800-78-5] (1) (1) Synthesis (Trachsel et al., 2006).
Biochemistry
Release of [ 3H]-labeled serotonin from rat hippocampal slices and [ 3H]-labeled dopamine
from rat caudate nucleus slices was seen (Johnson et al., 1986) . GC / MS analysis of human
urine has shown that the methylenedioxy ring of BDB opens to give DH-a-Et-PEA and
HM-a-Et-PEA as metabolites (Maurer, 1 996) . Qualitative and quantitative GC / MS with
trifluoroacetic anhydride derivatization was used to analyze mixtures containing MBDB,
BDB, MOMA, MDA, and MDE; BDB was detected in the urine of MBDB users (Kronstrand,
1996) . The conversion of MBDB to BDB in human trials involving urine, saliva, and sweat,
was quantitatively analyzed based on GC / MS (Kintz, 1 997) . MBDB, administered orally
to male rats at 20 mg / kg, was excreted in part unchanged, and as the three metabolites
BDB, GEA, and N-Me-GEA (Kanamori et al., 1998a) . MBDB and its metabolite BDB were
assayed in rat urine following oral administration (Nagai et al., 2002).
Pharmacology
Mescaline, DMPEA, MDPEA, TMA, MDA, DMA, BDB, and MOMA were compared phar
macologically in five animal species (Hardman et al., 1973) . MDA, MOMA, BDB, and
MBDB were compared in a two-lever drug discrimination study to distinguish saline from
LSD (Nichols et al., 1986a). BDB, MBDB, and MMBDB were compared to one another in
the newly hatched chicken (Bronson et al., 1995a), and on the chicken embryo and the one
day-old chicken (Bronson et al., 1994b). The effects of BDB and MDA were compared with
cathinone (stimulant) and 2C-B (psychedelic) activity in newly hatched chickens (Bronson
et al., 1995b).
Metabolic pathways were described in the rat and in humans, and GC / MS procedures
were developed for use in toxicological analysis; a major urinary metabolite of BDB is the
catechol metabolite (Maurer et al., 2000). A review of studies on the metabolism including
cytochrome P450 isoenzyme dependency, and on screening procedures for detection of
MDA, MOMA, MDE, BDB, and MBDB has been published (Maurer and Kraemer, 2002).

B-DFLY
BDB was among several homologues of MDA that appeared in the street drug market in
Italy (Furnari et al., 1998) .
Orally active in humans at 150-230 mg; duration 4-8 hours (Shulgin and Shulgin, 1991).
Legal Status
BDB is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#10. B-DFLY
1-( 8-B romobenzo [ 1,2-b:4,5-b' ] difuran-4-y1 )propan-2-amine
1-( 8-Bromobenzo [ 1,2-b ;4,5-b'] difuran-4-y1 )-2-aminopropane
Bromodragonfly
DOB-Dragonfly
Registry Numbers
CAS #
dl-HCl salt [219986-78-4]
dZ-Freebase [219986-94-4]
R-(-)-Isomer HCl salt [332012-24-5] Br
5-( +)-Isomer HCl salt [332012-25-6]
R-(-)-Isomer freebase [502759-67-3]

From FLY (see #68) (with trifluoroacetic anhydride) t o FLY-trifluoroacetamide; (with bro
mine) to B-FLY-trifluoroacetamide; (with dichlorodicyanobenzoquinone, DDQ) to B-DFLY
trifluoroacetamide; (with NaOH) to B-DFLY (Parker et al., 1 998a) .
alanine; (with oxalylchloride, tetrahydrobenzo[l,2-b;4,5-b'] difuran and AlCl) to R- (or S-)

From optically active (R- or S-) alanine (with CF3 C02Et) to R- (or S-) N-trifluoroacetyl
N-trifluoroacetyl-2,3,6,7-tetrahydro-4-alanylbenzo[l,2-b;4,5-b'] difuran; (with triethylsi

lane) to R- (or S-) N-trifluoroacetyl-l-(2,3,6,7-tetrahydrobenzo[l,2-b;4,5-b'] difuran-4-yl)-2-
aminopropane; (with Br2 ) to R- (or S-) 1-(8-bromo-2,3,6,7-tetrahydrobenzo[l,2-b:4,5-b'] difu
ran-4-yl)-2-trifluoroacetoamidopropane); (with DDQ) to R- (or S-) 1-(8-bromobenzo[ l,2-
b:4,5-b ']difuran-4-yl)-2-trifluoroacetamidopropane; (with NaOH) to R- (or S-) B-DFLY
(Chambers et al., 2001 ) .

ml z : 293.0051 (100.0% ), 295.0031 (97.3%), 294.0085 (14. 1 % ), 296.0064 (13.7% )
Elemental Analysis: C, 53.08; H, 4.11; Br, 27.16; N, 4.76; 0, 1 0.88
R-(-) HCl salt 290 °C (dee) [a] � -20.1° (Chambers et al., 2001)
5-( +) HCl salt 291 °C (dee) [a] �o +20.8° (Chambers et al., 2001)
Mass spectra of 2C-BFLY, B-FLY and B-DFLY were reported (Reed and Kiddon, 2007) .
History
The "FLY" name was inspired by the two dihydrofuran rings that extend oppositely from
the sides of the benzene ring. When the side rings are aromatized to furans, they are pla
nar with the benzene ring and the code name is "DRAGONFLY"; they are listed as DFLY
derivatives.

B-DFLY / BEATRICE
Biochemistry
B-DFLY is an extremely potent agonist at the 5-HT2A receptor (Parker et al., 1 998a) .
Pharmacology
Synthesis, and evaluation of activity in the two-lever drug discrimination paradigm in rats
trained to discriminate saline from LSD (Monte et al., 1996) . B-DFLY was the first arylethyl
amine found that surpassed LSD in potency in a behavioral assay (Parker et al., 1 998a), and
was noted as the first compound with LSD-like activity to have an aromatic nucleus other
than benzene or indole.
B-DFLY was compared with six pharmacologically related compounds in a 3D-QSAR

study (Schulze-Alexandru et al., 1999) .
The enantiomorphic isomers of B-DFLY were evaluated as agonists for 5-HT2 A and 5-HT2c
receptors, and compared with DFLY and TFM-DFLY as well as with the tetrahydro
analogues FLY, B-FLY, and TFM-FLY (Chambers et al., 2001 ) . B-DFLY was included in a
study of serotonin receptor-mediated activation of phospholipase A2 and C (Kurrasch
Orbaugh et al., 2003)
B-DFLY was first reported to be active in humans via i.m. administration at about 1 00 µg;
it was initially reported without oral activity at this dose (Shulgin, 2003). However, recent
reports of severe oral overdose reactions, including fatalities in Europe and the United
States, have also been attributed to this compound (Thorlacius et al., 2008; Erowid, 2009).
Legal Status
B-DFLY is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#11. BEATRICE
1 -(2,5-Dimethoxy-4-methylphenyl)-N-methylpropan-2-amine
2,5-Dimethoxy-N,4-dimethylamphetamine
N-Methyl-DOM
N-Me-DOM
R-N-Me-DOM
Registry Numbers
CAS# CAS #
HCl salt [25505-68-4] R-Isomer [92282-59-2]
Freebase [92206-37-6] [ 11 C]-Labeled isomer [201162-24-5]

From DOM (with benzaldehyde, then Me2S04) to N-benzylidinyl-N-methyl-(2,5-dime
thoxy-4-methylamphetamine)-yl quaternary salt; (with Hp) to BEATRICE (Ho et al.,
1970b).
From DOM (with ethyl formate) to 2,5-dimethoxy-N-formyl-4-methylamphetamine; (with

LAH) to BEATRICE (Shulgin and Shulgin, 1991).

m / z: 223. 1572 (100.0%), 224.1606 (14. 1 % )
Elemental Analysis: C, 69.92; H, 9.48; N , 6.27; 0, 14.33

BEATRICE / B-FLY
HCl salt m.p. 125-126 °C (Ho et al., 1970b)

HCl salt m.p. 136-137 °C (Shulgin and Shulgin, 1991) (EtOAc)
Infra-red distinguishable polymorphs exist. The quaternary salt procedure yields a hydro
chloride salt with a m.p. 125-126 °C, which, on recrystallization from ethyl acetate has a
different crystal structure and a m.p. of 1 36-137 °C. The formyl reduction procedure pro
duced only the latter form.
11
[ C]-labeled analogues were synthesized for PET studies (Solbach et al., 1 997a).
Homologues
N- a- Name CAS # Ref
Me Me BEATRICE (this entry) (1) Behavioral effects studied in rats
Me2 Me N,N-Me-DOM [26070-49-5) (1) (Smythies et al., 1970) .
(2) The N-ethyl homologue has been
Et Me N-Et-DOM [53581-78-5) (2) synthesized (Aldous et al., 1974).
History
BEATRICE was the second of the ten classic ladies. See ARIADNE ( # 7) for a discussion of
this naming convention.
Biochemistry
Research evidence for the involvement of serotonin in the mechanism of the action of psy
chedelic drugs has been presented (Glennon et al., 1984b).
Pharmacology
BEATRICE disrupted conditioned responses in rats, and potentiated the phenobarbital
sleeping time in mice (Ho et al., 1970b) . The 5-HT 1 and 5-HT2 binding properties of this
compound have also been studied (Shannon et al., 1984) .
Threshold activity in humans at 30 mg, but negative side-effects from that dose stopped
investigation of higher doses; duration 6-1 0 hours (Shulgin and Shulgin, 1991 ) .
Legal Status
BEATRICE is not a scheduled compound under federal drug law, or under District of Co
# 12. B-FLY
1-( 8-Bromo-2,3,6, 7-tetrahydrobenzo[1,2-b: 4,5-b'] di fur an-4-y1)propan-2-amine
1-( 8-Bromo-2,3,6, 7-tetrahydrobenzo [ 1,2-b: 4,5-b'] difuran-4-y1)-2-aminopropane
8-Bromo-2,3,6,7-tetrahydro-a-methylbenzo[l,2-b:4,5-b' ] difuran-4-ethanamine
3C-B-FLY
Bromo-fly
DOB-FLY
Registry Numbers
CAS # Br
HCI salt [1 78557-19-2]
Freebase [219986-75-1] CAS #
R-(-)-Isomer HCl salt [332012-1 8-7) R-Isomer freebase [740790-11-8)
S-(+)-Isomer HCl salt [332012-19-8) S-Isomer freebase [766498-58-2)

B-FLY

From hydroquinone (with 1-chloro-2-bromoethane) to 1,4-bis(2-chloroethoxy)ben
zene; (with Br2) to 1,4-bis(2-chloroethoxy)-2,5-dibromobenzene; (with butyl lithium) to
2,3,6,7-tetrahydrobenzo[ l,2-b:4,5-b'] difuran; (with dichloromethyl methyl ether) to 4-for
myl-2,3,6,7-tetrahydrobenzo[l,2-b;4,5-b']difuran; (with nitroethane, acetic acid, and am
monium acetate) to 4-(2-nitro-1 -propenyl)-2,3,6,7-tetrahydrobenzo[l,2-b:4,5-b'] difuran;
(with LAH) to 1 -(2,3,6,7-tetrahydrobenzo[l,2-b:4,5-b' ] difuran-4-yl)-2-aminopropane; (with
Br2) to B-FLY (Monte et al., 1996) .
From optically active (R- or S-) alanine (with CF 3C02Et) to R- (or S-) N-trifluoroacetylala
nine; (with oxalylchloride, tetrahydrobenzo[l,2-b;4,5-b'] difuran and A1Cl3 ) to R- (or S-) N
trifluoroacety1-2,3,6,7-tetrahydro-4-alanylbenzo[ l,2-b;4,5-b'] difuran; (with triethylsilane)
to R- (or S-) N-trifluoroacetyl-l -(2,3,6,7-tetrahydrobenzo[l,2-b;4,5-b'] difuran-4-yl)-2-amino
propane; (with Br2) to R- (or S-) N-trifluoroacetyl-1-(8-bromo-2,3,6,7-tetrahydrobenzo[l,2-
b;4,5-b']-difuran-4-yl)-2-aminopropane; (with NaOH) to R- (or S-) B-FLY (Chambers et al.,
2001 ) .

ml z : 297.0364 (100.0% ), 299.0344 (97.3% ), 298.0398 (14. 1 % ), 300.0377 (13.7% )
Elemental Analysis: C, 52.36; H, 5.41; Br, 26.80; N , 4.70; 0, 10.73
dl-HCl salt m.p. 244-245 °C (Monte et al., 1996) (EtOH / EtOAc)

R-(-)-Isomer m.p. 282-283 °C [a] � -10.82° (Chambers et al., 2001) (IPA)
5-( +)-Isomer m.p. 282-283 °C [a] � + 10.80° (Chambers et al., 2001) (IPA)
Mass spectra of 2C-B-FLY, B-FLY, and B-DFLY were reported (Reed and Kiddon, 2007) .
History
The "FLY" name was inspired by the two dihydrofuran rings that extend oppositely from
the sides of the benzene ring. When they are aromatized to furan rings they are planar
with the benzene ring, and the base code name is "DRAGONFLY"; they are listed as DFLY
derivatives.
Pharmacology
Five "FLY" compounds (2C-FLY, 2C-B-FLY, FLY, B-FLY, and DOM-FLY) were assayed in
a drug discrimination paradigm with LSD-trained rats, and in interactions with various
serotonin receptors (Monte et al., 1996) . B-FLY is an extremely potent agonist for the 5-HT2A
receptor and among the first arylethylamine derivatives known to surpass LSD in potency
in behavioral assays (Parker et al., 1998a) . The optical isomers of each of three "FLY"
compounds (FLY, B-FLY, and TFM-FLY) and their DFLY counterparts (DFLY, B-DFLY, and
TFM-DFLY) were assayed for their affinity to 5-HT2A and 5-HT2c receptors (Chambers et
al., 2001); these novel benzodifuran analogues were found to be potent 5-HT2A receptor
agonists, with ocular hypotensive activity (Feng et al., 2007) .
B-FLY is orally active in humans at about 1 mg (Shulgin, 2003).
Legal Status
B-FLY is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.

BOB
#13. BOB
2-(4-Bromo-2,5-dimethoxyphenyl)-2-methoxyethanamine
4-Bromo-f3,2,5-trimethoxyphenethylamine
f3,2,5-Trimethoxy-4-bromophenethylamine
Registry Numbers
CAS # CAS#

From 4-bromo-2,5-dimethyoxybenzaldehyde (with nitromethane) to 1 -(4-bromo-2,5-
dimethoxyphenyl)-2-nitroethene; (with sodium methoxide) to 4-bromo-2,5-dimethoxy-a
nitroacetophenone; (with AlH3 ) to BOB (Lemaire et al., 1985) .

m / z: 289.0314 (100.0%), 291.0293 (97.3% ), 290.0347 (11 .9% ), 292.0327 (11.6% )
Elemental Analysis: C, 45.53; H, 5.56; Br, 27.54; N, 4.83; 0, 16.54
HCl salt m.p. 1 87-1 88 °C (Lemaire et al., 1985)

2- a- [3- Name CAS # Ref
(1) Compared with DOB as agonist
MeO H Meo BOB (this entry) to 5-HT2A receptor. Experiments
MeO Me HO [3-HO-DOB [ 677277-49-5] (1) with administration to ocular hy
pertensive monkeys (Glennon et
MeO Me MeO [3-MeO-DOB [677277-53-1] (1) al., 2004) .
Biochemistry
Preparation and interaction with serotonin receptors (Torres et al., 1995) . Studies showed
both serotonergic and adrenergic receptor effects on isolated rat thoracic aorta (Torres et
al., 1 998) .
Pharmacology
Orally active in humans at about 12.5 mg (Lemaire et al., 1 985), and at 1 0-20 mg; duration
1 0-20 hours (Shulgin and Shulgin, 1991).
Legal Status
BOB is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#14. BOD
2-(2,5-Dimethoxy-4-methylphenyl)-2-methoxyethanamine
4-Methyl-2,5, f3-trimethoxyphenethylamine
f3,2,5-Trimethoxy-4-methylbenzeneethanamine
f3-Methoxy-2C-D
Registry Numbers
CAS #
HCl salt [98537-38-3]
Freebase [98537-41-8]

BOD / BOH
Synthesis
From 2,5-dimethoxy-4-methylbenzaldehyde (with nitromethane) to 1-(2,5-dimethoxy-
4-methylphenyl)-2-nitroethene; (with sodium methoxide) to 4-methyl-a-nitro-2,5-dime
thoxyacetophenone; (with AlH3 ) to BOD (Lemaire et al., 1985) .

m / z: 225.1365 (100.0% ), 226.1398 (13.0% )
Elemental Analysis: C, 63.98; H, 8.50; N, 6.22; 0, 21 .31
HCl salt m.p. 1 71-172 °C (Lemaire et al., 1985)

2- 4- 5- 13 - Name CAS # Ref
MeO -- Meo Meo BODM [168783-21-9] (1-3)
MeO Br MeO EtO BOBE [168783-22-0] (1,2)
MeO I Meo MeO BOI [168783-26-4] (1,2)
MeO N02 Meo Meo BON [168783-27-5] (1,2)
MeO Me MeO MeO BOD (this entry)
Meo Et Meo Meo BOE [ 168783-38-8] (1,2)
Meo MeO Meo MeO BOT [168783-25-3] (1)
MeO PrS MeO MeO BOPS [168783-23-1] (1,2)
(1) Preparation and interaction with serotonin receptors (Torres et al., 1995).
(2) Studies showed both serotonergic and adronergic receptor effects on isolated rat thoracic aorta
(Torres et al., 1998).
(3) Analogues of B03M were studied for their hypotensive effects (Howe et al., 1966) .
Biochemistry
Preparation and interaction with serotonin receptors has been reported (Torres et al., 1 995).
Both serotonergic and adrenergic receptor effects were observed on isolated rat thoracic
aorta (Torres et al., 1998) .
Pharmacology
This drug has been evaluated in extensive QSAR studies (Clare, 1 998; Beuerle et al., 1 997) .
Reported orally active in humans at 20 mg (Lemaire et al., 1 985), and at 15-25 mg; duration
8-1 6 hours (Shulgin and Shulgin, 1991 ) .
Legal Status
BOD is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#15. BOH
2-(Benzo[d] [l,3] dioxol-5-yl)-2-methoxyethanamine
�-Methoxy-3,4-methylenedioxyphenethylamine
�-Methoxy-1,3-benzodioxole-5-ethanamine

BOH / BOM
Registry Numbers
CAS # CAS # CAS #
HCl salt [98537-37-2] Freebase [73304-06-0] Oxalate [65615-17-0]

From piperonal (with nitromethane) to 1-(3,4-methylenedioxyphenyl)-2-nitroethene;
(with sodium methoxide) to 3,4-methylenedioxy-a-nitroacetophenone; (with AlH 3 ) to
BOH (Lemaire et al., 1985) .

m / z: 195.0895 (100.0%), 196.0929 (10.8% )
Elemental Analysis: C, 61 .53; H, 6.71; N, 7. 1 8; 0, 24.59
HCl salt m.p. 152-153 °C (Lemaire et al., 1985)
History
BOH was a synthetic intermediate in the synthesis of papaverine and related compounds
(Mannich and Walther, 1927) .
Biochemistry
Preparation and interaction with serotonin receptors (Torres et al., 1 995). Both serotonergic
and adrenergic receptor effects observed on isolated rat thoracic aorta (Torres et al., 1 998).
Pharmacology
Reported orally active in humans at 130 mg (Lemaire et al., 1985), and at 80-1 20 mg; dura
tion 6-8 hours (Shulgin and Shulgin, 1991).
Legal Status
BOH is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#16. BOM
2-Methoxy-2-(3,4,5-trimethoxyphenyl)ethanamine
�,3,4,5-Tetramethoxyphenethylamine
�-Methoxymescaline
Registry Numbers
CAS # CAS#
HCI salt [98537-36-1] Freebase [98537-40-7]

From 3,4,5-trimethoxybenzaldehyde (with nitromethane) to 1 -(3,4,5-trimethoxyphenyl)-2-
nitroethene; (with sodium methoxide) to �,3,4,5-tetramethoxy-a-nitroacetophenone; (with
AlH3) to BOM (Lemaire et al., 1985) .

m / z: 241 . 1314 (100.0% ), 242.1348 (13.0% )
Elemental Analysis: C, 59.73; H, 7.94; N, 5.81; 0, 26.5
HCI salt m.p. 198.5-199.5 °C (Lemaire et al., 1985)

BOM / B-SF
Biochemistry
Preparation, and interaction with serotonin receptors (Torres et al., 1995); studies found
both serotonergic and adrenergic receptor effects on isolated rat thoracic aorta (Torres et
al., 1998) .
Pharmacology
BOM produced experimental catatonia in cats (Noteboom, 1 934) .
Not active in humans at 200 mg orally (Lemaire et al., 1985; Shulgin and Shulgin, 1991 ) .
Legal Status
BOM is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#17. B-SF
1-(7-Bromo-5-methoxy-2,3-dihydrobenzofuran-4-yl)propan-2-amine
1-(7-Bromo-5-methoxy-2,3-dihydrobenzofuran-4-yl)-2-aminopropane
7-Bromo-2,3-dihydro-5-methoxy-a-methyl-4-benzofuranethanamine
Bromo-semi-fly
B-Semi-fly
OCH3
F-4A5,7B
Registry Numbers
CAS #
Methanesulfonate [ 130933-09-4] Br
Freebase [1 78557-10-3]

From 2,5-dihydroxybenzyl bromide (with K2C03, then with allyl bromide) t o 5-hydroxy
dihydrobenzofuran allyl ether; (with heat) to a mixture of the 4-allyl and the 6-allyl iso
mers; the 4-allyl isomer (with methyl iodide) to the methyl ether; (with KOH at reflux) to
the propenyl isomer; (with AgN02, 12, triethylamine) to the nitrovinyl intermediate; (with
LAH) to B-SF (Nichols et al., 1991)
From the Claisen rearrangement of 5-allyloxy-2,3-dihydrobenzofuran with methylation

and isomerization (Waldman et al., 1996) .

Molecular Weight: 286. 1 7
m / z: 285.0364 (100.0% ), 287.0344 (97.3% ), 286.0398 (13.0% ), 288.0377 (12.6% )
Elemental Analysis: C, 50.37; H, 5.64; Br, 27.92; N, 4.89; 0, 1 1 . 1 8
Methanesulfonate m . p . 191-193 ° C (Nichols e t al., 1991) (EtOH / Etp)
History
The removal of one of the two dihydrofuran rings from FLY (q.v.) leads to a family of com
pounds called semi-flys (SF). The "meta" suffix is sometimes used, and indicates that new
ring has the oxygen atom meta to the aliphatic chain. The loss of the other ring, instead,
leaves an oxygen ortho to the aliphatic chain. This ring structure also imposes its own sub
stituent numbering scheme (see structure) .

B-SF I 2C-B

5- 6- 7- a- Name CAS # Ref
-- Meo Meo -- Me0-2C-ISF [194787-61-6) (1)
Meo -- -- Me SF [ 130933-03-8] (2,3)
Meo -- Br Me B-SF (this entry)
-
Meo - I Me I-SF [184473-66-3] (4-6)
(1) Me0-2C-I-SF and Me0-2C-I-FLY were compared with mescaline and escaline in several tests
including a two-lever discrimination assay in rats trained to distinguish LSD from saline (Monte
et al., 1997).
(2) Synthesis (Nichols et al., 1991; Waldman et al., 1996)
(3) SF, especially in the bromination analogue 4-B-SF, showed high potency in drug discrimination
studies in LSD-trained rats (Nichols et al., 1991).
(4) Synthesis (Waldman et al., 1996).
(5) 4-I-SF (and the bromo analogue) was found to be extremely potent in the rat in vivo assays, and
2
was evaluated for its ability to compete for [ 1 5I] DOI and [ 3 H] ketanserin binding to cells express
ing cloned human 5-HT2N 5-HT2w and 5-HT2c receptors (Nichols et al., 1991).
(6) Also known as F-4A5,71 .
Pharmacology
B-SF showed high potency (similar to that of DOB) in drug discrimination studies in LSD
trained rats (Nichols et al., 1991 ) . B-SF (and the iodo analogue), was found to be extremely
2
potent in rat in vivo assays, and was evaluated for its ability to compete for [ 1 5 1] DOI
and [ 3H] ketanserin binding to cells expressing cloned human 5-HT2 A 5-HT2w and 5-HT2c
'
receptors (Nichols et al., 1991 ) .
Human activity o f B-SF i s unknown.
Legal Status
B-SF is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#18. 2C-B
2-( 4-Bromo-2,5-dimethoxyphenyl)ethanamine
4-Bromo-2,5-dimethoxyphenethylamine
a-DESMETHYL-DOB
BDMPEA
Bees
Bromo
Erox
Nexus
See-bietjies (sea biscuits)
Ubulawu Nomathotholo
Venus
Registry Numbers
CAS # DEA
HCl salt [56281-37-9] 7392
Freebase [66142-81-2]

2C-B

From 2,5-dimethoxybenzaldehyde (with nitromethane) to 2,5-dimethoxy-f3-nitroethene;
(with LAH) to 2,5-dimethoxyphenethylamine; (with Br2) to 2C-B (Shulgin and Carter, 1975;

m l z : 259.0208 (100.0% ), 261 .0187 (97.3% ), 260.0241 (10.8%), 262.0221 (10.5%)
Elemental Analysis: C, 46. 1 7; H, 5.42; Br, 30.72; N, 5.38; 0, 12.30
HCl salt m.p. 237-239 °C (dee.) (Shulgin and Carter, 1975) (EtOH)
HBr salt m.p. 214.5-215 °C (Shulgin and Shulgin, 1991)
The identification of dimethoxyamphetamines by bromination and the IR spectra of the

products has been reported (Bailey et al., 1 976) . Analysis by HPLC was developed for iso
lation and quantitation of this chemical in urine samples (Helmlin and Brenneisen, 1 992) .
Screening of substituted amphetamine derivatives b y fluorescence polarization immuno
assay has been described (Cody and Schwarzhoff, 1993).
GC / MS analysis of 2C-B and its two homologues, DOB and 4C-B, was complicated by
the presence of synthetic precursor contaminations (DeRuiter et al., 1 995). Bromination
products of all six dimethoxyphenethylamines were isolated and characterized by GC /
MS (DeRuiter et al., 1998a) . Analysis without derivatization by HPLC / MS was reported
(Bogusz et al., 2000).
GC / MS analysis was developed to identify 2C-B, which had been made illegal in Japan in
July, 1998 (Maruyama et al., 2000). DOB was distinguished from 2C-B in street tablets being
sold in Italy (Furnari et al., 2001). Employing HPLC-PDA, HPLC-MS, TLC, and NMR, a
library of 35 illegal drugs was assembled and used to identify street samples (Nakashima
et al., 2005.) GC / MS was used to successfully identify 2C-B in human blood and urine
samples (Vorce and Sklerov, 2004) . Analysis of human urine by LC-MS-MS was reported
(Nordgren and Beck, 2004; Nordgren et al., 2005); 2C-B has been analyzed in human plas
ma by GC / MS of the heptafluorobutyramide (Habrdova et al., 2005).
Cross-reactivity of several substituted amphetamines with the Roche Abuscreen® radio

immunoassay for amphetamines was evaluated (Cody, 1 990a) . Several isomers and ana
logues were characterized by IR, GC-MS, HPLC, and NMR (Matsumoto et al., 2004). A
single HPLC-UV analysis of human urine could detect amphetamine (and its metabolite
PHA), MOMA (and its metabolite MDA), 2C-B, and MTA (Soares et al., 2004) . Analysis of
human whole blood by capillary electrophoresis with diode array detection was reported
(Nieddu et al., 2005), and an NMR procedure was described for the identification of several
drugs (Hays, 2005). An analytical process of human urine is described, involving electro
phoresis and mass spectroscopy (Boatto et al., 2005).
Positional Isomers *
2- 3- 4- 5- 6- Name CAS # Ref
--
Br MeO MeO -- 2,3,4-BMM [72912-40-4] (1)
-
Br MeO - MeO -- 2,3,5-BMM [200264-67-1 ] (2)
Br MeO -
- --
MeO 2,3,6-BMM -- (3)
Br -- MeO MeO -
- 2,4,5-BMM [ 63375-81-5] (2,4-6)

2C-B
2- 3- 4- 5- 6- Name CAS # Ref

-
Br -- MeO -- MeO 2,4,6-BMM - (3)
MeO Br MeO -- -- 2,3,4-MBM -- (3)
MeO Br -- MeO -- 2,3,5-MBM -- (3)
MeO Br -- -- Meo 2,3,6-MBM [ 200264-68-2] (2)
-- Br MeO MeO -- 3,4,5-BMM [92015-18-4] (7,8)
MeO MeO Br -- -- 2,3,4-MMB -- (3)
--
MeO -- Br MeO -- 2C-B (this entry)

MeO -- Br -- MeO 2,4,6-MBM -- (3)
-- MeO Br MeO -- 3,4,5-MBM [ 64778-73-0] (9-11 )
MeO - -
MeO Br -- 2,4,5-MMB [200264-66-0] (2)
MeO MeO -- Br -- 2,3,5-MMB [2074-96-6] (12,13)
MeO MeO -- -- Br 2,3,6-MMB [200264-65-9] (2)
*Note that all entries in this table are Schedule I compounds (see Legal Status, this entry).
(1) Employed as an intermediate in the synthesis of pharmacologicals (Bessho, 1963).
(2) The bromination products of all six dimethoxyphenethylamines were isolated, and character-
ized by GC / MS (DeRuiter et al., 1998a).
(3) Not in the published scientific literature.
(4) Synthesis, physical properties reported (Tolkachev et al., 1958).
(5) 2,4,5-BMM has been used in the synthesis of complex molecules (Hanaoka et al., 1991; Culbert
et al., 1995; Heim et al., 1997).
(6) Several isomers and analogues were characterized by IR, GC-MS, HPLC, and NMR (Matsumoto
et al., 2004).
(7) Synthesis (Tolkachev et al., 1964) .
(8) 3,4,5-BMM has been used in the synthesis of complex molecules (Kondo et al., 1958; Bessho,
1963; Horii et al., 1978).
(9) Synthesis (Nichols and Dyer, 1977).
(10) Molecular connectivity analysis gave excellent correlation to serotonin agonist activity in a large
number of phenethylamines and amphetamines (Kier and Glennon, 1978a).
(11) 3,4,5-MBM is more potent than mescaline in contracting sheep umbilical artery strips (Nichols
and Dyer, 1977) .
(12) Synthesis (Merchant and Mountwala, 1958).
(13) Synthesis (Voronin et al., 1965).

2- 4- 5- N- N- Name CAS # Ref
MeO Br MeO -- -- 2C-B (this entry)
MeO Br EtO -- -- 2C-B-5-Et0 -- (1)
MeO Br MeO -- Me 2C-B-M [ 155638-82-7] (2)
MeO Br MeO Me Me 2C-B-MM [155639-23-9] (2)
MeO Br MeO -- Et 2C-B-E [155639-24-0] (2)
MeO Br MeO -CCCCCC- pip-2C-B [155639-27-3] (2)
EtO Br MeO -- -- 2C-B-2-Et0 [207740-17-8] (3)
-
EtO Br EtO -- -- 2C-B-2,5-DIEtO - (1)

2C-B

(2) Binding studies of 2C-B with 5-HT2A and 5-HT2c receptors (Glennon et al., 1994).
(3) The one reference to this compound is a three-dimensional quantitative QSAR study. There is no
published pharmacology (Beuerle et al., 1997).
History
2C-B was identified as a street drug in the United States (Ragan et al., 1 985) . Biochemical
evidence was offered, indicating that 2C-B was a potential drug of abuse (Glennon et al.,
1 988c). In Switzerland, "Ecstasy" tablets were found that contained only 2-CB (Giraud et
al., 1 999; de Boer et al., 1999b). GC / FTIR analysis found that 2C-B, MOMMA, and MBDB
had appeared for sale in Belgium (Dirinck et al., 2000).
Biochemistry
Mutagenic activity was not detected for 2C-B in Salmonella typhimurium assays (White et
al., 1977) . 2C-B caused contraction of the thoracic aorta in the rat (Lobos et al., 1 992) .
In rats, 2C-B is metabolized by two major processes. Deamination leads to the ethanol
and acetic acid metabolites. 0-demethylation leads to either of the two phenols, which
are N-acetylated (Kanamori et al., 2002). The metabolism of 2C-B was studied in the he
patocytes of the mouse, rat, rabbit, dog, monkey, and humans; several new metabolites
were reported. Deamination to the ethanol, acetic acid, and benzoic acid occurred in all six
species; 2,5-dimethoxy-4-bromo-2-hydroxy-5-methoxyphenylethanol was observed in the
human, the monkey, and the rabbit, but not in the other three species (Carma et al., 2005).
The in vitro metabolism of methamphetamine and 2C-B in rats was compared to the in vivo
metabolism (Kanamori et al., 2005).
2C-B was less selective than DOB as to its serotonin receptor binding (Glennon et al., 1 988c) .
2
The 5-HT2 binding site of 2C-B was located with [ 1 51]-labeled 2C-I (Johnson et al., 1990b).
Binding was evaluated at the 5-HTic and 5-HT2 receptors (Glennon et al. 1 992) and at the
5-HT2A and 5-HT2c receptors (Glennon et al., 1994) . A series of psychedelic amphetamines
were compared to their phenethylamine counterparts, as agonists to 5-HT2A and 5-HT2c
receptors (Acuna-Castillo et al., 2002) . Possible 5-HT2A or 5-HT2c receptor antagonism was
investigated (Villalobos et al., 2004).
Pharmacology
Several phenethylamines and tryptamines were compared in studies with rats trained to
discriminate 5-MeO-DMT (Kier and Glennon, 1 978b). Using molecular connectivity analy
sis of ten psychedelic phenethylamines, the importance of the 2- and 5-positions of the
methoxy groups, and the 4-substituent was demonstrated (Glennon et al., 1 979a) .
The effects of 2C-B, cathinone, BOB, and MDA were compared in newly hatched chickens
(Bronson et al., 1 995b ), and the effects of morphine, MOMA, MDA, and 2C-B were observed
on conditioned place preference of newly hatched chickens (Bronson et al., 1 996). Baboons
that had been trained to self-inject cocaine, were switched to MDA, MDOH, DIMETH, and
2C-B; changes in behavior were noted (Sannerud et al., 1 996).
In 1 975, the first publication of the human activity of 2C-B and 2C-D in the scientific
literature was made (Shulgin and Carter, 1975) . 2C-B was among several psychedelic drugs
verified in the Japanese street drug scene (Katagi et al., 2002); along with TMA, TMA-2, 2C
T-2, and 2C-T-7, 2C-B was identified and distinguished by HPLC (Takahashi et al., 2003).

2C-B I 2C-C
Orally active in humans at about 20 mg (Lemaire et al., 1985), and at 1 2-24 mg; duration
4-8 hours (Shulgin and Shulgin, 1 991).
Legal Status
2C-B is a Schedule I hallucinogen under federal drug law (FR, 1994, 1 995), and under
District of Columbia and all state laws except for Alabama, Arkansas, California, Colorado,
Delaware, Georgia, Kansas, Kentucky, Louisiana, Maryland, Massachusetts, Michigan,
Minnesota, New Jersey, New Mexico, New York, Oklahoma, Pennsylvania, Rhode Island,
South Carolina, Texas, Vermont, and Washington.
#19. 2C-C
2-(4-Chloro-2,5-dimethoxyphenyl)ethanamine
4-Chloro-2,5-dimethoxyphenethylamine
2C-DOC
Registry Numbers
CAS # CAS #
Synthesis
From 2C-B (with phthalic anhydride) to phthalimide derivative; (with Cu2Cl2) to the chlo
roisomer; (with hydrazine) to 2C-C (Cheng and Castignoli, 1 984) .
From a solution o f freebase 2,5-dimethoxyphenethylamine (2C-H) i n cold glacial acetic

acid (with dropwise addition of liquid chlorine) to 2C-C (Shulgin and Shulgin, 1 99 1 ) .

m/ z : 215.0713 (100.0% ), 217.0684 (32.0%), 216.0747 (10.8% ), 218.0717 (3.5%)
Elemental Analysis: C, 55.69; H, 6.54; Cl, 16.44; N, 6.49; 0, 14.84
HCI salt m.p. 220-221 °C (Cheng and Castingnoli, 1984) (EtOH)

HCI salt m.p. 120-122 °C (Shulgin and Shulgin, 1991) (IPA)
Freebase b.p. 145-155 °C / 0.05 mm (Cheng and Castingnoli, 1984)

2- 3- 4- 5- a- Name CAS # Ref
Cl -- MeO MeO -- 2-Cl-4,5-DMPEA [27164-31-4] (1)
MeO -- Cl MeO -- 2C-C (this entry)
MeO -- MeO Cl -- 5-Cl-2,4-DMPEA -- (2)
Cl MeO MeO -- -- 2-Cl-3,4-DMPEA [67287-36-9] (3)
-- Cl MeO Cl -- 3,5-Cl-4-MPEA [27164-18-7] (1)
-- Cl MeO Cl Me 3,5-Cl-4-MA [27164-26-7]
-- Cl EtO Cl -- 3,5-Cl-4-EPEA [27164-20-1] (1)
-- Cl PrO Cl -- 3,5-Cl-4-PPEA [27164-22-3] (1)
-- Cl AlO Cl -- 3,5-Cl-4-ALPEA [27164-25-6] (1)
-- Cl BuO Cl -- 3,5-Cl-4-BPEA [27164-23-4] (1)
-- Cl MeO MeO -- 3-Cl-4,5-DMPEA [27164-28-9] (1,4,5)

2C-C I 2C-D
(1) Synthesized as a potential psychedelic (Hellot et al., 1970a).

(3) Synthetic intermediate (Burger and Poggio, 1956).
(4) Pharmacokinetics in rat brain, liver, and plasma (Cohen et al., 1974).
(5) The octanol-water partition coefficient may serve as a predictor of human psychedelic potency
(Nichols et al., 1977).
Employing HPLC-PDA, HPLC-MS, TLC, and NMR, a library of 35 illegal drugs was as
sembled and used to identify street samples (Nakashima et al., 2005). Isomers and ana
logues were characterized by IR, GC-MS, HPLC, and NMR (Matsumoto et al., 2004) .
Biochemistry
The neurotoxic property of the hydroquinone counterpart was studied (Cheng and Cast
agnoli, 1 984) .
A reproducible, simple, and small-scale method was developed for detecting the uptake
and release of the monoamines dopamine, serotonin, and norepinephrine, using rat brain
Pharmacology
This drug has been evaluated in extensive QSAR studies (Clare, 1 998; Beuerle et al., 1 997) .
Legal Status
2C-C is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
In August 2005, the DEA Diversion Control Section asked for information that might
support the placement of this chemical into Schedule I status (Tella, 2004).
#20. 2C-D
2-(2,5-Dimethoxy-4-methylphenyl)ethanamine
2,5-Dimethoxy-4-methyl phenethylamine
DMM-PEA
LE-25
Registry Numbers
CAS #
HCl salt [25505-65-1]
Freebase [24333-19-5]

From 2,5-dimethoxy-4-methylbenzaldehyde (with nitromethane) to 1-(2,5-dimethoxy-4-
methylphenyl)-2-nitroethene; (with LAH) to 2C-D (Ho et al., 1970b; Shulgin and Carter,
1 975) .
From 2,5-dimethoxy-4-methylbenzaldehyde (with NaBH4, then cone. HCI) t o 2,5-dime

thoxy-4-methylbenzyl chloride; (with NaCN) to 2,5-dimethoxy-4-methylbenzyl cyanide;
(with B2H6) to 2C-D (Standridge et al., 1976).

2C-D

m / z: 195.1259 (100.0% ), 196.1293 (11 .9% )
HCI salt m.p. 212-213 °C (Shulgin and Carter, 1975) (EtOH)
HCl salt m.p. 214-216 °C (Standridge et al., 1976) (IPA)
HCI salt m.p. 213-214 °C (Shulgin and Shulgin, 1991) (EtOH)
HBr salt m.p. 1 83-1 84 °C (Shulgin and Shulgin, 1991)
Analysis by HPLC employing fluorescamine derivatization for fluorescence detection has

been reported (Shimamine, 1 984) . Analysis of human whole blood by capillary electropho
resis with photodiode array detection has been reported (Nieddu et al., 2005). Quantitative
determination of human blood plasma was achieved by GC / MS analysis of the heptafluo
robutyrate amides (Habrdova et al., 2005). Blood analyses were developed, utilizing capil
lary electrophoresis with diode-array detection (Boatto et al., 2002), and electrophoresis
combined with mass spectroscopy (Boatto et al., 2005).
Homologues
2- 4- 5- f:I- N- Name CAS # Ref
MeO Me MeO -- -- 2C-D (this entry)
MeO Me MeO Me -- f:\-Me-2C-D [53581-74-1 ] (1)
MeO Me MeO Me2 -- f:\,f:\-Me-2C-D [53581-75-2] (1)
MeO Me MeO -- Me N-Me-2C-D [25505-67-3] (2-4)
MeO Me MeO -- Me2 N,N-Me-2C-D [24286-42-8] (2-4)
MeO Me EtO -- -- 2C-D-5-Et0 -- (5,6)
EtO Me EtO -- -- 2C-D-2,5-DIEtO -- (5,7)
EtO Me MeO -- -- 2C-D-2-Et0 -- (5,8)
(1) Synthesis (Aldous et al., 1974).
(2) Synthesis (Ho et al., 1970b).
(3) Disruption of conditioned responses in rats, and potentiation of the phenobarbital sleeping time
in mice (Ho et al., 1970b).
(4) Disruption of conditioned responses in the rat, potentiated sleep time in mice (Ho et al., 1970b).
(5) Synthesis (Shulgin and Shulgin, 1991), otherwise not in the published scientific literature.
(6) Orally active in humans at 40-50 mg; duration 12 hours (Shulgin and Shulgin, 1991).
(7) Orally active in humans at 55 mg; duration four hours (Shulgin and Shulgin, 1991).
(8) Orally active in humans at 60 mg; duration four hours (Shulgin and Shulgin, 1991).
Analogues
2- 4- 5- Other Name CAS # Ref
MeO F MeO -- 2C-F [207740-15-6] (1-3)
MeO N02 MeO -- 2C-N [261789-00-8] (2,4-6)
MeO FCC MeO -- 2C-EF -- (7,8)
MeO Me MeO -- 2C-D (this entry)
MeO Me MeO N-HO N-H0-2C-D [ 42203-91-8] (9)
MeO Pr MeO -- 2C-P [207740-22-5] (10-15)

2C-D
2- 4- 5- Other Name CAS# Ref

MeO C=C MeO 2C-VI -- (7)
MeO C=C MeO -- 2C-YN [ 633290-73-0] (16)
MeO HOC- Meo -- 2C-HM -- (17)
(1) The single reference in the chemical literature involves the calculation of the structure-activity
relationship with no experimental chemistry (Beuerle et al., 1997) .
(2) Synthesis (Shulgin and Shulgin, 1991).
(3) Not orally active in humans at 250 mg (Shulgin and Shulgin, 1991 ).
(4) Orally active in humans at 1 00-150 mg; duration 4-6 hours (Shulgin and Shulgin, 1991).
(5) Two patents; neither for pharmacological use (He and Mortellaro, 2000; Khasanov and Bell, 2002) .
(6) Analysis of human urine described, involving electrophoresis and mass spectroscopy (Boatto et
al., 2005).
(8) Orally active in humans at 6-10 mg; duration 12 hours (Mueller, 2006).
(9) Synthesis (Coutts and Malicky, 1973).
(10) Quantitative determination in human blood plasma by GC / MS of the heptafluorobutyrate
amides (Habrdova et al., 2005).
(11) Orally active in humans at 5 mg (Mueller, 2006).
(13) Pharmacology described (Weintraub et al., 1980).
(14) Synthesis (Barfknecht et al., 1978)
(15) Establishing the presence and amount of 2C-P in plasma samples (Habrdova et al., 2005).
(16) Synthesis (Trachsel, 2003b).
(17) Not in the published scientific literature. A logical metabolite of 2C-D.
Biochemistry
No mutagenic activity of 2C-D detected in Salmonella typhimurium assays (White et al., 1 977) .
Studies of the 5-HT 1 and 5-HT2 binding properties were conducted (Shannon et al., 1 984) .
The calculated electrostatic potential was related to that of serotonin (G6mez-Jeria et
al., 1 984), and adrenergic and 5-HT2 serotonergic effects on the rat thoracic aorta were
compared (Saez et al., 1994) . A series of psychedelic amphetamines were compared to their
phenethylamine counterparts, as agonists to 5-HT2A and 5-HT2c receptors (Acuna-Castillo
et al., 2002). Possible 5-HT2A or 5-HT2c receptor antagonism was investigated (Villalobos
et al., 2004).
Pharmacology
2C-D disrupted conditioned responses in rats, and potentiated the phenobarbital sleep
ing time in mice (Ho et al., 1 970b), whereas mescaline shortened it (Ho and Huang, 1 970) .
Several phenethylamines and tryptamines were compared i n studies with rats trained to
discriminate 5-MeO-DMT from saline (Kier and Glennon, 1 978b); using molecular con
nectivity analysis of ten psychedelic phenethylamines, the importance of the 2,5-positions
of the methoxy groups, and the 4-substituent was demonstrated (Glennon et al., 1979a).
In 1975, the first publication of the human activity of 2C-B and 2C-D in the scientific litera
ture was presented (Shulgin and Carter, 1975) . Clinical studies with both neurotic patients
and normal controls in the 40-120 mg range suggested value as an adjunct to psychotherapy;
2C-D is short-lived (maximum effect at two hours, base-line at four hours) Sensory enhance
ment was noted at 8-16 mg (Shulgin and Carter, 1975). 2C-D was reported an orally active
psychedelic in humans at about 40 mg (Lemaire et al., 1985), and a mild stimulant with some
psychedelic suggestions at 20-60 mg; duration 4-6 hours (Shulgin and Shulgin, 1991).

2C-D /2C- E
Legal Status
2C-D is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#21. 2C-E
2-(4-Ethyl-2,5-dimethoxyphenyl)ethanamine
2,5-Dimethoxy-4-ethylphenethylamine
Registry Numbers
CAS#
HCl salt [923013-67-6]
Freebase [71539-34-9]

From 1,4-dimethoxybenzene (with acetyl chloride, A1Cl3 ) to 2,5-dimethoxyacetophenone;
(with hydrazine, KOH) to 2,5-dimethoxy-1-ethylbenzene; (dichloromethyl methyl ether,
SnC12) to 2,5-dimethoxy-4-ethylbenzaldehyde; (with nitromethane) to 1 -(2,5-dimethoxy-4-
ethylphenyl)-2-nitroethene; (with LAH) to 2C-E (Shulgin and Shulgin, 1991).

m / z: 209.14 (100.0%), 210.14 (13.3%), 211.15 (l .2% )
HCI salt m.p. 208.5-210.5 °C (Shulgin and Daley, unpublished data) (IPA)
Analysis by HPLC employing fluorescamine derivatization for fluorescence detection has

been reported (Shimamine, 1984) . Quantitative determination in human blood plasma was
achieved by GC / MS analysis of the heptafluorobutyrate amides (Habrdova et al., 2005).
Biochemistry
Most citations to 2C-E in Chemical Abstracts are for computational structure-activity rela
tionships studies. There is essentially no biochemistry published. A reproducible, simple,
and small-scale method for detecting the re-uptake and release of monoamines (dopamine,
serotonin, and norepinephrine) using rat brain synaptosome was developed and applied
to 2C-E (Nagai et al., 2007) .
Pharmacology
Using molecular connectivity analysis of ten psychedelic phenethylamines, importance of
the 2,5-positions of methoxy groups, and the 4-substituent was demonstrated (Glennon et
al., 1979a).
Orally active in humans at 10-25 mg; duration 8-12 hours (Shulgin and Shulgin, 199 1 ) .
Legal Status
2C-E is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
In August, 2005, the DEA Diversion Control Section asked for information that might
support the placement of this chemical into Schedule I status (Tella, 2004) .

2C-E I 2C-H
#22. 2C-H
2-(2,5-Dimethoxyphenyl)ethanamine
2,5-Dimethoxyphenethylamine
2,5-DMPEA
DMPEA-4
NCS 168525
Registry Numbers
CAS # CAS # CAS #
HCl salt [3166-74-3] Sulfate [64610-33-9] Freebase [3600-86-0]
Picrate [108774-13-6] Acid salt [87059-70-9]

From 2,5-dimethoxybenzaldehyde (with malonic acid) to 2,5-dimethoxycinnamic acid;
(with Na, Hg) to 2,5-dimethoxypropionic acid; (with NH3) to 2,5-dimethoxypropionamide;
(with NaOCl) to 2C-H (Buck, 1932) .
From 2,5-dimethoxybenzaldehyde (with nitromethane) to 1-(2,5-dimethoxyphenyl)-2-ni

troethene; (with LAH; Cheng and Castagnoli, 1984) or (with Zn / HCl, Hg; Zhao et al., 2002)
to 2C-H.
Additional syntheses were described (Baltzly and Buck, 1940a; Leaf and Neuberger, 1 948) .

ml z : 181.1103 (100.0% ), 1 82.1136 (10.9%)
Elemental Analysis: C, 66.27; H, 8.34; N, 7.73; 0, 1 7.66
HCI salt m.p. 142-143 °C (Leaf and Neuberger, 1948) (EtOH)

HCl salt m.p. 138-139 °C (Cheng and Castagnoli, 1984) (EtOH)
Freebase b.p. 150 °C / 8 mm (Buck, 1932)
Freebase b.p. 100 °C / 0.5 mm (Leaf and Neuberger, 1948)
Synthesis, TLC and GC chromatographic properties, UV spectra, and other physical prop
erties reported (Ono et al., 1976) . Analysis by HPLC employing fluorescamine derivatiza
tion for fluorescence detection has been reported (Shimamine, 1 984) . Several isomers and
analogues were characterized by IR, GC / MS, HPLC and NMR (Matsumoto et al., 2004).
Techniques were explored for the analysis of street drugs without the use of primary refer
ence standards, with identification by means of liquid chromatography with time-of-flight
mass spectrometry, and quantitation based on liquid chromatography with chemilumines
cence nitrogen detection (Laks et al., 2004). The fragmentation patterns of some fifty-five
phenethylamines were determined by a variety of mass spectrometry techniques (Kolliker
and Oehme, 2004), and employing HPLC-PDA, HPLC-MS, TLC, and NMR, a library of 35
drugs was assembled and used to identify street samples (Nakashima et al., 2005).

2- 5- 13- N- Name CAS # Ref
HO Me HO -- j),2-H0-5-MePEA [857542-53-1 ] (1,2)
HO Me HO Me j),2-H0-5,N-MePEA [117886-34-7] (1,2)
HO Me C=O -- 2-H0-5-MePEA-!)k [860538-08-5] (1)

2C-H
2- 5- f)- N- Name CAS # - �- -

Ref
HO Me C=O Me 2-H0-5,N-MePEA-f)k [857618-30-5] (1)
HO MeO -- -- 2,5-HMPEA [74516-48-6] (3)
HO MeO -- Me2 N,N-Me-2,5-HMPEA [74516-50-0] (3)
HO MeO HO -- f),2-H0-5-MPEA [860511-14-4] (2,4,5)
HO MeO HO Me f),2-HO-N-Me-5-MPEA [117342-28-6] (2,4)
HO MeO C=O -- 2-H0-5-MPEA-f)k [857560-60-2] (4)
HO EtO HO -- f),2-H0-5-EPEA [857755-64-7] (4)
HO EtO HO Me f),2-HO-N-Me-5-EPEA [860510-57-2] (4)
HO EtO C=O -- 2-H0-5-EPEA-f)k [857560-64-6] (4)
HO EtO C=O Me 2-HO-N-Me-5-EPEA-f)k [857566-16-6] (4)
MeO Me HO -- f)-H0-2-M-5-MePEA [ 855271-83-9] (1,2)
MeO Me HO Me f)-HO-N-Me-2-M-5-MePEA [855273-01-7] (1,2)
MeO Me C=O -- 2-M-5-MePEA-f)k [ 860538-07-4] (1)
MeO HO HO Me f),5-HO-N-Me-2-MPEA [854179-26-3] (6)
MeO HO C=O Me 5-HO-N-Me-2-MPEA-f)k [857566-48-4] (6)
MeO MeO -- -- 2C-H (this entry)
MeO MeO C=O -- 2,5-DMPEA-f)k [ 860538-19-8] (7)
MeO MeO Me -- f)-Me-2,5-DMPEA [3490-01-5] (8-10)
MeO MeO -- Me N-Me-2,5-DMPEA [3489-95-0] (2,9, 11-14)
MeO MeO -- Me2 N,N-Me-2,5-DMPEA [64057-69-8] (7-9, 11, 15)
MeO MeO Me Me f),N-Me-2,5-DMPEA [3490-03-7] (8-10)
MeO MeO Me Me2 f),N,N-Me-2,5-DMPEA [3490-04-8] (8-10)
MeO MeO HO -- f)-H0-2,5-DMPEA [ 60407-53-6] (7,9, 16, 1 7)
MeO MeO HO Me f)-HO-N-Me-2,5-DMPEA [63991-17-3] (7,9)
MeO MeO HO Me2 f)-HO-N,N-Me-2,5-DMPEA [ 63991-16-2] (7,9)
MeO MeO HO,Me -- f)-HO,Me-2,5-DMPEA [ 63991-1 8-4] (7,9, 16)
MeO MeO HO Me f)-HO-f),N-Me-2,5-DMPEA [ 69766-13-8] (7,9)
MeO MeO C=O Me2 N,N-Me-2,5-DMPEA-f)k [85761 8-59-8 (7)
EtO EtO HO -- f)-H0-2,5-DEPEA [854168-07-3] (4)
EtO EtO HO Me f)-HO-N-Me-2,5-DEPEA [854178-50-0] (4)
EtO EtO C=O Me N-Me-2,5-DEPEA-f)k [ 855942-20-0 l (4)
(1) Synthesis (Ardis et al., 1946).

(2) The pulmonary circulation effects were measured in the dog (Aviado et al., 1957) .
(3) Synthesis and serotonin agonist evaluation (Glennon et al., 1980b).
(4) Synthesis and toxicology (Ide and Baltzly, 1948) .
(5) Also known as ST-1061 .
(6) Synthesis (Baltzly et al., 1950) .
(7) Synthesis (Baltzly and Buck, 1940b).
(8) Synthesis (Baltzly and Buck, 1940a) .

2C-H I 2C-I
(9) In vitro studies with isolated guinea pig and rabbit uteri and rabbit intestine, and in vivo pressor
studies in mice, were compared (Hjort et al., 1948).
(10) Synthesis (Ardis et al., 1946).
(11) Serotonin receptor site affinity was determined (Glennon et al., 1978).
(12) Synthesis (Buck, 1932) .
(13) The effectiveness of releasing cardiac norepinephrine was measured (Daly et al., 1966).
(14) Serotonin receptor binding was studied (Glennon et al., 1978).
(15) Serotonin receptor site affinity was determined (Glennon et al., 1980a).
(16) The effects on cardiac function were observed in the cat and dog (Ellis, 1965) .
(17) Synonyms are: Desglymidodrine, ST 1 059.
Homologues with Three-Carbon Chains

2- 5- N- Name CAS # Ref
Meo MeO Me homo-N-Me-2,5-DMPEA [ 66997-06-6] (1,2)
MeO MeO Me2 homo-N,N-Me-2,5-DMPEA [64057-69-8] (3)
(2) The serotonin receptor binding was studied (Glennon et al., 1978) .
(3) Synthesis (Baltzly and Buck, 1940a).
Biochemistry
In vitro studies with isolated guinea pig and rabbit uteri and rabbit intestine, and in vivo
pressor studies in mice, were compared (Hjort et al., 1 948) . Effects of ring methoxy groups
on oxidative deamination were evaluated (Clark et al., 1 965). Serotonin receptor site affin
ity was determined (Glennon et al., 1978, 1 980a) . Adrenergic and 5-HT2 serotonergic effects
on the rat thoracic aorta were compared (Saez et al., 1 994) . A series of psychedelic am
phetamines were compared to their phenethylamine counterparts, as agonists to 5-HT2A
and 5-HT2c receptors (Acuna-Castillo et al., 2002), and possible 5-HT2A or 5-HT2c receptor
antagonism was investigated (Villalobos et al., 2004).
Pharmacology
Studies on the enzymatic oxidative deamination and effects on cat behavior (Clark et al.,
1 964)
2C-H is not known to have central effects in humans.
Legal Status
2C-H is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#23. 2C-I
2-( 4-Iodo-2,5-dimethoxypheny l)ethanamine
2,5-Dimethoxy-4-iodophenethy lamine
SPICE
Registry Numbers
CAS #
HCl salt [64584-32-3]
Freebase [69587-11-7]
2
[ 1 5J ]-labeled [126210-33-1 ]

2C-I
History
In December 2004, "SPICE" was being offered for sale in Canada as a sacrament in the
Trans Human Church of Enlightenment.

From 2,5-dimethoxyphenethylamine (with phthalic anhydride) to N-[2-(2,5-dimethoxy
phenyl)ethyl]phthalimide; (with ICl) to N-[2-(2,5-dimethoxy-4-iodophenyl)ethyl]-phthali
mide; (with hydrazine) to 2C-I (Shulgin and Shulgin, 1991). The [ 1 3 1 1]-labeled isomer has
2
been prepared by this route (Braun et al., 1 977) and so has the [ 1 5 1]-labeled isomer (John
son et al., 1 990b).
From 2,5-dimethoxyphenethylamine (with AcOH, ICl) to 2C-I (Cozzi, 1 994) .

Molecular Weight: 307. 13
m / z : 307.0069 (100.0%), 308.0103 (10.8% )
Elemental Analysis: C, 39. 11; H, 4.59; I, 41.32; N, 4.56; 0, 10.42
HCI salt m.p. 246-247 °C (Shulgin and Shulgin, 1991) (Hp)
2C-I was used as a chemical intermediate in the synthesis of 2C-TFM (Nichols et al., 1 994) .
Employing HPLC-PDA, HPLC-MS, TLC, and NMR, a library o f 3 5 illegal drugs was
assembled and used to identify street samples (Nakashima et al., 2005) . Several isomers
and analogues were characterized by IR, GC / MS, HPLC, and NMR (Matsumoto et al.,
2004). Techniques were explored for the analysis of street drugs without the use of primary
reference standards, utilizing LC with time-of-flight mass spectrometry and LC with
chemiluminescence nitrogen detection (Laks et al., 2004). 2C-I was found in street drugs
in Japan, with confirmational analysis by GC / MS and LC-ESI-MS (Kikura-Hanajiri et al.,
2005). An NMR procedure was described for the identification of possibly illegal drugs
(Hays, 2005).
Human whole blood was analyzed by capillary electrophoresis with photodiode array
detection (Nieddu et al., 2005), and an analytical process for human urine was described,
involving electrophoresis and mass spectroscopy (Boatto et al., 2005). Quantitative deter
mination of human blood plasma was achieved by the GC / MS analysis of the heptafluo
robutyrate amides (Habrdova et al., 2005).
Biochemistry
A series of psychedelic amphetamines were compared to their phenethylamine counter
parts, as agonists to 5-HT2A and 5-HT2c receptors (Acuna-Castillo et al., 2002). Possible
5-HT2A or 5-HT2c receptor antagonism was investigated (Villalobos et al., 2004).
Pharmacology
In uptake studies in the rat and dog, utilizing the [ 1 3 1 1]-labeled compound, distribution to
the brain and lung were especially noted (Braun et al., 1 977). The 5-HT2 binding sites in
2
rats were located with [ 1 5 I]-labeled 2C-I (Johnson et al., 1 990b). Several phenethylamines
and tryptamines were compared in studies with rats trained to discriminate 5-MeO-DMT
from saline (Kier and Glennon, 1 978b). Using molecular connectivity analysis of ten psy
chedelic phenethylamines, the importance of the 2,5-positions of the methoxy groups, and
the 4-substituent was demonstrated (Glennon et al., 1979a) . This drug has been evaluated
in extensive QSAR studies (Clare, 1 998; Beuerle et al., 1 997) .

2C-I I mCPP
2C-I was reported as a component of street drugs sold in Japan (Nishioka et al., 2007) .
Orally active in humans at 14-22 mg; duration 6-1 0 hours (Shulgin and Shulgin, 1 991).
Legal Status
2C-I is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
support the placement of this chemical into Schedule I status (Tella, 2004).
r NH
#24. mCPP
r'Y N _J
1-(3-Chlorophenyl)piperazine
m-CPP
y
3-CPP
NSC 49307
Cl
Registry Numbers
CAS #
HCl salt [13078-15-4] CAS #
HBr salt [913701-64-1] Aspartate [135014-38-9]
di-HCI salt [51639-49-7] Acid salt [1 71415-32-0]
x-HCl salt [65369-76-8] Freebase [ 6640-24-0]
L-Glutamate [135014-37-8] 3-[ 1 4C]-Isomer [115923-74-5]

From 3-chloroaniline (diethanolamine, NaOH) to mCPP (Pollard and Wicker, 1 954) .

m / z: 196.0767 (100.0% ), 198.0738 (32.0%), 197.0801 (10.8%), 199.0771 (3.5% )
Elemental Analysis: C, 61 .07; H, 6.66; Cl, 18.03; N, 14.24
N-Acetyl derivative m.p. 42.2-44.2 °C (Pollard and Wicker, 1954)

Freebase b.p. 157.2-158.2 °C / 5 mm (Pollard and Wicker, 1954)
Plasma concentrations of trazodone and its metabolite mCPP were determined in humans
following a single oral dose (Caccia et al., 1982) . An HPLC method was developed for
analysis of plasma (Suckow et al., 1 990); plasma screening and quantitative GC / MS
analysis has been reported (Peters et al., 2003). Employing HPLC-PDA, HPLC-MS, TLC,
and NMR, a library of 35 illegal drugs was assembled and used to identify street samples
(Nakashima et al., 2005).

-- -- F --�-----,--
Ph 4-FPP [2252-63-3] (1,2)
Cl -- -- Ph oCPP
-------·-- -----
[135014-36-7] (3)
-- Cl -- Ph mCPP (this entry)
-- -- Cl Ph pCPP [934991-33-0] (3,4)
Main En try Compounds 33

mCPP

-- Cl HO Ph HO-mCPP [85474-76-6] (5)
-- -- -- naphthyl 1-NP [57536-86-4] (6-10)
-- -- -- 2-quinolyl Quipazine [4774-24-7] (11-15)
-- -- -- 2-pyrimidyl 2-PmP [20980-22-7] (16,17)
(1) 4-FPP was originally discovered as a metabolite of the hypnotic antihistamine Niaprazine (San
juan et al., 1983; Caccia et al., 1985), but was rediscovered in 2003 as a potential recreational
drug, and subsequently sold as an ingredient in "party pills" in New Zealand, under brand
names such as "The Big Grin" and "Mashed" (Wikipedia, 2007b).
(2) Synthesis (Ratouis et al., 1965).
(3) Synthesis and physical properties (Pollard and Wicker, 1954).
(4) Synthesis (Sriram et al., 2006).
(5) OH-mCPP is a metabolite of mCPP from human liver microsomes (Rotzinger et al., 1998) .
(6) The effects on serotonin agonist-induced head-twitching seen in rodents were studied (Simansky
and Schechter, 1988) .
(7) 1 -NP had high affinity for tritiated spiperone binding sites in rat brain cortex in vitro (Fuller,
1986) .
(8) Serotonin-antagonist effects o f I-NP o n operant behavior o f squirrel monkeys (McKearney, 1989).
(9) 1 -NP derivatives as potential atypical antipsychotic agents (Lowe et al., 1991).
(IO) In vitro and in vivo activity of 1-NP at terminal serotonin autoreceptors in guinea-pig brain
(Moret and Briley, 1995).
(11) This experimental antidepressant is an agonist to several 5-HT2 and 5-HT3 receptors. If taken
with a 5-HT3 antagonist, quipazine (blocking nausea / vomiting) it produces a full psychedelic
response (Anon., 2007).
(12) Regional differences in the sensitivity of cholinergic neurons to dopaminergic drugs and
quipazine in the rat striatum (Guyenet et al., 1977).
(13) Quipazine provides evidence of an interaction between serotonergic and cholinergic neurons in
the corpus striatum and hippocampus of the rat brain (Samanin et al., 1978).
(14) Quipazine provides evidence of serotonergic stimulation of pituitary-adrenal activity in the
mouse (Meyer et al., 1978) .
(15) Evidence for the role of noradrenaline in some effects of quipazine (Frances et al., 1980).
(16) A metabolite of the anxiolytic drug Buspirone (Ahern et al., 2004).
(17) The i.v. administration of 2-PmP to adult rhesus monkeys regularly elicited penile erections
(Szele et al., 1988).
Biochemistry
mCPP, the closely related 4-isomer pCPP, and the unsubstituted isomer PP, all have a cen
tral serotonergic action in rats, mice, and rabbits (Maj and Lewandowska, 1 980) . mCPP
is a metabolite of trazodone in the rat (Caccia et al., 1981), and the antidepressants tra
zodone, etoperidone, and mepiprazole were metabolized to mCPP in the rat (Fong et al.,
1 982) . mCPP itself is metabolized by hydroxylation to a chlorophenol (Staack and Maurer,
2003b), employing the cytochrome P450 enzyme CYP2D6 from human liver microsomes
(Rotzinger et al., 1 998).
Hypothermia was induced in mice by mCPP and mTFMPP (Maj et al., 1 988) . mCPP
induced anorexia was caused by increased release and / or direct stimulation of postsynap
tic serotonin receptors in the brain (Samanin et al., 1980) . Effects of mTFMPP and mCPP on
locomotor activity were reported (Lucki et al., 1989). At doses of 1-20 mg / kg hyperthermia
was evoked in rats at a high ambient temperature (28 °C) (Klodzinska and Chojnacka
Wojcik, 1 992) .

m CPP
mCPP, an agonist at central serotonin receptors, was a potent antagonist of serotonin re
ceptor-mediated contractions of the rat jugular vein (Cohen and Fuller, 1 983). Effects on
serotonin agonist-induced head-twitching were seen in rodents (Simansky and Schechter,
1 988) . mCPP interacted with serotonergic, adrenergic, and dopaminergic receptor systems
(Murphy et al., 1991; Hamik and Peroutka, 1989). Effects of TFMPP and mCPP were ob
served on the copulative behavior of rats (Mendelson and Gorzalka, 1 990).
A comparison was made of the effects of three different serotonin receptor agonists: PAT
(for 5-HT 1 A ), mCPP (for 5-HT 1 8), and DOI (for 5-HT2), on preweanling rat pups (Frambes et
al., 1990). Lack of cross-tolerance for hypophagia induced by DOI versus mCPP suggested
separate mediation by 5-HT2A and 5-HT2c receptors, respectively (Aulakh et al., 1 995). Ef
fects of adrenodemedullation and adrenalectomy on drug-induced hypophagia in rats was
evaluated with the 5-HT2 receptor agonists DOI and mCPP (Yamada et al., 1 996) . Isoteolin,
a putative serotonin antagonist, inhibited mCPP, but not DOI and PAT-induced increase of
serum prolactin levels (Zhelyazkova-Savova and Negrev, 2000) .
A reproducible, simple, and small-scale method for detecting the uptake and release of
monoamines, dopamine, serotonin, and norepinephrine, was developed using rat brain
synaptosome (Nagai et al., 2007) .
Pharmacology
Behavioral changes in basal locomotor activity and conditioned avoidance response were
studied in several strains of mice, with mCPP (Vetulani et al., 1982) . Neuroendocrine and
behavioral effects of m-chlorophenylpiperazine administration in rhesus monkeys were
described (Aloi et al., 1 984). Effects on locomotor activity and food intake in rats were
studied (Aulakh et al., 1 987) . Effects on rat behavior were observed (Kennett and Curzon,
1 988). Intravenous administration of mCPP to adult rhesus monkeys regularly elicited
penile erections (Szele et al., 1988). Effects of the 5-HT2 agonist 1 -NP on the behavior of
the squirrel monkey, either alone, or in combination with DOB, mCPP, or TFMPP, were
reported (McKearney, 1989). Serotonin syndrome has occurred following mCPP use
(Klaassen et al., 1998) .
of 0.5 mg I kg in human subjects, there were reports of both euphoria and anxiety (Mueller
mCPP has been extensively evaluated for potential therapeutic applications. At oral levels
et al., 1985, 1986) . Effects of mCPP were studied in agoraphobic or panic disorder patients
(Charney et al., 1 987), and patients with obsessive-compulsive disorder (Charney et al.,
1 988), in each case with healthy control subjects. mCPP was later explored by additional
researchers in patients with obsessive-compulsive disorder (Goodman et al., 1995; Hol
lander et al., 1995) . Effects of mCPP (at an oral dose of 0.5 mg / kg) on patients with eating
disorders, with healthy subjects as controls, were reported (Brewerton et al., 1988). The
action of mCPP in 15 elderly patients (ages 67-71 years) with various age-related disor
ders was studied (Lawlor et al., 1989a). mCPP was administered intravenously to 12 pa
tients with Alzheimer 's disease and ten age-matched controls (Lawlor et al., 1 989b). mCPP
was administered chronically to eight moderate to severely affected Alzheimer patients.
In doses up to 80 mg / day for 16 days, mCPP was well tolerated and resulted in small
but significant increases in energy depression-related symptoms, compared with placebo
(Lawlor et al., 1991). As a measure of central serotonergic responsivity, the behavioral and
neuroendocrine responses of older normal volunteers were compared to those of younger
normal volunteers. When mCPP was administered intravenously, older subjects showed
decreased behavioral responses but similar neuroendocrine responses, as compared to

mCPP I 2-CT
younger subjects (Lawlor et al., 1 989c) . mCPP was more effective against anxiogenic and
other mood and cognitive effects when administered intravenously (0.1 mg / kg) rather
than orally (0.5 mg / kg) to healthy subjects (Murphy et al., 1 989) . mCPP was studied in 20
normal subjects, administered orally at 0.25 and 0.50 mg / kg (Kahn et al., 1 990).
Six patients with major depression were treated for two weeks with mCPP, at 80 mg / day
in a double-blind, placebo-controlled, crossover-design pilot study. Two patients showed
clinically significant improvement in depressive symptoms (Mellow et al., 1 990). mCPP
(0.35 mg / kg) or placebo was administered orally after a three-week drug-free period to 22
chronic schizophrenic patients and 17 healthy control subjects. The schizophrenic patients
had blunted temperature responses compared with the healthy control subjects (Kahn et
al., 1 992) .
mCPP decreased slow-wave sleep in humans (Katsuda et al., 1 993), stimulated the release
of cortisol and prolactin, and could induce migraine-like headaches (Gordon et al., 1 993).
At 0.4 mg / kg, in 12 healthy female volunteers, mCPP significantly lowered food intake
(Walsh et al., 1 994) . Daily administration of mCPP to healthy human volunteers rapidly
attenuates many of its behavioral, hormonal, cardiovascular, and temperature effects (Ben
jamin et al., 1996) . mCPP was given to male subjects by i.v. infusion of 0.06 to 0.08 mg / kg
doses (Kalus et al., 1 992) .
Hormonal and subjective responses t o intravenous mCPP were observed i n bulimia ner
vosa patients (Levitan et al., 1 997), and alcoholic patients (Buydens-Branchey et al., 1 997) .
mCPP has been explored in patients with cluster headaches (Leone et al., 1 997), and in pa
tients with migraine headaches who were in drug abstinence programs (Kalkman, 1 997).
Pharmacokinetic and pharmacodynamic profiles of oral and intravenous mCPP were gen
erated in healthy volunteers (Gijsman et al., 1 998). Human studies compared mCPP with
MOMA in moderate MOMA users (Tancer and Johanson, 2001 ) . The action of mCPP on
normal adolescents was evaluated (Ghaziuddin et al., 2003).
Effects of mCPP were observed in healthy male volunteers (Feuchtl et al., 2004), in pa
tients with borderline personality disorder (Paris et al., 2004), and in autistic patients with
primary behavioral manifestations of repetitive behaviors, social deficits, and language
abnormalities (Novotny et al., 2004).
mCPP has appeared in Holland as an "Ecstasy" substitute (Bossong et al., 2005), and as a
street drug in France with the reputation of "amphetamine-like" action (Lecompte et al.,
2006).
Legal Status
mCPP is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#25. 2C-T
2-(2,5-Dimethoxy-4-(methy lthio )pheny l)ethanamine
� N H2
�-------�
2,5-Dimethoxy-4-methylthiophenethylamine
H3CO
Registry Numbers
CAS #
HCI salt [61638-10-6] Freebase
CAS #
[ 61638-09-3] C H 3S ��ru OCH3

2C-T

From benzoquinone with sodium thiosulfate to 2,5-dihydroxyphenylthiosulfate; (with zinc
powder, HCl) to 2,5-dihydroxythiophenol; (with methyl sulfate) to 2,5-dimethoxymethyl
thioanisole; (with SnC12, dichloromethyl methyl ether) to 2,5-dimethoxy-4-methylthiobenz
aldehyde; (with nitromethane) to 2-(2,5-dimethoxy-4-methylthio)-2-nitroethene; (with
LAH) to 2C-T (Nichols and Shulgin, 1 976) .

m / z: 227.0980 (100.0%), 228.1014 (11 .9% ), 229.0938 (4.5%)
HCI salt m.p. 240-241 °C (Nichols and Shulgin, 1976) (EtOH)

MeS MeO -- -- 2C-T (this entry)
EtS Meo -- HO HOT-2 [207740-38-3] (1)
FC2S Meo -- -- 2C-T-21 [ 207740-33-8] (2-4)
-
F 2C 2S Meo -- - 2C-T-21 .5 [648957-46-4] (5)
F 3 C 2S MeO -- -- 2C-T-22 [648957-48-6] (5)
PrS MeO -- HO HOT-7 [207740-39-4] (6)
iPrS MeO -- -- 2C-T-4 [207740-25-8] (2,7-11 )
cPrS Meo -- -- 2C-T-15 [952006-95-0] (12,13)
Bus Meo -- -- 2C-T-19 [648957-44-2] (5)
iBuS Meo -- -- 2C-T-25 [648957-50-0] (5)
sBuS MeO -- -- 2C-T-17 [207740-32-7] (14)
sBuS MeO -- HO HOT-17 [207740-40-7] (15)
tBuS Meo -- -- 2C-T-9 [207740-28-1] (2,16)
-
cPrMS MeO - -- 2C-T-8 [207740-27-0] (5,1 7)
MeOEtS MeO -- -- 2C-T-13 [207740-30-5] (2, 1 8)
MeAllylS MeO -- -- 2C-T-3 [ 648957-40-8] (5)
FC 3S Meo -- -- 2C-T-28 [648957-54-4] (5)
AllylS Meo -- -- 2C-T-16 [648957-42-0] (5)
FC4S Meo -- -- 2C-T-30 [648957-56-6] (5)
MeS -- MeO -- 'ljJ-2C-T -- (19)
iPrS -- MeO -- 'ljJ-2C-T-4 [952006-71-2] (2,12,20)
(1) Orally active in humans at 1 0-18 mg; duration 6-1 0 hours (Shulgin and Shulgin, 1991).
(4) Synthesis (Zhang et al., 2003c).
(5) Synthesis and spectrographic description (Trachsel, 2003a).

2C-T I 2C-T-2
(8) Employing HPLC-PDA, HPLC-MS, TLC, and NMR, a library of 35 illegal drugs was assembled
and used to identify street samples (Nakashima et al., 2005).
(9) Isomers and analogues characterized by IR, GC-MS, HPLC, and NMR (Matsumoto et al., 2004) .
(10) Present in street drugs in Japan. Analysis by GC / MS and LC-ESI-MS (Kikura-Hanajiri et al., 2005).
(11) Synthesis and analysis of 2C-T-4 and 2C-T-7 (Kawashima et al., 2006).
(12) A CAS # exists for this compound, but there are no references or catalog sources.
(13) Threshold activity in humans at 30 mg; duration many hours (Shulgin and Shulgin, 1991).
(14) Orally active in humans at 60-1 00 mg; duration 10-15 hours (Shulgin and Shulgin, 1991).
(17) Orally active in humans at 30-50 mg; duration 1 0-15 hours (Shulgin and Shulgin, 1991).
(19) Synthesis (Shulgin and Shulgin, 1991), otherwise not in the published scientific literature.
(20) Threshold activity in humans at 12 mg; duration "probably short" (Shulgin and Shulgin, 1991).
Biochemistry
The octanol-water partition coefficient served as a predictor of human psychedelic potency
(Nichols et al., 1977). Molecular connectivity analysis gave excellent correlation to serotonin
agonist activity in a large number of phenethylamines and amphetamines (Kier and Glen
non, 1978a).
Pharmacology
This drug has been examined in an extensive QSAR study (Clare, 1 998) . Orally active in
humans at 60-1 00 mg; duration 3-5 hours (Shulgin and Shulgin, 1 991 ) .
Legal Status
2C-T is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#26. 2C-T-2
2-(4-(Ethylthio)-2,5-dimethoxyphenyl)ethanamine
2,5-Dimethoxy-4-ethy lthiophenethylamine
Registry Numbers
CAS #
HCl salt [681160-71-4]
Freebase [207740-24-7]

From 1,4-dimethoxybenzene (with chlorosulfonic acid) to 2,5-dimethoxybenzenesulfonyl
chloride; (with zinc powder) to 2,5-dimethoxythiophenol; (with ethyl bromide, KOH) to
2,5-dimethoxyphenyl ethyl sulfide; (with POCly N-methylformanilide) to 2,5-dimethoxy-
4-ethylthiobenzaldehyde; (with nitromethane) to 2,5-dimethoxy-4-ethylthiophenyl-2-
nitroethene; (with LAH) to 2C-T-2 (Shulgin and Shulgin, 1 991; note that this synthesis was
patented in China in 2003, see Zhang et al., 2003b).
m / z: 241 . 1136 (100.0%), 242.1170 (13.0%), 243.1094 (4.5% )
Elemental Analysis: C, 59.72; H, 7.93; N, 5.80; 0, 13.26; S, 13.29
Salt (unspecified) m.p. 130 °C (Boatto et al, 2007)

HCl Salt m.p. 206.0-207.0 °C (Shulgin and Daley, unpublished data) (IPA)
'8 The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

2C-T-2 I 2C-T-7
Employing HPLC-PDA, HPLC-MS, TLC, and NMR, a library of 35 illegal drugs was
assembled and used to identify street samples (Nakashima et al., 2005). Several isomers
and analogues were characterized by IR, GC-MS, HPLC, and NMR (Matsumoto et al.,
2004) . 2C-T-2 was found in street drugs in Japan, with confirmational analysis by GC / MS
and LC-ESI-MS (Kikura-Hanajiri et al., 2005), and determined in human plasma by GC /
MS of the heptafluorobutyramide derivatives (Habrdova et al., 2005).
Biochemistry
Four urinary metabolites of 2C-T-2 were identified in the rat. Amine hydrolysis to 2,5-di
methoxy-4-ethylthiophenyl-2-ethanol, oxidative deamination to 2,5-dimethoxy-4-ethyl
thiophenylacetic acid, and acetamide formation with methoxy hydrolysis to give N-[2-
[4-(ethylthio)-2-hydroxy-5-methoxyphenyl]ethyl]acetamide and N-[2-[4-(ethylthio)-5-
hydroxy-2-methoxyphenyl]ethyl] acetamide (Lin et al., 2003). In the rat, 2C-T-2 generated
14 metabolites by several routes, including sulfoxidation, N-acetylation, and 0-demethyl
ation, based on urine analysis by GC / MS (Theobald et al., 2005b).
The effects of 2C-T-2 on nitric oxide production in mice, as well as the quantitative evalu
ation of urinary excretion in rats following i.p. administration, has been studied (Chiu et
al., 2004) .
Pharmacology
The appearance in Holland of two sulfur-containing street drugs (2C-T-2 and MTA)
prompted a GC / MS identification study (Bosman et al., 2000) . Analysis of street drugs in
Japan revealed the presence of 2C-T-2, in place of 2C-B, which became illegal in July 1 998
(Maruyama et al., 2000) . 2C-T-2 was among several psychedelic drugs verified in the Japa
nese street drug scene (Katagi et al., 2002). Five street drugs: TMA, TMA-2, 2C-B, 2C-T-2,
and 2C-T-7 were identified and distinguished by HPLC (Takahashi et al., 2003).
2C-T-2 is orally active in humans at 8-20 mg; duration 12-18 hours (Shulgin and Shulgin,
1 991).
Legal Status
2C-T-2 is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
support the placement of this chemical into Schedule I status (Tella, 2004) .
#27. 2C-T-7
2-(2,5-Dimethoxy-4-(propy 1thio )pheny1 )ethanamine
2,5-Dimethoxy-4-(n )-propylthiophenethylamine
Blue Mystic
T7
Tripstasy
Tweety-bird mescaline
Registry Numbers
CAS # DEA#
HCl salt [850140-15-7]
Freebase [207740-26-9] 7348

2C-T-7

From a methanol solution of 2,5-dimethoxythiophenol (see under the recipe for 2C-T-2)
and KOH (with n-propyl bromide and heat) to 2,5-dimethoxyphenyl-4-n-propyl sulfide;
(with POC13 and N-methylformanilide) to 2,5-dimethoxy-4-n-propylthiobenzaldehyde;
(with nitromethane and anhydrous ammonium acetate) to 2,5-dimethoxy-4-n-propylthio
phenyl-2-nitroethene; (with LAH) to 2C-T-7 (Shulgin and Shulgin, 1 991 ) .

m / z: 255.1293 (100.0% ), 256.1327 (14.1 % ), 257.1251 (4.5% )
HCl Salt m.p. 206.0-207.0 °C (Shulgin and Daley, unpublished data)
sembled and used to identify street samples (Nakashima et al., 2005). Several isomers and
analogues were characterized by IR, GC-MS, HPLC, and NMR (Matsumoto et al., 2004).
Five street drugs: TMA, TMA-2, 2C-B, 2C-T-2, and 2C-T-7 were identified and distin
guished by HPLC (Takahashi et al., 2003). 2C-T-7 was found in street drugs in Japan, with
confirmational analysis by GC / MS and LC-ESI-MS (Kikura-Hanajiri et al., 2005). GC / MS
has successfully identified 2C-T-7 in human blood and urine samples (Vorce and Sklerov,
2004), and human plasma was analyzed by the GC / MS of the heptafluorobutyramide de
rivatives (Habrdova et al., 2005). Additional syntheses and analysis of 2C-T-4 and 2C-T-7
were reported (Kawashima et al., 2006).
Positional Isomers*
2- 3- 4- 5- 6- Name CAS # Ref
-
nPrS Meo MeO -- - 3,4,2-2C-T-7 -- (1)
nPrS Meo -- Meo -- 3,5,2-2C-T-7 -- (1)
-
nPrS MeO - -- Meo 3,6,2-2C-T-7 -- (1)
nPrS -- Meo Meo -- 4,5,2-2C-T-7 -- (1)
nPrS -- Meo -- MeO 4,6,2-2C-T-7 -- (1)
MeO nPrS MeO -- -- 2,4,3-2C-T-7 -- (1)
MeO nPrS -- MeO -- 2,5,3-2C-T-7 -- (1)
MeO nPrS -- -- Meo 2,6,3-2C-T-7 -- (1)
MeO MeO nPrS -- -- 2,3,4-2C-T-7 -- (1)
-
Meo - nPrS Meo -- 2C-T-7 (this entry)
Meo -- nPrS -- Meo 'ljJ-2C-T-7 -- (1)
-- Meo nPrS MeO -- TP [90109-55-0] (1-3)
MeO -- MeO nPrS -- 2,4,5-2C-T-7 -- (1)
MeO MeO -- nPrS -- 2,3,5-2C-T-7 -- (1)
-- MeO Meo nPrS -- 3,4,5-2C-T-7 -- (1)
MeO MeO -- -- nPrS 2,3,6-2C-T-7 -- (1)

2C-T-7 I 2C-TFM

(2) Synthesis (Jacob and Shulgin, 1981).
(3) Syntheses, potency evaluations in humans (Jacob and Shulgin, 1984).
Biochemistry
2C-T-7 is metabolized in the rat by several routes, including propyl group hydroxylation,
N-acetylation, sulfur oxidation, and deamination to the alcohol, as well as oxidative con
version to the phenylacetic acid. Metabolites were identified through urine analysis by
GC / MS (Theobald et al., 2005a) .
Pharmacology
Human tissue and fluid levels were reported in a post-mortem analysis following the
reported insufflation of 35 mg of 2C-T-7 (Curtis et al., 2003).
Stimulus generalization studies of 2C-T-7, MTA, and MTMA in rats trained with DOM,
cocaine, and MOMA were reported (Khorana et al., 2004) . 2C-T-7 was tested in a drug
elicited head-twitch assay in mice and in several drug discrimination assays in rats (Fan
tegrossi et al., 2005).
Reported as a component of street drugs sold in Japan (Nishioka et al., 2007) . History and
patterns of use in Europe and the United States were discussed (Murple, 2001).
Legal Status
2C-T-7 is a Schedule I hallucinogen under federal drug law (FR, 2002, 2003, 2004), and un
der the state laws of Arizona, Connecticut, Hawaii, Indiana, Iowa, Missouri, Nevada, New
Hampshire, North Dakota, Oregon, Pennsylvania, South Dakota, Texas, Virginia, Wiscon
sin, and Wyoming.
#28. 2C-TFM
2-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)ethanamine
2,5-Dimethoxy-4-trifluoromethylphenethylamine
Registry Numbers
CAS #
HCl salt [159277-13-1]
Freebase [159277-08-4]

From 2C-I (with trifluoroacetic anhydride) to 1 -(2,5-dimethoxy-4-iodophenyl)-2-(trifluoro
acetamido)ethane; (with methyl chlorodifluoroacetate, KF, Cul) to 1-(2,5-dimethoxy-4-
trifluoromethylphenyl)-2-(trifluoroacetamido)ethane; (with KOH) to 2C-TFM (Nichols et
al., 1 994) .

m / z: 249.0977 (100.0% ), 250. 1010 (11.9%)
Elemental Analysis: C, 53.01; H, 5.66; F, 22.87; N, 5.62; 0, 12.84
HCl salt m.p. 260 °C (Nichols et al., 1994) (EtOH / EtOAc)

2C-TFM / DESMETHYL

The a-methyl homologue of 2C-TFM is DOTFM ( # 63); many related amphetamine homo
logues are listed there.
Of sixteen possible positional isomers of 2C-TFM, only this compound and 2-trifluoro
methyl-4,5-dimethoxyphenthylamine (CAS # 1 094886-59-5) appear in the scientific litera
ture, and the latter only as an intermediate for the synthesis of an antimicrobial agent in a
Chinese patent (Huang, 2008) .
Biochemistry
or 2C-I (Nichols et al., 1 994) . Several phenethylamine I phenylisoproplyamine "pairs" were

2C-TFM is a more potent serotonin receptor agonist than the two halogen analogues, 2C-B
evaluated as partial agonists of the phoshpholipase C signaling pathway in cloned rat and
human 5-HT2A receptors, expressed in mammalian cell systems (Parrish et al., 2005).
Pharmacology
Street use covers the range from 5--15 mg with some samples up to 50% contaminated with
the precursor material, 2C-I (Mueller, 2006).
2C-TFM is orally active in humans at 3-5 mg; duration 5-7 hours (Shulgin, 2003) .
Legal Status
2C-TFM is not a scheduled compound under federal drug law, or under District of Colum
#29. DESMETHYL
4-(2-Aminoethy 1)-2,6-dimethoxyphenol
3,5-Dimethoxy-4-hydroxyphenethylamine
3,5-Dimethoxytyramine
4-Desmethylmescaline
4-0-Desmethylmescaline
NSC 167759
Registry Numbers
CAS # CAS # CAS #
HCl salt [2176-14-9] Freebase [2413-00-5] a,�-[ 3H] 2 Freebase [802035-75-2]
Picrate [108774-54-5] a,�-[ 3H)i HCl salt [27954-91 -2] a-[ 1 4C] Isomer [802035-74-1 ]
Sulfate [94783-21-8] a-[ 1 4C] HCl salt [27954-82-1]
"Demethylated mescaline" [ 63241-19-0] (location unspecified)
Natural Sources
DESMETHYL was found i n the cactus Lophophora williamsii (Agurell and Lundstrom,
1 968), and was reported present in Trichocereus pachanoi and T. werdermannianus, where it
was suspected of being a possible biosynthetic precursor of mescaline (Agurell, 1 969b); it
was also reported in T. peruvianus (Pardanani et al., 1977). It was established as a being a
biosynthetic precursor of mescaline in L. williamsii (Paul, 1 973) and in Trichocereus pachanoi
(Lundstrom, 1 971b). The incorporation into mescaline in L. williamsii was noted as being
very low (Paul et al., 1 969) .
DESMETHYL was present as a major alkaloid in the cacti Opuntia echinocarpa, Polas
kia chende, Stenocereus beneckei, S. stellatus and S. treleasei with a concentration level (dry

DESMETHYL
weight) of > 0.01 % . It is present as a minor alkaloid in the cacti Escontria chiotilla, Neorai
mondia arequipensis, Opuntia acanthocarpa, 0. basilaria, 0. exaltata, Pterocereus foetidus, and P.
gaumeri with a concentration level (dry weight) of < 0.01 % . It was not present in the cacti
Melocactus maxonii, Opuntia bigelovii, 0. ramosissima, and Stenocereus eruca with a minimum
detection level (dry weight) of 0.001 % (Ma et al., 1 986) .
This compound was also reported to be present in Acacia berlandieri (Clement et al., 1 997),
and A. rigidula (Clement et al., 1998) .

From 3,5-dimethoxy-4-hydroxybenzaldehyde (with nitromethane) to 1 -(3.5-dimethoxy-4-
hydroxyphenyl)-2-nitroethene; (with LAH) to DESMETHYL (Benington et al., 1 954a) .
From mescaline (with Na, NH3 ) to DESMETHYL (Tomita and Takano, 1 959).
From 1-(3,5-dimethoxy-4-hydroxyphenyl)-2-nitroethene (with H2, Pd) to DESMETHYL

(Dyumaev and Belostotskaya, 1962) .
From mescaline (with HCl) to DESMETHYL (Brossi and Teitel, 1969) .
Additional synthesis (Lee et al., 1 969), and synthesis with [ 3H]- or [ 1 4C]-labeling (Lundstrom
and Agurell, 1 971 ) .

m / z: 197. 1 052 (100.0% ), 198.1085 (10.9%)
Elemental Analysis: C, 60.90; H, 7.67; N, 7. 1 0; 0, 24.34
Picrate m.p. 231-231 .5 °C (Benington et al., 1954a) (AcOH)

Pier ate m.p. 217-21 8 °C (Tomita and Takano, 1959)
HCl salt m.p. 256-257 °C (Dyumaev and Belostotskaya, 1962) (MeOH / EtOAc)
Bisulfate m.p. 143-144 °C (Dyumaev and Belostotskaya, 1962)
HCl salt m.p. 249-250 °C (Brossi and Teitel, 1969)

3- 4- 5- Other Name CAS # Ref--
HO HO HO -·---
-- 3,4,5-DESMETHYL [5720-26-3] (1-8)
HO HO HO N-Me N-Me-3,4,5-DESMETHYL [7391 7-91-6] (3)
--
HO HO MeO -- 3,4-DESMETHYL [5090-25-5) (1,2,11-14)

---------�� r-- --..-�-· --- �
HO HO MeO f3-Me0 f3-M-3,4-DESMETHYL [ 197504-48-6] (3,15)
MeO HO Br -- 5-Br-DESMETHYL [90485-24-8] (11) ----
Br HO Br -- 3,5-Br-DESMETHYL [ 13062-88-9] (5,16)

-
MeO HO MeO - DESMETHYL
------· -- ---·---- -·------·----"--
-· ----.-- --· ----- - --- ,,,_
(this entry)
-- ---··-- ------
Meo HO MeO N-Me DESMETHYL-M [24131-17-7) (17)

MeO HO Meo N-Me2 DESMETHYL-MM [26138-13-6] (18)
MeO HO MeO N-iPr
------- - --
DESMETHYL-iPr
- ---·--- -·---
- --
[ 42973-59-1] (19)
MeO HO MeO f3-HO f3-HO-DESMETHYL [24131-22-4] (17)
MeO FCCO- Meo -- FEM [501700-01-2] (20)

DESMETHYL

MeO F2CCO- MeO -- F2EM [501 700-02-3] (20)
MeO F 3CCO- MeO -- F 3EM [501 700-03-4] (20)
(1) Methylation of phenolics with 0-methyltransferase enzymes (Daly et al., 1962).
(2) Synthesis (Benington et al., 1955b).
(3) Reported to be present in Acacia rigidula (Clement et al., 1998).
(4) Synthesis (Leminger, 1972b).
(5) The effectiveness of releasing cardiac norepinephrine was measured. (Daly et al., 1966)
(6) The relationship between psychedelic activity and electronic configuration is established (Snyder
and Merril, 1965)
(7) The injection of a-[ 14C]-3,4,5-DESMETHYL into Lophophora williamsii leads to the biosynthesis
of mescaline whereas the injection of a-[ 14C]-dopamine gives a higher yield suggesting that
DMPEA may be an intermediate (Paul et al., 1969).
(8) [ 14 C]-labeled 3,4,5-DESMETHYL was used to explore the biosynthesis of mescaline in Lophophora
williamsii (Lundstrom and Agurell, 1968b).
(9) GEA (3-methoxytyramine, a metabolite of dopamine) is 5-hydroxylated in rat or rabbit liver
hydrogenates to form 3,4-DESMETHYL, a potential precursor to analogues of mescaline (Ben
nington and Morin, 1968).
(10) GEA, DESMETHYL, and 3,4-DESMETHYL were found to be biosynthetic precursors of mescaline
in Lophophora williamsii, but HMPEA and 3-DESMETHYL were not. The role of dopamine as a pre
cursor was proposed (Rosenberg et al., 1969)(11) Synthesis (Dyumaev and Belostotskaya, 1962).
(12) The principle biosynthetic pathway for mescaline in Lophophora williamsii is from dopamine
with 3-0-methylation to GEA, 5 hydroxylation to 3,4-DESMETHYL (Lundstrom, 1971a).
(13) Synthesis with [ 3H] or [ 14C] (Lundstrom and Agurell, 1971 ).
(14) The possible role of GEA and 3,4-DESMETHYL in the biosynthesis of mescaline and the iso-
quinolines in Lophophora williamsii (Lundstrom, 1971a).
(15) Reported to be present in Acacia berlandieri (Clement et al., 1997).
(16) Synthesis and pharmacological evaluation in cats (Benington et al., 1958a).
(17) Synthesis (Lee et al., 1969).
(18) Also called desmethyltrichocereine.
(19) Synthesis (Short et al., 1973).
(20) Synthesis (Trachsel, 2002).
Biochemistry
GEA, DESMETHYL, and 3,4-DESMETHYL were found to be biosynthetic precursors of
mescaline in Lophophora williamsii, but HMPEA and 3-DESMETHYL were not. The role of
dopamine as a precursor was proposed (Rosenberg et al., 1969) .
DESMETHYL and 3-DESMETHYL were shown to be metabolites of mescaline in humans

(Ratcliffe and Smith, 1959) . DESMETHYL was formed from mescaline by demethylation
with rat liver microsome preparations (Daly et al., 1 962) . The effectiveness of cardiac
norepinephrine by the mouse heart was measured (Daly et al., 1966). Biosynthsis by rat
liver supernatant of [ 1 4C]-labeled mescaline from DESMETHYL with adenosylmethionine
methyl-[ 1 4C] was also demonstrated (Friedhoff et al., 1972) . Mescaline demethylase can
remove either the 3-methoxy or the 4-methoxy methyl group (Datta and Ghosh, 1 977) .
Pharmacology
DESMETHYL producted experimental catatonia in cats (Noteboom, 1934) . Studies on the
oxidative deamination and effects on cat behavior were reported (Clark et al., 1964) . This
compound also generated a hypokinetic rigid syndrome in cats (Ernst, 1965a) . Studies
were made of injection into the rat optic nerve and the cat sciatic nerve (Paulson and Mc
Clure, 1973) .

DESMETHYL / 3-DESMETHYL
Human activity of DESMETHYL has not been reported in the scientific literature.
Legal Status
DESMETHYL is not a scheduled compound under federal drug law, or under District of
#30. 3-DESMETHYL
5-(2-Aminoethyl)-2,3-dimethoxyphenol
3-H ydroxy-4,5-dimethoxyphenethylamine
Registry Numbers
CAS #
HCl salt [13062-71-0]
Freebase [16046-07-4]
Natural Sources
Trace amounts of 3-DESMETHYL were found in Trichocereus pachanoi (Agurell and Lund
strom, 1 968); 3-DESMETHYL was found in Lophophora williamsii (Kapadia et al., 1 969), and
was identified as a bioprecursor to anhalamine to anhalonidine in this plant (Lundstrom,
1971a) . It was reported to be present in Acacia berlandieri (Clement et al., 1 997) and A. rigid
ula (Clement et al., 1998) .

From 4,5-dimethoxy-3-hydroxybenzaldehyde (with nitromethane) to 1 -(4,5-dimethoxy-3-
hydroxyphenyl)-2-nitroethene; (with LAH) to 3-DESMETHYL (Ratcliffe and Smith, 1 959).
Synthesis with [ 3H] or [ 1 4C] labels (Lundstrom and Agurell, 1971 ) .
Exact Mass: 197. 1 052

m / z: 197.1052 (100.0% ), 198. 1 085 (10.9% )
HCl salt m.p. 1 80 °C (Ratcliffe and Smith, 1959)
3-DESMETHYL is valuable in the synthesis of isoquinoline alkaloids (Spath, 1 923) .

HO MeO HO -- 3,5-DESMETHYL [5090-32-4] (1-3)
HO Meo MeO N-Me N-Me-3-DESMETHYL [24131-16-6] (4-7)
HO Meo MeO N-Me2 N,N-Me-3-DESMETHYL [38184-65-5] (4,5,8-11)
HO MeO MeO f3-HO [3,5-HO-DMPEA [24159-01-1] (7)
(1) Methylation of phenolics with 0-methyltransferase enzymes (Daly et al., 1962) .
(3) Synthesis with [ 3H] or [ 14C] (Lundstrom and Agurell, 1971 ).
(4) Present in the cactus Pelecyphora aselliformis (Neal et al., 1972).

3-DESMETHYL / DESOXY
(5) An immediate bioprecursor to pellotine and anhalidine in Lophophora williamsii (Lundstrom,

1971a).
(6) A bioprecursor to anhalamine to anhalonidine in Lophophora williamsii (Lundstrom, 1971a).
(7) Synthesis (Lee et al., 1969).
(8) Found in Lophophora williamsii (Lundstrom, 1971a) and Pelecyphora aselliformis (Bruhn and Bruhn,
1973; Neal et al., 1972).
(9) Present in the cacti Ariocarpus agavoides and Pelecyphora aselliformis (Bruhn and Bruhn 1973).
(10) Studies made of injection into rat optic nerve and cat sciatic nerve (Paulson and McClure, 1973).
(11) Reported to be a natural alkaloid in the cactus, Pelecyphora aselliformis (Neal et al., 1972).
Biochemistry
GEA, DESMETHYL, and 3,4-DESMETHYL were found to be biosynthetic precursors of
mescaline in Lophophora williamsii, but HMPEA and 3-DESMETHYL were not. The role
of dopamine as a precursor was proposed (Rosenberg et al., 1 969) . 3-DESMETHYL and
N-Me-GEA were shown by mass spectroscopy to be precursors of mescaline in the cac
tus Trichocereus cuzcoensis (Lindgren et al., 1971 ) . 3-DESMETHYL was among several com
pounds tested at the microgram levels as plant growth inhibitors (Mandava et al., 1981).
DESMETHYL and 3-DESMETHYL were identified as metabolites of mescaline in humans

(Ratcliffe and Smith, 1 959). Demethylation of mescaline to 3-DESMETHYL was demon
strated with rat liver microsome preparations (Daly et al., 1 962); phenolics were also meth
ylated with 0-methyltransferase enzymes. Mescaline demethylase could remove either
the 3-methoxy or the 4-methoxy methyl group (Datta and Ghosh, 1977) .
The effectiveness of releasing cardiac norepinephrine was measured in the mouse heart
(Daly et al., 1 966) .
Pharmacology
The pharmacology of 3-DESMETHYL is unknown, and there are no reports on human
effects of this compound.
Legal Status
3-DESMETHYL is not a scheduled compound under federal drug law, or under District of
#31. DESOXY
2-(3,5-Dimethoxy-4-methylphenyl)ethanamine
3,5-Dimethoxy-4-methylphenethylamine
4-Desoxymescaline
Registry Numbers
CAS #
HCI salt [4395-23-7]
Freebase [63037-49-0]

From 3,5-dihydroxytoluic acid (with methyl sulfate) to 3,5-dimethoxytoluic acid; (with
SOC12) to 3,5-dimethoxytoluoyl chloride; (with methylamine) to 2-diazo-3' ,5' -dimethoxy-
4' -methylacetophenone; (with AgN03 ) to 3,5-dimethoxy-4-methylphenylacetamide; (with
LAH) to DESOXY (Benington et al., 1960) .

DESOXY / DFLY

m / z: 195.1259 (100.0%), 196.1293 (11 .9% )
HCl salt m.p. 244-245 °C (Benington et al., 1960) (EtOH / EtOAc)

There are no reported homologues or analogues of this compound in the scientific literature.
Biochemistry
The calculated electrostatic potential was related to that of serotonin (G6mez-Jeria et al.,
1 984) .
Pharmacology
DESOXY produced a rage response in cats (Benington et al., 1 960). Studies on the oxidative
deamination and effects on cat behavior were performed (Clark et al., 1964) . Relationships
between serotonin level and sexual behavior were studied in the rat (Everitt and Fuxe,
1 977) .
Legal Status
DESOXY is not a scheduled compound under federal drug law, or under District of Co
#32. DFLY
1-(Benzo[ 1,2-b:4,5-b' ] difuran-4-yl)propan-2-amine
1 -(Benzo [ 1 ,2-b:4,5-b' ] difuran-4-y1)-2-aminopropane
a-Methyl-benzo[l,2-b:4,5-b' ]difuran-4-ethanamine
Registry Numbers
CAS #
di-Freebase [260809-94-7]
R-(-)-Isomer HCI salt [332012-22-3]
S-( +)-Isomer HCI salt [332012-23-4]
5-( +)-Isomer freebase [787538-82-3]
Synthesis
From optically active (R- or S-) alanine (with CF3C02Et) to R- (or S-) N-trifluoroacetyl
alanine; (with oxalyl chloride, tetrahydrobenzo[l,2-b;4,5-b']difuran and AlC13 ) to R- (or
S-) N-trifluoroacetyl-2,3,6,7-tetrahydro-4-alanylbenzo[l,2-b;4,5-b' ] difuran; (with Et3SiH) to
R- (or S-) N-trifluoroacetyl-1-(2,3,6,7-tetrahydrobenzo[l,2-b;4,5-b' ]difuran-4-yl)-2-amino
propane; (with 2,3-dichloro-5,6-dicyano-1,4-benoquinone, DDQ) to R- (or S-)-1-(benzo[ l,2-
b:4,5-b-] difuran-4-yl)-2-trifluoroacetamidopropane; (with NaOH) to R- (or S-) DFLY
(Chambers et al., 2001).

m / z: 215.0946 (100.0%), 216.0980 (14. 1 % )
Elemental Analysis: C , 72.54; H, 6.09; N , 6.51; 0, 14.87

DFLY
R-(-)-Isomer HCl salt m.p. 269 C [a] � -9.54° (Chambers et al., 2001) (IPA) (dee.)
S-( +)-Isomer HCl salt m.p. 270 C [a] � +9.58° (Chambers et al., 2001) (IPA) (dee.)
History
The "FLY" name was inspired by the two dihydrofuran rings that extend from the opposite
sides of the benzene ring. When they are aromatized (furan rings) they are planar with the
benzene ring, and the code name is "DRAGONFLY"; they are listed as DFLY derivatives.

4- a- Name CAS # Ref
- - -- 2C-DFLY [260809-97-0] (1)
-- Me DFLY (this entry)
Br -- 2C-B-DFLY [260809-98-1 ] (1)
I -- 2C-I-DFLY -- (4)
I Me I-DFLY [260809-95-8] (1)
Me Me DOM-DFLY [260809-96-9] (1)
CF3 Me TFM-DFLY [260809-99-2] (2,3)
(1) The single literature reference is a computational QSAR study, but no synthetic chemistry is
included (Schulze-Alexandru et al., 1999).
(2) Synthesis (Chambers et al., 2001).
(3) Optical isomers assayed for their affinity to 5-HT2A and 5-HT2c receptors (Chambers et al., 2001).
(4) Not in the published literature.
Biochemistry
The 5-HT2A receptor agonism is a potential measure of pharmacological potency (Schulze
Alexandru et al., 1 999). The optical isomers of each of three "FLY" compounds (FLY, B-FLY,
and TFM-FLY) and their DFLY counterparts (DFLY, B-DFLY, and TFM-DFLY) were assayed
for their affinity to 5-HT2A and 5-HT2c receptors (Chambers et al., 2001 ) .
Pharmacology
Acute toxicity cases attributed to the derivitive B-DFLY ( # 1 0) were reported from Europe,
associated with symptoms suggestive of severe vasoconstriction (Thorlacius et al., 2008) .
Legal Status
DFLY is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.

DHA
#33. DHA
4-(2-Aminopropyl)benzene-1,2-diol
3,4-Dihydroxyamphetamine
4-(2-Aminopropyl)-pyrocatechol
a-Methyl dopamine
HHA
a-MeDA
Registry Numbers
CAS # CAS #
HCl salt [828-06-8] R-Isomer HBr salt [1 72967-65-6]
HBr salt [3459-15-2] R-Isomer freebase [2743-78-4]
Acid salt [51080-00-3] 5-Isomer freebase [14513-20-3]
Freebase [555-64-6] a, f3-[d2 ] Isomer [76381-67-4]
R-Isomer HCl salt [1892-59-7] a, f3, f3-[H3 ]-pyrocatechol [19523-16-1]
5-Isomer HCl salt [4998-74-7]
Synthesis
From DMA (with P, HI) to DHA (Mannich and Jacobsohn, 1910).
From 3,4-dimethoxyamphetamine, DMA (with hydrogen iodide and C02 gas, silver
chloride) to DHA (Alles, 1 932) .

m/ z : 167.0946 (100.0%), 168.0980 (9.7% )
Unspecified form m.p. 190-192 °C (Mannich and Jacobsohn, 1910)

Unspecified form m.p. 192 °C (Alles, 1932)
Derivatives of phenylisopropylamine were prepared, configuration of optically active

DHA was determined (Pratesi et al., 1964); additional synthesis was described (Ensslin et
al., 1996b).

3- 4- a- f3- N- Name CAS # Ref
-
HO HO Me - -- DHA (this entry)
-
HO HO Me - Me DHMA [15398-87-5] (1,2)
HO HO Me -- Me2 N,N-Me-DHA [52370-69-1 ] (3)
HO HO Me -- Et DHEA [181425-74-1 ] (4-6)
HO HO Me -- HO DHAOH [ 13662-98-1 ] (7)
HO HO Me -- Me,HO DHMAOH [674368-64-0] (7)
HO HO Me HO -- f3-HO-DHA [6539-57-7] (8-11 )
HO HO Me HO Me f3-HO-DHMA [13032-27-4] (12,13)
HO HO Me C=O iPr N-iPr-DHA-f3k [530-1 0-9] (14)
HO HO Et -- -- DH-a-Et-PEA [2014-52-0] (15)
HO HO Et HO -- f3,3,4-HO-a-Et-PEA [3198-07-0] (14)

DHA
3- 4- a- f3- N- Name CAS # Ref

HO MeO Me -- -- HMA [52336-47-7] (16,17)
HO MeO Me -- Me HMMA [11 7652-27-4] (1 7-23)
HO MeO Me -- Et HMEA [210708-15-9] (24)
AcO AcO Me -- Me2 N,N-Me-DHA (diacetate) [52370-70-4] (3)
MeO HO Me -- HO MHAOH [674368-62-8] (7)
Meo HO Me -- Me, HO MHMAOH [674368-63-9] (7)
MeO HO Et -- -- HM-a-Et-PEA [181485-30-3] (15,25)
(1) DHMA as a major metabolite was investigated for possible association with the reported neu
rotoxicity of MDMA. Plasma and urine levels were measured and plasma levels were as high
as MDMA itself. The 24-hour urine recovery accounted for 1 7% of the administered MDMA
(Segura et al., 2001).
(2) DHMA and MHMA found to be metabolites of MDMA in humans by GC / MS (Maurer, 1996).
(3) N,N-Me-DHA is acetylated to N,N-Me-DHA (diacetate), which was tested in mice as a potential
anti-Parkinsonism agent (Borgman et al., 1974).
(4) DHEA has been evaluated as a dopamine agonist (Cannon et al., 1979).
(5) DHEA has been shown by GC / MS to be a metabolites of MDE in humans (Maurer, 1996; Ensslin
et al., 1996b), and is detectable in the urine for up to 60 hours after ingestion (Ensslin et al., 1996a).
(6) MDE is metabolized to DHEA in human liver microsomes containing CYP2D6 (Kreth et al.,
2000; Maurer et al., 2000).
(7) A metabolite of MDMA in the horse (Dumasia, 2003).
(8) Effects on rats injected s.c. with 10 mg / kg of f3-HO-DHA on serotonin and 5-HIAA levels were
observed and recorded (Yeh and Hsu, 1991).
(9) Action on the iris of the cat reported (Marley, 1962).
(10) Also known as: a-(1-aminoethyl)-3,4-dihydroxybenzyl alcohol, 3,4-dihydroxynorephedrine,
isoadrenaline, methylnoradrenaline, noradrenaline, and a-methylnorephinephrine.
(11) Kinetics of mydriatic action of f3-HO-DHA on the mouse iris (Freundt, 1973) .
( 1 2 ) Effects o n rats injected s . c . with 10 m g / kg o f f3-HO-DHMA o n serotonin and 5-HIAA levels were
observed and recorded (Yeh and Hsu, 1991).
(13) Effects on rat locomotor activity from s.c. administration of f3-HO-DHMA was reported (Yeh
and Hsu, 1991).
(14) Effectiveness of releasing cardiac norepinephrine was measured (Daly et al., 1966).
(15) A human metabolite of BDB (Maurer, 1996).
(16) Synthesis and serotonin receptor agonist evaluation (Glennon et al., 1980b).
(17) Analysis of oral fluids by GC / MS for MDMA, MDE, and their metabolites (Scheidweiler and
Huestis, 2006).
(18) HMMA has been shown to be a metabolite of MDMA in the rat (Yousif et al., 1990), and in
humans (Lim and Foltz, 1988, 1989; Jenkins et al., 2004).
(19) Found with several other drugs in the urine of Ecstasy users at raves (Zhao et al., 2001).
(20) GC / MS analysis (Helmlin et al., 1996).
(21 ) Assayed for neurochemical and stimulatory effects in rats (Yeh and Hsu, 1991 ).
(22) HMMA is a metabolite of PMMA in the rat (Staack et al., 2003a).
(23) Assayed in rats trained to discriminate between MDMA and saline (Glennon and Higgs, 1992).
(24) Detected as a urinary metabolite in the rat by HPLC (Matsushima et al., 1998).
(25) Identified as a metabolite of MBDB in the rat by TLC, IR, and GC / MS (Kanamori et al., 1998a,
1999).
Biochemistry
Action on isolated frog heart was studied (Ellis, 1949) . The effectiveness of releasing car
diac norepinephrine was measured in the mouse heart (Daly et al., 1966) . Potency as an

DHA / 2,3-DMA
inhibitor of phenethanolamine N-methyltransferase was determined (Fuller et al., 1971).

Correlation was made between chemical structure and phenethanolamine N-methyltrans
ferase reactivity (Hansch and Glave, 1 972) . In hypertensive and normal human subjects,
MHA and DHA were urinary metabolites of [ 1 4C]-labeled L-a-methyl-DOPA (Au et al.,
1972) . The catalytic conversion of MDA to DHA by rat liver microsomes may have involved
the NADPH-dependent cytochrome P450 hydroxylase (Marquardt and DiStefano, 1 974) .
Mechanisms for hyperactivity induction from the nucleus accumbens b y phenethylamine
derivatives were characterized (Cos tall et al., 1976) . MHA and DHA, the major metabolites
of MDA, did not produce serotonin depletion when injected into the brain of rats (McCann
and Ricaurte, 1991a). Effects on rats injected s.c. with 10 mg / kg of DHA on serotonin and
5-HIAA levels were observed and recorded (Yeh and Hsu, 1991). The effects of MDMA and
three of its metabolites (MHMA, DHA, and DHMA) on hormone release from the isolated
rat hypothalamus were measured (Forsling et al., 2002).
5-(+)-DHA is a human metabolite of a-methyldopa (Marshall and Castagnoli, 1 973) . Fol

lowing i.p. injection of [ 3H]-labeled MDA to rats, unchanged MDA was the major com
ponent in brain and liver, but after 24 hours DHA and MHA were the major metabolites
found (Marquardt et al., 1978c) . The metabolites of MDA in the dog and monkey were
DHA, MHA, and 3,4-dihydroxyphenylacetone. 3,4-methylenedioxybenzoate was also
present as a conjugate (Midha et al., 1978) . DHA was a urinary excretion product follow
ing administration of MDA (Schweitzer et al., 1978) and MDMA (Yousif et al., 1 990) in the
rat. In humans, DHA was a metabolite of MDMA (Lim and Foltz, 1989), MDE (Ensslin
et al., 1996a), and, with MHA, of MDA (Maurer, 1996). DH-a-Et-MA and MH-a-Et-MA
were shown by GC / MS to be metabolites of MBDB in humans (Maurer, 1996). The three
reported phenolic human urinary metabolites (MHMA, MHA, and DHA) and a new one,
DHMA, are excreted mainly as the glucuronides. The peak plasma levels of MDMA (300
ng / ml) and of MDA (15 ng / ml) were at two and six hours, respectively. Urine levels of
MDMA were up to 30 µg / ml (Helmlin et al., 1996) .
Pharmacology
Human activity of DHA has not been reported.
Legal Status
DHA is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#34. 2,3-DMA
1-(2,3-Dimethoxyphenyl)propan-2-amine
2,3-Dimethoxyamphetamine
2,3-Dimethoxy-a-methyl phenethylamine
2,3-Dimethoxyphenylisopropylamine
DMA-2
NSC 1 72189
Registry Numbers
dl-HCI salt
CAS # CAS # CAS #
R-Isomer HCI salt [50505-82-3]

[25068-96-6] Freebase [15402-81-0] R-Isomer freebase [744974-27-4]
S-Isomer HCI salt [50505-83-4]

Sulfate [64610-42-0] S-Isomer freebase [741616-71-7]
Acid salt [87059-55-0]

2,3-DMA

From 2,3-dimethoxybenzaldehyde (with nitroethane, acetic acid, and ammonium acetate)
to 1-(2,3-dimethoxyphenyl)-2-nitropropene; (with LAH) to 2,3-DMA (Ho et al., 1970a) .
From 2,3-dimethoxybenzaldehyde (with propionic anhydride) to 2,3-dimethoxycinnamic

acid; (with Na, Hg) to 2,3-dimethoxyphenyl-a-methylpropionic acid; (with NaOCl) to 2,3-
DMA (Ho et al., 1970a) .
From 2,3-dimethoxyphenyl acetone (with R- ( + ) - (or 5- ( - ) - ) a-methylbenzylamine, Raney

Ni, H) to R,R-(+)- (or 5,5-(-)-) N-(a-phenethyl)-2,3-dimethoxyphenylisopropylamine;
(with Pd / C, H2) to R-(-)- (or 5-(+)-) 2,3-DMA (Nichols et al., 1973).

m / z: 195. 1259 (100.0% ), 196.1293 (11.9%)
HCl salt m.p. 154-156 °C (Ho et al., 1970a)

HCl salt m.p. 154 °C (Govindachari and Lakshmikantham, 1957) (EtOH / Etp)
Freebase b.p. 125 / 1 mm (Govindachari and Lakshmikantham, 1957)
R-(-)-Isomer HCl salt m.p. 124-125 °C [aJ b0 -16.9 (Nichols et al., 1973)
S-(+)-Isomer HCl salt m.p. 123-l24 °C [aJ ;g1 +16.6 (Nichols et al., 1973)
The NMR spectrum of 2,3-DMA was obtained and intramolecular interactions analyzed
(Bailey et al., 1971), and the NMR spectrum of 2,3-DMA was analyzed for rotamer popula
tion distribution (Bailey, 1971 ) . The six dimethoxyamphetamines gave distinguishable GC /
MS patterns (Bailey, 1972); UV, MS, NMR, and IR spectra of all six DMAs were presented,
as well as TLC and gas-liquid chromatographic properties (Bailey et al., 1974a) . 2,3-DMA
was distinguished from other dimethoxyamphetamines by chromatographic analysis of its
bromination products (Bailey et al., 1976). Synthesis, TLC, and gas chromatographic prop
erties, UV spectra, and other physical properties were reported (Ono et al., 1976). NMR
spectral shifts with europium reagents were studied (Smith et al., 1976). Urine and plasma
samples were analyzed as the pentafluorobenzamide derivatives by GC with electron cap
ture detection (Midha et al., 1979a). The [ 13C]-NMR spectra for methoxyamphetamines
were shown to be distinctive and suitable for identification (Bailey et al., 1981; Bailey and
Legault, 1 983) . HPLC analysis employing fluorescamine derivatization for fluorescence
detection has been reported (Shimamine, 1984) . The dimethoxy substitution pattern was
confirmed by bromination (DeRuiter et al., 1998b). Fragmentation patterns of some fifty
five phenethylamines were determined by a variety of mass spectrometry techniques (Kol
liker and Oehme, 2004).

2- 3- a- N- Name CAS # Ref
a-CC- HO -- Pr2 5-HO-PPAT [ 68593-96-4] (1-3)
HO Me -- -- 2,3-HMePEA [188851-99-2] (4)
HO Me -- Me 2,3-HMeMPEA [188852-00-8] (4)
HO Me -- Me2 2,3-HMeMMPEA [188852-01-9] (4)
HO Me Me -- 2,3-HMeA [188852-11-1] (4)
52 The 5hulgin Index - Psychedelic Phenethylamines and Related Compounds

2,3-DMA

HO Me Me Me 2,3-HMeMA [ 188852-12-2] (4)
HO Me Me Me2 2,3-HMeMMA [188852-13-3] (4)
HO HO -- -- 2,3-DHPEA [ 1972-58-3] (5)
HO HO -- Me2 N,N-Me-2,3-DHPEA [ 13075-89-3] (5)
HO MeO -- -- 2,3-HMPEA [ 1986-12-5] (5-7)
MeO Me Me -- 2,3-MMeA [ 188852-1 0-0] (4)
MeO Me Me Me 2,3-MMeMA [ 105338-61-2] (4)
MeO Me Me Me2 2,3-MMeMMA [ 107410-19-5] (4)
MeO MeO Me -- 2,3-DMA (this entry)
MeO Meo Me Me N-Me-2,3-DMA [93675-26-4] (8)
MeO MeO Et -- 4C-2,3-DMPEA [722550-56-3] (9)
(1) In reserpinized rats, the 8-hydroxy compound PPAT is a serotonin receptor agonist with no do
pamine receptor action, where as the 5-0H, 6-0H, and 7-0H analogues are dopamine receptor
agonists with no serotonergic activity (Arvidsson et al., 1981).
(2) R- (and 5-) 5-hydroxy-2-(dipropylamino)tetralin (5-HO-PPAT) were assayed for dopamine activ
ity (Karlsson et al., 1990).
(3) PPAT and related compounds were investigated as central serotonin receptor agonists (Arvidsson
et al., 1984).
(4) Synthesis and tissue distribution of radioiodine-labeled psychoactive drugs (Ghaffari et al., 1997).
(6) Synthesis (Voronin et al., 1965)
(7) Synthesis (Ramirez and Burger, 1950).
(8) Identification of methoxy-N-methylamphetamines (Clark, 1984).
mass spectrometry techniques (Kolliker and Oehme, 2004).
Biochemistry
The potency of 2,3-DMA as an inhibitor of phenethanolamine N-methyltransferase was de
termined (Fuller et al., 1971), and correlation of chemical structure with reactivity has been
studied for this enzyme (Hansch and Glave, 1972) . Correlations were made between the
potency of 2,3-DMA, 2,5-DMA, TMA-3, and TMA-6, and the EEG arousal location in rabbit
brain (Fujimori et al., 1 971 ) . Inhibition of uptake of metaraminol and efflux of noradrena
line by rabbit atria was observed (Paton, 1975) . Relationships between drug-induced dis
ruption of behavior and thermoregulation were studied (Kuhlemeier et al., 1 977) .
Action on the uptake and release of serotonin by human blood platelets (Tseng and Loh,
1977), and serotonin receptor site affinity were evaluated (Glennon et al., 1980a) .
Pharmacology
The pharmacology of 2,3-DMA was evaluated for toxicity, effects on barbiturate sleeping
time, and ability to disrupt mouse behavior (Ho et al., 1970a).
Rats trained to discriminate 5-MeO-DMT from saline were tested with several psychoac
tive phenylisopropylamines (Glennon et al., 1981b). Rats trained to distinguish between
DOM and saline in a two-lever drug discrimination task were tested with a series of me
thoxylated amphetamines, showing that 2,4-DMA, 2,3,4-, 2,3,5-, 2,4,6- and 3,4,5-TMA to

2,3-DMA I 2,4-DMA
be active isomers, but that 2,3-, 2,6- and 3,5-DMA were relatively inactive (Glennon and
Young, 1982) . A comparison of the behavioral properties in rats were reported (Glennon
et al., 1 982b), and additional discrimination stimulus studies were presented (Glennon et
al., 1985).
Human potency affected by changes in substitution patterns was demonstrated (Shul

gin et al., 1969). A correlation was made between the energy of the highest occupied
molecular orbital of the drug and potency in humans (Kang and Green, 1970). Positive
correlation was made between psychedelic potency and the degree of native fluorescence
of methoxy derivatives in humans (Antun et al., 1971), stability of molecular complexes
(as determined by NMR) (Sung and Parker, 1972), and lower ionization potential as
measured by photoelectron spectroscopy (Domelsmith and Houk, 1 978) . In a large number
of methoxylated amphetamines, the rabbit hyperthermia response paralleled human
psychedelic potency (Anderson et al., 1978b) . A series of amphetamines were studied for
correlation between 5-HT2 affinity, charge complex stability, rabbit hyperthermia, and
human activity (Domelsmith et al., 1981).
Legal Status
2,3-DMA is a positional isomer of 2,5-DMA, and therefore a Schedule I hallucinogen under
federal drug law, and in states where isomers are included in the controlled drug definition.
#35. 2,4-DMA
1 -(2,4-Dimethoxyphenyl)propan-2-amine
2,4-Dimethoxy-a-methylphenethylamine
DMA-3
Registry Numbers
CAS # CAS # CAS #
HCl salt [33189-36-5] Acid salt [87059-56-1 ] R-Isomer [67313-94-4]
Sulfate [ 64610-43-1 ] Freebase [23690-13-3]

From 2,4-dimethoxy-2-aminopropiophenone (with Pd / C, H2) to 2,4-dimethoxy-13-hy
droxy-a-methylphenethylamine; (with Pd / BaS04 HC104 ) to 2,4-DMA (Glennon et al.,
'
1980a) .

m / z: 195. 1259 (100.0% ), 196.1293 (11.9%)
HCI salt m.p. 150-152 °C (Glennon et al., 1980a) (EtOH)
Ultraviolet absorption spectra and apparent acidic dissociation constants were reported
(Kappe and Armstrong, 1965) . The six dimethoxyamphetamines gave distinguishable
GC / MS patterns (Bailey, 1972) . The UV, MS, NMR, and IR spectra of all six DMAs were
presented; TLC and gas-liquid chromatographic properties are also provided (Bailey et al.,
1974a) . Synthesis, TLC, and gas chromatographic properties, UV spectra, and other physi
cal properties were reported (Ono et al., 1976) . 2,4-DMA was distinguished from other

2,4-DMA
dimethoxyamphetamines by chromatography of its bromination products (Bailey et al.,

1976); the dimethoxy substitution pattern was confirmed by bromination (DeRuiter et al.,
1998b). HPLC analysis employing fluorescamine derivatization for fluorescence detection
was reported (Shimamine, 1984) .
The NMR spectrum was used for analysis of intramolecular interactions (Bailey et al.,
1971) and analysis of rotamer population distribution (Bailey, 1971 ) . [ 13 C] NMR spectra for
methoxyamphetamines were later shown to be distinctive and suitable for identification
(Bailey et al., 1981; Bailey and Legault, 1 983) . Fragmentation patterns of some fifty-five
phenethylamines were determined by a variety of mass spectrometry techniques (Ki::i l liker
and Oehme, 2004) .
Reaction of 2,4-DMA with [ 1 8F] acetyl hypofluorite gave 5-F-2,4-DMA (Mathis et al., 1 986a);
2,4-DMA could be N-methylated to form 2,4-DMMA (Glennon et. al., 1 987b).

2- 4- N- Other Name CAS # Ref
F F -- -- 2,4-DFA [2021-64-9] ( 1,2)
-
Cl Cl -- - 2,4-DCA [32560-77-3] ( 1,2)
a-CC- HO Pr2 -- 6-HO-PPAT [7501 7-01-5] (3,4)
HO MeO -- -- 2,4-HMA [no CAS # assigned] (5)
MeO Cl -- -- 4-Cl-2-MA [53581-61-6] (6)
--
MeO I -- 4-I-2-MA [166820-02-6] (7)
-
MeO MeO -- - 2,4-DMA (this entry)
MeO MeO Me -- 2,4-DMMA [93675-27-5] (8-11 )
MeO MeO Me2 -- 2,4-DNNA [102145-22-2] (10, 12, 13)
MeO MeO -- a-Et 4C-2,4-DMPEA [722550-57-4] (14)
MeO MeO -- �-C=O 2,4-DMA-�k [72739-16-3] (15)
Meo Me -- -- 2,4-MMA [53581-59-2] (16-19)
MeO Me Me -- 4,N-Me-2-MA [166820-00-4] (16)
Meo Br -- -- 4-Br-2-MA [99632-51 -6] (16)
EtO MeO -- -- 2,4-EMPEA [109036-67-1 ] (20)
(1) Potency as an inhibitor of phenethanolamine N-methyltransferase determined (Fuller et al., 1971).
(2) Correlation of a chemical structure and the phenethanolamine N-methyltransferase reactivity
(Hansch and Glave, 1972).
(3) In reserpinized rats, the 8-hydroxy compound PPAT is a serotonin receptor agonist with no do
pamine receptor action, where as the 5-0H, 6-0H, and 7-0H analogues are dopamine receptor
agonists with no serotonin activity (Arvidsson et al., 1981).
(4) PPAT and related compounds as central serotonin receptor agonists (Arvidsson et al., 1984).
(5) Synthesis and serotonin agonist evaluation (Glennon et al., 1980b).
(6) Structure-activity relations in psychedelic phenylalkylamines (Aldous et al., 1974).
(7) The binding at 5-HT 1 c and 5-HT2 receptors was studied (Glennon et al., 1992) .
(8) The synthesis, infra-red spectra, NMR, and GC / MS data are presented (Clark, 1984) .
(9) This was assayed i n rats trained t o discriminate from saline. I t did not show stimulatory effects
(Glennon et al., 1987b).
(10) The heavier N-substituents (ethyl, propyl, isopropyl, hexyl, and N,N-diethyl homologues) were

2,4-DMA
explored as radiolabeling precursors, but are not in the published scientific literature (Shulgin
and Shulgin, 1991).
(11) Several N-methylated psychedelics were compared to methcathinone in stimulant-trained rats
( 12) Synthesis, and reaction with [ 1 8F] acetyl hypofluorite (Mathis et al., 1986a).
(13) Used as a precursor to radiolabeled tracers (Mathis et al., 1986b).
(15) Serotonin receptor site affinity was determined (Glennon et al., 1980a).
(16) Synthesis and binding at 5-HT 1 c and 5-HT2 receptor studied (Glennon et al., 1992).
(17) Synthesis (Ho et al., 1970a).
(18) 2-Methoxy-4-methylamphetamine has been synthesized and assayed in rabbit hyperthermia
(Aldous et al., 1974).
(19) The pharmacology was evaluated for toxicity, effects on barbiturate sleeping time, and ability to
disrupt mouse behavior (Ho et al., 1970a).
Biochemistry
2,4-DMA effects on mouse behavior and the activity of the brain enzymes MAO and DOPA
decarboxylase were evaluated (De Ropp and Kastl, 1970) . Potency as an inhibitor of phe
nethanolamine N-methyltransferase was determined (Fuller et al., 1971); later, chemical
structure was correlated with reactivity with this enzyme (Hansch and Glave, 1 972) . Stud
ies are reported on the action of several psychedelic drugs on perfused vascular strips of
the dorsal metatarsal vein of the dog (Cheng et al., 1974b). Inhibition of uptake of meta
raminol and efflux of noradrenaline by rabbit atria (Paton, 1975).
Using calculated energy interactions between several amphetamines and a model com
pound (3-methylindole) allowed the development of a receptor model for psychedelics
(DiPaolo et al., 1978) . Several compounds were synthesized and assayed for their ability
to inhibit MAOA and MAOB. Most were potent against MAOA; none were appreciably
active against MAOB (Gallardo-Godoy et al., 2005).
Action on the uptake and release of serotonin by human blood platelets has been stud
ied (Tseng and Loh, 1 977) . Serotonin receptor site affinity was measured (Glennon et al.,
1980a). The 5-HT2 receptor was the preferred site of psychedelic action, as its radiolabeled
marker (tritiated DOB) was preferentially targeted. The three controls (appropriately ra
diolabeled 5-HT 1 A 5-HT 1 w and 5-HT 1 c were not as strongly stimulated (Titeler et al., 1 988);
'
binding at 5-HT 1 c and 5-HT2 receptor was also studied (Glennon et al., 1992) .
Pharmacology
Effects observed in rats trained to respond to food presentation schedules (Harris et al.,
1 978) . Several psychedelic drugs were found to elicit myoclonic jumping behavior in the
guinea pig (Carvey et al., 1989) .
tive phenylisopropylamines (Glennon et al., 1981b); rats trained to distinguish between
DOM and saline in a two-lever drug discrimination task with a series of methoxylated am
phetamines, showed 2,4-DMA, 2,3,4-, 2,3,5-, 2,4,6-, and 3,4,5-TMA to be active isomers, but
2,3-, 2,6-, and 3,5-DMA to be relatively inactive (Glennon and Young, 1982); 2,4-DMA sub
stitued for the training drug, but 2,3-DMA did not. 2,4-DMA was assayed in rats trained to
discriminate amphetamine from saline, and did not exhibit substitution for the stimulant

2,4-DMA I 2,5-DMA
Human psychedelic potency was affected by changes in substitution patterns (Shulgin et

al., 1 969). Positive correlations were made between potency in humans and the energy of
the highest occupied molecular orbital of the drug (Kang and Green, 1970), the degree of
native fluorescence (Antun et al., 1971), and the stability of molecular complexes (as deter
mined by NMR; Sung and Parker, 1 972) . For the compounds PMA, 2,4-DMA, 2,5-DMA,
TMA, TMA-2, and TMA-3 (but not for DMA and TMA-6), the lower energy of the rt-rt*
transition and the increased probability of it occurring was positively correlated with hu
man potency (Bailey and Verner, 1972) . A correlation between the octanol-water partition
coefficient and psychedelic potency was determined, and an optimum lipophilicity could
be found for maximum psychedelic activity in humans (Barfknecht et al., 1 975) . In a series
of psychoactive compounds, those with greater potency had lower ionization potential as
measured by photoelectron spectroscopy (Domelsmith and Houk, 1978) . For a large num
ber of methoxylated amphetamines, the rabbit hyperthermia response paralleled human
psychedelic potency (Anderson et al., 1978b); 5-HT2 affinity, charge complex stability, and
rabbit hyperthermia were also positively correlated with human potency (Domelsmith et
al., 1981 ) .
2,4-DMA was initially reported a s orally active i n humans a t 6 0 m g (Shulgin e t al., 1 969),
later reported to only have threshold activity at 60 mg; duration "short" (Shulgin and
Shulgin, 1 991).
Legal Status
#36. 2,5-DMA
2,5-Dimethoxy-a-methyl-phenethylamine
1 -(2,5-Dimethoxyphenyl)-2-aminopropane
1-(2,5-Dimethoxyphenyl)isopropylamine
2-(2-Aminopropyl)hydroquinonedimethylether
DMA*
DMA-4
NSC 367445
*this code appears occasionally in the literature, but usually refers to 3,4-DMA
Registry Numbers
CAS # CAS # DEA# CAS #
HCl salt [24973-25-9] Sulfate [ 64610-44-2] S-( +)-Isomer [ 58993-80-9]
HBr salt [71832-30-9] Acid salt [87059-57-2] 7396 R-Isomer HCl salt [50505-84-5]
Acetate [ 182189-03-3] Freebase [2801-68-5] S-Isomer HCl salt [50505-85-6]
Oxalate [69321-45-5] R-(-)-Isomer [58993-81 -0]
Oxalate [52948-31-9]
(unstated ratio)

From 2,5-dimethoxyphenylacetone (with NH40Ac, Raney Ni, H2, elevated temperature
and pressure) to 2,5-DMA (Green, 1965).

2,5-DMA

to 1-(2,5-dimethoxyphenyl)-2-nitro-propene; (with LAH) to 2,5-DMA (Ho et al., 1 970a).
From 1,4-dimethoxybenzene (with propylene oxide) to 2-(2-hydroxypropyl)-1,4-dime

thoxybenzene; (with tosyl chloride) to 2-(2-tosyloxypropyl)-1,4-dimethoxybenzene; (with
liq. NH3 ) to 2,5-DMA (Yutilov et al., 1999).
Additional syntheses described (Baltzly and Buck, 1940a; Coutts and Malicky 1973; Shul
gin and Dyer, 1975).
From 2,5-dimethoxyphenyl acetone (with R-(+)- (or 5-(-)) a-methylbenzylamine, Raney

Ni, Hz) to R,R-(+)- (or 5,5-(-)-) N-(a-phenethyl)-2,5-dimethoxyphenylisopropylamine
(with Pd / C, Hz) to R-(-)- (or 5-(+)-) 2,5-DMA (Nichols et al., 1 973) .

m / z: 195.1259 (100.0% ), 196.1293 (11.9%)
HCl salt m.p. 107-108 °C (Shulgin and Dyer, 1975) (acetic anhydride)
HCl salt m.p. 114-116 °C (Shulgin and Shulgin, 1991) (EtOH)
HCI salt m.p. 111 .5-112.5 °C (Ho et al., 1970a) (IPA / Etp)
R-(-)-Isomer HCI salt m.p. 145-146 °C [aJ i51 -18.7 (Nichols et al., 1973)
m.p. 144-145 °C [aJ i51 +18.0

(acetone I HzO -or- acetone / IPA)
S-( +)-Isomer HCl salt (Nichols et al., 1973)
(acetone, HzO -or- acetone, IPA)
The NMR spectrum was obtained and intramolecular interactions analyzed (Bailey et al.,
1971), and the NMR spectrum of 2,5-DMA was used to determine rotamer population dis
tributions (Bailey, 1 971 ) . NMR spectral shifts with europium reagents was studied (Smith
et al., 1976). The conformation of the aryl methoxy groups of several psychedelics was es
tablished by [ 13C]-NMR spectral analysis (Knittel and Makriyannis, 1981), and [ 13 C]-NMR
spectra for methoxyamphetamines were shown to be distinctive and suitable for identifi
cation (Bailey et al., 1981; Bailey and Legault, 1983). The electrochemistry of TMA-2, DOB,
DOM, and DON were compared with the 4-unsubstituted 2,5-DMA (Squella et al., 1992).
HPLC separation techniques were described for the identification of drugs (Cashman et
al., 1 973) . Resolution of 2,5-DMA into its optical isomers has been achieved (Aldous et
al., 1974) . UV, MS, NMR, and IR spectra of all six DMAs were reported, along with TLC
and GC properties (Bailey et al., 1974a) . Synthesis, TLC and GC chromatographic proper
ties, UV spectra, and other physical properties were reported (Ono et al., 1976). 2,5-DMA
was distinguished from other dimethoxyamphetamines by chromatographic analysis of
its bromination products (Bailey et al., 1976); the dimethoxy substitution pattern was con
firmed by bromination (DeRuiter et al., 1998b). TLC and color tests were defined for the
identification of substituted amphetamines (O'Brien et al., 1982); methods for rapid fo
rensic identification of illicit phenethylamines were described using TLC in six different
solvent systems and five color reactions for visualization (Neuninger, 1987) . Analysis by
HPLC employing fluorescamine derivatization for fluorescence detection was reported
(Shimamine, 1984) . Cross-reactivity of several substituted amphetamines with the Roche
Abuscreen® (Cody, 1990a) and the Diagnostic Products Corporation radioimmunoassays for
amphetamines was evaluated (Cody, 1990b). Substituted amphetamine derivatives were

2,5-DMA
screened by fluorescence polarization immunoassay (Cody and Schwarzhoff, 1993), and

rapid screening identification was possible with planar chromatography (Fater et al.,
1998). Identification by FTIR spectral analysis (Praisler et al., 2000) and analysis of human
whole blood by capillary electrophoresis with photodiode array detection (Nieddu et al.,
2005) were reported.
The six dimethoxyamphetamines gave distinguishable GC / MS patterns (Bailey, 1 972) .

Urine and plasma samples were analyzed a s the pentafluorobenzamide derivatives, by
GC with electron capture detection (Midha et al., 1979), and identification by GC of hep
tafluorobutyl derivatives was described (Lillsunde and Korte, 1 991). Quantitation in bio
logical fluids using chemical ionization GC / MS was reported (Mariani et al., 1999). The
fragmentation patterns of some fifty-five phenethylamines were determined by a variety
of mass spectrometry techniques (Kolliker and Oehme, 2004) . Detection in urine by MS
(Nordgren and Beck, 2004), and analyses of human urine by LC-MS-MS methods were re
ported (Nordgren et al., 2005). Analysis of human urine involved electrophoresis and mass
spectroscopy (Boatto et al., 2005).
Positional Isomers*
2- 3- 4- 5- 6- Name Entry
MeO MeO -- -- -- 2,3-DMA #34
MeO -- MeO -- -- 2,4-DMA #35
Meo -- -- MeO -- 2,5-DMA this entry
MeO - -
-- -- MeO 2,6-DMA #37
-
-- MeO Meo - -- DMA #38
-- Meo -- Meo -- 3,5-DMA #39
*All compounds in this table are Schedule I (see Legal Status, this entry), and have separate entries.

2- 5- f3- N- Name CAS # Ref
F F -- -- 2,5-DFA (32560-78-4] (1,2)
Br MeO -- -- 2-Br-5-MA (32156-24-4] (3,4)
I MeO -- -- 2-I-5-MA (99254-51-0] (5)
a-CC- HO -- Pr2 7-HO-PPAT (74938-11-7] (6,7)
HO Me HO -- f3,2-H0-5-MeA (857543-23-8] (8,9)
HO Me HO Me f3,2-H0-5,N-DMeA [ 110556-08-6] (8)
-
HO MeO -- - 2,5-HMA [74516-49-7] (2)
HO MeO -- Me2 N,N-Me-2,5-HMA (74516-51-1] (2)
HO MeO HO -- f3,2-H0-5-MA (14722-93-1 ] (10,11)
HO MeO HO Me f3,2-HO-N-Me-5-MA [110492-80-3] (9, 10)
HO EtO HO -- f3,2-H0-5-EA [110492-83-6] (10)
HO EtO HO Me f3,2-HO-N-Me-5-EA (108746-20-9] (9, 10)
HO EtO C = O Me 2-HO-N-Me-5-EA-f3k [857983-04-1 ] (10)
MeO I -- -- 5-1 -2-MA [159432-44-7] (12)

2,5-DMA

MeO Me HO -- f3-H0-2-M-5-MeA [110612-15-2] (8,9)
MeO Me HO Me f3-H0-2-M-N-Me-MeA [717108-44-6] (8,9)
Meo HO -- Me 2,5-MH-MMA [61866-76-0] (13)
-
Meo MeO -- - 2,5-DMA (this entry)
Meo MeO -- Ac 2,5-DMA-Ac [42311-16-0] (15,16)
MeO MeO -- Me 2,5-DMMA [54687-43-3] (9, 1 7-21)
MeO MeO -- Me2 2,5-DNNA [67707-78-2] (15, 19,23-25)
Meo MeO HO -- f3-H0-2,5-DMA [25351-11-5] (1,11,26-32)
MeO MeO HO Me f3-HO-N-Me-2,5-DMA [108746-19-6] (17,25)
MeO MeO HO Me2 [3-HO-N,N-Me-2,5-DMA [3489-99-4] (9,16,25,32)
MeO MeO HO iPr f3-H0-2,5-DMIPA [550-53-8] (34)
MeO MeO C=O -- 2,5-DMA-f3k [854685-37-3] (25)
MeO Meo C=O Me 2,5-DMMA-f3k [ 854685-49-7] (25)
EtO EtO HO -- [3-H0-2,5-DEA [105652-59-3] (9,27)
EtO EtO HO Me f3-HO-N-Me-2,5-DEA [3489-98-3] (9,10)
EtO EtO C=O -- 2,5-DEA-f3k [ 856814-48-7] (17)
(1) The potency as an inhibitor of phenethanolamine N-methyltransferase was determined; no
chemical data presented (Fuller et al., 1971).
(2) Synthesis, and 5-HT2A receptor binding affinities characterized (Parker et al., 2008).
(3) A correlation has been made between the degree of native fluorescence and psychedelic potency
of the methoxy derivatives in humans (Antun et al., 1971) .
(4) Synthesis; pharmacology o n conditioned avoidance response i n rats (Barfknecht and Nichols,
1971) .
(5) Synthesis from 3-MA with 12, Ag2S04 (Sy, 1993).
(6) PPAT and related compounds as central serotonin receptor agonists (Arvidsson et al., 1984).
(7) In reserpinized rats, the 8-0H compound PPAT is a serotonin receptor agonist with no dopamine
receptor action, where as the 5-0H, 6-0H, and 7-0H analogues are dopamine receptor agonists
with no serotonin activity (Arvidsson et al., 1981).
(8) Synthesis, and comparitive pharmacology in the rabbit and guinea pig (Ardis et al., 1946).
(9) The pulmonary circulation effects were measured in the dog (Aviado et al., 1957).
(10) Synthesis (Ide and Baltzly, 1948).
(11) The effects on cardiac function were observed in the cat and the dog (Ellis, 1965).
(12) Synthesis from 2-MA with 12, Ag2S04 (Sy, 1993).
(13) Metabolite of 2-MMA (Roy et al., 1984).
(15) Biotransformation by Cunninghamella echinulata (Foster et al., 1992).
(16) In vitro studies with isolated guinea pig and rabbit uteri and rabbit intestine, and in vivo pressor
studies in mice, were compared (Hjort et al., 1948).
(18) Synthesis (Baltzly and Buck, 1940a).
(19) Discrimination stimulus studies against racemic amphetamine (Glennon et al., 1985).
(20) Serotonin receptor binding was studied (Glennon et al., 1978).
(21) 2,5-DNNA reacts with the appropriate radioactive hypohalites to form 4-iodo-2,5-dimethoxy
N,N-dimethylamphetamine (IDNNA) and 4-fluoro-2,5-dimethoxy-N,N-dimethylamphetamine
(FDNNA). (Shulgin and Shulgin, 1991)
(22) Serotonin affinity of 2,5-DNNA was determined (Glennon et al., 1978).

2,5-DMA
(23) Synthesis and reaction with [ 1 8F] acetyl hypofluorite (Mathis et al., 1986a).
(24) Syntheses described (Baltzly and Buck, 1940a).
(25) Action on the CNS of the chicken (Dewhurst and Marley, 1965).
(26) Effects on the renal blood flow in dogs (Aviado et al., 1958).
(27) Action on the iris of the cat (Marley, 1962).
(28) Synthesis (Ohshita and Ando, 1992).
(29) The effectiveness of releasing cardiac norepinephrine was measured (Daly et al., 1966) .
(30) Derivatization with heptafluorobutyryl-L-proline allowed chiral analysis by GC (Srinivas et al.,
1989).
(31) A quantitative colorimetric urine screening is described for urine analysis (Rutter, 1972) .
(32) Synthesis (Baltzly and Buck, 1940b).
(33) 2,5-DMIPA with a �-hydroxyl group (erythro-2,5-dimethoxy-�-hydroxy-N-(i)-propylamphet
amine, BW 61-43, N-isopropylmethoxamine) is a pharmaceutical �-adrenergic blocking agent
(Blinks, 1967).
Biochemistry
In vitro studies with isolated guinea pig and rabbit uteri and rabbit intestine, and in vivo
press or studies in mice, were compared (Hjort et al., 1 948) . 2,5-DMA effects on cardiac
function were observed in the cat and dog (Ellis, 1 965) . 2,5-DMA effects on mouse behavior
and the activity of the brain enzymes MAO and DOPA decarboxylase were evaluated (De
Ropp and Kastl, 1970) . Correlations were made between the potency of 2,3-DMA, 2,5-
DMA, TMA-3, and TMA-6, and the EEG arousal location in rabbit brain (Fujimori et al.,
1971 ) . The action of several psychedelic drugs on perfused vascular strips of the dorsal
metatarsal vein of a dog was reported (Cheng et al., 1 974b). Mutagenic activity in Salmonella
typhimurium was evaluated (White et al., 1 977) .
Both PMA and 2,5-DMA, administered to rats, increased the activation of myoclonic twitch
activity of suprahyoideal muscle, which was reported previously to involve central seroto
nergic and dopaminergic mechanisms (Tseng, 1978) . Using calculated energy interactions
between several amphetamines and a model compound (3-methylindole) allowed the de
velopment of a receptor model for psychedelics (DiPaolo et al., 1 978) . Several compounds
were synthesized and assayed for their ability to inhibit MAOA and MAOB . Most were
potent against MAOA; none were appreciably active against MAOB (Gallardo-Godoy et
al., 2005).
Serotonin agonist activity was detected in sheep umbilical preparations (Shulgin and Dyer,
1975) . Action on the uptake and release of serotonin by human blood platelets was de
scribed (Tseng and Loh, 1977) . Serotonin receptor binding was studied (Glennon et al.,
1 978; Glennon et al., 1980a; Glennon et al., 1 982a), 5-HT 1 and 5-HT2 binding properties
were reported (Shannon et al., 1 984), affinity to 5-HT2 receptors was measured and com
pared to structurally related compounds (Seggel et al., 1 990), and binding at 5-HTl C and
5-HT2 receptors was reported (Glennon et al., 1992) . The 5-HT2 receptor was the preferred
site of psychedelic action as its radiolabeled marker (tritiated DOB) was preferentially tar
geted; the three controls (appropriately radiolabeled 5-HT 1 N 5-HT 1 w and 5-HT 1 c) were
not as strongly stimulated (Titeler et al., 1988) . A large study of psychedelic compounds
showed that the lipophilicity of the 4-position substituent was of primary importance in
determining 5-HT2 receptor affinity (Glennon and Seggel, 1989) . A series of psychedelic
amphetamines were compared to their phenethylamine counterparts, as agonist to 5-HT2A
and 5-HT2c receptors (Acuna-Castillo et al., 2002). The affinity to cloned human 5-HT2N
5-HT2w and 5-HT2c receptors was measured and compared to structurally related com
pounds (Nelson et al., 1 999). Binding at 5-HT2A receptors was compared to binding affinity

2,5-DMA
of several [3-carbolines (Glennon et al., 2000). Evidence was presented for the involvement
of serotonin in the mechanism of action of psychedelic drugs (Glennon et al., 1 984b).
Pharmacology
A series of mono-, di- and tri-substituted amphetamines were tested on rats trained with
various avoidance programs. Potency increased with the loss of methoxy groups. Of the
tri-substituted compounds tested, TMA-2 > TMA > TMA-6 >> TMA-3; with the di-sub
stituted derivatives 2,3-DMA, 2,5-DMA, 3,4-DMA, and 3,5-DMA, only 3,4-DMA showed
activity. PMA was the most potent of the three mono-substituted amphetamines (Smythies
et al., 1967b). 2,5-DMA disrupted conditioned responses in rats, and potentiated the phe
nobarbital sleeping time in mice (Ho et al., 1970a) . Rabbit hyperthermia responses were de
scribed for 2,5-DMA and its optical isomers (Aldous et al., 1 974) . Drug-induced disruption
of behavior and thermoregulation was studied in a series of tryptamines, and mono- and
di-substituted amphetamines; the di-substituted amphetamines were intermediate in ac
tivity with respect to the other two compound groups (Kuhlemeier et al., 1977) . A pharma
cologic comparison of reflex responses to 2,5-dimethoxyamphetamine and LSD was made
in the chronic spinal dog (spinal cords surgically transected; Vaupel et al., 1 977) .
The decreased frequency of rat limb flicks correlated well with a drop off in potency of
several 2,5-dimethoxy compounds: DOM, R-DOB, and 2,5-DMA were the most effective,
S-DOB and DOET were weaker, and 4C-M was almost without activity (Rusterholz et al.,
1977) . Effects were observed on acute toxicology and gross behavior in rodents, dogs, and
monkeys (Davis et al., 1 978), on integrated sensory functions and active startle in male rats
(Geyer et al., 1 978), and on rats trained to respond to food presentation schedules (Harris
et al., 1 978) . Inhibition of food intake was observed in the dog (Vaupel et al., 1979) .
Discriminative stimulus studies in rats trained with d-amphetamine reported (Huang and
Ho, 1 974a). Serotonin receptor affinities were determined in isolated rat fundus prepara
tions, and studies were performed with rats trained to discriminate 5-MeO-DMT from
saline (Glennon et al., 1981a, 1981b). Rats trained with racemic amphetamine were tested
with several mono- and di-substituted amphetamines; none of the di-substituted com
pounds completely generalized the amphetamine response of these animals (Glennon et
al., 1 985) . Drug discrimination studies with rats trained with LSD has been performed by
others (Nichols et al., 1991).
A number of studies have attempted correlation between molecular parameters, organ-lev

el responses, or whole-animal responses, and psychedelic potency in humans. Correlations
were made between psychedelic potency and the energy of the highest occupied molecular
orbitals of the drug (Kang and Green, 1970), the degree of native fluorescence (Antun et
al., 1 971 ), the stability of molecular complexes (as determined by NMR; Sung and Parker,
1 972), an optimum lipophilicity (as determined by the octanol-water partition coefficient;
Barfknecht et al., 1975), partition coefficients, steric bulk, and in vitro activity (Nichols et al.,
1977), ionization potentials as measured by photoelectron spectroscopy (Domelsmith and
Houk, 1978), and the electron withdrawing or donating nature of the 4-position substitu
ent (Neuvonen et al., 2006). For the compounds PMA, 2,4-DMA, 2,5-DMA, TMA, TMA-2,
and TMA-3 (but not for DMA and TMA-6), the lower energy of the rt-rt* transition and the
increased probability of it occurring was positively correlated with human potency (Bai
ley and Verner, 1 972) . Stereoisomers of five psychedelic amphetamines contracted isolated
strips of sheep umbilical arteries, the R-(-)- being more active than the S-( +)-isomers; there
was a general correlation between the smooth muscle contracting ability and the psychoac-

2,5-DMA I 2,6-DMA
tivity of the compounds (Dyer et al., 1973) . A series of amphetamines were studied for cor
relation between 5-HT2 affinity, charge complex stability, rabbit hyperthermia, and human
activity (Anderson et al., 1978b; Domelsmith et al., 1981). A comparison of steric properties
with animal and human potency of several phenethylamines, tryptamines, and lysergide
derivatives has been made (Nichols, 1986) .
2,5-DMA was identified as a component in seizures of recreational drugs before it was

placed in Schedule I in 1973 (Shaler and Padden, 1972) .
2,5-DMA was reported t o be orally active i n humans a t 4 0 m g (Shulgin e t al., 1 969) . 2,5-
DMA produced stimulant effects similar to those produced by MDA, LSD, and cocaine
(Glennon and Young, 1984a); an effective dose range from 75 to 110 mg was reported (Cas
sels and G6mez-Jeria, 1985) . In the 80-160 mg range there were physical effects (cardio
vascular stimulation and mydriasis), but no sensory enhancement or psychedelic effects;
duration 6-8 hours (Shulgin and Shulgin, 1991).
Legal Status
2,5-DMA is a Schedule I hallucinogen under federal drug law, and under District of
Columbia and all state laws except for Delaware, Kentucky, Massachusetts, New Mexico,
Pennsylvania, and Vermont. There are five additional positional isomers that are also
Schedule I, and these are treated in separate entries.
#37. 2,6-DMA
2,6-Dimethoxy-a-methylbenzeneethanamine
2-(2,6-Dimethoxyphenyl)-1-methylethylamine
DMA-5
Registry Numbers
CAS # CAS # CAS #
HCl salt [3904-11-8] Acid salt [87059-58-3] Freebase [23690-14-4]
Synthesis and Chemisty

to 1-(2,6-dimethoxy)phenyl-2-nitropropene; (with LAH) to 2,6-DMA (Shulgin and Shulgin,
1991).
Synthesis described, proceeding from rescorcinol (1,3-benzenediol) (Shamshurin and

Revenko, 1 962) .

m / z: 195.1259 (100.0%), 196.1293 (11.9%)
HCI salt m.p. 1 85-1 86 °C (Shamshurin and Revenko, 1962) (EtOH / EtOAc)
Six dimethoxyamphetamines gave distinguishable GC / MS patterns (Bailey, 1 972) . The UV,

MS, NMR, and IR spectra of all six DMAs were given, along with TLC and GC properties
(Bailey et al., 1974a). 2,6-DMA was distinguished from other dimethoxyamphetamines

2,6-DMA
dimethoxy substitution pattern was confirmed by bromination (DeRuiter et al., l 998b ). The
by chromatographic analysis of its bromination products (Bailey et al., 1 976), and the
[ 13 C]-NMR spectra for methoxyamphetamines are distinctive and suitable for identification
(Bailey et al., 1981; Bailey and Legault, 1983).

Cl Cl Me -- 2,6-DCA [32560-79-5] (1,2)
MeO Br Me -- 6-Br-2-MA [139102-29-7] (3)
Meo Meo Me -- 2,6-DMA (this entry)
MeO MeO Me Me N-Me-2,6-DMA [93675-28-6] (4)
MeO MeO Me Me2 2,6-DNNA [ 1 05363-36-8] (5,6)
(3) The binding at 5-HT 1 c and 5-HT2 receptors has been studied (Glennon et al., 1992).
(4) The synthesis, infra-red spectra, NMR, and GC / MS data are presented (Clark, 1984) .
(5) Synthesis, and reaction with [ 18F] acetyl hypofluorite (Mathis et al., 1986a).
Biochemistry
Action on the uptake and release of serotonin by human blood platelets (Tseng and Loh,
1 977) . The pressor-activity rating was predicted by pattern recognition of molecular struc
tures (Zotov and Altymyshev, 1980) .
Serotonin receptor site affinity was determined (Glennon et al., 1980a), and interaction at
human brain 5-HT2 receptors was evaluated (Sadzot et al., 1989) .
Pharmacology
Rats trained to distinguish between DOM and saline in a two-lever drug discrimination
task with a series of methoxylated amphetamines, showed 2,4-DMA, 2,3,4-, 2,3,5-, 2,4,6-,
and 3,4,5-TMA to be active isomers, but 2,3-, 2,6-, and 3,5-DMA to be relatively inactive
(Glennon and Young, 1982) . Rats trained with racemic amphetamine were tested with
several mono- and di-substituted amphetamines; none of the di-substituted compounds
completely generalized the amphetamine response of these animals (Glennon et al., 1985).
Drug discrimination studies with rats trained with LSD were performed by others (Nichols
et al., 1991).
A number of studies have attempted correlation between molecular parameters, organ

level responses, or whole-animal responses, and psychedelic potency in humans. Cor
relations have been made between psychedelic potency and changes in substitution
patterns (Shulgin et al., 1969), the energy of the highest occupied molecular orbital of
the drug (Kang and Green, 1970), the degree of native fluorescence (Antun et al., 1971),
ionization potential as measured by photoelectron spectroscopy (Domelsmith and Houk,
1978), and the stability of molecular complexes (as determined by NMR; Sung and Parker,
1972) . A series of amphetamines were studied for correlation between 5-HT 2 affinity, charge
complex stability, rabbit hyperthermia, and human activity (Domelsmith et al., 1981).
Human activity of 2,6-DMA is unknown.

2,6-DMA / OMA
Legal Status
#38. DMA
a-Methyl-3,4-dimethoxyphenethylamine
1-(3,4-Dimethoxyphenyl)-2-aminopropane
1 -(3,4-Dimethoxyphenyl)-2-propylamine
2-Amino-1-(3' ,4' -dimethoxyphenyl)propane
a-Methylhomoveratrylamine
3,4-DMA
EA-1316
NSC 14471 7
Registry Numbers
CAS # CAS #
HCl salt [13078-75-6] S-( +)-Isomer HCl salt [2811-24-7]
Bisulfate [91340-28-2] R-Isomer sulfate [161121-04-6]
Oxalate [58379-90-1 ] R-Tolylsulfonyl-L-prolinate [199527-10-1 ]
Sulfate [64610-45-3] S-Tolylsulfonyl-L-prolinate [199527-11-2]
Acid salt [87059-59-4] R-(-)-Isomer freebase [ 64778-78-5]
Freebase [120-26-3] S-( +)-Isomer freebase [ 1 7279-41-3]
R-(-)-Isomer HCl salt [2656-14-6]

From 3,4-dimethoxyphenylacetone (with hydroxylamine) to 3,4-dimethoxyphenylacetone
oxime; (with NaH or Na, Hg) to DMA (Mannich and Jacobsohn, 1910).
From 3,4-dimethoxyphenylacetone (with formamide, HCl) to DMA (Govindan, 1957) .
From 3,4-dimethoxyaldehyde (with nitroethane, acetic acid, and ammonium acetate) to

1-(3,4-methoxyphenyl)-2-nitropropene; (with electrolysis, Hg / Pd; Alles, 1 932), or (with
LAH; Ho et al., 1970a) to DMA.
From 3,4-dimethoxyphenyl acetone (with R-(+)- (or 5-(-)-) a-methylbenzylamine, Raney

Ni, Hz) to R,R-(+) (or 5,5-(-)-) N-a-phenethyl)-3,4-dimethoxyphenylisopropylamine; (with
Pd / C, Hz) to R-(-)- (or 5 -( + )-) DMA (Nichols et al., 1973) .

m / z: 195.1259 (100.0%), 196. 1293 (11.9%)
Elemental Analysis: C, 67.66; H, 8.78; N, 7. 17; 0, 16.39
HCl salt m.p. 144 °C (Mannich and Jacobsohn, 1910)

HCl salt m.p. 147.5-148 °C (Ho et al., 1970a) (EtOH / Etp)
Sulfate salt m.p. 312-315 °C (Ho et al., 1970a)

OMA
S-(+)-Isomer, HCI salt m.p. 141-142 °C [aJ g1 +23.1 (Nichols et al., 1973)
Freebase b.p. 166-168 °C / 20 mm (Mannich and Jacobsohn, 1910)
Freebase b.p. 148-150 °C / 3 mm (Govindan, 1957)
The UV, MS, NMR (proton magnetic resonance), and IR spectra of all six DMAs were given,
along with TLC and GC chromatographic properties (Bailey et al., 1 974a) . Synthesis, TLC,
and gas chromatographic properties, UV spectra, and other physical properties were re
ported (Ono et al., 1 976) . DMA was distinguished from other dimethoxyamphetamines by
chromatographic analysis of its bromination products (Bailey et al., 1976); the dimethoxy
substitution pattern was later confirmed by bromination (DeRuiter et al., 1 998b). Analysis
by HPLC employing fluorescamine derivatization for fluorescence detection was reported
(Shimamine, 1984) . Analysis and identification by capillary electrophoresis was reported
(Trenerry et al., 1995) . Identification has been performed with IR spectra, analyzed with a
neural network alone, and coupled with principal component analysis (Gosav et al., 2005) .
1971); the NMR spectrum of DMA was used to determine rotamer population distribu
tion (Bailey, 1971 ) . NMR spectral shifts with europium reagents were studied (Smith et al.,
1976) . The [ 13C]-NMR spectra for methoxyamphetamines were shown to be distinctive and
suitable for identification (Bailey et al., 1981; Bailey and Legault, 1983). An NMR procedure
was described for the identification of possibly illegal drugs (Hays, 2005) .
The six dimethoxyamphetamine gave distinguishable GC / MS patterns (Bailey, 1972) .

Urine and plasma samples were analyzed as the pentafluorobenzamide derivatives, by
GC with electron capture detection (Midha et al., 1979a) . Derivatization with heptafluoro
butyryl-L-proline allowed chiral analysis by GC (Srinivas et al., 1989), and GC based iden
tification was possible with the heptafluorobutyl derivative (Lillsunde and Korte, 1 99 1 ) .
GC / MS analysis was made o f several N-substituted derivatives o f DMA (Noggle e t al.,
1991a). The fragmentation patterns of some fifty-five phenethylamines were determined
by a variety of mass spectrometry techniques (Kolliker and Oehme, 2004).
The optically active form was synthesized from the corresponding ketone by a bacteria
culture (Sato et al., 1990) . Microbial synthesis of R- and 5-3,4-dimethoxyamphetamines
through stereoselective transamination (Iwasaki et al., 2003), and microbial synthesis of
DMA at >99% enantiomeric excess has been performed (Iwasaki et al., 2006).

3- 4- a- N- Other Name CAS # Ref
F F Me -- -- DFA [31338-32-6] (1,2)
Cl Cl Me -- -- DCA [4806-87-5] (1,2)
Cl Cl Me Me -- N-Me-DCA [ 32633-68-4] (1)
Cl HO Me -- -- 3-Cl-PHA [31338-31-5] (1-3)
Br HO Me -- -- 3-Br-PHA [ 32560-72-8] (1,2)
Br MeO Me -- -- 3-Br-PMA [32156-22-2] (4,5)
-
I MeO Me -- - 3-I-PMA [159432-45-8] (6)
Me MeO -- -- -- a,a,3-Me-MPEA [ 198226-60-7] (7,8)
Me MeO Me Me -- 3-Me-PMMA [827611-22-3] (7,8)

OMA
3- 4- a- N- Other Name CAS # Ref

Me MeO Et -- -- 3-Me-a-Et-MPEA [827611-24-5] (7,8)
MeO Cl Me -- - -
4-Cl-3-MA [27572-11-8] (9, 10)
-
MeO Br Me -- - 4-Br-3-MA [32156-23-3] (4,5)
MeO MeO Me -- -- DMA (this entry)
MeO MeO Me -- [3-HO [3-HO-DMA [3046-92-2] (11)
MeO MeO Me HO -- DMAOH [ 58380-00-0 l (21)
Meo MeO Me Me -- DMMA [33236-61 -2] (13-19)
MeO MeO Me Me2 -- N,N-Me-DMA [58993-77-4] (17)
MeO MeO Me Et -- DMEA [ 33236-63-3] (17-20)
MeO MeO Me Me,HO -- DMMAOH [58379-99-0] (12)
MeO MeO Me Pr -- DMPA [33236-63-4] (21)
MeO MeO Me Bz -- DMBZ [2980-07-6] (12, 22)
Meo MeO Et -- -- 4C-DMPEA [55174-55-5] (3,23)
MeO EtO Me -- -- MEA [32560-70-6] (2,24)
EtO MeO Me -- -- EMA [ 872810-48-5] (25)
-
EtO EtO Me - -- DEA [94640-33-2] (25)
(Hansch and Glave, 1972)
(3) In rats, PCA is metabolized with the "NIH" shift to yield 3-chloro-4-hydroxyamphetamine (ParIi
and Schmidt, 1975) .
(4) A correlation was made between the degree of native fluorescence and the psychoactivity of the
methoxy derivatives in humans (Antun et al., 1971).
(5) Synthesis described; pharmacology on conditioned avoidance response in rats (Barfknecht and
Nichols, 1971 ).
(6) Synthesis from PMA with I2, Ag2S04 (Sy, 1993).
(7) Analysis by non-polar GC and MS, and comparison to MDMA (Aalberg et al., 2004).
(8) Analysis by LC and ESI-MS-MS, and comparison to MDMA (Pihlainen et al., 2005).
(10) Synthesis (Carlsson et al., 1970).
(11) Synthesis (Ohshita and Ando, 1992) .
(12) Synthesis (Morgan and Beckett, 1975).
(13) Impurity in MDMA made from sassafras oil (Noggle et al., 1991a).
(14) The synthesis, infra-red spectra, NMR and GC / MS data are presented (Clark, 1984).
(15) Assayed in rats trained to discriminate from saline. No stimulatory effects shown (Glennon et
al., l 987b ).
(17) GC / MS analysis of several N-substituted derivatives of DMA (Noggle et. al., 1991a).
(18) Assayed in rats trained to discriminate between MDMA and saline (Glennon and Higgs, 1992).
(19) Threshold activity in humans at 250 mg; duration unknown (Shulgin and Shulgin, 1991).
(20) The code name DMEA has been used in the literature for MEM.
(21) Correlation made between structure and locomotor activity of mice (van der Schoot et al., 1962).
(22) Synthesis (Muszynski, 1965).

DMA
(24) Potency as an inhibitor of phenethanolamine N-methyltransferase determined (Fuller et al.,

1971).
(25) Synthesis (Shepard et al., 1952).
Homologues and Analogues with Three-Carbon Chains

OH OH -- -- homo-Dopamine [52336-30-8] (1)
MeO MeO a -Me -- homo-DMA [27487-78-1 ] (2,3)
(1) Potential cardiovascular drug (Winn et al., 1975) .
(2) The behavioral effects in rats were compared with those produced by LSD, mescaline, and am
phetamine (Buxton, 1972) .
(3) Synthesis (Aldous et al., 1974) .
Biochemistry
Action of DMA on isolated rabbit intestine (Mercier et al., 1948a) and on isolated frog heart
(Ellis, 1949) has been reported. Effects on the oxidation of tyramine by amine oxidase were
studied (Fellows and Bernheim, 1950), as were the effects on alkaline phosphatase activity
and pyruvate utilization in rat brain homogenates (Clark et al., 1 956). The effectiveness
of releasing cardiac norepinephrine by the mouse heart was measured (Daly et al., 1966) .
Effects on spontaneous brain electrical activity in the cat (Fairchild et al., 1967), and EEG
response in the rabbit brain following i.v. administration (Fujimori and Himwich, 1 969)
have also been reported. The potency of DMA as an inhibitor of phenethanolamine N
methyltransferase was determined (Fuller et al., 1971), and correlation of chemical struc
ture and reactivity with this enzyme has also been reported (Hansch and Glave, 1972) .
Action o f DMA o n the salivary gland o f the adult blowfly was compared with the action
of serotonin (Berridge and Prince, 1973) . Studies were reported on the action of DMA and
several other psychedelic drugs on perfused vascular strips of the dorsal metatarsal vein
of the dog (Cheng et al., 1974b). Action on the uptake and release of serotonin by human
blood platelets was also studied (Tseng and Loh, 1977) . Serotonin receptor site affinity was
determined (Glennon et al., 1980b), and 5-HT 1 and 5-HT2 binding properties have been
reported (Shannon et al., 1984) . Several compounds were synthesized and assayed for their
ability to inhibit MAOA and MAOB . Most were potent against MAOA; none were appre
ciably active against MAOB (Gallardo-Godoy et al., 2005).
PCA is metabolized to OMA in the rat brain (Sherman and Gal, 1976; Silverman and Ho,
1 979), and the primary metabolite of DMA, in both the dog and the monkey, is MHA
(3-methoxy-4-hydroxyamphetamine; Midha et al., 1979b). Microorganisms fed L-alanine
were effective in converting 3,4-dimethoxyphenyl-acetone to the S-( +)-isomer of DMA
(Nakamichi et al., 1990) .
Pharmacology
DMA produced an experimental catatonia in cats (Noteboom, 1 934) . At 5-10 mg / kg, i.v.,
DMA produced a hypotensive response in dogs (Mercier and Mercier, 1944) . There was an
amphetamine-like awakening of barbital-narcotized rats when treated with DMA, unless
the dose is 1,000 times higher (Mercier et al., 1948b). Pulmonary circulation effects were
measured in the dog (Aviado et al., 1957), and effects on cardiac function were observed
in the cat and dog (Ellis, 1965) . Pharmacology was evaluated for toxicity, effects on barbi
turate sleeping time, and ability to disrupt mouse behavior (Ho et al., 1 970a) . Mescaline,

DMA
DMPEA, MDPEA, TMA, MDA, DMA, BDB, and MDMA were compared pharmacologi
cally in five animal species (Hardman et al., 1973) . The optical isomers of PMMA, DOM,
MBDB, MDMA, and DMA were compared as stimulants in rats (Rangisetty et al., 2001).
A series of mono-, di- and tri-substituted amphetamines was tested on rats trained with
various avoidance programs. Potency increased with the loss of methoxy groups. Of the
tri-substituted, TMA-2 > TMA > TMA-6 >> TMA-3. With the di-sustituted derivatives,
2,3-DMA, 2,5-DMA, 3,4-MDA, and 3,5-MDA, only the DMA showed activity. Of the three
mono-substituted amphetamines, PMA was the most potent (Smythies et al., 1967b). With
rats trained with various avoidance programs, of the several dimethoxy isomers tried only
DMA showed activity (Smythies et al., 1967b). The 5-(+)- and R-(-)-isomers of DMA did
not exhibit the characteristic effects of racemic DMA and mescaline on conditioned avoid
ance response in rats (Barfknecht and Nichols, 1972). Effects were observed in rats trained
to respond to food presentation schedules (Harris et al., 1978) . This compound was among
about a dozen psychedelics compared to stimulants evaluated in rats trained for condi
tioned avoidance (Davis and Hatoum, 1987).
tive phenylisopropylamines (Glennon et al., 198lb). Rats trained to distinguish between
DOM and saline were tested with a series of methoxylated amphetamines, showing 2,4-
DMA, 2,3,4-, 2,3,5-, 2,4,6-, and 3,4,5-TMA to be active isomers, but 2,3-, 2,6-, and 3,5-DMA
to be relatively inactive (Glennon and Young, 1982) . Rats trained with racemic amphet
amine were tested with several mono- and di-substituted amphetamines; none of the di
substituted compounds completely generalized the amphetamine response of these ani
mals (Glennon et al., 1 985) . DMA was assayed in rats trained to discriminate between
MDMA and saline (Glennon and Higgs, 1992) .

level responses, or whole-animal responses, and psychedelic potency in humans. Correla
tions were made between psychedelic potency and mouse behavioral responses (Corne
and Pickering, 1 967), changes in substitution patterns (Shulgin et al., 1969), the energy
of the highest occupied molecular orbital of the drug (Kang and Green, 1970), the degree
of native fluorescence (Antun et al., 1971), and the stability of molecular complexes (as
determined by NMR; Sung and Parker, 1972) . For the compounds PMA, 2,4-DMA, 2,5-
DMA, TMA, TMA-2, and TMA-3 (but not for DMA and TMA-6), the lower energy of the
*
rt-rt transition and the increased probability of it occurring was positively correlated with
human potency (Bailey and Verner, 1972) . The relationship between partition coefficients
(Barfknecht et al., 1975), steric bulk, and in vitro activity (Nichols et al., 1977) was used to
predict potency in humans. For a large number of methoxylated amphetamines, the rabbit
hyperthermia response paralleled psychedelic potency in humans (Anderson et al., 1978b ),
and correlations between 5-HT2 affinity, charge complex stability, rabbit hyperthermia, and
human activity reported (Domelsmith et al., 1981).
Intravenous trials of DMA in humans were made in doses up to 700 mg, with reports
of mescaline-like effects (at the Army Medical Center; see Fairchild, 1 963) . Oral levels of
160 mg produce a hypertensive responses and slight mydriasis (Fairchild et al., 1967) .
Speculation is that the orally active level is perhaps a few hundred mg; duration unknown
(Shulgin and Shulgin, 1991).

2,5-DMA I 3,5-DMA
Legal Status
OMA is a positional isomer of 2,5-DMA, and therefore a Schedule I hallucinogen under
m
y
#39. 3,5-DMA
H3CO NH2
C H3
DMA-6 OCH3
NSC 660980
Registry Numbers
CAS # CAS #
HCl salt [24973-29-3] R-(-)-Isomer HCI salt [153379-46-5]
Sulfate [6461 0-46-4] S-( +)-Isomer HCl salt [104371-23-5]
Acid salt [87920-96-5] R-(-)-Isomer freebase [1 77971-34-5]
Freebase [15402-82-1 ] S-( +)-Isomer freebase [104371-22-4]

From 3,5-dimethoxybenzaldehyde (with nitroethane) to 1-(3,5-dimethoxyphenyl)-2-nitro
propene; (with LAH) to 3,5-DMA (Ho et al., 1970a).

m / z: 195.1259 (100.0%), 196.1293 (11.9%)
Elemental Analysis: C, 67.66; H, 8.78; N, 7. 1 7; 0, 16.39
HCl salt m.p. 160-161 °C (Ho et al., 1970a) (EtOH / Etp)
The NMR spectrum was obtained and intramolecular interactions analyzed. (Bailey et al.,
1971); the NMR spectrum of 3,5-DMA was used to determine rotamer population distribu
tion (Bailey, 1 971 ) . The UV, MS, NMR, and IR spectra of all six DMAs were given, along
with TLC and GC chromatographic properties (Bailey et al., 1 974a). [ 13 C]-NMR spectra for
methoxyamphetamines were shown to be distinctive and suitable for identification (Bailey
et al., 1981; Bailey and Legault, 1983) . Synthesis, TLC, and gas chromatographic proper
ties, UV spectra, and other physical properties were reported (Ono et al., 1 976). 3,5-DMA
was distinguished from other dimethoxy-amphetamines by chromatographic analysis
of its bromination products (Bailey et al., 1976); the dimethoxy substitution pattern was
confirmed by bromination (DeRuiter et al., 1998b). Analysis by HPLC employing fluores
camine derivatization for fluorescence detection has been reported (Shimamine, 1 984) . The
six dimethoxyamphetamines gave distinguishable GC / MS patterns (Bailey, 1972) . Frag
mentation patterns of some fifty-five phenethylamines were determined by a variety of
mass spectrometry techniques (Kolliker and Oehme, 2004) .
Homologues and Analogues --- --- ---

- -
-
MeO MeO Me - 3,5-DMA (this entry) - --·-·--
MeO MeO Me Me N Me-3 5-DMA

- , [93675-30-0]
------· -
(1)

3,5-DMA / DMAP

MeO MeO Me Me2 3,5-DNNA [ 105363-38-0 l (2,3)
MeO MeO Et -- 4C-3,5-DMPEA [129556-97-4] (4)
(1) Synthesis, infra-red spectra, NMR and GC / MS data are presented (Clark, 1984) .
(2) Synthesis and reaction with [ 1 8F] acetyl hypofluorite (Mathis et al., 1986a) .
mass spectrometry techniques (Ki:illiker and Oehme, 2004).
Biochemistry
Inhibition by 3,5-DMA of uptake of metaraminol and efflux of noradrenaline by rabbit
atria was reported (Paton, 1975) . Action on the uptake and release of serotonin by human
blood platelets was studied (Tseng and Loh, 1977), and serotonin receptor site affinity was
determined (Glennon et al., 1980a) .
Pharmacology
Studies on the oxidative deamination, and effects on cat behavior were presented (Clark
et al., 1964) . The pharmacology was evaluated for toxicity, effects on barbiturate sleeping
time, and ability to disrupt mouse behavior (Ho et al., 1970a) . Drug-induced disruption of
behavior and thermoregulation was studied in a series of tryptamines, and mono- and di
substituted amphetamines; the di-substituted amphetamines were intermediate in activity
with respect to the other two compound groups (Kuhlemeier et al., 1977) .
Rats trained to distinguish between DOM and saline in a two-lever drug discrimination
task with a series of methoxylated amphetamines, showed 2,4-DMA, 2,3,4-, 2,3,5-, 2,4,6-,
and 3,4,5-TMA to be active isomers, but 2,3-, 2,6-, and 3,5-DMA to be relatively inactive
(Glennon and Young, 1982) Rats trained with racemic amphetamine were tested with
several mono- and di-substituted amphetamines; none of the di-substituted compounds
completely generalized the amphetamine response of these animals (Glennon et al., 1985).

level responses, or whole-animal responses, and psychedelic potency in humans. Correla
tions were made between psychedelic potency and changes in substitution patterns (Shul
gin et al., 1969), the energy of the highest occupied molecular orbital of the drug (Kang
and Green, 1970), the degree of native fluorescence (Antun et al., 1971), and the stability of
molecular complexes (as determined by NMR; Sung and Parker, 1972) .
Human activity of 3,5-DMA has not been reported.
Legal Status
3,5-DMA is a positional isomer of 2,5-DMA, and is therefore a Schedule I hallucinogen
under federal drug law, and in states where isomers are included in the controlled drug
definition.
#40. DMAP
2-(Dimethylamino )-1-phenylpropan-1-one
2-Dimethylaminopropiophenone
N-Methylephedrone
Dimethylpropion

DMAP
Metamfepramone
Metamfepyramone
DMPI
MG 559
NSC 234706
UR 1430
Registry Numbers
CAS# CAS #
HCl salt [10105-90-5] R-Isomer HCl salt [ 35026-80-3]
Camphoric acid salt [115121-90-9] 5-Isomer HCl salt [35026-79-0]
Diacetyltartrate [102321-77-7] 5-Isomer dibenzoyl tartrate [35026-78-9]
2,3-Dimethoxysuccinate [108479-33-0] 5-(-)-Isomer diacetate tartrate [ 444289-41 -2]
Picrate [857982-44-6] 5-(-)-Isomer dibenzoate tartrate [121316-76-5]
N-Di-trideutero isomer [160977-87-7] 5-Isomer freebase [35026-77-8]
Perdeuterophenyl isomer [87258-67-1 ]

From 1-bromopropiophenone (with HOAc) to 1 -acetoxypropiophenone; (with K2C03 ) to
1 -hydroxypropiophenone; (with dimethylamine) to DMAP (Iwao et al., 1 954) .
Synthesis and motor stimulation in mice (van der Schoot et al., 1 962) .
Unusual decomposition occurred with GC analysis on KOH coated columns (Beckett and
Stanojcic, 1983) .

ml z: 177.1154 (100.0% ), 178.1187 (11.9%)
HCl salt m.p. 202-204 °C (Iwao et al., 1954)

a- N- Name CAS # Ref
-- -- AA [613-89-8] (1)
-- Me MAA [35534-19-1] (1,2)
-- Me2 DMAA [103030-62-2] (1,3-5)
Me Me2 DMAP (this en try)
Me Et EAP [1 8259-37-5] (1,6)
Me Etz DEAP [90-84-6] (1,7-11)
Me Pr PAP [52597-14-5] (7)
Me i-Pr i-PAP [52597-15-6] (7,12)
Me Bu BAP [52597-16-7] (7)
Me t-Bu t-BAP [ 34509-36-9] (7,12)
Me -CCCC- PPP [19134-50-0] (13)
-- --- -�----�-·

DMAP / DMCPA

Me -CCCCC- PIAP [58759-28-7] (3)
Me -CCNMeCC- PZAP [4863-51-8] (3)
(1) Anorexigenic activity in rats, and spontaneous motor activity in mice evaluated (Sanchez et al.,
1979.
(2) Also called UR 1432.
(3) Synthesis (Iwao et al., 1954).
(4) Also called NSC 129395, UR 1428.
(5) Found in Desmodium gangeticum (Ghosal and Bhattacharaya, 1972).
(6) Also called UR 1424.
(7) Correlation made between structure and locomotor activity of mice (van der Schoot et. al., 1962) .
(8) Also known as DEPI and Diethylpropion.
(9) Both EMAP and DEAP can be absorbed percutaneously (Markantonis et al., 1986b).
(10) Human metabolites were identified by mass spectrometry (Pokrafac et al., 1991).
(11) Also known as: Adiposon, Amfepramone, Amphepramone, Cegramine, Derfon, Diethpropion,
Magrene, Neobes, Nopropiophenone, Obesitx, Silutin, UR 1423.
(12) Synthesis and behavioral testing in rats as potential antidepressants (Foley and Cozzi, 2003).
(13) Metabolism and toxicology (Springer et al., 2003c).
Biochemistry
Stereoselective metabolism of DMAP demonstrated in humans (Markantonis et al., 1 986a) .
Both DMAP and DEAP (diethylaminopropiophenone) could be absorbed percutaneously
(Markantonis et al., 1 986b); reduction of the carbonyl group or the loss of a methyl group
was the primary in vitro metabolic fate of DMAP in tissue homogenates (Markantonis et
al., 1989). Human metabolites were identified by mass spectral fragmentation (Pokrafac et
al., 1991).
Pharmacology
The anorexigenic activity was determined in rats and the spontaneous motor activity in
mice (Sanchez et al., 1979) . The pharmacology of the resolved optical isomers has been
studied (Dal Cason, 1 997) . Animal studies compared the S-isomer of several active am
phetamine analogues with their �-keto counterparts (Dal Cason et al., 1997b).
DMAP evaluated in human studies for the treatment of orthostatic syndrome (Soholing,
1982).
Active in humans by insufflation, smoking, injection, or orally; extensive kiosk sales in

Israel led to its being made illegal there, effective April, 2006 (Siegel-ltzkovich, 2006). Reli
able reports of human doses for psychedelic effects are not yet available.
Legal Status
DMAP is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#41. DMCPA
2-(2,5-Dimethoxy-4-methylphenyl)cyclopropan
amine
trans-2-(2,5-Dimethoxy-4-methylphenyl)cyclo
propylamine
4-Methyl-2,5-methoxycyclopropylamine

DMCPA
Registry Numbers
CAS # CAS #
Unspecified Isomer [ 69854-49-5] R,S-trans-(-)-Isomer freebase [714903-64-7]
R,S-trans-(-)-Isomer HCl salt [67890-16-8] R,R-cis-Isomer freebase [101468-37-5]
R,S-trans-(-)-Isomer HCl salt [53581-71-8] S,R-trans-( +)-Isomer freebase [ 69980-36-5]
S,R-trans-(+)-Isomer dibenzoyl tartrate [ 69980-3 7-6] R,S-trans-(-)-Isomer freebase [ 69980-34-3]
R,S-trans -(-)-Isomer dibenzoyl tartrate [ 69980-35-4] R,S-trans-( +)-Isomer freebase [ 67890-1 7-9]
Synthesis
From 2,5-dimethoxy-4-methylbenzaldehyde (with malonic acid) to 2,5-dimethoxy-4-meth
ykinnamic acid; (with isobutene, H2S04 ) to t-butyl-2,5-dimethoxy-4-methykinnamate;
(with dimethylsulfoxonium methylide) to trans-2-(2,5-dimethoxy-4-methylphenyl)cyclo
propanecarboxylic acid; (with Et3N, Pd / C, H2) to DMCPA (Shulgin and Shulgin, 1991 ) .

m / z: 207. 1259 (100.0% ), 208.1293 (13.0% )
HCl salt 211-213 °C (Aldous et al., 1974)

HCl salt 210-211 °C (Shulgin and Shulgin, 1991) (EtOH / EtzO)
Resolution and absolute configuration determination of the optical isomers of DMCPA

was reported (Nichols et al., 1 979) .

2- 3- 4- 5- a- I �- Name CAS # Ref
-- -- Cl -- -C- CCPA [26568-25-2] (1-4)
- -
-- - Br - -C- BCPA [26568-24-1 ] (1)
-- MeO MeO -- -C- 3,4-DMCPA [61114-45-2] (5,6)
-- -OCO- -- -C- MDCPA [ 54719-10-7] (7)
MeO -- Me MeO -C- DMCPA (this entry)
Meo -- Me MeO -CMe- DMMCPA [811 77-10-8] (8)
MeO -- MeO MeO -C- TM CPA [773 790-48-0 l (1)
-- MeO MeO MeO -C- MCPA [17061 -21-1] (9-13)
(2) Synonym: SKF 6279A.
(3) Effects on serotonin concentration and MAO activity in the rat brain (Fuller and Kaiser, 1980).
(4) The effects of CCPA on rat behavior (Smith, 1978).
(5) Synonym of SKF 1 0714.
(6) Synthesis (Burger and Fitchett, 1952).
(7) Synthesis (Burger, 1960).
(8) Chemistry and pharmacology (including the optical isomers) (Jacob and Nichols, 1982).
(9) Has been referred to by the code name TMT in the literature.
(10) No evidence of oral activity in humans at 13 mg (Shulgin and Shulgin, 1991).
(11) Mescaline, MCPA, and tranylcypromine were compared with LSD as to effects on motor behav
ior in mice (Walters and Cooper, 1968) .
(12) Synthesis of the cis- and trans- isomers (Cooper, 1970).
(13) Mescaline was compared to MCPA in rat hyperactivity assays (Cooper and Walters, 1972).

DMCPA / DMeA
Biochemistry
2
The 5-HT2 binding site of DMCPA was located with [ 1 5 1]-labeled 2C-I (Johnson et al.,
1 990b).
Pharmacology
The correlation of rabbit hyperthermia and human psychedelic activity has been studied
(Aldous et al., 1974) . The optical isomers of DMCPA were compared to the corresponding
isomers of DOM in mice and cats (Nichols et al., 1978) .
A comparison of steric properties with animal and human potency of several phenethyl
amines, tryptamines, and lysergide derivatives was made (Nichols, 1986a) .
Orally active in humans at 1 5-20 mg; duration 4-8 hours (Shulgin and Shulgin, 1991 ) .
Legal Status
DMCPA is not a scheduled compound under federal drug law, or under District of Colum
#42. DMeA
1 -(3,4-Dimethylphenyl)propan-2-amine
3,4-Dimethylamphetamine
a,3,4-Trimethylphenethylamine
X ylopropamine
3,4-DMeA
Registry Numbers
CAS # CAS # CAS #
HCl salt [6009-73-0] Bisulfate [61079-92-3] Freebase [102-31-8]
HBr salt [861007-60-5] Sulfate [14543-76-1] (+)-Isomer [124866-26-8]
Bifumarate [5973-70-6] x-Sulfate [7437-51-6] (-)-Isomer [124866-27-9]

From 3,4-dimethylphenylacetone (with NHy H2, Ni) to DMeA (Schnider, 1945) .

m / z: 163.1361 (100.0%), 164. 1395 (11.9%)
Elemental Analysis: C, 80.93; H, 10.50; N, 8.58
HBr salt m.p. 132-133 °C (Schnider, 1945)

Freebase b.p. 116-118 °C / 12 mm (Schnider, 1945)
The physical properties and spectra of the six positional isomers of DMeA were report
ed (Bailey et al., 1977) . The [ 1 3 C]-NMR spectra of ring mono- and dimethylated amphet
amines were obtained and compared (Bailey and Legault, 1981 ) .

2- 3- 4- 5- 6- N- Name CAS # Ref
Me Me -- -- -- -- 2,3-DMeA [34332-74-2] (1-4)
Me -- Me - -
- -
-- 2,4-DMeA [32560-84-2] (1-6)

DMeA
2- 3- 4- 5- 6- N- Name CAS # Ref

Me -- NMe2 -- -- -- Amiflamine [55875-51-9] (7-9)
Me -- -- Me -- -- 2,5-DMeA [19064-48-3] (1-6, 1 0-15)
Me -- -- Me -- Me N-Me-2,5-DMeA -- (16)
Me -- -- Me -- Me2 N,N-Me-2,5-DMeA [ 105466-90-8] (17)
Me -- -- -- Me -- 2,6-DMeA [63223-62-1 ] (1,2)
-- Me Me -- -- -- DMeA (this entry)
-- Me -- Me -- -- 3,5-DMeA [32156-16-4] (1,2,4, 1 8)
-- Me Me -- -- Me N-Me-DMeA [105254-13-5] (19)
-
-- -CCC- -- -- - IAP [13396-94-6] (20-24)
-- -CCC- -- Me -- IMA -- (16,25)
-- -CCCC- -- -- -- TAP [3160-20-1 ] (24,26)
(1) The physical properties and spectra of the six positional isomers of DMeA were recorded (Bailey
et al., 1977).
(2) The [ 1 3 C]-NMR spectra of ring mono- and dimethylated amphetamines were obtained and com
pared (Bailey and Legault, 1981).
(3) NMR spectrum was obtained and intramolecular interactions analyzed (Bailey et al., 1971) .
(4) Urine and plasma samples were analyzed a s the pentafluorobenzamide derivatives, b y GC with
electron capture detection (Midha et al., 1979a).
(6) Correlation of a chemical structure and the phenethanolamine N-methyltransferase reactivity.
(7) Also known as: FLA-336, Astra FLA-336.
(8) This is a substrate for MAO (and stereoselectively inhibits MAO activity) in human brain region
homogenates (Fowler and Oreland, 1981).
(9) Amiflamine (an MAO inhibitor) relieves hypertension in humans following oral doses of tyra
mine in excess of more than 200 mg (Grind et al., 1986).
(10) Synthesis (Milstein, 1968).
(11) The 2,5-dimethyl- analogue, 2,5-MeA, has been studied in the mouse, dog, and humans as an
anorexic (Marsh and Herring, 1950); synthesis as for 2,5-DMA, except for the use of 2,5-dimeth
ylbenzaldehyde as the starting material.
(12) An HPLC method was developed for the isolation and quantification in urine samples (Helmlin
and Brenneisen, 1992).
(13) Orally active in humans at 50 mg, providing appetite suppression without side-effects (Hoff
mann-La Roche, 1959).
(14) The nitroalkene precursor to 2,5-MeA (1-(2,5-dimethylphenyl)-2-nitropropene) was reduced to
the phenylacetone, which was reductively aminated with dimethylamine to the N,N-dimethyl
homologue, 2,5,N,N-tetramethylamphetamine (N,N-Me-2,5-DMeA). Protected as the trifluoro
acetamide, 2,5-DMeA was the precursor of carrier-free [77Br]-labeled DOB (Coenen, 1981 ).
(15) Procedures employing HPLC and photodiode-array detection were developed to analyze plant
and urine samples for phenylalkylamine materials (Helmlin and Brenneisen, 1992) .
(16) Not in the published chemical literature.
(17) Synthesis and reaction with [ 1 8F]-acetyl hypofluorite (Mathis et al., 1986a).
(18) A correlation was made between the degree of native fluorescence and psychedelic potency in
humans (Antun et al., 1971 ).
(19) Synthesis (Schnider, 1945).
(20) Synthesis (Monte et al., 1993).
(21) IAP was first synthesized in 1993 but appeared on the Internet about ten years later. It is referred
to by the DEA as API (Tella, 2004).

DMeA / DMePEA
(22) Orally active in humans at 40-80 mg (Igor, 2006).

(23) Currently not a scheduled drug. In August 2005, the DEA Diversion Control Section asked for
information that might support placement of this chemical into Schedule I status (Tella, 2004) .
(24) Evaluated in rats for discriminative stimulus effects (Monte et al., 1993).
(25) Qualitatively "quite a negative response" (Anon., 2006).
(26) The tetramethylene homologue, TAP [3160-20-1] [152623-96-6] is known, with an HCl salt m.p.
of 216 °C (Monte et al., 1993).
Biochemistry
Correlation of chemical structure and reactivity with phenethanolamine N-methyltransfer
ase was studied (Hansch and Glave, 1972) .
Pharmacology
Animal studies performed in the mouse, dog, and in humans, evaluating anorectic activity
(Marsh and Herring, 1950). DMeA was compared with methamphetamine in its effects on
spider web building (Witt, 1 956). Studies were performed in rats on edema, pain threshold,
and anti-inflammatory action (Randall et al., 1957) . A correlation has been made between
the degree of native fluorescence and psychedelic potency in humans (Antun et al., 1971 ) .
Orally active i n humans a t 10 m g a s a n analgesic but, unlike amphetamine, not active a s an

analeptic (stimulant) (Harris, 1957) .
Legal Status
DMeA is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#43. DMePEA
2-(3,4-Dimethylphenyl)ethanamine
3,4-Dimethylphenethylamine
Registry Numbers
CAS # CAS #
Picrate [17283-15-7]

From a-xylene (with formaldehyde, HCI) to 3,4-dimethylbenzylchloride; (with sodium
cyanide) to 3,4-dimethylbenzyl cyanide; (with LAH) to DMPEA (Benington et al., 1960).

m / z: 149.1204 (100.0% ), 150.1238 (10.8%)
Elemental Analysis: C, 80.48; H, 10. 13; N, 9.39
HCl salt m.p. 222-223 °C (Benington et al., 1960) (EtOH)

2- 3- 4- 5- 6- [) - N- Name CAS # Ref
Me Me -- -- -- - -
-- 2,3-DMePEA [67685-71-6] (1)
Me -- Me -- -- -- -- 2,4-DMePEA [76935-60-9] (2)
--
Me -- -- Me -- -- 2,5-DMePEA [ 6632-32-2] (2)

DMePEA / DMMDA
2- 3- 4- 5- 6- �- N- Name CAS # Ref

Me -- -- -- Me -- -- 2,6-DMePEA [76935-78-9] (3)
-
-- Me Me -- -- - -- DMePEA (this entry)
-- Me Me -- - -
HO -- �-H0-3,4-MePEA [100131-59-7] (4)
-- Me Me -- -- HO Me �-H0-3,4,N-MePEA [40807-91-8] (4)
-
- Me -- Me -- -- -- 3,5-DMePEA [6632-31-1] (2,5)
(1) Blockage of glial cell transport of serotonin (Suddith et al., 1978).
(2) Studies on enzymatic oxidative deamination and effects on cat behavior (Clark et al., 1964).
(3) Effects on the cardiovascular system and on sedation were compared (Savala et al., 1988).
(4) Synthesis and pharmacological evaluation in cats (Benington et al., 1958a) .
(5) Synthesis (Prasad et al., 1992).
Pharmacology
DMePEA has been shown to produce a strong rage response in cats (Benington et al., 1960),
also oxidative deamination and effects on cat behavior (Clark et al., 1964) . Relationships
between serotonin levels and sexual behavior studied in the rat (Everitt and Fuxe, 1977) .
Administration to rats (i.p.) produced immediate body tremors and salivation (Schweitzer
et al., 1969).
Human activity of DMePEA has not been reported.
Legal Status
DMePEA is not a scheduled compound under federal drug law, or under District of Co
#44. DMMDA
1-(4,7-Dimethoxybenzo[ d] [ 1,3 ] dioxol-5-yl)propan-2-amine
2,5-Dimethoxy-3,4-methylenedioxyamphetamine
4,7-Dimethoxy-a-methyl-1,3-benzodioxole-5-ethanamine
Registry Numbers
CAS #
HCl salt [15183-24-1 ]
Freebase [15183-13-8]
R-Isomer freebase [67313-98-8]

2,5-Dimethoxy-3,4-methylenedioxyallylbenzene (apiole from oil of parsley) (with KOH) to
2,5-dimethoxy-3,4-methylenedioxypropenylbenzene (isoapiole); (with tetranitromethane)
to 1-(2,5-dimethoxy-3,4-methylenedioxyphenyl)-2-nitropropene; (with LAH) to DMMDA
(Shulgin and Sargent, 1967) .

m / z: 239. 1158 (100.0% ), 240.1191 (13.0% )
Elemental Analysis: C, 60.24; H, 7. 16; N, 5.85; 0, 26.75
HCI salt m.p. 165-1 75 °C (Shulgin and Shulgin, 1991) (Etp)

DMMDA

2- 3- 4- 5- 6- a- N- Name CAS # Ref
MeO -OCO- MeO -- -- -- 2C-DMMDA [33542-94-8] (1,2)
MeO -OCO- MeO -- -- Me N-Me-2C-DMMDA [ 33543-08-7] (1)
MeO -OCO- MeO -- Me -- DMMDA (this entry)
MeO -OCO- MeO -- Me Me Methyl-DMMDA -- (3)
MeO MeO -OCO- -- 2C-DMMDA-2 [33542-95-9] (1)
MeO MeO -OCO- -- Me N-Me-2C-DMMDA-2 [ 33543-09-8] (1)
MeO MeO -OCO- Me -- DMMDA-2 [15183-25-2] (4-7)
-OCO- MeO MeO -- -- -- 2C-DMMDA-3 [ 33542-96-0 l (1)
-OCO- -- MeO MeO -- Me N-Me-2C-DMMDA-3 [33543-10-1] (1)
-OCO- -- MeO MeO Me -- DMMDA-3 -- (8)
MeO -OCO- -- MeO -- -- 2C-DMMDA-4 -- (8)
MeO -OCO- -- MeO Me -- DMMDA-4 -- (8)
-OCO- MeO -- MeO -- -- 2C-DMMDA-5 -- (8)
-OCO- MeO -- MeO Me -- DMMDA-5 -- (8)
-OCO- -- MeO MeO -- -- 2C-DMMDA-6 -- (8)
-OCO- -- MeO Meo Me -- DMMDA-6 -- (8)
(1) Synthesis (Dallacker et al., 1971 ).
(2) 2C-DMMDA in the mouse causes respiratory paralysis, in the cat causes a drop in blood pressure
and heart dilation, in the frog causes irregular heartbeat and acceleration of respiratory movements;
responses are similar to those produced by mescaline (Supniewski, 1932).
(3) Also called DMMDMA; synthesis (Shulgin and Shulgin, 1991), otherwise not in chemical litera-
ture.
(4) Synthesis (Shulgin and Sargent, 1967; Dallacker, 1969)
(5) Studies on the release of serotonin and dopamine (McKenna et al., 1991).
(6) Orally active in humans at 50-80 mg (Shulgin and Sargent, 1967).
(7) Perhaps orally active in humans at - 50 mg; duration unknown (Shulgin and Shulgin, 1991).
(8) Naming convention discussed (Shulgin and Shulgin, 1991), otherwise not in the scientific litera
ture.
Biochemistry
Use of calculated energy interactions between several amphetamines and a model com
pound (3-methylindole) allowed the development of a receptor model for hallucination
(DiPaolo et al., 1978) .
Pharmacology
Human psychedelic potency is affected by changes in substitution patterns (Shulgin et al.,
1969).
Orally active in humans at 20-25 mg (Shulgin and Sargent, 1967), and at 30-75 mg; duration
6-8 hours (Shulgin and Shulgin, 1991).
Legal Status
DMMDA is not a scheduled compound under federal drug law, or under District of Co

a,N-DMMDBA
#45. a,N-DMMDBA
1-(Benzo[d] [l,3]dioxol-5-yl)-N-methylethanamine
a,N-Dimethylpiperonylamine
a,N-Dimethyl-3,4-methylenedioxybenzylamine
a,N-Dimethyl-1,3-benzodioxole-5-methanamine
MDMlEA
Registry Numbers
CAS # CAS #
Freebase [121734-65-4] (-)-Isomer [109881-35-8]
(+)-Isomer [109922-33-0]

From piperonyl methyl ketone (with methyl amine via reductive alkylation) to a,N
DMMDBA (Noggle et al., 1 989b).

m / z: 179.0946 (100.0%), 1 80.0980 (10.8%)
m.p. unknown

-- Me N-MMDBA [15205-27-3] (1)
-- Me2 N,N-DMMDBA [58995-64-5] (1)
Me -- a-Me-MDBA [121734-64-3] (2,3)
Me Me a,N-DMMDBA (this entry)
Me Me2 a,N,N-TMMDBA [112101-18-5] (3)
Me Et a-Me-N-Et-MDBA [121 734-66-5] (3)
Me Pr a-Me-N-Pr-MDBA [121 734-67-6] (3)
Me iPr a-Me-N-iPr-MDBA [121 734-68-7] (3)
Me2 -- a,a-DMMDBA [556053-68-0] (3-5)
Me2 Me a,a,N-TMMDBA -- (6)
Me2 Me2 a,a,N,N-TMMDBA -- (6)
(1) Potential impurity in MDMA (Cimeno et al., 2005).
(2) Affects on the chicken embryo and the one-day-old chicken (Bronson et al., 1994b).
(3) Synthesis and GC / MS analysis was reported (Noggle et al., 1989b).
(4) Heterocyclic acridone inhibitors of inosine monophosphate dehydrogenase for use in therapy of
IMPDH-associated disease (Chen et al., 2003).
(5) Used in preparation of acridones as inhibitors of inosine monophosphate dehydrogenase
(IMPDH), useful against psoriasis, transplant rejection, and rheumatoid arthritis.
Biochemistry
Administration of serotonin uptake inhibitors including a,N-DMMDBA and MDBP de
crease the effectiveness of MOMA in the rat brain (Hashimoto et al., 1992b), and in mice

a,N-DMMDBA I 2,3-DMPEA
(Hashimoto et al., 1993) . This compound is a weak serotonin uptake inhibitor, but not
effective in protecting rats from developing neurotoxicity from exposure to MOMA (Ha
shimoto et al., 1992b).
Pharmacology
This compound partially substituted for MOMA in MOMA-trained rats (Bronson et al.,
1994a) .
Human activity of this compound has not been reported.
Legal Status
a,N-DMMDBA is not a scheduled compound under federal drug law, or under District of
#46. 2,3-DMPEA
DMPEA-2
Registry Numbers
CAS# CAS #
HCl salt [ 3166-89-0 l Sulfate [64610-31-7]
Oxalate [669-36-3] Acid salt [87059-68-5]
Picrate [14480-1 0-5] Freebase [3213-29-4]

(with Na, Hg, ammonia) to 2,3-dimethoxypropionamide; (with NaOCl) to 2,3-DMPEA
(Buck, 1932) .
Exact Mass: 1 8 1 . 11 03
Molecular Weight: 1 81 .23
m / z: 181 . 11 03 (100.0%), 1 82.1136 (10.9%)
Picrate m.p. 1 77-1 78 °C (Spath et al., 1948)

Freebase b.p. 138 °C / 8 mm (Buck, 1932)
Synthesis, TLC and GC properties, UV spectrum, and other physical properties were re
ported (Ono et al., 1976). The [ 13 C]-NMR spectra for methoxylated phenethylamines and
amphetamines were shown to be distinctive and suitable for identification (Bailey and
Legault, 1983) . An additional synthesis was descibed (Liu and Cui, 2002). The fragmenta
tion patterns of some fifty-five phenethylamines were determined by a variety of mass
spectrometry techniques (Kolliker and Oehme, 2004).

2- 3- 13 - N- Other Name CAS # Ref
Cl Meo MeO -- -- B03M2C [24550-13-8] (1)
MeO Meo -- -- -- 2,3-DMPEA (this entry)

2,3-DMPEA I 2,4-DMPEA
2- 3- f3- N- Other Name CAS # Ref

MeO MeO -- Me -- N-Me-DMPEA-2 [3490-09-3] (2-5)
MeO MeO -- Me2 -- N,N-Me-DMPEA-2 [3494-01-7] (5,6)
EtO MeO -- -- -- 2,3-EMPEA [87790-87-2] (2)
EtO MeO -- Me -- N-Me-2,3-EMPEA [ 1 05339-86-4] (2)
EtO MeO -- Me2 -- N,N-Me-2,3-EMPEA [4981 8-52-2] (4)
(1) Analogues of B03M were studied for their hypotensive effects (Howe et al., 1966) .
(2) Pulmonary circulation effects were measured in the dog (Aviado et al., 1957).
(3) Synthesis (Buck, 1932).
(4) Synthesis (Buck et al., 1938).
(5) Effectiveness of releasing cardiac norepinephrine was measured (Daly et al., 1966).
(6) Effects on cardiac function were observed in the cat and dog (Ellis, 1965).
Biochemistry
The effects on rat brain enzymes were observed (Clark et al., 1956), and effects of ring
methoxy groups on oxidative deamination were evaluated (Clark et al., 1965).
Pharmacology
Studies reported on oxidative deamination and effects on cat behavior (Clark et al., 1 964);
several compounds were compared for their effectiveness in producing a catatonic state in
cats (Ernst, 1965a) . The effectiveness of releasing cardiac norepinephrine from the mouse
heart was measured (Daly et al., 1966).
Human activity of this compound is has not been reported.
Legal Status
2,3-DMPEA is not a scheduled compound under federal drug law, or under District of
#47. 2,4-DMPEA
2-(2,4-Dimethoxyphenyl )ethanamine
DMPEA-3
Registry Numbers
CAS# CAS #
Acid salt [87059-69-6] 4-( C[ d 3 ]0) [ 88204-73-3]
Bisulfate [64610-32-8]

From 2,4-dimethoxybenzaldehyde (with nitromethane) to 1-(2,4-dimethoxyphenyl)-2
nitroethene; (with electrolytic reduction) to 2,4-DMPEA (Kondo et al., 1928).

(with Na, Hg, ammonia) to 2,4-dimethoxypropionamide; (with NaOCl) to 2,4-DMPEA
(Buck, 1932) .

2,4-DMPEA

m/ z : 1 8 1 . 11 03 (100.0% ), 1 82.1136 (10.9%)
Freebase b.p. 140 °C / 1 mm Hg (Kondo et al., 1928)

Freebase b.p. 1 00-11 0 °C (Weinstock, 1987)
(Kappe and Armstrong, 1965). Synthesis, TLC and GC properties, UV spectra, and other
physical properties were reported (Ono et al., 1976). The [ 13C]-NMR spectra for methoxyl
ated phenethylamines and amphetamines were shown to be distinctive and suitable for
identification (Bailey and Legault, 1983). Analysis by HPLC employing fluorescamine de
rivatization for fluorescence detection reported (Shimamine, 1984) . The fragmentation pat
terns of fifty-five phenethylamines were determined by a variety of mass spectrometry
techniques (Kolliker and Oehme, 2004).

2- 4- 13 - N- Name CAS # Ref
N02 HO -- -- 2-N02-HPEA [2419-60-5] (1)
HO OH -- -- 2,4-DHPEA [2039-62-5] (2,3)
-
Meo Br -- - 4-Br-2-MPEA [139102-26-4] (4)
Meo Me -- -- 2,4-MMPEA [139102-20-8] (4)
MeO HO -- -- 2,4-MHPEA [34536-15-7] (5)
MeO HO Me -- j),2-MHPEA-3 [91252-21 -0] (6)
MeO MeO -- -- 2,4-DMPEA (this entry)
MeO MeO -- Me2 N-Me-DMPEA-3 [3600-89-3] (2,7)
-
EtO EtO - -- 2,4-DEPEA [101787-05-7] (8)
(1) Also called 2-nitrotyramine.
(3) Ultraviolet absorption spectra, and apparent acidic dissociation constants (Kappe and Armstrong,
1965).
(4) The binding at 5-HT 1 c and 5-HT2 receptor has been studied (Glennon et al., 1992) .
(5) An alkaloid found in Trichocereus peruvianus (Pardanani et al., 1977).
(6) Studies of both agonist and antagonist activity with dopamine j)-oxidase (Creveling et al., 1962).
(7) Synthesis (Buck, 1932)(8) Synthesis (Merchant and Mountwala, 1958).
Biochemistry
Studies were reported on oxidative deamination and effects on cat behavior (Clark et al.,
1964), and the effects of ring methoxy groups on oxidative deamination (Clark et al., 1965) .
Spasmolytic activity on isolated rabbit small intestine (Stolyarchuk et al., 1975) . Binding to
5-HT 1 c and 5-HT2 receptors was studied (Glennon et al., 1992) .
Human activity of 2,4-DMPEA is unknown.
Legal Status

2,6-DMPEA
#48. 2,6-DMPEA
DMPEA-5
Registry Numbers
CAS# CAS #
Acid salt [87059-71-0] Freebase [486-95-3]

From (2-acetylresorcinol) (with NH20H.HC1, and NaOH) to 2,6-dimethoxyacetophenone
oxime; (with Na, Hg) to 2,6-DMPEA (Shamshurin, 1945) .

m/ z: 181. 1103 (100.0% ), 1 82.1136 (10.9%)
HCl salt m.p. 1 82-1 83 °C (Shamshurin, 1945) (1,2-dichloroethane)

N-benzoyl salt m.p. 1 05.5-106.5 °C (Shamshurin, 1945) (petr. ether)
Oxalate m.p. 1 70-1 71 °C (Shamshurin, 1945) (EtOH)
Picrate m.p. 1 85.5-186.5 °C (Shamshurin, 1945) (MeOH)
Freebase b.p. 204-205 °C (Shamshurin, 1945)
Synthesis, TLC, and GC properties, UV spectra, and other physical properties were
reported (Ono et al., 1976) . The [ 13C] -NMR spectra for methoxylated phenethylamines and
amphetamines were shown to be distinctive and suitable for identification (Bailey and
Legault, 1983) . Analysis by HPLC employing fluorescamine derivatization for fluorescence
detection was reported (Shimamine, 1984) .

OH OH -- -- 2,6-HPEA [54942-65-3] (1)
OH MeO -- -- 2,6-HMPEA -- (2)
Meo MeO -- -- 2,6-DMPEA (this entry)
MeO MeO -- Me N-Me-2,6-DMPEA -- (2)
Meo Meo -- Me2 N,N-Me-2,6-DMPEA -- (2)
MeO Meo HO -- f3-H0-2,6-DMPEA [145412-89-1 ] (3)
MeO MeO HO Me f3-HO-N-Me-2,6-DMPEA [ 3490-1 0-6] (4)
(1) Action of norepinephrine uptake into cardiac tissue (Rotman et al., 1975).
(3) Action on the octopamine receptors in cockroach ventral nerve cords (Hirashima et al., 1992).
(4) Effects of sympathomimetic drugs on pulmonary circulation; with special reference to a new pul
monary vasodilator (Aviado et al., 1957).
Biochemistry
Action on the iris described (Marley, 1962). Oxidative deamination, effects on behavior and
general pharmacology in the cat was evaluated (Clark et al., 1964); effects of ring methoxy

2,6-DMPEA / DMPEA
groups on oxidative deamination were studied (Clark et al., 1965). Synthesis and oxidative
deamination in rabbit liver was reported (Clark et al., 1965). 2,6-DMPEA was among several
compounds compared for effectiveness in producing a catatonic state in cats (Ernst, 1965a).
Action of norepinephrine uptake into cardiac tissue studied (Rotman et al., 1975) .
Pharmacology
Studies on the generation of a hypokinetic rigid syndrome in cats (Ernst, 1965a) .
Legal Status
# 49 . DMPEA
Di-0-methyldopamine
Dopamine dimethyl ether
Homoveratrylamine
DIMPEA
3,4-DMPEA
DMPE
NSC 6328
NSC 16948
NSC 26152
NSC 113958
NSC 14471 7
Registry Numbers
CAS # CAS # CAS #
HCl salt [635-85-8] x-Sulfate [14457-28-4] a-[ 3H] HCl salt [95864-24-7]
HCl salt dihydrate [102092-07-9] Thiocyanate [ 639806-99-8] a-[ 3H] Freebase [732945-89-0]
HBr salt [54373-56-7] p-Toluenesulfonate [124154-09-2] 13-[ 3H] HCl salt [95864-22-5]
Bicarbonate [42047-49-4] Trifluroacetate [107326-31-8] 13-[ 3H] Freebase [740759-57-3]
Bioxalate [54373-57-8] Acid salt [87059-72-1] 13-[ 3H] 2 Freebase [70097-40-4]
Bisulfate [5006-63-3] Freebase [120-20-7] a-[11C] Freebase [765846-80-8]
Carbonate [63286-43-1] 13-[ d] Freebase [27167-81-3] a-[1 3C] HCI salt [157333-18-1 ]
3,5-Dinitrobenzoate [440124-92-5] a-[d2] Freebase [37699-47-1] a-[1 3C] Freebase [123283-21-6]
Methylsulfonate [99275-26-0] 13-[d2] HCI salt [85479-74-9] 13-[1 3C] Freebase [157333-16-9]
Nitrate [37852-37-2] 13-[ d2] Freebase [27160-05-0] a-[1 4C] freebase [79563-88-5]
Picrate [265323-73-7] 3-(C[d 3]0) Freebase [88204-74-4] 13-[1 4C] Freebase [55323-11-0]
x-Picrate [14456-33-8] a,13,N-[ d6] Freebase [85226-30-8] [1 3N] Freebase [111045-19-3]
Sulfate [64610-34-0]
Natural Sources
DMPEA was found in Lophophora wiliamsii (Lundstrom and Agurell, 1968a). DMPEA was
present in Trichocereus pachanoi and T. werdermannianus, and was a possible biosynthetic
precursor of mescaline in this plant (Agurell, 1969b; Lundstrom, 1970a). Other cacti report
ed to contain DMPEA include T. peruvianus (Pardanani et al., 1977), Echinocereus merkeri
(Agurell et al., 1969), Pachycereus pecten-aboriginum (Bruhn and Lindgren, 1976), Carnegiea

DMPEA
gigantea (Bruhn and Lundstrom, 1 976), Pilosocereus maxonii (Pummangura et al., 1977), and
Islaya minor, Pereskia corrugata, P. tampicana, and Pereskiopsis scardens (Doetsch et al., 1980) .
The cactus Opuntia spinosior contained DMPEA (Pardanani et al., 1978, as did several spe
cies in the Opuntia subgenus Cylindropuntia (Meyer et al., 1980) . DMPEA was present as a
major alkaloid in the cacti Opuntia acanthocarpa, 0. echinocarpa, Polaskia chende, Pterocereus
foetidus, P. gaumeri, Stenocereus beneckei, S. stellatus, and S. treleasei. It was present as a minor
alkaloid in the cacti Neoraimondia arequipensis, Opuntia exaltata and 0. ramosissima with a
concentration level (dry weight) of < 0.01 % . It was not present in the cacti Escontria chiotilla,
Melocactus maxonii, Opuntia basilaria, 0. bigelovii, and Stenocereus treleasei with a minimum
detection level (dry weight) of 0.001% (Ma et al., 1986) .
DMPEA was found i n the legume Desmodium tiliaefolium (Ghosal and Srivastava, 1973a),
and was reported to be present in Acacia rigidula (Clement et al., 1998).
DMPEA was been found in the urine of human schizophrenic patients (15 out of 19), but
it was absent in the urine of normal human subjects (Friedhoff and Van Winkle, 1962);
the use of isotopically labeled material indicated an endogenous source of DMPEA in the
urine of schizophrenic patients (Friedhoff and Van Winkle, 1 962, 1967) . Other researchers
also found it to be in the urine of schizophrenic patients, but not in normal subjects (Sen
and McGeer, 1964), and DMPEA was found in urine of schizophrenic patients more often
than in the urine of normal subjects (Takesada et al., 1963).
DMPEA, bufotenine, and N-methylepinephrine were observed in the urine of psychotic

children (Perry, 1963); DMPEA was not present in the urine of schizophrenic patients who
had controlled diets and were off of medication (Perry et al., 1964) .

From methylvanillin (with ethyl acetate) to dimethylcaffeic acid; (with H2, catalyst) to di
hydrodimethylcaffeic acid amide; (with KOBr) to DMPEA (Pictet and Finkelstein, 1909).
From 3,4-dimethoxybenzaldehyde (with MeMgl) to 3,4-dimethoxyphenylethene (with

HgO, 12) to 3,4-dimethoxyphenylacetaldehyde; (with hydroxylamine) to 3,4-dimethoxy
phenylacetaldehyde oxime; (with NaH) to DMPEA (Mannich and Jacobsohn, 1910).
From veratraldehyde (with nitromethane) to 3,4-dimethoxyphenyl-B-nitroethene; (with

electrolytic reduction) to DMPEA (Kondo and Kondo, 1928) .
From 3,4-dimethoxyhydrocinnamamide (Kindler, 1931).
From 3,4-dimethoxybenzaldehyde (with HCN) to a-cyano-3,4-dimethoxybenzylalcohol;

(with H2, catalyst) to DMPEA (Kindler et al., 1935).
From veratrol (with formaldehyde, HCl) to veratryl chloride; (with sodium cyanide) to
homoveratrylcyanide; (with Raney Ni, H2) to DMPEA (Bide and Wilkinson, 1945).
From 4-allylveratrol (with KMn04 ) to 3,4-dimethoxybenzylglycol; (with Pb(OAc4 ) to

3,4-dimethoxyphenylacetaldehyde; (with hydroxylamine) to 3,4-dimethoxybenzaldehyde
oxime; (with Na) to DMPEA (Kaufman et al., 1946) .
From 3,4-dimethoxybenzaldehyde (with nitromethane ) to 3,4-dimethoxyphenyl-B-nitro

ethene; (with 10% Pd / C, H2) to DMPEA (Wang et al., 1983) .

DMPEA
From o-dimethoxybenzene (with 2-chloroethanol) to veratryl chloride; (with sodium cya

nide) to 3,4-dimethoxyphenylacetonitrile; (with H2) to DMPEA (Viel, 1963; Zhang, 2000).
Synthesis achieved by the reduction of the 2-nitrophenylethane with Fe powder in ethanol

in the presence of ammonium chloride (Ran et al., 2000). Additional syntheses (Ho et al.,
1970a; Liu and Cui, 2002).

m / z: 181.11 03 (100.0% ), 1 82.1136 (10.9%)
HCI salt m.p. 154-155 °C (Mannich and Jacobsohn, 1910) (EtOH, acetone)
Chloroplatinate m.p. 1 73-1 74 °C (Pictet and Finkelstein, 1909)
Chloroplatinate m.p. 196 °C (Kondo and Kondo, 1928)
Picrate m.p. 165 °C (Kindle et al., 1935)
Sulfate m.p. 312-315 °C (Ho et al., 1970a)
Freebase b.p. 155 °C / 12 mm (Kindle et al., 1935)
Freebase b.p. 1 88 °C / 15 mm (Mannich and Jacobsohn, 1910)
Freebase b.p. 125-127 °C / 5 mm (Bide and Wilkinson, 1945)
A number of salts and derivatives were described for identification purposes (Jansen,
1931). Reaction with sodium and ammonia gave the 3-demethylated product, HMPEA (To
mita and Takano, 1959). Synthesis, TLC and GC chromatographic properties, UV spectra,
and other physical properties were reported (Ono et al., 1976). The [ 13 C]-NMR spectra for
methoxylated phenethylamines and amphetamines were shown to be distinctive and suit
able for identification (Bailey and Legault, 1983) . HPLC analysis employing fluorescamine
derivatization for fluorescence detection was reported by (Shimamine, 1984) . Several iso
mers and analogues were characterized by IR, GC / MS, HPLC, and NMR (Matsumoto et
al., 2004). The fragmentation patterns of some fifty-five phenethylamines were determined

3- 4- f3- N- Other Name CAS# Ref
Cl Cl -- -- -- DCPEA [21581-45-3] (1-3)
Cl Cl -- Me -- N-Me-3-Cl-MPEA [7569-59-7] (4)
Cl HO -- -- -- 3-Cl-4-HPEA [32560-53-5] (7)
N02 HO -- -- -- 3-N02-HPEA [49607-15-0] (5)
HO HO -- -- 1-C DHBA [1124-40-9] (6)
chain
HO HO -- Me -- N-Me-DHPEA [501-15-5] (4,6-8)
HO HO -- Me2 -- N,N-Me-DHPEA [21581-37-3] (9,10)
HO HO -- Me 3 -- Coryneine [7224-66-0] (11)
HO HO -- Me,iPr -- N-Me,N-iPr-DHPEA [57303-11-4] (6)
HO HO -- Et -- N-Et-DHPEA [21987-94-0] (12)
HO HO -- Bu -- N-Bu-DHPEA [13076-06-7] (4)
HO HO -- iBu -- N-iBu-DHPEA [65341-01-7] (13)

DMPEA
3- 4- 13 - N- Other Name CAS # Ref

HO HO Me -- -- 13-Me-DHPEA [66432-25-5] (14)
HO HO HO iPr -- 13 -HO-N-iPr-DHPEA [7683-59-2] (6,15, 1 6)
HO HO HO Me2 -- 13,3,4-HO-N,N-MePEA [554-99-4] (17)
HO HO HO Et -- 13,3,4-HO-N-Et-PEA [51 79-72-6] (4)
HO HO C=O -- -- DHPEA- 13k [499-61-6] (18)
HO HO C=O Me -- N-Me-DHPEA- 13 k [62-13-5] (14,19)
HO HO C=O iPr -- N-iPr-DHPEA- 13 k [13076-1 0-3] (20)
HO Meo -- -- -- HMPEA [645-33-0] (4,20-2 6)
HO MeO HO -- -- HME [32655-70-2] (4,27)
HO Meo HO Me -- N-Me-HME [29866-04-4] (4,27)
HO MeO HO Me2 -- N,N-Me-HME [ 63504-04-1 ] (27,28)
HO MeO C=O -- -- HMPEA- 13k [13061-68-5] (4)
HO Meo C=O Me -- N-Me-HMPEA- 13 k [13062-69-6] (4)
HO Meo -- Me -- N-Me-HMPEA [35266-68-3] (21)
HO MeO -- Me 3 -- Salicifoline [ 6882-07-1 ] (29-31 )
MeO HO Me -- -- 13 -Me-GEA [ 69478-40-6] (32,33)
Meo HO -- Me -- N-Me-GEA [32602-66-7] (21,34,35,36)
Meo HO -- Me a-Et N-Me-a-Et-GEA [181485-31-4] (37)
MeO HO -- Me2 -- MM-GEA [35266-63-8] (34,38,39)
Meo HO HO iPr -- 13-HO-N-iPr-GEA [1420-27-5] (4)
Meo HO C=O -- -- GEA- 13k [13062-63-0] (4)
MeO HO C=O Me -- N-Me-GEA- 13k [13062-64-1 ] (4)
MeO MeO -- -- -- DMPEA (this entry)
MeO MeO Me -- -- 13-Me-DMPEA [55174-61-3] (32)
Meo Meo HO -- -- DME [6924-15-8] (4,40-44)
MeO MeO HO Me -- N-Me-DME [5653-66-7] (39,43-49)
Meo MeO HO Me,CHO -- N-Me,CHO-DME [41688-37-3] (39,50)
Meo Meo HO Me2 -- N,N-Me-DME [19751-75-8] (39,49,51,52)
MeO MeO MeO -- -- 13,3,4-TMPEA [4722-08-1 ] (53)
MeO Meo MeO Me -- N-Me- 13,3,4-TMPEA [56120-35-5] (48,54)
MeO MeO MeO Me2 -- N,N-Me- 13,3,4-TMPEA [52910-84-6] (48,55)
MeO MeO -- Me -- N-Me-DMPEA [3490-06-0] (4,21,34,38,39,
44,48,51,56-62)
Meo Meo -- Me2 -- N,N-Me-DMPEA [3490-05-9] (4,9,44,47,58,
61,63)
Meo MeO -- Et -- N-Et-DMPEA [13078-77-8] (4)
MeO EtO HO -- -- 13 -HO-EMPEA [ 861078-09-3] (64,65)
MeO EtO -- Me2 -- N,N-Me-4,3-EMPEA [861008-09-5] (9)

DMPEA
3- 4- 13- N- Other Name CAS # Ref

MeO AllylO -- -- -- MAPEA [39201-81-5] (66)
EtO MeO -- -- -- EMPEA [86456-97-5] (1)
EtO Meo -- Me -- N-Me-EMPEA [21581-47-5] (67)
EtO MeO -- Me2 -- N,N-Me-3,4-EMPEA [861008-11-9] (9)
EtO EtO -- -- -- DEPEA [61381-04-2] (41,64,68)
-
EtO EtO HO - -- DEE [861078-07-1] (64)
EtO EtO -- Me -- N-Me-DEPEA [21581-36-2] (41,68)
EtO EtO -- Me2 -- N,N-Me-DEPEA [854908-22-8] (9)
-
AcO AcO -- Me - N-Me-DHPEA-AA [13075-96-2] (14)
AcO AcO -- Me2 -- N,N-Me-DHPEA-AA [54719-11-8] (69)
(1) Found in Corydalis cava (Spath and Dobrowsky, 1925).
(2) Produced a strong rage response in cats (Henington et al., 1960).
(3) Synthesis (Henington et al., 1960).
(4) Effectiveness of releasing cardiac norepinephrine from mouse heart (Daly et al., 1 966) .
(5) Isolated from the unripe and ripe fruit of the cactus Cereus validus (Nieto et al., 1982) .
(6) Characterization of mechanisms for hyperactivity induction from the nucleus accumbens by
phenethylamine derivatives (Costall et al., 1976).
(7) Potency as inhibitor of phenylethanolamine N-methyltransferase determined (Fuller et al., 1971).
(8) Reported present in Acacia rigidula (Clement et al., 1998).
(10) The trimethylammonium salt has been reported as being present in the stem of the legume
Alhagi pseudalhagi (Ghosal and Srivastava, 1973b).
(11) Found in Desmodium triflorum (Ghosal et al., 1973).
(12) Synthesis (Pyman, 1910).
(13) Potential anti-Parkinson compound (Ginos et al., 1978).
(14) Studies made of agonist and antagonist activity with dopamine 13-oxidase (Creveling et al., 1962).
(15) Action on the iris of the cat (Marley, 1962) .
(16) Also known as: N-isopropyl- 13 -3,4-trihydroxyphenethylamine, 3,4-dihydroxy-a-(isopro-pyl
amino)methylbenzyl alcohol, 3,4-dihydroxy- 13-hydroxy-N-isopropylphenethylamine, Aludrine,
Asiprenol, Asmalar, Assiprenol, Bellasthman, Isoproterenol, Isorenin, Isupren, Lomupren,
Respifral, ICI 46399, NSC 9975, and NSC 33791.
(17) DMPEA, bufotenine, and N-methylepinephrine found in urine of psychotic children (Perry,
1963).
(18) Found in human urine after death (Tormey et al., 1999).
(19) Synthesis (Fodor et al., 1951).
(20) GEA, DESMETHYL and 3,4-DESMETHYL found to be biosynthetic precursors of mescaline
in Lophophora williamsii, but HMPEA and 3-DESMETHYL were not. The role of dopamine as a
precursor was proposed (Rosenberg et al., 1969).
(22) Studies on the generation of a hypokinetic rigid syndrome in cats (Ernst, 1965a).
(23) The relationship between psychedelic activity and electronic configuration is established (Sny
der and Merril, 1965).
(24) Dopamine and [ 14C]-labeled S-adenosylmethionine, incubated in rat liver, formed GEA and
HMPEA, but no DMPEA (Kuehl, 1967).
(25) Synthesis (Ramirez and Burger, 1950).
(26) Discovered in the cactus Pachycereus pecten-aboriginum (Strombom and Bruhn, 1978a).
(27) Passage through the blood brain barriers of the rat was determined (Evans and Vogel, 1977).
(28) UV absorption spectra and acidic dissociation constants (Kappe and Armstrong, 1965).

DMPEA
(29) Found in Magnolia grandiflora (Nakano, 19S4), M. officialis (Cui et al., 1988), M. kobus (Tomita and
Kakano, 19S2), M. sprengeri (Chen and Wang, 1981), and M. acuminata (Kapadia and Shah, 1992).
(30) There are three natural products in the literature with the trivial name salicifoline, and they are
best recognized by a chemical class name: [A] Salicifoline (terpene), [BJ Salicifoline (lignan), and
this alkaloid, called Salicifoline.
(31 ) Salicifolia, MM-GEA and the isoquinoline magnocurarine are components of the Chinese
medicine Hou-po, from the plant Magnolia officialis (Cui et al., 1988).
(32) Discriminative stimulus properties observed in rats trained to discriminate DOM from saline
(Glennon et al., 1982c)
(33) Optical isomers described (Glennon et al., 1982c).
(34) Pilosocereus maxonii contains MM-GEA and N-Me-GEA (Pummangura et al., 1977).
(3S) MBDB, administered orally to male rats at 20 mg / kg was excreted partly unchanged, and as the
three metabolites BDB, GEA, and N-Me-GEA (Kanamori et al., 1998a) .
(36) 3-DESMETHYL and N-Me-GEA were shown by mass spectroscopy to be precursors of mescaline
in cactus (Lindgren et al., 1971).
(37) Synthesis and spectral characterization of MBDB, BDB, GEA, N-Me-a-Et-GEA (Kanamori et al.,
1999).
(38) Found in the cacti Ariocarpus agavoides and Pelecyphora aselliformis (Bruhn and Bruhn, 1973) .
(39) Found i n the cactus Coryphantha macromeris var. runyonii (Keller e t al., 1973).
(40) Threshold oral activity in humans, llS mg; duration unknown (Shulgin and Shulgin, 1991).
(41 ) Synthesis and physical properties (Kindler et al., 193S).
(42) Effect on the sensitivity of acetylcholine-reactive receptors in the peripheral vascular systems
(Matthies, 19S7) .
(43) An 0-methylated metabolite of catecholamines (Axelrod and Kopin, 1961).
(44) Evaluated as inhibitor of monoamine oxidase activity in the rat brain (Keller and Ferguson, 1977).
(4S) Observation of cataleptic activity in mice (Michaux and Yerly, 1963).
(46) Also known as Normacromerine.
(47) Found in the legume Desmodium tiliaefolium (Ghosal and Srivastava, 1973a) .
(48) Found in the cactus Coryphantha greenwoodii (Bruhn, 197S).
(49) Inhibition of synaptosomal neurotransmitter uptake by psychedelics (Whipple et al., 1983) .
(SO) Also known a s N-formylnormacromerine.
(Sl) Isolated from Coryphantha spp. (Hornemann et al., 1972) .
(S2) Also known as macromerine.
(S3) Production of experimental catatonia in cats (Noteboom, 1934).
(S4) Also known as 0-Me-normacromerine.
(SS) Also known as 0-Me-macromerine.
(S6) Isolation of hordenine and N-methyl-3,4-dimethoxy-�-phenethylamine from Ariocarpus trigonus
(Speir et al., 1970).
(S7) Present in the cactus Pelecyphora aselliformis (Neal et al., 1972).
(S8) The cactus Echinocereus merkeri contains DMPEA, N-Me-DMPEA, N,N-Me-DMPEA, Hordenine,
and GEA (Agurell et al., 1969).
(S9) In Trichcereus pachanoi, radiolabeled dopamine is 3-0-methylated to give GEA, which leads to
both DMPEA and mescaline (Lundstrom, 1970b).
(60) Also known as NSC 1 87772.
(61) Found in the cactus Ariocarpus scapharostrus (Bruhn, 197S) .
(62) Isolated from Coryphantha (Neobessya) missouriensis (Pummangura et al., 1981 ).
(63) Effect on alkaline phosphatase activity and pyruvate utilization in rat brain homogenates (Clark
et al., 19S6).
(64) Synthesis and physical properties (Kindler et al., 193S).
(6S) Threshold oral activity in humans at 4.6 mg; duration unknown (Shulgin and Shulgin, 1991).
(67) Synthesis (Ide and Buck, 1937).
(68) Pulmonary circulation effects measured in the dog (Aviado et al., 19S7).
(69) Among a number of compounds shown to stimulate behavioral changes via dopaminergic
mechanisms (Costall et al., 1974) .

DMPEA
Biochemistry
[ 1 4 C]-labeled DMPEA was used to explore the biosynthesis of mescaline in Lophophora
williamsii (Lundstrom and Agurell, 1968b); injection of a-[ 1 4 C]-3,4,5-DESMETHYL into L.
williamsii led to the biosynthesis of mescaline whereas the injection of [ 1 4 C]-DMPEA gave
a higher yield, suggesting that dopamine might be an intermediate, giving rise to DMPEA
through 0-methylation (Paul et al., 1969) . Radiolabeled dopamine was 3-0-methylated to
give GEA in Trichocereus pachanoi, which lead to both DMPEA and mescaline (Lundstrom,
1970a) .
Alpha [ 1 4 C]-labeled DMPEA, following i.p. injection into a male rat, was metabolized by
oxidative deamination to the dimethoxyphenylacetic acid (Schweitzer and Friedhoff, 1965).
Metabolism of mescaline and DMPEA were compared in eight human subjects (Friedhoff
and Hollister, 1966). The metabolism of a-[ 1 4 C]-DMPEA in rats produced 3,4-dimethoxy
phenylacetic acid (77% ) . There was also 4-demethylation (as the N-acetylamine and the
glucuronide); N-acetyl-DMPEA, and the dimethoxy and 4-demethylated phenylethanols,
were also formed (Schweitzer and Friedhoff, 1966) . Rat studies with 4-[ 1 4 C]-Me0-, and
separately, 3-[ 1 4 C]-Me0-labeled DMPEA, showed the 4-MeO group was metabolized at 1 5
times the rate o f the 3-MeO group based o n expired C02 (Sargent e t al., 1967). Dopamine
and [ 1 4 C]-labeled 5-adenosylmethionine, incubated in rat liver, formed GEA and HMPEA
but no DMPEA (Kuehl, 1967) . With [ 1 4 C]-labeled DMPEA, urine, plasma and cerebrospinal
fluid (CSF) levels were determined in humans; urine levels of the two major metabolites,
DMPAA and GEA, were also reported (Charalampous and Tansey, 1967). Metabolism of
mescaline and DMPEA were compared in humans (Charalampous, 1971 ) . The organ distri
bution and metabolic fate of nitrogen in N-[3-PEA, N-octylamine, and DMPEA was studied
in mice, utilizing [ 13N]-labeled materials (Tominaga et al., 1987) .
DMPEA effects on alkaline phosphatase activity and pyruvate utilization in rat brain ho
mogenates were described (Clark et al., 1 956) . Studies were made of both agonist and an
tagonist activity with dopamine [3-oxidase (Creveling et al., 1962) . DMPEA was not formed
by the action of 0-methyltransferase on dopamine but both monomethoxy derivatives
were products (Kuehl et al., 1964). Effects of ring methoxy groups on oxidative deamina
tion were described (Clark et al., 1965). The sensitivity of acetylcholine-reactive receptors
in peripheral vascular systems was evaluated (Matthies, 1957); DMPEA affected serotonin
turnover in rat brain and spinal cord (Anden et al., 1974) .
4-MPEA was a specific substrate for type B monoamine oxidase (MAO) i n rat brain mito
chondria, whereas DMPEA was a common substrate for both types of MAO (Suzuki et al.,
1980) . Serotonin receptor site affinity was determined (Glennon et al., 1980a) . Adrenergic
and 5-HT2 serotonergic effects on rat thoracic aorta were compared (Saez et al., 1994).
DMPEA (100 mg), but not mescaline, caused a 20% rise in arterial blood pressure in the
cat (Geesink and Jager, 1939). The dog peroneal tibialis anticus nerve muscle responded to
treatment with DMPEA (Schopp and Walsh, 1964); this compound was effective in releasing
cardiac norepinephrine from mouse hearts (Daly et al., 1966), and with i.p. injection
into rats, increased the dopamine concentration at the central grey nucleus (Barbeau et
al., 1965a, 1965b). DMPEA injections influenced catecholamine metabolism in rats and
monkeys (Barbeau et al., 1966b), and dopamine metabolism in rats and dogs (Barbeau et
al., 1967) . Histamine responses to DMPEA in mice, rats, and guinea pigs has been studied
(Lusvarghi et al., 1967), and antihistamine properties of DMPEA were examined in guinea
pigs, dogs, and rabbits (VanderWende and Johnson, 1 967) . DMPEA injection effects on
dopamine metabolism in rats and dogs were studied (Barbeau et al., 1967). DMPEA

DMPEA
evoked cortical potentials in the rat (Dear and Malcolm, 1967), and serotonin mediated the
action of mescaline, DMPEA, and DOM on plasma prolactin production in rats (Meltzer
et al., 1978). DMPEA had no effect on isolated human ceruloplasmin-catalyzed serotonin
oxidation, in vitro (Barrass and Coult, 1972) .
Pharmacology
DMPEA produced an experimental catatonia in cats (Noteboom, 1 934; Michaux and Ces
sion-Fossion, 1964). The toxicology and pharmacology of p-MPEA, m-MPEA, MDPEA,
and DMPEA were studied in mice and with excised animal organs (Epstein et al., 1932) .
Cataleptic activity was produced by DMPEA in mice (Michaux and Yerly, 1963) . Studies
were reported on the enzymatic oxidative deamination and effects on cat behavior (Clark
et al., 1964). DMPEA was studied in relationship to a compulsive gnaw syndrome in the rat
(Ernst, 1965b), and behavioral responses and pharmacology of DMPEA were studied fol
lowing i.v. injection of DMPEA into both dogs and cats (Brown et al., 1965). A hypokinetic
rigid syndrome was generated by DMPEA in cats (Ernst, 1965a) . Rabbits with brain tran
sections at various positions showed electroencephalographic arousal when DMPEA was
administered (Takeo and Himwich, 1965). Akinesia was generated following i.p. injection
of DMPEA into rats, mice, monkeys, and rabbits (Barbeau et al., 1966a) .
Chronic administration of 3,4-dimethoxyphenethylamine and mescaline influenced the

rope climbing performance of rats (Carlini et al., 1 967) . Cortical responses, manic behavior,
and catatonia were produced by 3,4-dimethoxyphenethylamine and its N-acetyl deriva
tive in cats (Bindler et al., 1968). Continuous intrastriatal injection of DMPEA in awake,
freely moving rats produced motor dysfunction similar to those produced by cholinergic
stimulation (Little and Dill, 1969). Effects of DMPEA on operant behavior of trained rats
were studied before and after pretreatment of the animals with phenelzine, an inhibitor of
monoamine oxidase (Bueno et al., 1969).
The pharmacology of DMPEA was evaluated for toxicity, effects on barbiturate sleeping
time, and ability to disrupt mouse behavior (Ho et al., 1 970a) . Mouse behavior was com
pared with the activity of the brain enzymes MAO and DOPA decarboxylase (De Ropp
and Kastl, 1970) . Pharmacological effects were followed after i.v. administration of 1 mg to
a cat (Talalaenko, 1 971 ), and mescaline, DMPEA, MDPEA, TMA, MDA, OMA, BOB, and
MOMA were compared pharmacologically in five animal species (Hardman et al., 1 973) .
Both DMPEA and TMA-2 were labeled with [ 1 4 C] a t the methoxyl groups, t o correlate be
havior with 1 4 C02 respiration as evidence of metabolism (Sargent et al., 1 976) .
O f the 21 compounds tested, only 4-Cl-PEA, 4-MPEA, DMPEA, and 4-EPEA were syn
ergistic with acute subliminal doses of p-chlorophenylalanine in inducing male-to-male
mounting behavior in sexually naive rats (Segal et al., 1977); chronic administration of
4-MPEA and DMPEA also induced this behavior. The conditioned avoidance responses of
the rat were studied for both Trichocereine and DMPEA, and related to that of mescaline
(Smythies and Sykes, 1966). Serotonin was involved in the jumping contest changes result
ing from the s.c. injection of 4-MPEA and DMPEA into rats (Hallasmoeller et al., 1973).
In rats trained with mescaline as a discriminative stimulus, DMPEA did not substitute for
the training compound (Winter, 1974). Mescaline and DMPEA were compared as facilita
tors and disruptors of shock avoidance in trained rats (Gorelick and Bridger, 1 977) .
There was substantial interest generated in the mid-1960s when the possibility that a "pink
spot" observed in the TLC analysis of schizophrenic patients' urine might be DMPEA,
and that the compound could become a biochemical marker for schizophrenia. However,

DMPEA
many people subsequently encountered conflicting results. Patients with acute rather than
chronic schizophrenia had no DMPEA in urine analyses (Faurbye and Pind, 1 964) . Twenty
two schizophrenic patients had no DMPEA in their urine, assayed by a TLC method with
a limit of detection of 1 0-15 mg / 24 hour sample (Williams et al., 1966); assays of the urine
samples of 13 psychotic children showed no DMPEA, with a detection sensitivity of 2
mg / 24 hour sample (Faurbye and Pind, 1 966) . Another chromatographic assay of 31 urine
samples from schizophrenic patients also confirmed that the "pink spot" was not DMPEA
(Boulton and Felton, 1966) .
A metabolite of chlorpromazine, still being excreted 25 days after cessation, had a color
test identical to reference DMPEA (Pind and Faurbye, 1966). The relationship between the
"pink spot" and the pharmacology of DMPEA was reviewed (Barbeau, 1967; Friedhoff and
Van Winkle, 1967; Vogel, 1967) .
Mass spectrometric analysis of chromatographic isolates, converted to the dansyl deriva

tives, supported the identification of DMPEA in the urine of two schizophrenic patients
(Creveling and Day, 1967). Using a fluorimetric analysis DMPEA was found in some (but
not all) of the Parkinson' s disease patients, and some (but not all) of the control subjects
(Rinne and Sonninen, 1967) . Free and conjugated DMPEA appeared in the urine of both
schizophrenics and normal subjects, and at comparable levels (Siegel and Tefft, 1971 ) . Over
1 00 urine samples from normal and schizophrenic subjects were analyzed by GC / MS, and
DMPEA was not detected in any of them (Narasimhachari et al., 1972) .
Using controlled diets, i t appeared that urinary DMPEA had tea a s its origin (Stabenau
et al., 1970) . No DMPEA was found in the urine of normal humans, schizophrenic pa
tients, or other psychiatric patients with detection limits of 2 µ g / g creatinine. Excretion
of DMPEA in fasting controls, schizophrenics, and normal patients showed similar urine
content for all three groups, thus DMPEA appeared to be a normal endogenous metabolite
(Knoll et al., 1978) . A control study, with parenterally administered radiolabeled DMPEA
in humans, showed 75% excreted as 3,4-dimethoxyphenylacetic acid and 20% excreted
unchanged (Hempel et al., 1982) .
Studies have attempted correlation between molecular parameters, organ-level respons

es, or whole-animal responses, and psychedelic potency in humans. Positive correlations
were made between psychedelic potency and electronic configuration (Snyder and Merril,
1 965), changes in substitution patterns (Shulgin et al., 1969), partition coefficients, steric
bulk, and in vitro activity (Nichols et al., 1977), and lower ionization potential (as measured
by photoelectron spectroscopy (Domelsmith and Houk, 1978) . Using molecular connectiv
ity analysis of ten psychedelic phenethylamines, the importance of the 2,5-positions of the
methoxy groups, and the 4-substituent was demonstrated (Glennon et al., 1979a) .
In human subjects, DMPEA shows no psychoactivity at oral doses that are active for mes
caline. This is ascribed to its relatively complete conversion to an acid by oxidative de
amination (Hollister and Friedhoff, 1966) . Acute oral administration of 550 mg produced
no psychedelic effects, nor did the consumption of 900 mg over the course of seven days
(Shulgin et al., 1966). Active oral dose is certainly greater than 1,000 mg; duration un
known (Shulgin and Shulgin, 1991)
Legal Status
DMPEA is not a scheduled compound under federal drug law, or under District of Colum

3,5-DMPEA
# 50. 3,5-DMPEA
DMPEA-6
Registry Numbers
CAS # CAS #
HCI salt [637-26-3] Acid salt [87059-73-2]
Picrate [93023-05-3] Freebase [3213-28-3]
Sulfate [64610-35-1]
Natural Sources
3,5-DMPEA was present in the cactus Pelecyphora aselliformis (Neal et al., 1972) .

From 3,5-dimethoxy benzoic acid (with thionyl chloride) to 3,5-dimethoxy benzyl chlo
ride; (with diazomethane) to 3,5-dimethoxybenzyldiazoketone; (with AgN03, ammonia)
to 3,5-dimethoxyphenylacetamide; (with LAH) to 3,5-DMPEA (Benington et al., 1958a).
Exact Mass: 181.11 03

m / z: 181.11 03 (100.0%), 1 82.1136 (10.9% )
HCl salt m.p. 156-157 °C (Benington et al., 1958a)
Synthesis, TLC and GC chromatographic properties, UV spectra, and other physical prop
erties were reported (Ono et al., 1976) . Analysis by HPLC employing fluorescamine de
rivatization for fluorescence detection was described (Shimamine, 1984) . The [ 13 C]-NMR
spectra for methoxylated phenethylamines and amphetamines were shown to be distinc
tive and suitable for identification (Bailey and Legault, 1983). The fragmentation patterns
of some fifty-five phenethylamines were determined by a variety of mass spectrometry

3- 5- J)- N- Name CAS # Ref
HO HO -- -- 3,5-HPEA [29866-11-3] (1)
HO MeO -- -- 3,5-HMPEA (2)
MeO MeO -- -- 3,5-DMPEA (this entry)
Meo Meo -- Me N-Me-3,5-DMPEA [75689-33-7] (3)
MeO MeO -- Me2 N,N-Me-3,5-DMPEA [37108-92-2] (4)
MeO MeO HO -- J)-H0-3,5-DMPEA [91252-41 -4] (5,6)
MeO MeO HO Me J)-HO-N-Me-3,5-DMPEA [582-31 -0] (7)
MeO MeO HO Me2 J)-HO-N,N-Me-3,5-DMPEA [100252-59-3] (7)
(1) Synthesis (Bailey et al., 1952).
(3) Patented as an agent to lower heart rate (Kehrbach et al., 1996) .
(4) Synthetic intermediate (Maeda et al., 1994).
(5) Action on the iris of the cat (Marley, 1962).

3,5-DMPEA / DOAM
(6) Action on the octopamine receptors in cockroach ventral nerve cords (Hirashima et al., 1992).
(7) Synthesis (Abe et al., 1956) .
This chemical is also included in the homologue list for DESOXY.
Biochemistry
Effects of ring methoxy groups on oxidative deamination were studied (Clark et al., 1 965).
Pharmacology
Pharmacological evaluations in cats were reported (Benington et al., 1958a; Clark et al.,
1964); action on the iris of the cat was reported (Marley, 1962). 3,5-DMPEA was among
several compounds compared for their effectiveness in producing a catatonic state in cats
(Ernst, 1965a), and was studied in relationship to the compulsive gnaw syndrome in the rat
(Ernst, 1965b).
Legal Status
#51. DOAM
1 -(2,5-Dimethoxy-4-pentylphenyl)propan-2-amine
4-Amy 1-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-pentylamphetamine
Registry Numbers
CAS #
HCl salt [54975-72-3]
Freebase [ 63779-90-8]
R-Isomer [64813-1 7-8]
Synthesis
From p-dimethoxybenzene (with valeric acid, polyphosphoric acid) to 2,5-dimethoxy
valerophenone; (with Zn, Hg) to 2,5-dimethoxyamylbenzene; (with N-methylformanilide
and POC13 ) to 2,5-dimethoxy-4-amylbenzaldehyde; (with nitroethane, acetic acid, and
ammonium acetate) to 1 -(4-amyl-2,5-dimethoxyphenyl)-2-nitropropene; (with LAH) to
DOAM (Shulgin and Dyer, 1 975) .

ml z : 265.2042 (100.0%), 266.2075 (1 7.4% ), 267.2109 (1 .4% )
HCI salt m.p. 145-146 °C (Shulgin and Dyer, 1975)
Biochemistry
Serotonin receptor affinities were determined in isolated rat fundus preparations, and
in rats trained to discriminate 5-MeO-DMT from saline, only partial generalization was
observed with DOAM (Glennon et al., 1 981a). A large study of psychedelic compounds
showed that the lipophilicity of the 4-position substituent was of primary importance in

DOAM / DOB
determining 5-HT2 receptor affinity (Glennon and Seggel, 1989); the affinity to 5-HT2 recep
tors was measured and compared to structurally related compounds (Seggel et al., 1990).
Pharmacology
DOAM was among DOM homologues assayed for behavioral effects in rats trained with
an avoidance paradigm; DOPR was the most active, and the t-butyl and n-amyl deriva
tives were inactive (Morin et al., 1975) . Relationships between drug-induced disruption of
behavior and thermoregulation were presented (Kuhlemeier et al., 1977) . Effects on inte
grated sensory functions and active startle in male rats were observed (Geyer et al., 1978).
DOAM only partially generalized for the training response in rats that discriminated 1 .0
mg / kg of (±)-DOM from saline (Glennon et al., 1982b).
The octanol-water partition coefficient served as predictor of human psychedelic potency

(Nichols et al., 1977). Molecular connectivity analysis gave excellent correlation to serotonin
agonist activity in a number of phenethylamines and amphetamines (Kier and Glennon,
1978a, 1978b).
Threshold oral activity in humans at 1 0 mg; duration unknown (Shulgin and Dyer, 1 975;
Legal Status
DOAM is not a scheduled compound under federal drug law, or under District of Colum
#52. DOB
1 -(4-Bromo-2,5-dimethoxyphenyl)propan-2-amine
1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane
4-Bromo-2,5-dimethoxyphenylisopropylamine
4-Bromo-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-bromoamphetamine
Brolamfetamine
BDA
4-Bromo-DMA
4-Br-DPIA
Registry Numbers
CAS # DEA# CAS #
HCl salt [29705-96-2] R-Isomer HBr salt [53581-79-6]
HBr salt [53581-53-6] 5-Isomer HBr salt [53581-80-9]
Freebase [64638-07-9] 7391 a,f3-[ 3H]-Tritiated freebase [770733-79-4]
Freebase [52432-70-9]* [77Br] Freebase [55181-90-3]
R-Isomer HCI salt [50505-92-5] R-(-)-[77Br] Isomer freebase [114167-06-5]
2
5-Isomer HCI salt [50505-93-6] [8 Br] Freebase [55181-91-4]
5-(+)-Isomer freebase [43061-16-1]
*A Chemical Abstracts oddity: In the text of abstracts, this CAS # occasionally appears immediately
following the term 4-bromo-2,5-dimethoxyamphetamine, but when entered as a synonym, the first
structure that is shown (and the first printed name) is that of the chain isomer 4-bromo-2,5-dime
thoxy-[3-methylphenethylamine.

DOB

From 2,5-dimethoxyamphetamine (with HOAc, Br2) to DOB (Shulgin et al., 1971 ) .
From 4-bromo-2,5-dimethoxybenzaldehyde (with nitroethane, acetic acid, and ammo

nium acetate) to 1 -(2,5-dimethoxy-4-bromophenyl)-2-nitropropene; (with LAH) to DOB
(Barfknecht and Nichols, 1971).
Synthesis (see general method in #54 and #58; Coutts and Malicky, 1973); product of bro
mination of 2,5-DMA (Bailey et al., 1976) .
2
Synthesis o f radiolabeled DOB with [77Br] and [8 Br] (Sargent e t al., 1975). High specific
activity tritiation (Ahern et al., 2004).

m / z : 273.0364 (100.0%), 275.0344 (97.3% ), 274.0398 (11 .9% ), 276.0377 (11 .6% )
Elemental Analysis: C, 48.19; H, 5.88; Br, 29. 15; N, 5.11; 0, 11 .67
HCl salt m.p. 207-208 °C (Shulgin et al., 1971) (IPA)

HBr salt m.p. 145-146 °C (Aldous et al., 1974) (EtOAc)
R-(-)-lsomer HCl salt m.p. 203.5-204 °C [a] � -13.7° (Nichols et al., 1973)
5-( +)-Isomer HCl salt m.p. 204-205 °C [a] � +13.7° (Nichols et al., 1973)
From the individual optical isomers of 2,5-DMA (see #36) with bromination as mentioned
in the above synthesis, the R-(-)- and the S-(+)-isomers were synthesized (Nichols et al.,
1973). Resolution of DOB into its optical isomers has also been reported (Aldous et al.,
1 974) . HPLC separation techniques for the identification of illicit drugs was described
(Cashman et al., 1973); analysis by gas chromatography was described (Canfield et al.,
1977) . Urine and plasma samples were analyzed as the pentafluorobenzamide derivatives,
by GC with electron capture detection (Midha et al., 1979a). High specific activity, carrier
free [77Br]-DOB (>8 Ci / µmole) was synthesized via the trifluoroacetamide (Coenen, 1981).
Synthesis and analysis by UV, IR, HPLC, GC / MS, and NMR was described (Shimamine et
al., 1989). DOB was among several substituted amphetamines evaluated for cross-reactiv
ity with the Roche Abuscreen® (Cody, 1990a), and the Diagnostic Products Corporation (Cody,
1990b) radioimmunoassays. GC identification was achieved using heptafluorobutyl deriv
atives (Lillsunde and Korte, 1991). Electrochemistry of TMA-2, DOB, DOM, and DON was
compared with the 4-unsubstituted 2,5-DMA (Squella et al., 1992) . An HPLC method was
developed for the isolation and quantification of this chemical in urine samples (Helmlin
and Brenneisen, 1992). Substituted amphetamine derivatives were screened by fluores
cence polarization immunoassay (Cody and Schwarzhoff, 1993). GC / MS analysis of 2C-B
and its two homologues, DOB and 4C-B, was complicated by the presence of precursor
contaminations (DeRuiter et al., 1 995) . DOB was one of the products of the bromination
of dimethoxyamphetamine, for confirmational LC / MS analysis (DeRuiter et al., 1998b).
Urine screening procedures by GC / MS were described (Battu et al., 1998), and rapid pla
nar chromatographic screening method facilitated identification (Fater et al., 1998). DOB
was distinguished from 2C-B in street tablets sold in Italy (Furnari et al., 2001). Identifica
tion and quantification by capillary zone electrophoresis (CE) was achieved (Trenerry et
al., 1 995; Esseiva et al., 1997), along with analysis of human whole blood by CE with diode
array detection (Nieddu et al., 2005). An analytical process for human urine was described,
involving electrophoresis and mass spectroscopy (Boatto et al., 2005). Analysis was de-

DOB
scribed for human urine by LC-MS-MS methods (Nordgren and Beck, 2004; Nordgren et
al., 2005), analysis of serum by extraction, derivatization with trifluoroacetic anhydride,
and GC / MS (Hidvegi et al., 2006).
History
DOB first synthesized and evaluated in humans in 1967 (Shulgin, 1967; unpublished data),
and reported in 1971 (Shulgin et al., 1971). Origin and early history of DOB reviewed (Shul
gin, 1981). DOB appeared in Australia, and had popular use (Delliou, 1980). Forensic de
scriptions of DOB in Australia (Delliou, 1983; Bowen et al., 1983; Buhrich et al., 1983; Ragan
et al., 1985). DOB first reported on the street in Germany in 1981 (Gielsdorf and Klug, 1981).
2- 3- 4- 5- 6- N- Name CAS # Ref
Br MeO MeO -- -- -- 2,3,4-DOB -- (1)
Br MeO -- Meo -- -- 2,3,5-DOB [204776-50-1 ] (2)
Br MeO -- -- MeO -- 2,3,6-DOB -- (1,3)
Br -- MeO MeO -- -- o-DOB [32156-25-5] (2-9)
-
Br -- Meo - Meo -- 2,4,6-DOB -- (1)
Meo Br MeO -- -- -- 3,2,4-DOB -- (1)
MeO Br -- MeO -- -- 3-DOB [72739-13-0] (10-13)
MeO Br -- -- MeO -- 3,2,6-DOB [60887-75-4] (2,14,15)
MeO Br -- -- MeO Me2 N,N-Me-3,2,6-DOB [105466-92-0] (16)
-- Br MeO MeO -- -- 3,4,5-DOB [32156-34-6] (1)
- -
MeO Meo Br -- - - 4,2,3-DOB -- (1)
Meo -- Br Meo -- -- DOB (this entry)
-
MeO -- Br -- MeO - 4,2,6-DOB [ 82789-71-7] (17)
- -
-- MeO Br MeO - - 4,3,5-DOB [ 64778-79-6] (6,7, 1 8-21 )
Meo -- Meo Br -- -- m-DOB [6091 7-67-1] (2-5,8,9,22-25)
MeO MeO -- Br -- -- 5,2,3-DOB -- (1)
MeO MeO -- -- Br -- 6,2,3-DOB [60887-73-2] (2,3, 14,23)
*Note that all entries in this table are Schedule I compounds (see Legal Status, this entry), with the
exception of N,N-Me-3,2,6-DOB, which is a homologue.
(2) One of the products of the bromination of dimethoxyamphetamine for LC I MS analysis (DeRuiter
et al., 1998b ).
(3) Product of bromination of DMA (Bailey et al., 1976).
(4) Studied for correlation between 5-HT2 affinity, charge complex stability, rabbit hyperthermia, and
(5) Synthesized and assayed for ability to inhibit MAOA and MAOB (Gallardo-Godoy et al., 2005).
(6) Correlation made between the degree of native fluorescence and psychedelic potency in humans
(Antun et al., 1971).
(7) Synthesis and pharmacology on conditioned avoidance response in rats (Barfknecht and Nichols,
1971 ).
(8) Synthesis described. Orally active in humans at about 100 mg, with an MDA-like action (Sepul
veda et al., 1972); a subsequent paper reported toxicity (flushing, nausea, diarrhea), anxiety, and
paranoia at 50-80 mg (Cassels and G6mez-Jeria, 1985).

DOB
(9) In a large series of methoxylated amphetamines, rabbit hyperthermia response paralleled

human potency as psychedelics (Anderson et al., 1978b).
(10) Serotonin receptor site affinity determined (Glennon et al., 1980a).
(11) Also called SL 7161 .
(12) In Chemical Abstracts the structure of 3-DOB was written out, but the reference led to DOB itself,
not 3-DOB.
(13) Rats trained to discriminate 5-MeO-DMT from saline were tested with several psychoactive
phenylisopropylamines (Glennon et al., 1981b).
(14) Urine and plasma samples were analyzed as the pentafluorobenzamide derivatives, by GC with
electron capture detection (Midha et al., 1979a).
(15) Product of bromination of 2,6-DMA (Bailey et al., 1976).
(16) Synthesis and reaction with [ 1 8F] acetyl hypofluorite (Mathis et al., 1986a). Note that this
compound is not a positional isomer, but a homologue of DOB.
(17) The two references to 2,6,4-DOB are QSAR studies, but the compound has not yet been synthe
sized (Bindal et al., 1982; Schulze-Alexandru et al., 1999).
(18) 5-HT2A and 5-HT2c are used in a study of receptor agonism (Dowd et al., 2000).
(19) The relationship between partition coefficients, steric bulk, and in vitro activity was used to
predict potency in humans (Nichols et al., 1977).
(20) The octanol-water partition coefficient may serve as a predictor of human psychedelic potency
(21) Orally active in humans at 4-1 0 mg; duration 8-12 hours (Shulgin and Shulgin, 1991).
(22) This drug has been studied in an extensive QSAR study (Clare, 1998).
(23) Product of bromination of 2,3-DMA (Bailey et al., 1976) .
(24) Behavioral properties i n trained rats were correlated with structural components (Glennon and
Young, 1982).
(25) Orally active in humans at 50-100 mg; duration 5-6 hours (Shulgin and Shulgin, 1991 ).

a- f3- N- Name CAS # Ref
Me -- -- DOB (this entry)
Me C=O -- DOB-f3k -- (1)
Me -- Ac DOB-Ac [42203-75-8] (2)
Me -- Me N-Me-DOB [155638-80-5] (3-7)
Me -- Me2 N,N-Me-DOB [107271-31-8] (8)
Me -- Pr N-Pr-DOB [99632-47-0] (3,8)
--
-
Et -- - 4C-DOB [ 69294-23-1 ] (9-13) --
(1) Orally active at 20 mg, it had an action similar to DOB but lasting just 6-8 hours (Igor, 2006); not
reported in the published scientific literature.
(3) Binding at 5-HT c and 5-HT2 receptor studied (Glennon et al., 1987a, 1992).
1
(4) Synthesis of the [ 1 1 C]-labeled compound described (Solbach et al., 1997a) .
(5) Another literature code name is MDOB (Ewald et al., 2006a).
(6) Metabolized in the rat by 0-demethylation and 0,0-bisdemethylation, and N-demethylation to
DOB (Ewald et al., 2006a).
(7) Threshold oral activity in humans 8 mg; duration "probably rather long" (Shulgin and Shulgin,
1991).
(8) Affinity to cloned human 5-HT2 A' 5-HT2w and 5-HT2c receptors was measured and compared to
structurally related compounds (Nelson et al., 1999).
(10) GC / MS analysis of 2C-B and its two homologues DOB and 4C-B is complicated by the presence
of precursor contaminations (DeRuiter et al., 1995).

DOB
(11) 4-substituted 2,5-dimethoxyphenylbutanes (including 4C-B, 4C-Cl (see #54), 4C-T (see #3), and
4C-HM (see #118)) were patented for use in geriatric patients for increasing mental alertness
without stimulant side-effects (Partyka et al., 1978).
(12) Orally active in humans at 60 mg (Armalista, 1994).
(13) A synonym for 4C-DOB is 4C-B.
Biochemistry
Metabolism in the rat leads to 0-demethylation followed by oxidative deamination to the
phenylacetone, with reduction to the corresponding alcohol. Also there is bis-0-demethyl
ation to the 2-(2-hydroxypropyl)hydroquinone (Ewald et al., 2006a) . Mutagenic activity of
DOB was not detected in Salmonella typhimurium (White et al., 1 977) . Interaction with im
idazolium chloride was noted (Makriyannis et al., 1993) . Several compounds were synthe
sized and assayed for their ability to inhibit MAOA and MAOB . Most were potent against
MAOA; none were appreciably active against MAOB (Gallardo-Godoy et al., 2005).
Studies were reported on the action of several psychedelic drugs, including the optical
isomers of DOM and DOB, on perfused vascular strips of the dorsal metatarsal vein of the
l 980a). Molecular connectivity analysis gave excellent correlation to serotonin agonist ac
dog (Cheng et al., 1974b) . Serotonin receptor binding was studied (Glennon et al., 1978,
tivity in a large number of phenethylamines and amphetamines (Kier and Glennon, 1978a,
1978b) . Serotonin binding to rat brain membranes was inhibited by DOB (De Jong et al.,
1982) . Binding of DOB at the 5-HT 1 and 5-HT2 receptors was reported (Shannon et al.,
1984) . Evidence for involvement of serotonin in the mechanism of action of psychedelic
drugs (Glennon et al., 1984b).
Tritiated DOB was used to label 5-HT2 receptors in a particulate fraction prepared from rat
frontal cortex tissue homogenates (Lyon et al., 1987) . DOB was a potent 5-HT2 agonist in
guinea pig trachea receptors (Heller and Baraban, 1987). A correlation was made between
the electron orbitals at the 4- position and serotonin receptor binding (G6mez-Jeria et al.,
1 987) . 2C-B was found to be less selective than DOB in its serotonin receptor binding speci
ficity (Glennon et al., 1988c). The 5-HT2 receptor was the preferred site of psychedelic ac
tion as its radiolabeling marker (tritiated DOB) was preferentially targeted; three controls
(appropriately radiolabeled 5-HT 1 N 5-HT 1 w and 5-HTic) were not as strongly stimulated
(Titeler et al., 1988) . Interaction with human brain 5-HT2 receptors was reported (Sadzot et
al., 1 989) . In a large study of active psychedelics, the lipophilicity of the 4-position substitu
ent was of primary importance in determining 5-HT2 receptor affinity (Glennon and Seg
gel, 1989) . DOB affinity for 5-HT2 receptors was measured and compared to structurally
related compounds (Seggel et al., 1990) . Tritiated DOB and ketanserin labeled two affinity
states of the cloned human 5-HT2 receptors (Branchek et al., 1990) . DOB stimulated the
5-HT2 system that regulates the hypothalamic-pituitary-adrenal axis (Owens et al., 1 991b);
evidence for tolerance was reported (Owens et al., 1991a). An argument was made for the
involvement of 5-HT ic in the mechanism of psychedelic action, in that the potency of DOB,
DOM, DOI, and MDA as psychedelics decreased in parallel to their potency as agonists at
this site (Sanders-Bush and Breeding, 1991). Binding at 5-HTic and 5-HT2 receptors was
reported (Glennon et al., 1992). DOB affinity to cloned human 5-HT2N 5-HT2w and 5-HT2c
receptors was measured and compared to structurally related compounds (Nelson et al.,
1 999), and binding at 5-HT2A receptors was compared to binding of several f3-carbolines
(Glennon et al., 2000). DOB was among a series of psychedelic amphetamines compared
to their phenethylamine counterparts, as agonists to 5-HT2A and 5-HT2c receptors (Acufi.a
Castillo et al., 2002).
1 00 The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

DOB
DOB inhibited synaptosomal neurotransmitter uptake (Whipple et al., 1983) . Diffuse vas
cular spasm associated with ingestion of DOB (Bowen et al., 1983) . Autoradiography of
2
[ 1 5I]-labeled DOI and LSD-I displacement with 2,5-DMA, DOB, DOI, and LSD permitted
localization of binding regions in the rat brain (McKenna and Saavedra, 1987), and the
R-isomer of DOB, labeled with [77Br], was used to label membrane-associated recognition
sites in rat brain (Wang et al., 1988; Peroutka et al., 1988a) . Binding affinities of LSD, DMT,
DOB, and DOI were compared at nine neurotransmitter binding sites in the human cortex
(Pierce and Peroutka, 1989) . With R-DOB, telemetric recordings were made of field poten
tials from frontal cortex, hippocampus, striatum, and reticular formation of freely moving
rats (Dimpfel et al., 1989) .
Functional selectivity of serotonin receptor subtypes for a series of substituted phenyliso

propylamines and phenethylamines was studied in hamster ovary cells expressing cloned
human receptors, and through behavioral tests with rats (Moya et al., 2007) .
Pharmacology
Stereoisomers of five psychedelic amphetamines contracted isolated strips of sheep um
bilical arteries, the R-(-)- being more active than the 5-( +)-isomers. There was a general
correlation between the smooth muscle contracting ability and the psychedelic potency of
the compounds (Dyer et al., 1973) . The R-(-)-isomer of DOB was more toxic than the 5-(+)
isomer in the rat, and also more active in an avoidance task test (Benington et al., 1973) .
Rabbit hyperthermia studies compared responses to DOB and its optical isomers (Aldous
et al., 1974) . Decreased frequency of rat limb flicks correlated well with the drop off in
potency of several 2,5-dimethoxy compounds: DOM, R-DOB and 2,5-DMA were the most
effective, 5-DOB and DOET were weaker, and 4C-M was almost without activity (Ruster
holz et al., 1977) . With (i.p.) administration, the R-(-)-isomer was more effective than the
5-( +)-isomer in the disruption of behavior in cats (Rusterholz et al., 1978) . Acute toxicol
ogy and gross behavioral effects were studied in rodents, dogs, and monkeys (Davis et al.,
1978), and in squirrel monkeys (McKearney, 1988) . Inhibition of food intake was studied
in the dog (Vaupel et al., 1979). Amphetamine, and to a greater extent several psychedelics
(PMA, MDA, DOM, DOB, and 4C-M) protected rats from electroshock seizure (Davis et al.,
1982) . A comparison of behavioral responses in rats of racemic, R- and 5-isomers of DOB
was reported (Glennon et al., 1982b). Effects were reported of the 5-HT2 agonist 1-NPP on
the behavior of the squirrel monkey either alone or in combination with DOB, mCPP, or
TFMPP (McKearney, 1989) .
Pharmacology and conditioned avoidance response tests in rats were reported (Barfknecht
and Nichols, 1971 ) . Rats trained to discriminate 5-MeO-DMT from saline were tested with
several psychoactive phenylisopropylamines (Glennon et al., 1981b). DOB was among
about a dozen psychedelics compared to stimulants in rats trained in a conditioned avoid
ance study (Davis and Hatoum, 1987) . DOB and LSD substituted fully for DOI in mice
using the two-lever discrimination procedure (Smith et al., 2003).
2
After (i.v.) injection of [8 Br]-labeled 4-bromo-2,5-dimethoxyphenyl-isopropylamine to hu
man subjects, there was a first-pass accumulation of radioactivity in the lungs. After re
lease from the lung, radioactivity accumulated in the liver with a peak at one hour. Radio
activity in the blood plasma and brain were maximal at two and three hours, respectively;
kinetics were also studied after oral administration (Kalbhen et al., 1974) . Demonstrating
the potential of DOB as a brain-scanning agent, i.v. and oral administration of [77Br]- and
2
[8 Br]-labeled DOB to human subjects was performed (Sargent et al., 1975) .

DOB / DOB U

level responses, or whole-animal responses, and psychedelic potency in humans. Positive
correlations were made between psychedelic potency and the degree of native fluores
cence (Antun et al., 1971), lipophilicity (measured as the octanol-water partition coeffi
cient; Barfknecht et al., 1975; Nichols et al., 1977), the rabbit hyperthermia response (An
derson et al., 1978b), ionization potentials (as measured by photoelectron spectroscopy;
Domelsmith and Houk, 1978), and the electron withdrawing or donating nature of the
4-position substituent (Neuvonen et al., 2006). A series of amphetamines were studied for
correlation between 5-HT2 affinity, charge complex stability, rabbit hyperthermia, and hu
man activity (Domelsmith et al., 1981), and a comparison of steric properties with animal
and human potency of several phenethylamines, tryptamines and lysergide derivatives
was made (Nichols, 1986a) .
A death was ascribed to DOB use (Winek et al., 1981). The autopsy of a man who died from
a fall following the consumption of DOB showed stomach contents of 37.5 µg and tissue
levels of from 0.2 to 65 ng / g, with identification and analysis by IR, MS, and NMR (Binder
et al., 1981 ) . Two men overdosed on DOB; onset of action was 15 minutes, with intense hal
lucinations and vomiting. Both were in comas for several days. One survived, the other did
not. DOB was verified by gastric and urinary GC / MS analysis (Balikova, 2005).
The effective dose of DOB varies from 1 . 6 milligrams to 2.3 milligrams (freebase; Cassels
and G6mez-Jeria, 1985) . Several people have reported on activity and duration. DOB is an
active psychedelic in humans in the 1-2 mg range; increased dose extends activity up to
24 hours (Shulgin et al., 1971 ) . Reported orally active at about 1 mg (Lemaire et al., 1985),
and at 3.5 mg (Cassels and G6mez-Jeria, 1985), at 1-3 mg; duration 18-30 hours (Shulgin
and Shulgin, 1991).
Legal Status
DOB is a Schedule I hallucinogen under federal drug law, and under District of Columbia
and all state laws except for Delaware, Kentucky, New Mexico, and Vermont.
#53. DOBU
1-( 4-Butyl-2,5-dimethoxyphenyl)propan-2-amine
4-Butyl-2,5-dimethoxyamphetamine
�co
4-Butyl-2,5-dimethoxy-a-methylphenethylamine
1-(2,5-Dimethoxy-4-n-butylphenyl)-2-aminopropane
c
Registry Numbers
CAS # N H2
HCI salt [ 54749-54-1 ]
Freebase [ 63779-89-5]
R-Isomer [64813-16-7]

From p-dimethoxybenzene (with butyric acid, polyphosphoric acid) to 2,5-dimethoxy
butyrophenone; (with Zn, Hg) to 2,5-dimethoxy-butylbenzene; (with N-methylformanilide
and POC13 ) to 2,5-dimethoxy-4-butyl-benzaldehyde; (with nitroethane, acetic acid, and
ammonium acetate) to 1-(4-butyl-2,5-dimethoxyphenyl)-2-nitropropene; (with LAH) to
DOBU (Shulgin and Dyer, 1975) .

DOB U
Exact Mass: 251 . 1 885

m / z: 251 . 1 885 (100.0% ), 252.1919 (16.2% ), 253.1952 ( 1 .2%)
Elemental Analysis: C, 71 .67; H, 1 0.02; N, 5.57; 0, 12.73
HCl salt m.p. 151-152 °C (Shulgin and Dyer 1975) (MeCN)
The three butyl isomers, DOIB, DOSB, and DOTB, are listed in #60.
Biochemistry
Serotonin agonist activity was measured in sheep umbilical preparation (Shulgin and Dyer,
1975) . Molecular connectivity analysis gave excellent correlation to serotonin agonist activ
ity in a large number of phenethylamines and amphetamines (Kier and Glennon, 1978a,
1978b). The 5-HT2 receptor was the preferred site of psychedelic action as its radiolabeling
marker (tritiated DOB) was preferentially targeted; the three controls (appropriately radio
labeled 5-HT 1 N 5-HT 1 w and 5-HTic) were not as strongly stimulated (Titeler et al., 1988) .
A large study of psychedelic compounds showed that the lipophilicity of the 4-position
substituent was of primary importance in determining 5-HT2 receptor affinity (Glennon
and Seggel, 1 989); affinity to 5-HT2 receptors was measured and compared to structurally
related compounds (Seggel et al., 1990) . Binding at 5-HTic and 5-HT2 receptors has also
been studied (Glennon et al., 1992) .
Pharmacology
Six DOM homologues were assayed for behavioral effects in trained rats; DOPR was the
most active (Morin et al., 1975) . Drug-induced disruption of behavior and thermoregula
tion was studied in a series of tryptamines, and mono- and di-substituted amphetamines;
the di-substituted amphetamines were intermediate in activity with respect to the other
two compound groups (Kuhlemeier et al., 1977) . Effects on integrated sensory functions
and active startle was studied in male rats (Geyer et al., 1978) . Six compounds were as
sayed for psychedelic activity in trained rats, as determined by disruption of discriminated
avoidance responding. Of DOET, DOPR, DOIP, DOTB, DOBU, and DOAM, DOPR was the
most potent (Morin et al., 1975) .
Serotonin receptor affinities determined i n isolated rat fundus preparations, and studied
in rats trained to discriminate 5-MeO-DMT from saline (Glennon et al., 1981a) . Behavioral
effects studied with rats trained to discriminate 1 . 0 mg / kg of (±)-DOM from saline (Glen
non et al., 1982b).
The octanol-water partition coefficient served as a predictor of human psychedelic potency

(Nichols et al., 1977) . Research evidence was presented for the involvement of serotonin in
the mechanism of the action of psychedelic drugs (Glennon et al., 1984b).
The orally active level in humans was initially reported at about 8 mg (Shulgin and Dyer,
1975), then later reported as uncertain, but greater than 3 mg; duration "very long" (Shulgin
and Shulgin, 1991).
Legal Status
DOBU is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.

DOC
#54. DOC
1 -(4-Chloro-2,5-dimethoxyphenyl)propan-2-amine
2,5-Dimethoxy-4-chloroamphetamine
Registry Numbers
CAS # CAS #
HCl salt [ 42203-77 -0 l S-Isomer HCl salt [53626-24-7]
R-Isomer HCl salt [53626-23-6] S-Isomer freebase [756418-21-0]

From 2,5-dimethoxybenzaldehyde (with ammonium acetate, nitroethane) to 1-(2,5-di
methoxyphenyl)-2-nitropropene; (with LAH) to 1-(2,5-dimethoxyphenyl)-2-aminopro
pane; (with acetic anhydride) to N-acetyl-1-(2,5-dimethoxyphenyl)-2-aminopropane; (with
HN031 NaN02) to N-acetyl-1 -(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane; (with Pd / C,
H2) to N-acetyl-1-(4-amino-2,5-dimethoxyphenyl)-2-aminopropane; (with NaN02, KCl) to
N-acetyl-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminopropane; (with NaOH, ethylene gly
col) to 1-(2,5-dimethoxy-4-chlorophenyl)-2-aminopropane (Coutts and Malicky, 1973) .
From 2,5-dimethoxyamphetamine (with HOAc, Cl2) to DOC (Shulgin and Shulgin 199 1 ) .

m / z: 229.0870 (100.0% ), 231 .0840 (32.0% ), 230.0903 (11 .9% ), 232.0874 (3.8% )
Elemental Analysis: C, 57.52; H, 7.02; Cl, 15.43; N, 6.10; 0, 13.93
HCl salt m.p. 193-194.5 °C (Coutts and Malicky, 1973) (EtOH / Etp)
HCl salt m.p. 187-188 °C (Aldous et al., 1974) (Acetone / EtOH)
S-Isomer HCl salt m.p. 198 °C [a] � + 16° (Aldous et al., 1974)
R-Isomer HCl salt m.p. 195 °C [a] � -14° (Aldous et al., 1974)
Resolution of DOC into its optical isomers was reported (Aldous et al., 1974) . Analysis of
human whole blood by capillary electrophoresis with diode array detection was described
(Nieddu et al., 2005). An analytical method for human urine involved electrophoresis and
mass spectrometry (Boatto et al., 2005).

2- 4- 5- a- N- Name CAS # Ref
-
MeO Cl MeO Me - DOC (this entry)
MeO Cl MeO Me Ac DOC-Ac [42203-74-7] (1)
MeO Cl Meo Et -- 4C-Cl [ 69294-22-0] (2-4)
(2) Studied in cat behavior (Standridge et al., 1980).
(3) Synthesis (Stanridge et al., 1980).
Biochemistry

DOC / DOCN
and Seggel, 1989) . Affinity for 5-HT2 receptors was measured and compared to structurally
related compounds (Seggel et al., 1990) . Relative binding affinity to 5-HT2A' 5-HT2w and
5-HT2c receptors was determined (Nelson et al., 1999) . Binding at 5-HT2A receptors was
compared to binding affinity of several f3-carbolines (Glennon et al., 2000) . Possible 5-HT2A
or 5-HT2c receptor antagonism was investigated (Villalobos et al., 2004) .
Pharmacology
Relationship of hyperthermia induced by DOC (and its optical isomers) to psychedelic
activity was investigated (Aldous et al., 1 974) . The electron withdrawing or donating
nature of the 4-position substituent was correlated with the human potency of the com
pound (Neuvonen et al., 2006).
DOC was identified as a new designer drug in Canada by NMR (Dawson and Neville, 1989) .
Orally active in humans at 1 . 5-3.0 mg; duration 12-24 hours (Shulgin and Shulgin, 199 1 ) .
Legal Status
DOC is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#55. DOCN
4-(2-Aminopropyl)-2,5-dimethoxybenzonitrile
4-Cyano-2,5-dimethoxyamphetamine
Registry Numbers
CAS #
HCl salt [125903-49-3]
Freebase [125903-74-4]

From DOB (with phthalic anhydride) to 1-(4-bromo-2,5-dimethoxyphenyl)-2-phthalimido
propane; (with CuCN) to 1-(4-cyano-2,5-dimethoxyphenyl)-2-phthalimidopropane; (with
hydrazine) to DOCN (Seggel et al., 1 990) .

m / z: 220.1212 (100.0% ), 221 . 1 245 (13. 1 % )
HCl salt m.p. 236-238 °C (Seggel et al., 1990) (EtOH / Etp)

MeO C02H MeO -- 2C-CA [88441-11-6] (1)
Meo CN MeO -- 2C-CN [88441-07-0] (1,2)
MeO C02H MeO Me DOCA [29907-75-3] (3-11 )
MeO C02Pr MeO Me DOCEP [ 125903-50-6] (5, 13)
MeO C02Bu MeO Me DOC EB [125903-53-9] (5)
Main Entry Compounds 1 05

DOCN / DOET

Meo COMe MeO Me DOAC [222022-54-0] (13)
Meo COEt MeO Me DOCOE [125926-1 8-3] (5)
MeO CONHPr MeO Me DOCONHP [125903-56-2] (5)
MeO CN MeO Me DOCN (this entry)
(1) Synthesis described; HCl salt m.p. 220-222 °C (Cheng and Castagnoli, 1984).
(2) The neurotoxic property of the hydroquinone counterpart studied (Cheng and Castagnoli, 1984).
(3) Synthesis from DOB (Seggel et al., 1990), or from formyl-DMA (Ho and Tansey, 1971; Matin et al.,
1974).
(4) DOCA is a major metabolite of DOM in the rabbit (Matin et al., 1974; Nagamatsu et al., 1978) and
the guinea pig (Nagamalsu et al., 1978). It is a minor metabolite of DOM (28% ) in the rat (Ho and
Tansey, 1971 ).
(5) The affinity to 5-HT2 receptors was measured and compared to structurally related compounds
(Seggel et al., 1990).
(6) Metabolite of DOM in the rat (Ho et al., 1971b).
(7) Stereochemical aspects of DOM metabolism following i.p. administration to the rabbit reported
(Matin et al., 1974).
(8) A metabolite of DOM in the guinea pig and rabbit (Nagamatsu et al., 1978).
(9) Melting points: 194-196 °C (Seggel et al., 1990), and 196-198 °C (Matin et al., 1974) .
(10) The acid DOCA, a s well a s the propyl and butyl esters and the propylamide, were assayed as
5-HT2 receptor binding compounds (Seggel et al., 1990).
(11) A study of psychedelic compounds showed that the lipophilicity of the 4- position substituent
was of primary importance in determining 5-HT2 receptor affinity (Glennon and Seggel, 1989b).
(12) Binding at 5-HT 1 c and 5-HT2 receptors studied (Glennon et al., 1992).
(13) Relative binding affinity to 5-HT2N 5-HT2w and 5-HT2c receptors determined (Nelson et al., 1999).
Biochemistry
and Seggel, 1989) . The affinity to 5-HT2 receptors was measured and compared to structur
ally related compounds (Seggel et al., 1990); affinity to cloned human 5-HT2N 5-HT281 and
5-HT2c receptors was similarly measured (Nelson et al., 1999).
Pharmacology
Relative binding affinity to 5-HT2N 5-HT281 and 5-HT2c receptors was determined. It was
found that introduction of more polar substituents at the 4-position led to lower affinity
when compared to their hydrophilic counterparts (Nelson et al., 1999) .
Human psychedelic activity of DOCN is unknown.
Legal Status
DOCN is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#56. DOET
1-(4-Ethyl-2,5-dimethoxyphenyl)propan-2-amine
2,5-Dimethoxy-4-ethy!amphetamine
1-(2,5-Dimethoxy-4-ethylphenyl)-2-aminopropane
DMEA

DOET
Registry Numbers
CAS # DEA # CAS #
HCl salt [22139-65-7] R-(-)-Isomer HCI salt [42011-76-7]
Bisulfate [22702-18-7] 5-( +)-Isomer HCl salt [50505-91-4]
x-Sulfate [30100-54-0] R-(-)-Isomer freebase [57116-37-7]
Freebase [22004-32-6] 7399 5-( +)-Isomer freebase [ 53305-83-2]

From p-dimethoxybenzene (with acetic acid, polyphosphoric acid) to 2,5-dimethoxyace
tophenone; (with Zn, Hg) to 2,5-dimethoxyethylbenzene; (with N-methylformanilide and
POC13 ) to 2,5-dimethoxy-4-ethylbenzaldehyde; (with nitroethane, acetic acid, and ammo
nium acetate) to 1-(2,5-dimethoxy-4-ethylphenyl)-2- nitropropene; (with LAH) to DOET
(Shulgin and Dyer, 1975) .
From 2,5-dimethoxyethylbenzene (with dichloromethyl methyl ether, SnC14 ) to 2,5-di

methoxy-4-ethylbenzaldehyde; (with nitroethane, acetic acid, and ammonium acetate) to
1-(2,5-dimethoxy-4-ethylphenyl)-2-nitropropene; (with Fe, HCI) to 2,5-dimethoxy-4-ethyl
phenylacetone; (with R-( + )- (or 5-(-)-) a-methylbenzylamine, Raney Ni, H2) to R,R-( + )- (or
5,5-(-)-)-N-(a-phenethyl)-2,5-dimethyl-4-ethylphenylisopropylamine; (with Pd / C, H2) to
R-(-)- (or 5-(+)-) DOET (Nichols et al., 1973) .

m / z: 223.1572 (100.0% ), 224.1606 (14. 1 % )
HCl salt m.p. 188-190 °C (Aldous et al., 1974)

HCl salt m.p. 194-195 °C (Shulgin and Dyer, 1975) (MeCN)
m.p. 226.5-227 °C [a] � -16. 1 °

Freebase m.p. 61-61.5 °C (Shulgin, 1970)
R-(-)-Isomer HCI salt (Nichols et al., 1973) (IPA / Etp)
5-( +)-Isomer HCI salt m.p. 225.5-226.5 ° C [a] � +16.0° (Nichols et al., 1973) (IPA / Etp)
The crystalline structure was determined (Kennard et al., 1974), and correlated with bio
logical activity (Horn et al., 1 975) . Synthesis, TLC and GC chromatographic properties,
UV spectra, and other physical properties were reported (Ono et al., 1976) . TLC and color
tests were defined for the identification of substituted amphetamines (O' Brien et al., 1982) .
An additional synthesis was reported (Jacob and Shulgin, 1983) . DOET was analyzed by
HPLC employing fluorescamine derivatization for fluorescence detection (Shimamine,
1 984) . Rapid forensic identification of illicit phenethylamines was described, using TLC in
six different solvent systems, and five color reactions for specific visualization (Neuninger,
1987) . The 4-position substituent was identified by NMR analysis (Dawson and Avdovich,
1987), and optical purity was demonstrated by NMR (Hatzis and Rothchild, 1987) . Syn
thesis, and analysis by UV, IR, HPLC, GC / MS, and NMR was reported (Shimamine et al.,
1989) . Among several substituted amphetamines evaluated for cross-reactivity with the
Roche Abuscreen® radioimmunoassay (Cody, 1990a), and the Diagnostic Products Corporation
radioimmunoassay for amphetamines (Cody, 1990b). GC identification was performed
with the heptafluorobutyl derivative (Lillsunde and Korte, 1991). An HPLC method was
developed for the isolation and quantification of this chemical in urine samples (Helmlin
and Brenneisen, 1992) . DOET was identified by a rapid planar chromatographic screening
method (Fater et al., 1998) . Serum was analyzed by extraction, derivatization with trifluo
roacetic anhydride, and GC / MS (Hidvegi et al., 2006).

DOET
2- 3- 4- 5- 6- Name CAS # Ref
Et MeO MeO -- -- 2,3,4-DOET -- (1)
Et MeO -- MeO -- 2,3,5-DOET -- (1)
Et MeO -- -- MeO 2,3,6-DOET -- (1)
Et -- MeO Meo -- 2,4,5-DOET [910382-26-2] (2)
-
Et -- MeO -- MeO 2,4,6-DOET - (1)
MeO Et MeO -- -- 3,2,4-DOET -- (1)
MeO Et -- MeO -- 3,2,5-DOET -- (1)
MeO Et -- -- MeO 3,2,6-DOET -- (1)
-- Et MeO MeO -- 3,4,5-DOET -- (1)
Meo Meo Et -- -- 4,2,3-DOET -- (1)
MeO -- Et MeO -- DOET (this entry)
MeO -- Et -- MeO 4,2,6-DOET -- (1)
-
- MeO Et MeO -- 4,3,5-DOET -- (1)
-
Meo - MeO Et -- 5,2,4-DOET -- (1)
-
MeO MeO -- Et -- 5,2,3-DOET - (1)
- -
MeO MeO - -- Et 6,2,3-DOET - (1)
(2) This compound is referenced by CAS # in the catalog of Rare Chemicals, GmbH; Schauenburg
erstr. 116; Kiel, 24118; Germany; http: / / www.rarechem.de. Otherwise not found in the scientific
literature.

Meo Me MeS -- 2C-5-TOM -- (1)
MeO Et MeO Me (this entry)
MeO Et MeS -- 2C-5-TOET -- (1)
MeO Et MeS Me 5-TOET [84910-93-0] (2,3)
MeS Me MeO -- 2C-2-TOM -- (1)
MeS Et MeO Me 2-TOET [779279-63-9] (2,4)
- -
MeS Et MeO - 2C-2-TOET - (1)
MeS Et MeS Me BIS-TOET -- (1)
(2) Synthesis, human pharmacology (Jacob and Shulgin, 1983).
(4) Threshold oral activity in humans at 65 mg; duration unknown (Shulgin and Shulgin, 1991).
Biochemistry
Studies were made with DOET, comparing mouse behavior and the activity of the brain
enzymes MAO and DOPA decarboxylase (De Ropp and Kastl, 1970) .

DOET
Serotonin agonist activity was measured in sheep umbilical preparations (Shulgin and
Dyer, 1975). Molecular connectivity analysis gave excellent correlation with serotonin ago
nist activity in a large number of phenethylamines and amphetamines (Kier and Glennon,
1978a, 1978b). Serotonin receptor site affinity was determined (Glennon et al., 1980a), and
DOET was shown to inhibit serotonin binding to rat brain membranes (De Jong et al.,
1982) . 5-HT 1 and 5-HT2 binding properties were studied (Shannon et al., 1984) . Evidence
for the involvement of serotonin in the mechanism of the action of psychedelic drugs was
summarized (Glennon et al., 1984b). Correlations made between the electron orbital state
at the 4-position and serotonin receptor binding (G6mez-Jeria et al., 1 987) . Actions of a
number of psychedelics on the 5-HT2 receptors in the guinea pig trachea were evaluated
(Heller and Baraban, 1987) . The 5-HT2 receptor was the preferred site of psychedelic action,
as its radiolabeling marker (tritiated DOB) was preferentially targeted; the three controls
(appropriately radiolabeled 5-HTl A' 5-HT 1 w and 5-HT 1 c receptors) were not as strongly
stimulated (Titeler et al., 1988) . Interactions at human brain 5-HT2 receptors were observed
(Sadzot et al., 1989). A large study of psychedelic compounds showed that the lipophilic
ity of the 4-position substituent was of primary importance in determining 5-HT2 receptor
affinity (Glennon and Seggel, 1989) . The affinity for 5-HT2 receptors was measured and
compared to structurally related compounds (Seggel et al., 1990). Acute behavioral effects
of psychedelics in rats were 5-HT2 receptor-mediated (Wing et al., 1990) . Binding at 5-HT 1 c
and 5-HT2 receptors was studied (Glennon et al., 1 992), and binding at 5-HT2A receptors
was compared to the affinity of several f3-carbolines (Glennon et al., 2000).
Pharmacology
DOET altered learned responses of the squirrel monkey (Uyeno, 1969), and nest-building
behavior of mice (Schneider and Chenoweth, 1 970) . The potencies of several psychedelics
were rated in prolonging the latency of initiating an escape behavior of trained rats (Uyeno,
1971 ) . Behavioral effects in rats were compared with those produced by LSD, mescaline, and
amphetamine (Buxton, 1972) . Mescaline, DOM, DOET, and DOIP induced dose-dependent
scratching response in mice, in increasing potency; DOTB was inactive (Kulkarni, 1973) .
Hyperthermia was induced in rabbits with DOET (Aldous et al., 1 974), and effects were
observed on the locomotor activity of mice and rats (Huan and Ho, 1975) . Drug-induced
disruption of behavior and thermoregulation was studied in a series of tryptamines, and
mono- and di-substituted amphetamines; the di-substituted amphetamines were inter
mediate in activity with respect to the other two compound groups (Kuhlemeier et al.,
1977) . Decreased frequency of rat limb flicks correlated well with the drop off in potency of
several 2,5-dimethoxy compounds: DOM, R-DOB, and 2,5-DMA were the most effective,
S-DOB and DOET were weaker, and 4C-M was almost without activity (Rusterholz et al.,
1977) . Effects were noted on integrated sensory functions, and active startle in male rats
(Geyer et al., 1978), and effects on general behavior of rats were studied (Geyer et al., 1979) .
A comparison of the behavioral responses of DOET was reported in rats (Glennon et al.,
1982b).
DOET was evaluated in rats that were trained to discriminate d-amphetamine from sa
line (Huang and Ho, 1974) . A comparison was made between DOM, DOET, cocaine, and
amphetamine in rats trained to recognize mescaline (Winter, 1975). Six compounds were
assayed for psychedelic activity in trained rats as determined by disruption of conditioned
avoidance responses; of DOET, DOPR, DOIP, DOTB, DOBU, and DOAM, DOPR was the
most potent (Morin et al., 1975) . DOET was positively recognized in rats trained to distin
guish DOM from saline (Silverman and Ho, 1978), and reacted positively to DOET and
mescaline (Silverman and Ho, 1980) . DOET serotonin receptor affinities were determined

DOET / DOF
in isolated rat fundus preparations; studies in rats trained to discriminate 5-MeO-DMT

from saline were also included (Glennon et al., 198lb) . The same methodology was ap
plied to several psychoactive phenylisopropylamines including R- and S-isomers of DOET
(Glennon et al.,198lb, 1982b). Discrimination studies with animals trained to discriminate
amphetamine from saline were conducted (Corrigall et al., 1992a) .
Studies have attempted correlation between molecular parameters, organ-level responses,

or whole-animal responses, and psychedelic potency in humans. Stereoisomers of five psy
chedelic amphetamines contracted isolated strips of sheep umbilical arteries; the R-(-)-iso
mers being more active than the S-( +)-isomers. There was a general correlation between the
smooth muscle contracting ability and the psychedelic potency of the compounds (Dyer et
al., 1973) . Positive correlations were made between psychedelic potency and the drug lipo
philicity (determined by octanol-water partition coefficient; Barfknecht et al., 1975; Nichols
et al., 1977), and the electron withdrawing or donating nature of the 4-position substituent
(Neuvonen et al., 2006).
DOET was patented as a CNS stimulant (Shulgin, 1969) . Ten normal human subjects were
given 1 . 5 mg DOET or 10 mg d-amphetamine in a double-blind experiment. DOET pro
duced subjective feelings of mild euphoria and enhanced self-awareness in the absence
of perceptual distortion or psychedelic changes. Those effects began 1 . 5 hours after drug
administration, peaked at 3-4 hours, and subsided by 5-6 hours. DOET did not markedly
alter pulse rate, oral temperature, or blood pressure (Snyder et al., 1969). The effects of
LSD, DOM, and DOET were compared in human subjects (Snyder et al., 1970); further hu
man studies compared DOET (at 1 .5 mg orally) with DOM (at 3 mg orally) (Snyder et al.,
1970) . Effects of different doses were evaluated in human subjects (Snyder et al., 1971 ) . In
human studies, the R-(-)-isomer was about four times as potent as the S-( +)-isomer (Snyder
et al., 1974) .
Orally active as a psychedelic in humans at 3 mg (Shulgin and Dyer, 1975), and at 2-6 mg;
Legal Status
DOET is a Schedule I hallucinogen under federal drug law (FR, 1993a) and under all state
laws except for Alabama, Alaska, California, Delaware, the District of Columbia, Kansas,
Kentucky, Louisiana, Maine, Maryland, Michigan, Minnesota, Montana, New Jersey, New
Mexico, Oklahoma, Rhode Island, South Carolina, Vermont, and Washington.
#57. DOF
1-( 4-Fluoro-2,5-dimethoxyphenyl)propan-2-amine
2,5-Dimethoxy-4-fluoroamphetamine
1-(2,5-Dimethoxy-4-fluoropheny I )-2-aminopropane
Registry Numbers
CAS #
Freebase [125903-69-7]
(+)-Isomer HCI salt [ 82830-43-1 ]
(+)-Isomer freebase [ 697731-15-4]

From 2-fluorophenol (with persulfate) to fluorohydroquinone; (with methyl sulfate) to
2,5-dimethoxyfluorobenzene; (with dichloromethyl methyl ether, SnC14) to 2,5-dimethoxy-

DOF / DOI
4-fluorobenzaldehyde; (with nitroethane, acetic acid, and ammonium acetate) to 1-(2,5-di

methoxy-4-fluorophenyl)-2-nitropropene; (with LAH) to DOF (Glennon et al., 1982a) .

m / z: 213.1165 (100.0% ), 214.1199 (11 .9%)
Elemental Analysis: C, 61 .95; H, 7.56; F, 8.91; N, 6.57; 0, 15.01
HCl salt m.p. 166-167 °C (Glennon et al., 1982a) (Etp / EtOAc/ EtOH)
Biochemistry
A large study of psychedelic compounds showed the lipophilicity of the 4-position sub
stituent was of primary importance in determining 5-HT2 receptor affinity (Glennon and
Seggel, 1989) . Affinity for 5-HT2 receptors (Seggel et al., 1990), 5-HT 1, and 5-HT2 receptors
(Shannon et al., 1984), and for cloned human 5-HTzN 5-HT281 and 5-HTzc receptors (Nelson
et al., 1999) was measured and compared to structurally related compounds.
Pharmacology
A comparison of the serotonin receptor affinity and the behavioral properties of DOF was
reported (Glennon et al., 1982a); further research provided evidence for the involvement
of serotonin in the mechanism of the action of psychedelic drugs (Glennon et al., 1984b).
Animal studies suggest that DOF is of high potency, only four to six times less potent than
DOB and DOI. No human trials have been reported (Shulgin and Shulgin, 1991).
Legal Status
DOF is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#58. DOI
1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-amine
2,5-Dimethoxy-4-iodoamphetamine
1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane
Registry Numbers
CAS # CAS #
2
HCl salt [ 42203-78-1 ] [ 1 3I]-Isomer freebase [65756-99-2]
2
HBr salt [188576-64-9] [ 1 5 I]-Isomer freebase [111381-00-1]
Freebase [ 64584-34-5] [ 3 1 I]-Isomer freebase
1 [65756-98-1 ]
2
S-Isomer HCl salt [ 99665-05-1 ] [ 1 3I], R-Isomer freebase [122419-39-0]
2
R,R-Tartrate salt [99632-42-5] [ 1 3I], S-Isomer freebase [122419-40-3]
2
R-(-)-Isomer freebase [ 82864-06-0 l [ 1 5 I], R-Isomer freebase [122167-34-4]
1 25
S-( +)-Isomer freebase [ 99665-04-0 l [ I], S-Isomer freebase [122167-35-5]
2
[ 1 5 I] HCl salt [111381-06-7] a,j3-[d2] HCl salt [64584-31-2]
2
[ 1 3I] HCl salt [72299-69-5]

From 2,5-dimethoxybenzaldehyde (with ammonium acetate, nitroethane) to 1-(2,5-di
methoxyphenyl)-2-nitropropene; (with LAH) to 1-(2,5-dimethoxyphenyl)-2-aminopro
pane; (with Ac20) to N-acetyl-1-(2,5-dimethoxyphenyl)-2-aminopropane; (with HN031
NaN02) to N-acetyl-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane; (with Pd / C, H2)

DOI
to N-acetyl-1-(4-amino-2,5-dimethoxyphenyl)-2-aminopropane; (with NaN02, KI) to N

acetyl-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane; (with NaOH, ethylene glycol) to
1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (Coutts and Malicky, 1973).
From 1-(2,5-dimethoxyphenyl)-2-aminopropane (with phthalic anhydride) to N-[2-(2-5-

dimethoxyphenyl)-1-methylethyl]phthalimide; (with ICl) to N-[2-(2-5-dimethoxy-4-iodo
phenyl)-1-methylethyl]phthalimide; (with hydrazine) to DOI (Braun et al., 1977) . This pa
per also describes synthesis with [ 131 I]-labeled ICl to yield the radiolabeled isomer; [ 131 I]
DOI with a-deuterium and a, f3-dideutero substitution was also described.
From 2,5-DMA (with acetic anhydride) to N-acetyl-2,5-dimethoxyamphetamine; (with io

dine, silver trifluoroacetate) to N-acetyl-2,5-dimethoxy-4-iodoamphetamine; (with NaOH)
to DOI (Glennon et al., 1982a) .
From 2,5-DMA (with I2, Ag2SO) to DOI (Sy, 1993) .

2
Syntheses of radiolabeled [ 131 I]-DOI (Braun et al. 1977), [ 1 3I]-DOI (Braun et al., 1978b),
22 2
[ 1 I]-DOI (Sargent et al., 1984a), and [ 1 5 I]-DOI (Johnson et al., 1990b) were described.
2 2
Syntheses of high specific activity of R- and S-DOI, with both [ 1 5I] and [ 1 3I], also reported
(Mathis et al., 1988) .
Exact Mass: 321 .0226

Molecular Weight: 321 . 1 6
m / z: 321 .0226 (100.0%), 322.0259 (11 .9% )
Elemental Analysis: C, 41. 14; H, 5.02; I, 39.52; N, 4.36; 0, 9.96
HCl salt m.p. 199.5-201 °C (Coutts and Malicky, 1973)

HCl salt m.p. 200.5-201.5 °C (Braun et al., 1977) (EtOH / Etp)
R-(-) Isomer HCl salt m.p. 218-219 °C [a] � -12.0°

HCl salt m.p. 196 °C (Glennon et al., 1982b) (EtOH / Etp)
(Glennon et al., 1982b)
S-( +) Isomer HCl salt m.p. 232 °C (Mathis, 1988)
DOI was used as a chemical intermediate in the synthesis of DOTFM ( #63) (Nichols et al.,
1994) . Analysis was described for human urine by LC-MS-MS (Nordgren and Beck, 2004;
Nordgren et al., 2005), and combined electrophoresis and mass spectroscopy (Boatto et al.,
2005). Human whole blood analyzed by capillary electrophoresis with diode array detec
tion (Nieddu et al., 2005).

4- a- N- Name CAS # Ref
I -- 2-MeOBz INBMeO [919797-19-6] (1,2)
I -- 2,3-MDOBz INBMDO [919797-25-4] (1)
I Me -- DOI (this entry)
I Me Ac DOI-Ac [82830-50-0] (3)
I Me Me 2,5-IDNA [ 844888-63-7] (4)
I Me [ 1 1 C]Me 2,5- 11 CIDNA [844888-61-5] (5)
I Me M_:L __ _ r---·-
2,5-IDNNA [ 85563-10-6]
-- -----
(6)
-
I Me [ 11 C]Me,Me -� �-··--
2,5- 1 1CIDNN A [844888-62-6]
,_____
__ �--�------·
(7)
--�

DOI
-
a-
-�� ----
4- N- Name CAS # Ref
1 221 Me 1 22
2,5- IDNNA [ 85563-11-7] (8)
!----�-�
1 3 11 Me Me 2,5- 1 3 1 IDNA [90064-53-2] (9)

1 31 J Me NH2 2,5- 1 3 1 lNAA [90064-59-8] (9)
1 3 11 Me HO 2,5- 1 3 1 lNHA [ 90064-60-1] (9)
1 31 J Me CH2CN 2,5- 1 3 1 lNCNMA [90064-61-2] (9)
1 3 11 Me MeOEt 2,5- 1 3 1 lNMeOEtA [90064-67-8] (9)
1 3 11 Me CCCNMe2 2,5- 1 3 1 IDMAPA [90064-62-3] (9)
1 3 11 Me iPr 2,5- 1 3 1 lNiPrA [90064-54-3] (9)
1 3 11 Me CH2cP 2,5- 1 31 INCPMA [90064-55-4] (9)
1 31 1 Me He 2,5- 1 3 1 INHeA [ 90064-56-5] (9)
rn 1 Me Do 2,5- 1 3 1lNDoA [90064-57-6] (9)
1 3 11 Me Me2 2,5- 1 31 IDNNA [90064-52-1 ] (9,10)
1 3 11 Me Me,iPr 2,5- 1 3 1 IDMNiPrNMeA [90064-64-5] (9)
1 3 11 Me Et2 2,5- 1 3 1 lNNEA [ 90064-63-4] (9)
1 3 11 Me He,Me 2,5- 1 3 1 lNHeNMeA [90083-1 8-4] (9)
l Et -- 4C-l [ 64584-33-4] (9-12)
(1) One of a new class of extremely potent N-benzyl serotonin receptor agonists, examined with an
h5-HT2A receptor homology module (Braden et al., 2006).
(2) Synthesis, as a high specific activity tritium-labelled isomer (Nichols et al., 2008).
(4) Synthesis (Schmaljohann et al., 2004).
(5) Radiosynthesis and in vitro evaluation of 2,5- 11 CIDNA for PET (Schmaljohann et al., 2004).
(6) Threshold oral activity in humans, 2.6 mg; duration unknown (Shulgin and Shulgin, 1991).
(7) In vitro labeling of serotonin receptors for PET scanning (Schmaljohann et al., 2004).
22
(8) [ 1 1] -labeled material used to study brain uptake and plasma flow in dogs, employing PET
scanning (Sargent et al., 1983).
(9) Synthesis, organ distribution in the rat, and brain absorbtion and blood clearance in the dog
were measured (Sargent et al., 1984b ).
(10) The body distribution of [ 1 3 11] -labeled 4C-l determined in the rat and dog (Braun et al., 1977).
(11) Studied in cat behavior (Standridge et al., 1980).
(13) Synthesis of [ 1 3 11] -labeled 4C-l (Braun et al., 1977).
Biochemistry
DOI has been intensively studied for its specific actions at serotonin receptors, however,
there has been much less research into its metabolic fate and general biochemistry. DOI, at
0.5-2 mg / kg s.c. increased brain tryptophan levels in the rat (Chaouloff et al., 1992), and it
increased plasma glucose levels in the rat without changing insulin levels (Chaouloff et al.,
1990; Baudrie and Chaouloff, 1992). DOI effects on plasma glucose and glucagon levels of
rats were also studied (Sugimoto and Yamada, 2000). DOI altered the expression of cyclo
oxygenase-2 in the rat parietal cortex (Mackowiak et al., 2002), and increased cortical ex
tracellular glutamate levels in rats (Scruggs et al., 2003). Several compounds were synthe
sized and assayed for their ability to inhibit MAOA and MAOB. Most were potent against

DOI
The R-isomer of DOI was more potent than the racemate in binding to the 5-HT2 receptor
prepared from rat cortex (Shannon et al., 1984) . Evidence was presented for the involve
ment of serotonin in the mechanism of the action of psychedelic drugs (Glennon et al.,
1 984b). DOI was found active on the 5-HT2 receptors in rats (Glennon, 1986a). The rat
5-HT2 receptor was the preferred site of psychedelic action, as its radiolabeling marker
(tritiated DOB) was preferentially targeted; the three controls (appropriately radiolabeled
5-HT 1 N 5-HT 1 B' and 5-HT 1 c) were not as strongly stimulated (Titeler et al., 1988). A series
of arylpiperazines was examined for structure-function relationships at the human plate
let serotonin receptor activated by DOI (Britt et al., 1988) . DOI was referred to as a mixed
agonist / antagonist at postjunctional 5-HT2 receptors in the pithed rat (Dabire et al., 1989b).
Chronic treatment with DOI downregulated 5-HT2 receptors in rat brain (McKenna et al.,
1989b), and induced changes in human platelet shape that reflected 5-HT2 agonism (Mc
Clue et al., 1989) . A large study of psychedelic compounds showed that the lipophilicity
of the 4-position substituent was of primary importance in determining 5-HT2 receptor
affinity (Glennon and Seggel, 1989) . DOI was shown to interact with isolated human brain
5-HT2 receptors (Sadzot et al., 1989) .
The serotonin-related mechanisms for cardiovascular activation of respiration were stud

ied by the separate activation of the three major agonists: PAT for 5-HT 1 N TFMPP for
5-HT 1 B' and DOI for 5-HT2 (King and Holtman, 1990) . A comparison was also made of the
effects of these agonists (in this case: PAT for 5-HT 1 N mCPP for 5-HT 1 B' and DOI for 5-HT2)
on preweanling rat pups (Frambes et al., 1990). Effects of DOI and PAT were compared
with those of the 5-HT2 antagonist ritanserin in rats implanted for chronic sleep recordings
(Monti et al., 1990), and PAT and DOI effects were compared, on monosynaptic transmis
sion in spinalized rats (Hasegawa and Ono, 1996) . 5-HT2 binding sites of R-DOI and 5-DOI
2 2
were located with [ 1 5 I]-labeled 2C-I (Johnson et al., 1990b). [ 1 5 I]-labeled DOI was an ef
fective marker of 5-HT2 receptors in the rat brain (Appel et al., 1990). Evidence in the rat
showed that DOI increased renin secretion and blood pressure through both central and
peripheral 5-HT2 receptors (Rittenhouse et al., 1991).
The affinity for 5-HT2 receptors was measured and compared to structurally related com
pounds (Seggel et al., 1990), and affinity to cloned human 5-HT2N 5-HT2B' and 5-HT2c
receptors was measured, and also compared to related structures (Nelson et al., 1999). The
receptor agonist mechanisms underlying the cardiovascular effects of central and periph
eral administration of DOI were studied in conscious rats (Dedeoglu and Fisher, 1991). An
argument is made for the involvement of 5-HT 1 c in the mechanism of psychedelic action,
in that the potency of DOB, DOM, DOI, and MDA as psychedelics decreases parallel to
their potency as agonists for this receptor (Sanders-Bush and Breeding, 1991). Binding at
5-HT 1 c and 5-HT2 receptors was studied (Glennon et al., 1992) . Neuroendocrine responses
to DOI were differentially modified by three 5-HT 1 A agonists (Li et al., 1992) .
Behavioral and biochemical evidence was given, indicating that glucocorticoids are not
involved in DOI-elicited 5-HT2 receptor down-regulation (Chaouloff et al., 1993). LSD and
DOI were potent partial agonists at 5-HTzA receptors on interneurons in rat piriform cortex
(Marek and Aghajanian, 1996) . Mechanisms of tolerance development to DOI in rats in
cluded down-regulation of the 5-HT2A receptor, but not 5-HT2c (Smith et al., 1999). Binding
at rat 5-HT2A receptors was compared to binding affinity of several f3-carbolines (Glennon
et al., 2000). Blockade of DOI-induced corticosterone secretion in rats by diverse antide
pressant agents reflected antagonist properties at 5-HT2A receptors (Rivet et al., 2001 ), and
a series of psychedelic amphetamines were compared to their phenethylamine counter-

DOI
parts, as agonists to 5-HT2A and 5-HT2c receptors (Acuna-Castillo et al., 2002). DOI activity
implicated 5-HT2A subtype receptors in the four-plate test-retest paradigm in mice (Ripoll
et al., 2006). Functional selectivity of serotonin receptor subtypes for a series of substituted
phenylisopropylamines and phenethylamines was studied in hamster ovary cells express
ing cloned human receptors, and through behavioral tests with rats (Moya et al., 2007) .
The distribution of [ 131 I]-labeled DOI in the rat was studied (Sargent et al., 1984b), and us
ing the same labeled material, brain and lung uptake were especially noted (Braun et al.,
2
1977) . Locations of binding sites in the rat brain were identified with (±)-[ 1 5 I]-DOI (McK
enna et al., 1987; Johnson et al., 1987b; Glennon et al., 1988b). DOI produced an increase
in spontaneous sympathetic nerve discharge recorded from the inferior cardiac nerve in
2
chloralose anesthetized cats (McCall and Harris, 1988) . Binding in the rat brain of [ 1 5 I]
labeled DOI and LSD-I was studied by displacement with 2,5-DMA, DOB, DOI, and LSD
2
(McKenna and Saavedra, 1987) . The localization of high-specific activity R- and S-[ 1 5 I]
2
DOI was compared with that of [ 1 5 I]-labeled LSD (McKenna et al., 1989a) . DOI (1-100 µ g /
kg, i.v.) induced a n increase i n mean blood pressure i n the anaesthetized rats (Dabire et
2
al., 1989a) . Binding sites for the R- and 5- isomers of [ 1 5 I]-DOI were identified in the rat
brain (Nazarali et al., 1989) . Effects were noted of DOI on medial prefrontal cortical cells
(Ashby et al., 1989). Binding affinities of LSD, DMT, DOB, and DOI were compared at nine
neurotransmitter binding sites in human cortex (Pierce and Peroutka, 1989). Radioligand
2
binding characteristics of [ 1 5I] -R-(-)-DOI and [ 3H]-ketanserin were compared in rat and
bovine cortical membranes (McKenna and Peroutka, 1989).
With R-DOI, telemetric recordings were made of field potentials from frontal cortex, hip
pocampus, striatum, and reticular formations of freely moving rats (Dimpfel et al., 1989).
2
Human platelet binding sites for [ 1 5I]-R-(-)-DOI were quantified (Himeno and Saavedra,
1990) . DOI' s effects on arterial pressure, heart rate, renal blood flow, and plasma renin
activity were determined in conscious rats (Alper, 1990a) . In male rats with indwelling
arterial and venous catheters, DOI (500 µg / kg, i.v.) increased plasma corticosterone levels
six- to seven-fold (Alper, 1990b). Systemic i.v. administration of DOI to a rat inhibited dor
sal raphe neuronal firing (Wright et al., 1990), and increased plasma glucose levels in the
rat without changing insulin levels (Chaouloff et al., 1990; Baudrie and Chaouloff, 1992) .
DOI ' s effects on plasma glucose and glucagon levels of rats were studied (Sugimoto and
Yamada, 2000).
Administration of DOI (i.v.) to anesthetized cats increased sympathetic activity recorded

from the inferior cardiac nerve (Clement and McCall, 1990) . Intrarenal infusions of DOI
at a rate of 5 µ g / min in anesthetized dogs resulted in increased renal blood flow (Shoji et
al., 1990) . DOI depressed end-plate current amplitude, in an in vitro assay utilizing sciatic
nerve-sartorius muscle preparations from frogs (Rana pipiens; Bhattacharyya et al., 1991);
DOI effects on nerve conduction in the isolated frog sciatic nerve trunk were also examined
(Martin et al., 1991). Studies were conducted of effects of repeated DOI treatment on the
autoregulatory control of cortical serotonin release and dorsal raphe nucleus neuronal fir
ing in the rat (Kidd et al., 1991).
DOI and 5-HO-AMT (5-hydroxy-a-methyltryptamine), both 5-HT2 agonists, acted on phos

phatidylinositol metabolism in the rat fronto-cingulate and entorhinal cortex (Edwards et
al., 1992) . Their contractile activities in certain smooth muscle preparations (Cohen et al.,
1993), and their vascular and cardiac effects were mediated by different serotonin recep
tors in the pithed rat ( Chaouche-Teyara et al., 1993), and systemic and regional effects were

DOI
noted in the anaesthetized rat (Chaouche-Teyara et al., 1994) . DOI caused differential sym
patho-excitation in nerves supplying the heart in anesthetized cats (Ramage et al., 1 993),
and restored extensor excitability in the acute spinal cat (Miller et al., 1996).
DOI effects were observed on skeletal muscle specimens from malignant hyperthermia
susceptible patients (Wappler et al., 1996). Isoteolin, a putative serotonin antagonist, inhib
its mCPP but not DOI- and PAT-induced increase of serum prolactin levels (Zhelyazkova
Savova and Negrev, 2000). DOI induced activation of the cortex, and was dependent on
5-HT2A heteroceptors on thalamocortical glutamatergic neurons (Scruggs et al., 2000). DOI
attenuated clozapine-induced cortical dopamine release (Ichikawa et al., 2001). Prolactin
responses to DOI were noted, in rats maintained on a low tryptophan diet (Franklin and
Cowen, 2001). 5-HT2A receptor stimulation by DOI potentiated amphetamine-induced do
pamine release in rat medial prefrontal cortex and nucleus accumbens (Kuroki et al., 2003).
Chronic stress created long-lasting effects on DOI-induced hyperthermia in male rats (Ma
tuszewich and Yamamoto, 2003). DOI was effective in lowering intraocular pressure in
monkey (May et al., 2003).
A reproducible, simple, small-scale method for detecting uptake and release of mono
amines (dopamine, serotonin, and norepinephrine), using rat brain synaptosomes was de
veloped (Nagai et al., 2007).
Pharmacology
Drug-induced disruption of behavior and thermoregulation was studied in a series of
tryptamines, and mono- and di-substituted amphetamines; the di-substituted amphet
amines were intermediate in activity with respect to the other two compound groups
(Kuhlemeier et al., 1977) .
DOI-induced head-twitching was inhibited by PAT (Arnt and Hyttel, 1989) . Mice were
injected once daily for 13 days with (±)-DOI and the induced head-twitch response was
observed (Darmani et al., 1990a) . DOI-induced head-twitch response in supersensitive
mice was used as a tool for studying the mechanism of the action of cocaine (Darmani,
1993), and anti-AIDS agents (Dursun et al., 1993). R-(-)-DOI was over six times more po
tent than S-( +)-DOI in inducing the ear-scratch response in mice (Darmani et al., 1990b).
In naive rats, DOI induced dose-dependent shaking behavior, the novel behavior "skin
jerks" (paraspinal muscle contractions), and forepaw tapping of the serotonin syndrome
(Pranzatelli, 1990). In pigs, DOI at 0.8 mg / kg induced psychotic behavior, i.e.: grimac
ing, backwards locomotion, blank staring, and muscular syndromes known as malignant
hyperthermia in both pigs and humans. Studies were also conducted with DOI, LSD, and
5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine), which each produced a malignant hy
perthermia syndrome in pigs, that included muscular rigidity and temperature elevation;
the condition could be blocked with 5-HT2 antagonists ketanserin or ritanserin (Loscher et
al., 1990) . Administration of DOI to rats produced dose-related decreases in food intake in
a food-deprivation paradigm (Aulakh et al., 1992) . Behavioral effects of DOI in the rat were
evaluated with the elevated plus-maze test (Onaivi et al., 1995), and a comparison of the
effectiveness of several antipsychotic drugs was made, employing the behavioral effects in
rats produced by DOI (Wettstein et al., 1999) .
A comparison was made of serotonin receptor affinity and behavioral properties of (±)
DOI and R-DOI (Glennon et al., 1982a, 1982b). Anorexic action exerted by DOI in rats was
blocked by 5-HT2 antagonists (Schechter and Simansky, 1988), and acute behavioral effects

DOI / DOIP
of psychedelics were found to be mediated by 5-HT2 responses in rats (Wing et al., 1990) .
A variety of 5-HT2 antagonists blocked the inhibition of male rat copulatory behavior in
duced by DOI (Watson and Gorzalka, 1991). Acute immobilization stress reduced (±)-DOI
induced, 5-HT2-mediated head shakes in rats (Yamada et al., 1993). Testosterone and DOI
influenced male sexual behavior of rats (Padoin and Lucion, 1995), and DOI effected fe
male rat sexual behavior (Rossler et al., 2006).
DOI disrupted prepulse inhibition of startle in the rat; this was mediated by 5-HT2A and
not by 5-HT2c receptors (Sipes and Geyer, 1995) . Lack of cross-tolerance for DOI-induced
hypophagia in the rat versus mCPP suggested separate mediation by 5-HT2A and 5-HT2c
receptors, respectively (Aulakh et al., 1995) . DOI- and mCPP-induced hypophagia in rats
was influenced by adrenodemedullation and adrenalectomy (Yamada et al., 1996).
DOB and LSD substituted fully for DOI in mice using the two-lever discrimination pro
cedure (Smith et al., 2003). The electron withdrawing or donating nature of the 4-position
substituent was correlated with the human potency of the compound (Neuvonen et al.,
2006).
Orally active in humans at 1 .5-3.0 mg; duration 16-30 hours (Shulgin and Shulgin, 199 1 ) .
Legal Status
DOI is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#59. DOIP
1-(4-Isopropyl-2,5-dimethoxyphenyl)propan-2-amine
2,5-Dimethoxy-4-isopropylamphetamine
1-(2,5-Dimethoxy-4-isopropylphenyl)-2-aminopropane
Registry Numbers
CAS #
HCl salt [53581-56-9]
Freebase [42306-96-7]

From 2,5-dimethoxyacetophenone (with MeMgI followed by dilute H2S04 ) to 2-(2,5-dime
thoxyphenyl)propene; (with H2, Pd / C) to 2,5-dimethoxyisopropylbenzene; (with N-meth
ylformanilide and POC13 ) to 2,5-dimethoxy-4-isopropylbenzaldehyde; (with nitroethane,
acetic acid, and ammonium acetate) to 1-(2,5-dimethoxy-4-isopropylphenyl)-2-nitropro
pene; (with LAH) to DOIP (Shulgin and Shulgin, 1991).

m / z: 237.1 729 (100.0% ), 238.1762 (15.1%), 239.1796 (1.1%)
HCI salt m.p. 183-184 °C (Aldous et al., 1974) (EtOH / acetone)

HCl salt m.p. 182-183 °C (Morin et al., 1975)
HCl salt m.p. 1 83-184 °C (Shulgin and Shulgin, 1991)

DOIP / DOM
Biochemistry
Drug-induced disruption of behavior and thermoregulation studied in a series of trypt
amines, and mono- and di-substituted amphetamines; the di-substituted amphetamines
were intermediate in activity with respect to the other two compound groups (Kuhlemeier
et al., 1977) .
and Seggel, 1989). The affinity to 5-HT2 receptors was measured and compared to structur
ally related compounds (Seggel et al., 1990) .
Pharmacology
Mescaline, DOM, DOET, and DOIP induced a dose-dependent scratching response in
mice, in increasing potency; DOTB was inactive (Kulkarni, 1973). Rabbit hyperthermia
studies were conducted with DOIP (Aldous et al., 1974). Six compounds were assayed for
psychedelic activity in trained rats, as determined by disruption of discriminated avoid
ance responding. Of DOET, DOPR, DOIP, DOTB, DOBU, and DOAM, DOPR was most
potent (Morin et al., 1975) .
DOIP is less potent than DOPR; i t was reported t o have threshold oral activity i n humans
at 20-30 mg (Anon., 1983; Shulgin and Shulgin, 1991).
Legal Status
DOIP is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#60. DOM
1 -(2,5-Dimethoxy-4-methylphenyl)propan-2-amine
2,5-Dimethoxy-4-methylamphetamine
DMMTA*
a-Me-2C-D
STP
*This code is also used for ALEPH (see #3)
Registry Numbers
CAS # DEA# CAS #
HCI salt [15589-00-1 ] 4-C[d 3] HCI salt [61552-35-0]
Acetate [22702-23-4] 4-C[d 3] Freebase [736876-81 -6]
Freebase [15588-95-1 ] 7395 (C[d3 ]0)2 HCI salt [60124-80-3]
R-(-)-Isomer HCI salt [ 50505-88-9] (C[d 3 ]0)2 Freebase [60124-87-0]
S-( +)-Isomer HCI salt [ 50505-89-0 l (C[d3 ]0)2, R-Isomer freebase [ 59262-02-5]
R-(-)-Isomer freebase [43061-13-8] (C[d3 ]0)2, S-Isomer freebase [ 59262-03-6]
S-( +)-Isomer freebase [43061-14-9] f:l,f:l-[ 3Hlz Freebase [343323-59-1 ]
a, f:\-[d2]-R-Isomer HCI salt [59262-04-7] f:l, f:1 -[ 3H]-a-C[ 3H] 3 Freebase [70097-37-9]
a,f:l-[d2]-S-Isomer HCI salt [ 58262-05-8] f:l-[ 1 4C] Freebase [53197-60-7]
a, f:\-[d2]-R-Isomer freebase [754921-26-1]
a, f:\-[ d2]-S-Isomer freebase [ 61471-46-3]

From 2,5-dimethoxy-4-methylbenzaldehyde (with nitroethane, acetic acid, and ammo
nium acetate) to 1-(2,5-dimethoxy-4-methylphenyl)-2-nitropropene; (with LAH) to DOM
(Shulgin, 1970) .

DOM
From m-cresol (with hexamine) to 2-hydroxy-4-methylphenol; (with the J. Renz reaction)

to 2,5-dihydroxy-4-methylbenzaldehyde; (with MezS04 ) to 2,5-dimethoxy-4-methylbenz
aldehyde; (to DOM, as described above) (Ono et al., 1973b).
From 2,5-dimethoxy-4-methylphenyl acetone (with R-( +)- (or 5-(-)-) a-methylbenzylamine,

Raney Ni, Hz) to R,R-(+)- (or 5,5-(-)-) N-(a-phenethyl)-2,5-dimethoxy-4-methylphenyliso
propylamine; (with Pd / C, Hz) to R-(-)- (or 5-(+)-) DOM (Nichols et al., 1973).
From racemic DOM (with N-benzyloxycarbonyl-L- (or D-) phenylalanine p-nitrophenyl

ester) to the corresponding amides, purification by recrystallization; (with hydrogenation,
phenylisothiocyanate) to R-(-)- (or 5-(+)-) DOM (Aldous et_al., 1974) .
Racemic DOM has been resolved into its optical isomers with the use of the salts formed
with (+) or (-) o-nitrotartranilic acid (Matin et al., 1974) .

m / z: 209.1416 (100.0% ), 210.1449 (13.0% )
HCl salt m.p. 1 89-189.5 °C (Shulgin, 1970) (IPA / Etp)

HCl salt m.p. 188-190 °C (Shulgin and Dyer, 1975) (IPA / Etp)
HCI salt m.p. 187-1 88 °C (Shulgin and Shulgin, 1991)
Sulfate m.p. 131 °C (Klug, 1971)
204-205 °C [a] � -1 7.2°

Freebase m.p. 60.5-61 °C (Shulgin, 1970)
R-(-)-Isomer HCI salt m.p. (Nichols et al., 1973)
5-( +)-Isomer HCl salt m.p. 204-205 °C [a] � +l 7.2° (Nichols et al., 1973)
The first published paper addressing the chemistry of DOM was a report on TLC and GC
identification of the compound (Genest and Hughes, 1968), although this was prior to
the first publication of its synthesis. Mass spectral and NMR analyses of DOM were re
ported (Phillips and Mesley, 1969) . Identification of picogram levels was possible, by GC /
MS analysis of the isothiocyanate derivatives (Brandenberger and Schnyder, 1 972) . Mass
spectra of DOM (Cornell and Fenselau, 1971), and GC / MS analysis of DOM quickly fol
lowed (Frigerio et al., 1972) .
Thin-layer electrophoretic behavior was described (Cavallaro and Elli, 1972), along with
quantitative colorimetric urine screening methods (Rutter, 1972), color tests (Fitzgerald
and Walaszek, 1973), TLC (Bussey and Backer, 1974), HPLC (Chan et al., 1974), quantitative
TLC analysis (Niwaguchi and Inoue, 1976), and analysis by GC (Canfield et al., 1977) .
Synthesis, TLC and Gas chromatographic properties , UV spectra, and other physical
properties were reported (Ono et al., 1976). GC / MS techniques for detecting drugs of
abuse in physiological fluids were described (Foltz, 1978) . Optical isomers of DOM were
detected in plasma by HPLC (Goto et al., 1979) . The conformation of the aryl methoxy
groups of several psychedelics was established by [ 13C]-NMR spectral analysis (Knittel and
Makriyannis, 1981). TLC and color tests were defined for the identification of substituted
amphetamines (O'Brien et al., 1982) . DOM enantiomers were resolved with LC and four
chiral reagents (Miller et al., 1984). HPLC employing fluorescamine derivatization for
fluorescence detection was reported (Shimamine, 1984) . Rapid forensic identification of
illicit phenethylamines was described, using TLC in six different solvent systems, and
five color reactions for specific visualization (Neuninger, 1987) . Synthesis and analysis by
UV, IR, HPLC, GC / MS, and NMR was reported (Shimamine et al., 1989). HPLC methods

DOM
were developed for isolation and quantification in urine samples (Helmlin and Brenneisen,
1992) . Electrochemical comparisons of TMA-2, DOB, DOM, and DON were made with
the 4-unsubstituted 2,5-DMA (Squella et al., 1992) . Identification and quantification by
capillary zone electrophoresis (Esseiva et al., 1997), and rapid planar chromatographic
screening methods were described (Fater et al., 1998) . Urine screening procedures by GC /
MS were reported (Battu et al., 1998) .
Sensitive and specific radioimmunoassays for DOM in body fluids were developed (Rice
berg et al., 1974; Nagamatsu et al., 1977). Cross-reactivity of several substituted amphet
amines was evaluated with the Roche Abuscreen® (Cody 1990a), and the Diagnostic Products
Corporation (Cody, 1990b) radioimmunoassays for amphetamines. Fluorescence polariza
tion immunoassay was used to screen substituted amphetamine derivatives (Cody and
Schwarzhoff, 1993).
A sensitive method for determining levels of R-(-)-DOM in brain tissue utilized d-amphet
amine as an internal standard for GC / MS (Eckler et al., 2001). Human whole blood ana
lyzed by capillary electrophoresis with diode array detection (Nieddu et al., 2005), human
urine analyzed with methods involving combined electrophoresis and mass spectroscopy
(Boatto et al., 2005).
History
A short history of DOM (STP) notes that the original synthesis took place in 1963, psycho
logical effects were discovered the following year, and that the compound had appeared
in the Haight-Ashbury scene of mid-1967 (Shulgin, 1977b). The known congeners of DOM
were reviewed for structure-activity relationships (Barfknecht et al., 1978) .
Positional Isomers*
2- 3- 4- 5- 6- Name CAS # Ref
MeO Meo Me -- -- 4-Me-2,3-DOM -- (1)
- -
MeO MeO -- Me - 5-Me-2,3-DOM - (1)
MeO MeO -- -- Me 6-Me-2,3-DOM -- (1)
Meo Me MeO -- -- 3-Me-2,4-DOM [25068-97-7] (2-4)
MeO -- Meo Me -- m-DOM [79440-50-9] (5-8)
MeO -- MeO -- Me 6-Me-2,4-DOM [84294-84-8] (7)
MeO Me -- Meo -- 3-DOM [72739-11-8] (9, 10)
-
MeO -- Me MeO - DOM (this entry)
Meo Me -- -- MeO 3-Me-2,6-DOM -- (1)
-
Meo -- Me - Meo 'ljJ-DOM [ 80888-36-4] (9, 11-14)
Me MeO MeO -- -- 2-Me-3,4-DOM -- (1)
-
-- Meo MeO Me -- 5-Me-3,4-DOM - (1)
Me MeO -- MeO -- 2-Me-3,5-DOM -- (1)
-- Meo Me MeO -- 4-Me-3,5-DOM -- (1)
Me MeO -- -- MeO 2-Me-3,6-DOM -- (1)
-
Me - MeO MeO -- o-DOM [ 56966-33-7] (5,6)

DOM

(2) Also called 3-Me-DOM.
(4) Disruption on conditioned responses in rats, and potentiated the phenobarbital sleeping time in
mice (Ho et al., 1970a).
(5) A series of amphetamines were studied for correlation between 5-HT2 affinity, charge complex
stability, rabbit hyperthermia, and human activity (Domelsmith et al., 1981).
(6) In a large number of methoxylated amphetamines, rabbit hyperthermia paralleled human po
tency as psychedelics (Anderson, 1978b).
(7) Behavioral properties in trained rats correlated with structural components (Glennon and
Young, 1982).
(8) LC resolution with four chiral reagents (Miller et al., 1984).
(9) Rats trained to discriminate 5-MeO-DMT from saline were tested with several psychoactive
(12) This compound has the code names 1jl-DOM and Z-7.
(13) Synthesis (Shulgin, 1970).
(14) The potency of several polysubstituted phenethylamine psychedelics was changed by the relo
cation of just one substituent (Chambers et al., 2002) .
Homologues
2- 4- 5- a- 13 - Name CAS # Ref
HO Me HO Me -- 2,5-DES-Me-DOM [52336-29-5] (1,2)
HO Me MeO Me -- 2-DES-Me-DOM [52336-49-9] (3,4)
MeO Me HO Me -- 5-DES-Me-DOM [788100-96-9] (4-7)
-
MeO Me MeO Me - DOM (this entry)
Meo Me Meo Me -- homo-DOM [38910-34-8] (8)
MeO Me MeO Me Me 13 -Me-DOM [53581-76-3] (9)
MeO Me MeO Me Me2 13, 13-Me-DOM [53582-16-4] (9)
MeO Me MeO Me2 -- a-Me-DOM -- (10-12)
MeO Me MeO Me2 Me a, 13 -Me-DOM -- (13)
MeO Me MeO Me2 Me2 a, 13, 13-Me-DOM -- (13)
Meo Me EtO Me -- IRIS [952016-59-0] (14)
-
MeO iBu MeO -- -- 2C-IB - (15,16)
-
MeO iBu MeO Me - DOIB [89556-64-9] (17-20)
MeO sBu MeO Me -- DOSB [89556-69-4] (17,18,20-22)
MeO tBu MeO Me -- DOTB [53581-57-0] (19,20,23-31)
MeO c6 MeO Me -- DOHE [125903-45-9] (14,25,26,30-33)
MeO C7 MeO Me -- DOHP -- (13)
-
MeO Cs MeO Me - DOOC [125903-46-0] (14,25,30,33)
MeO C9 MeO Me -- DONO -- (13)
EtO Me MeO Me -- FLORENCE [22702-19-8] (13,14,31,32)
EtO Me EtO Me -- DOM-2,5-DIEtO [22702-15-4] (31,32)
BuO He BuO Me -- BHB [22702-21-2] (31,32)

DOM
(1) Metabolite of DOM (Jacob et al., 1979).

(2) Auto-oxidation at pH 7.4 produces the quinone, which immediately forms the bicyclic iminoqui
none (Jacob et al., 1979).
(3) Research evidence for the involvement of serotonin in the mechanism of the action of psychedelic
drugs (Glennon et al., 1984b).
(4) The DOM metabolites 2-DES-Me-DOM and 5-DES-Me-DOM active in LSD-trained rats (Eckler
et al., 2003).
(5) Serotonin agonist evaluation (Glennon et al., 1980a, 1980b).
(6) Studies on the in vitro metabolism of DOM (Weinkam et al., 1976).
(7) The metabolism of DOM in rabbit liver (Castagnoli et al., 1976) .
(8) Three-carbon side-chain homologue of DOM. The behavioral effects in rats were compared with
those produced by LSD, mescaline, and amphetamine (Buxton, 1972).
(10) Pharmacology (Weintraub et al., 1980); note that although this compound was reported here, a
structure-search in Chemical Abstracts does not produce a CAS registry number.
(11) Chemical Abstracts produces an abstract, but a search for the structure and registry number fails.
(12) Chemistry discussed (Barfknecht et al., 1978).
(14) Synthesis (Shulgin and Shulgin, 1991), otherwise no references in the scientific literature.
(15) Synthesis (from 2,5-dimethoxyisobutylbenzene) (Mueller, 2006); although this compound was
reported here, a structure-search in Chemical Abstracts does not produce a CAS registry number
(16) Threshold activity in humans at 5 mg orally; long duration (about 20 hours; Mueller, 2006).
(17) Animal discrimination studies based on LSD (Oberlender et al., 1984).
(18) Synthesis (Oberlender et al., 1984).
(19) Serotonin receptor affinities determined in isolated rat fundus preparation, and studies in rats
trained to discriminate 5-MeO-DMT from saline (Glennon et al., 1981b).
(20) A comparison of steric properties with animal and human potency of several phenethylamines,
tryptamines, and lysergide derivatives was made (Nichols, 1986a).
(21 ) The sec-butyl R- and S-isomers were synthesized and compared as to serotonin receptor agonist
activity (Oberlender et al., 1995).
(22) Synthesis, physical properties described (Shulgin, 1970). Not orally active in humans at 25 mg
(Shulgin and Shulgin, 1991 ).
(23) Six compounds were assayed for psychedelic activity in trained rats as determined by disruption
of discriminated avoidance responses. Of DOET, DOPR, DOIP, DOTB, DOBU, and DOAM,
DOPR was the most potent (Morin et al., 1975).
(24) Mescaline, DOM, DOET, and DOIP induce a dose-dependent scratching response in mice, in
increasing potency. DOTB was inactive (Kulkarni, 1973).
(25) Affinity to 5-HT2 receptors measured and compared to structurally related compounds (Seggel
et al., 1990).
(26) Affinity to cloned human 5-HT2N 5-HT2w and 5-HT2c serotonin receptors was measured and
compared to structurally related compounds (Nelson et al., 1999).
(27) Serotonin agonist activity in sheep umbilical preparation (Shulgin and Dyer, 1975).
(28) The octanol-water partition coefficient served as a predictor of human psychedelic potency
(29) Behavioral effects on rats trained to discriminate 1 .0 mg / kg of (±)-DOM from saline (Glennon et
al., 1982b).
(30) A large study of psychedelic compounds showed that the lipophilicity of the 4-position sub
stituent was of primary importance in determining 5-HT2 receptor affinity (Glennon and Seggel,
1989).
(31 ) Patented as a CNS stimulant (Shulgin, 1969).
(33) Study on the biotransformation products of TMA, MEM, MPM, and ALEPH by Cunninghamella
echinulata (Foster et al., 1992).

DOM
Analogues
MeO Me MeO -- DOM (this entry)
MeO Me MeO a-C-6 DOMAI [51806-87-2] (1-5)
MeO Me MeO a-C-6,N-Me2 N,N-Me-DOMAI [52428-22-5] (2)
MeO Me MeO a-CH=CH-6 DOMAD [77886-58-9] (6,7)
MeO Me Meo a-CC-a a-CP-2C-D -- (8)
MeO Me MeO a-CC-6 DOMAT [51806-86-1] (2-5,9)
MeO Me MeO N-HO N-HO-DOM [43022-01-1] (10-14)
MeO Me MeSO -- 5-TOMSO [84910-95-2] (15,16)
MeO CHpH MeO -- DOHM [29907-74-2] (17-18)
MeO FC MeO -- DOFM [ 260810-05-7] (19)
MeO HOCC MeO -- DOEH [121649-04-5] (20)
MeO FCC MeO -- DOEF [121649-01-2] (21 )
MeO C=C MeO -- DOVI -- (8)
MeO C=C Meo -- DOYN [ 633290-70-7] (22)
Meo Bz Meo -- DOBZ [158721-63-2] (23,24)
MeO PhCCC MeO -- DOPh3 [125903-47-1] (23)
(1) With the a-C-2 (aminoindane) nomenclature, the substitution pattern for this molecule is 3-MeO,
5-Me, 6-MeO.
(2) Synthesis (Coutts and Malicky, 1974a).
(3) Stimulation of dog vascular strips and of serotonin receptors (Cheng et al., 1974b).
(4) Rats to discriminate between either LSD and saline, or MDMA and saline, were tested with
MDAI, MDAT, 4,5-MDAI, 5,6-MDAT, DOMAI, and DOMAT (Nichols et al., 1990).
(5) Synthesis, and assay in rats where it appeared to show little psychedelic activity when com
pared to DOM (Nichols et al., 1974).
(6) DOMAD is less effective than DOMAT (or DOM itself) as a serotonin agonist with rat fundus
preparations (Kothari et al., 1981). See Appendix A for ring numbering for DOMAD.
(7) The totally aromatic naphthalenamine is not in the published scientific literature.
(9) See Appendix A for ring numbering, as for DOMAD.
(10) The mutagenic activity in Salmonella typhimurium has been studied (White et al., 1977).
(11) A metabolite of DOM in the rabbit (Gal et al., 1975).
(12) Studies of the optical isomers of DOM and N-HO-DOM with rabbit liver cytochrome P-450
(McGraw and Castagnoli, 1981).
(13) Synthesis (Coutts and Malicky, 1973b).
(15) Synthesis and human pharmacology described (Jacob and Shulgin, 1983).
(16) Activity in humans at greater than 150 mg orally, or 1 00-150 mg with alcohol; duration 10-16
hours (Shulgin and Shulgin, 1991).
(17) 2,5-Dimethoxy-4-hydroxymethylamphetamine (DOHM) was synthesized as a possible metabo
lite of DOM (Matin et al., 1974). A major metabolite in the rat (Ho and Tansey 1971; Ho et al.,
1971b).
(18) A metabolite of DOM in the guinea pig and rabbit (Nagamatsu et al., 1978).
(19) A potentially psychedelic compound, not yet synthesized (Schulze-Alexandru et al., 1999).
(20) Synthesized as intermediate in the preparation of DOEF (Gerdes et al., 1988).
(21 ) Synthesis (Gerdes et al., 1988).

DOM

(24) The affinity to cloned human 5-HT2N 5-HT2w and 5-HT2c serotonin receptors was measured and
compared to structurally related compounds (Nelson et al., 1999) .
Biochemistry
Metabolism of DOM in the rat compared with that of tyramine (Tacker, 1 969). In the rat, the
primary metabolic attack was upon the 4-methyl group; in 24 hours, 50% was excreted as
DOHM (free and conjugated), 28% as DOCA, and 8% was excreted unchanged (Ho et al.,
1971 ) . A trace of the oxidation deamination product 1-(2,5-dimethoxy-4-methylphenyl)-2-
propiophenone was present (Ho et al., 1971; Ho and Tansey, 1971 ) . Four possible metabolites
of DOM synthesized: 1-(2,5-dimethoxy-4-methylphenyl)-2-propanone, 1-(2,5-dimethoxy )-
4-methylphenyl-2-propanol, 1-(2,5-dimethoxy-4-methylphenyl)-2-propanone oxime, and
N-HO-DOM (Coutts and Malicky, 1973b) . In the rabbit, oxidation of the 4-methyl group of
DOM to the carboxylic acid (DOCA) was the primary metabolic transformation, at about
40%; only about 1 % was excreted unchanged (Matin et al., 197 4) in a study of stereochemical
aspects of DOM metabolism following i. p. administration to the rabbit. In rat and rabbit liver
preparations, DOM was metabolized by 5-demethylation, 2-demethylation, and 2,5-bis
demethylation (Zweig and Castagnoli, 1975, 1977; Castagnoli et al., 1976) . Spectral and
kinetic metabolic studies of the interaction of DOM and its N-hydroxy metabolite utilized
rabbit liver microsomal preparations (McGraw, 1977) . In the rabbit and the guinea pig,
urinary metabolites were DOHM, the �-alcohol and �-ketone resulting from deamination,
the oxidation of the propyl chain giving 2,5-dimethoxy-4-methyl benzoic acid, and the
oxidation of the 4-methyl group to a carboxy group. This latter compound, DOCA, was
the major metabolite (Nagamatsu et al., 1978) . DOM metabolically bis-demethylated to
2,5-DES-Me-DOM (Jacob et al., 1979). Interaction of optical isomers of DOM and N-HO
DOM with rabbit liver cytochrome P450 studied (McGraw and Castagnoli, 1981).
DOM affected the metabolism of biogenic amines in the rat brain (Leonard, 1973), and
interacted with serotonin turnover in rat brain and spinal cord (Anden et al., 1 974) . In a
study of its metabolic fate, DOM was chemically converted to 5-hydroxy-2,6-dimethylin
dole by demethylation with HBr followed by treatment with base (Zweig and Castagnoli,
1974) . The metabolism of the R- and 5-DOM were compared to the dl-racemate in rat liver
homogenate (McGraw et al., 1977) . Stereospecific metabolism was facilitated by GC / MS
analysis of the (S)-a-methoxy-a-(trifluoromethyl)phenylacetylamides (Gal, 1978) .
Interactions of DOM and other mescalinoids with monoamine oxidase were studied (Hel
lot et al., 1970b) . DOM had no effect on isolated human ceruloplasmin-catalyzed serotonin
oxidation, in vitro (Barrass and Coult, 1972) . No mutagenic activity was caused by DOM in
Salmonella typhimurium (White et al., 1977), but teratogenic effects of DOM on the chick em
bryo were detected (Spindler and Garcia Monge, 1970) . Several compounds were synthe
sized and assayed for their ability to inhibit MAOA and MAOB. Most were potent against
DOM and other psychedelics, including LSD, had effects on serotonin metabolism (Freed
man et al., 1970). Stereoisomers of five psychedelic amphetamines contracted isolated
strips of sheep umbilical arteries, the R-(-)- being more active than the 5-( +)-isomers; there
was a general correlation between the smooth muscle contracting ability and the known
psychedelic potency of the compounds (Dyer et al., 1973) . Binding to dopamine neurore-

DOM
ceptors was measured (Whitaker and Seeman, 1977) . Serotonin receptor binding was first
reported in 1 978 (Glennon et al., 1978) . The R-isomer of DOM was more potent than the
racemate in binding to the 5-HT2 receptor (Shannon et al., 1984) . DOM affected uptake and
release of [ 1 4 C]-serotonin by rabbit blood platelets (Huang et al., 1974) . The action of DOM
and several other psychedelic drugs on perfused vascular strips of the dorsal metatarsal
vein of a dog was reported (Cheng et al., 1974b) . Serotonin agonist activity was measured
in sheep umbilical preparations (Shulgin and Dyer, 1975) . Effects of R-DOM, R-4C-M, and
serotonin were compared with non-innervated vascular smooth muscle (Dyer, 1976).
DOB, DOM, and 5-MeO-DMT were behaviorally the most potent compounds of a large
series of phenethylamines and tryptamines, and had the highest serotonin receptor site af
finities in a rat fundus preparation (Glennon et al., 1978); receptor affinities determined in
the rat fundus model, and studies in rats trained to discriminate 5-MeO-DMT from saline
expanded on these results (Glennon et al., 1981a). Molecular connectivity analysis gave
excellent correlation to serotonin agonist activity for a large number of phenethylamines
and amphetamines (Kier and Glennon, 1978a; Glennon et al., 1980a, 1982a). Evidence for
the involvement of serotonin in the mechanism of the action of psychedelic drugs was
summarized (Glennon et al., 1984b).
Inhibition of serotonin binding to rat brain membranes has been noted (De Jong et al.,
1982) . A correlation was made between the electron orbital at the 4-position and serotonin
receptor binding (G6mez-Jeria et al., 1987) . Action of a number of psychedelics on 5-HT2 re
ceptors were studied in the guinea pig trachea (Heller and Baraban, 1987) . 5-HT2 receptors
were the preferred site of psychedelic action, as its radiolabeling marker (tritiated DOB)
was preferentially targeted; three controls (appropriately radiolabeled 5-HTIN 5-HT 1 81 and
5-HT 1 c) were not as strongly stimulated (Titeler et al., 1988) .
Interactions at human brain 5-HT2 receptors were studied (Sadzot et al.,1989) . DOM treat
ment rapidly desensitized and down-regulated 5-HT2 receptors (Leysen et al., 1989). A
large study of psychedelic compounds showed that the lipophilicity of the 4-position sub
Seggel, 1989). Affinity to 5-HT2 receptors was measured and compared to structurally re
lated compounds (Seggel et al., 1990) . The release of serotonin and dopamine from synap
tosomes isolated from rat brain was characterized (McKenna et al., 1991). DOM binding
at 5-HTic and 5-HT2 receptors was measured (Glennon et al. 1992), and binding at 5-HT2A
receptors compared to the affinity of several (3-carbolines (Glennon et al., 2000) . The role of
various serotonin receptor subtypes in mediating neuroendocrine effects of DOM in rats
has been explored (Aulakh et al., 1994a) . A series of psychedelic amphetamines were com
pared to their phenethylamine counterparts, as agonists for 5-HT2 A and 5-HT2c receptors
(Acuna-Castillo et al., 2002). The assignment of DOM as a 5-HT2 or 5-HTic agonist was dis
cussed (Ismaiel et al., 1993). Functional selectivity of serotonin receptor subtypes for DOM
and a series of substituted phenylisopropylamines and phenethylamines was studied in
hamster ovary cells expressing cloned human receptors, and through behavioral tests with
rats (Moya et al., 2007) .
Effects were observed on EEG response in rabbit brain following i.v. administration (Fu
jimori and Himwich, 1969, 1970) . Tissue distribution of DOM was studied in male mice
(Idanpaan-Heikkila and Mcisaac, 1970) . DOM levels were determined in monkey and rat
brain following i.v. injection (Ho et al., 1971a). Pressor action of DOM in rats (Huang and
Ho, 1972), cardiovascular effects in rats and dogs (Boissier et al., 1972), and neuropharma-

DOM
cological effects of DOM in the cat (Wallach et al., 1972b) were monitored. DOM increased
the amplitude of contraction and decreased the rate of contraction of perfused rat hearts
(Huang and Ho, 1974b). DOM had effects on sensory discrimination behaviors maintained
by electrical stimulation of the brain in the rat (Vincent and Lenzer, 1976). Action of R- and
5-DOM on colonic temperature in the rat at various ambient temperatures was noted (Bea
ton et al., 1976) .
Serotonin mediated the action of mescaline, DMPEA and DOM on plasma prolactin of rats
(Meltzer et al., 1978), while DOM produced a rise in blood pressure and heart rate when
injected into the cerebral ventricles of anesthetized rats (Friedman et al., 1978) . Effects on
dorsal and median raphe neurons were studied (Geyer and Mandell, 1979; Geyer, 1980).
Psychedelics inhibited synaptosomal neurotransmitter uptake (Whipple et al., 1983), and
stereochemical effects were noted, of 3,4-methylenedioxymethamphetamine (MOMA),
DOM, and related amphetamine derivatives on inhibition of uptake of [ 3H]monoamines
into synaptosomes in different regions of rat brain (Steele et al., 1987) . A comparison of
DOM, mescaline and d-amphetamine was made on the rat dorsal raphe neurons (Pening
ton and Reiffenstein, 1986a); DOM was also possibly involved with serotonin receptors
in the facilitatory effect on single facial motoneurons (Penington and Reiffenstein, 1986b).
With R-DOM, telemetric recordings of field potentials were made from frontal cortex, hip
pocampus, striatum, and reticular formation of freely moving rats (Dimpfel et al., 1 989) .
DOM had effects o n uterine and umbilical blood flow i n conscious pregnant sheep (Zhang
et al., 1991 ). Transport of DOM by crown-ether macroheterocycles across erythrocyte mem
branes prevents natural homolysis (Karaseva et al., 1993) .
Pharmacology
DOM altered learned responses of the squirrel monkey (Uyeno, 1969). DOM produced sei
zures in rabbits at 1-2 mg / kg orally (Florio et al., 1969); EEG and other behavioral effects
were also reported. Additional behavioral responses in rats (Smythies et al., 1970), effects
on nest-building behavior of mice (Schneider and Chenoweth, 1970), toxicity, effects on
barbiturate sleeping time, and ability to disrupt mouse behavior were reported (Ho et al.,
1970a) . DOM action on single midbrain raphe neurons was compared with several isopro
pylamines, phenethylamines, tropanes, and other agents (Aghajanian et al., 1970) .
Correlations were made between potency o f psychedelic methoxyamphetamines and their

inhibition of [ 3H]-normetanephrine uptake in rat cerebral cortex (Hendley and Snyder,
1971 ) . The potencies of several psychedelics were rated in prolonging the latency of initiat
ing an escape behavior of trained rats (Uyeno, 1971), and in the behavior of rats in competi
tion for food (Uyeno, 1972a) . DOM effects were also observed in rats responding to a timed
food presentation schedule (Harris et al., 1977) . Behavioral and neurochemical effects were
observed in neonate chicks (Wallach et al., 1972a), and behavioral effects in rats were
compared with those produced by LSD, mescaline, and amphetamine (Buxton, 1972) . The
R-(-)-isomer was more toxic than the 5-(+)-isomer in the rat, and also more active in the
avoidance task test (Benington et al., 1973) . Studies were made of injection into the rat optic
nerve and the cat sciatic nerve (Paulson and McClure, 1973) . Rabbit hyperthermia studies
were reported for DOM and its optical isomers (Aldous et al., 1974) .
Behavioral and neuropharmacological analysis of amphetamine and DOM in rats reported

(Tilson, 1975). R-DOM and R-4C-M were compared with amphetamine in the dog (Buyni
ski et al., 1974) and the rat (Tilson et al., 1977b). DOM (0. 1-1 .5 mg / kg) injections decreased
dominance behavior of male rats (Uyeno, 1972b), and caused cardiovascular stimulation
on vagotomized dogs (Uyeno, 1973) . Cardiovascular effects of DOM were also observed
1 26 The 5hulgin Index - Psychedelic Phenethylamines and Related Compounds

DOM
in pentobarbital-anesthetized cats (Tadepalli et al., 1975) . Effects of DOM on behavior and

metabolism of biogenic amines in the rat brain were reported (Leonard, 1973) . Mescaline,
DOM, DOET, and DOIP induced a dose-dependent scratching response in mice, in increas
ing potency; DOTB was inactive (Kulkarni, 1973) . DOM effects were compared with those
of mescaline and methamphetamine in rats and mice (Yamamoto and Ueki, 1975). DOM
and d-amphetamine were compared for in vivo efflux of catecholamines from rat brain
(Vrbanac et al., 1975) .
DOM and 119-tetrahydrocannabinol were approximately equipotent i n their effect o n rat

sexual dominance behavior (Uyeno, 1976) . The decreased frequency of rat limb flicks cor
related well with the drop off in potency of several 2,5-dimethoxy compounds: DOM, R
DOB, and 2,5-DMA were the most effective, S-DOB and DOET were weaker, and 4C-M
was almost without activity (Rusterholz et al., 1977) . DOM was among several psychedelic
drugs compared in effects on cat behavior (Jacobs et al., 1977) . Drug-induced disruption of
behavior and thermoregulation was studied in a series of tryptamines, and mono- and di
substituted amphetamines; the di-substituted amphetamines were intermediate in activity
with respect to the other two compound groups (Kuhlemeier et al., 1977) .
Effects on integrated sensory function and active startle in male rats (Geyer et al., 1978),
and behavioral changes induced by DOM in primate dyads (Tyler et al., 1978) were re
ported. Acute toxicology and gross behavioral effects were described in rodents, dogs,
and monkeys (Davis et al., 1978) . Optical isomers of DMCPA were compared to the cor
responding isomers of DOM in mice and cats (Nichols et al., 1978), and effects on the
behavior of rats were studied (Geyer et al., 1979) . DOM inhibited food intake in the dog
(Vaupel et al., 1979).
Rats trained to discriminate between d-amphetamine and saline, did not generalize to ei
ther MDA or DOM (Shannon, 1980), although rats trained to distinguish DOM from saline
reacted positively to DOET and mescaline (Silverman and Ho, 1980). Amphetamine, and
to a greater extent several psychedelics (PMA, MDA, DOM, DOB, and 4C-M) protected
rats from electroshock seizure (Davis et al., 1982) . Behavioral effects of intracerebroventric
ular administration of LSD, DOM, mescaline, or lisuride (Mokler and Rech, 1984), and ac
tivity of serotonin-containing neurons in the nucleus centralis superior and nucleus raphe
pallidus were reported in studies of freely moving cats (Trulson et al., 1984) . Intravenous
self-administration of cathinone and DOM was observed in rhesus monkeys (Yanagita,
1986). Effects were reported on intracranial administration of DOM and other psychedel
ics on operant behavior in the rat (Mokler et al., 1987a) . Several psychedelic drugs were
found to elicit myoclonic jumping behavior in the guinea pig (Carvey et al., 1 989) . Effects
of DOM and other phenethylamines were reported in rhesus monkeys (Woolverton and
English, 1997) .
Mouse behavior was compared with the effect of several phenethylamines on activity
of the brain enzymes MAO and DOPA decarboxylase (De Ropp and Kastl, 1970) . DOM
was evaluated with a discriminative stimulus method in rats that had been trained to re
spond to d-amphetamine (Huang and Ho, 1974) . Relationships between serotonin levels
and sexual behavior were reported in the rat (Everitt and Fuxe, 1977) . DOM was studied
with respect to the role of central serotonergic mechanisms on head-twitch and backward
locomotion induced by psychedelic drugs (Yamamoto and Ueki, 1981). Serotonin recep
tor affinity and the behavioral properties of DOM were reported (Glennon et al., 1982a),
and behavioral properties could be correlated with structural modifications (Glennon and
Young, 1982) . This background served to justify the use of DOM as a model training com-

DOM
pound in numerous studies of other suspected psychoactive compounds; for example,

behavioral effects in rats trained to discriminate 1 .0 mg / kg of (±)-DOM from saline were
used for measuring the disruption caused by related psychedelic amphetamines (Glennon
et al., 1982c).
Effects of the 5-HT2 agonist 1-NP on the behavior of the squirrel monkey either alone or in
combination with DOB, mCPP, or TFMPP were reported (McKearney, 1989). 5-HT2 medi
ated acute behavioral effects of psychedelics in rats (Wing et al., 1990). An argument was
made for the involvement of 5-HT 1 c in the mechanism of psychedelic action, in that the
potency of DOB, DOM, DOI, and MDA as psychedelics decreases in parallel to their po
tency as agonists (Sanders-Bush and Breeding, 1991). Evidence was presented that DOM
induced hypophagia and hyperthermia in rats was mediated by 5-HT2A receptors (Aulakh
et al., 1994b ) .
DOB and other psychedelics decreased response rates i n rats i n a lever-press assay, while
stimulants increased response rates (Ando, 1975) . Discriminative stimulus properties of
R-DOM and 5-amphetamine were compared in the rat (Tilson et al., 1975) . DOM, DOET,
cocaine, and amphetamine responses were compared in rats trained with mescaline (Win
ter, 1975). The discriminative response of rats trained to distinguish DOM from saline had
commonality with other psychedelics (Silverman and Ho, 1978) . Rats trained to discrimi
nate 5-MeO-DMT from saline were tested with several psychoactive phenylisopropyl
amines including (R)- and (5)-isomers of DOM (Glennon et al., 1981b). DOM, DOIB, and
DOSB were compared in discrimin-ation studies based on training with LSD (Oberlender
et al., 1984) . Rats trained to discriminate DOM from saline only partially generalized to
PMA (Glennon et al., 1985). Mechanistic studies were presented on DOM as a discrimina
tive stimulus (Glennon and Hauck, 1985) .
Biochemical and behavioral studies with MDMA and MBDB gave similar results, but dif
fered from both stimulants (amphetamine) and psychedelics (DOM, LSD). This prompted
the creation of a new class name: "entactogens" (Nichols, 1986b). In establishing defini
tions of entactogen, hallucinogen, and stimulant, using drug discrimination-trained rats,
(MDMA or 5-(+)-amphetamine), the optical isomers of MDA, MDMA, MBDB, amphet
amine, LSD, and DOM were compared (Oberlender and Nichols, 1988, 1990) . DOM and
other substituted isopropylamines were evaluated in drug discrimination studies with rats
trained with LSD (Nichols et al., 1991). The replacement of the a-methyl group with an a
ethyl group eliminated psychedelic action, but maintained the MDMA-generalized stimu
lus responses in rats (DOM homologized to 4C-M, a-MT (a-methyltryptamine) to a-ET
(a-ethyltryptamine); Glennon, 1993). Antipsychotic drugs were evaluated with the DOM
discriminative stimulus response of rats (Fiorella et al., 1997) . Optical isomers of PMMA,
DOM, MBDB, MDMA, and DMA were compared as stimulants in rats (Rangisetty et al.,
2001), and effects in trained rats compared sulfur-containing psychoactive materials with
DOM (Khorana et al., 2004). The 2-0-desmethyl and 5-0-desmethyl metabolites of DOM
(2-DM-DOM and 5-DM-DOM) (Zweig and Castagnoli, 1977) were pharmacologically ac
tive, and positively substituted for LSD in discrimination tests (Eckler et al., 2003).

correlations were made between psychedelic potency and changes in substitution patterns
(Shulgin et al., 1969), the energy of the highest occupied molecular orbital of the drug (Kang
and Green, 1970), the degree of native fluorescence (Antun et al., 1971), and lipophilicity
(as determined by octanol-water partition coefficient; Barfknecht et al., 1975; Nichols et

DOM / DON
al., 1977) . In a separate series of psychoactive compounds, those with greater potency had
lower ionization potential as measured by photoelectron spectroscopy (Domelsmith and
Houk, 1978) . Rabbit hyperthermia paralleled human psychedelic potency (Anderson et al.,
1978b), and human activity was correlated between 5-HT2 affinity, charge complex stabil
ity, and rabbit hyperthermia (Domelsmith et al., 1981 ) . A comparison was made of steric
properties with animal and human potency of several phenethylamines, tryptamines, and
lysergide derivatives (Nichols, 1986a) . The electron withdrawing or donating nature of
the 4-position substituent was correlated with the human potency of the compound (Neu
vonen et al., 2006) .
DOM was patented as an experimental CNS stimulant (Shulgin, 1970) . Human studies
were reported, comparing DOET (at 1 .5 mg orally) with DOM (at 3 mg orally; Snyder et
al., 1970), and studies involving human visual integrity were reported (Weingartner et al.,
1971 ) . The R-(levo)-isomer showed activity at sub-milligram amounts in humans, twice
the potency of the racemate; the 5-(dextro)-isomer at 2.5 mg showed no sympathomimetic
stimulation, and at no level was there a psychedelic syndrome (Shulgin, 1973). Human re
sponses to oral doses of 2 to 14 mg, showed that tolerance rapidly developed with chronic
use (Hollister et al., 1969; Angrist et al., 1974) .
Deception took place in street sales in New York and other East Coast cities, with DOM
being sold as mescaline, at doses of approximately 4 mg (Cheek et al., 1 970) .
Initial reports o f oral activity i n humans gave a level o f 1-2 m g a s the effective dose (Sny
der et al., 1967; Shulgin et al., 1969) . Reports from the period had indicated chlorproma
zine worsened "bad trips" induced by this drug, but this was not observed in human
trials (Snyder et al., 1967) . At doses above 4 mg, the central sensory effects become marked
(Weingartner et al., 1971 ) . DOM was reported to be orally active in humans at about 5 mg
(Shulgin and Dyer, 1975; Lemaire et al., 1985), and at 3-1 0 mg; duration 14-20 hours (Shul
gin and Shulgin, 1991).
Legal Status
DOM is a Schedule I hallucinogen under federal drug law, and under District of Columbia
and all state laws except for Montana.
#61. DON
1 -(2,5-Dimethoxy-4-ni tropheny1)propan-2-amine
1-(2,5-Dimethoxy-4-nitrophenyl)-2-aminopropane
2,5-Dimethoxy-4-nitroamphetamine
Registry Numbers
CAS # CAS #
HCl salt [42203-79-2] R-(-)-Isomer HCl salt [82830-45-3]
Freebase [67460-68-8] R-Isomer freebase [64778-74-1 ]

From 2,5-dimethoxybenzaldehyde (with ammonium acetate, nitroethane) to 1 -(2,5-dime
thoxy-phenyl)-2-nitropropene; (with LAH) to 1-(2,5-dimethoxyphenyl)-2-aminopropane;
(with acetic anhydride) to N-acetyl-1-(2,5-dimethoxyphenyl)-2-aminopropane; (with
HN031 NaN02) to N-acetyl-1-(2,5-dimethoxy-4-nitro-phenyl)-2-aminopropane; (with
NaOH, ethylene glycol) to DON (Coutts and Malicky, 1973) .

DON
From 2,5-DMA (with HN03 ) to DON (Glennon et al., 1982a) . The same procedure has been
employed starting with the R-(-)-isomer of 2,5-DMA, producing the R-(-)-isomer of DON
(Glennon et al., 1982a) .

m / z: 240.1110 (100.0%), 241 .1144 (11 .9%)
Elemental Analysis: C, 54.99; H, 6.71; N, 11 .66; 0, 26.64
HCl salt m.p. 203-204 °C (Coutts and Malicky, 1973) (EtOH / Etp)
HCl salt m.p. 207-209 °C (Glennon et al., 1982a) (EtOH / Etp)
R-(-)-Isomer HCl salt m.p. 231-232 °C (Glennon et al., 1982a) (EtOH / Etp) (dee.)
Analysis of human whole blood by capillary electrophoresis with diode array detection
was performed (Nieddu et al., 2005). An analytical process for human urine was described
involved electrophoresis and mass spectrometry (Boatto et al., 2005).

2- 3- 4- 5- a- N- Name CAS # Ref
N02 -- MeO MeO Me -- a-DON [142893-52-5] (1-3)
Meo N02 -- MeO Me -- 3-DON [146269-95-6] (4)
MeO -- NH2 MeO Me -- DONH [42203-80-5] (5-9)
MeO -- NH2 MeO Me Ac DONHAc [42203-73-6] (10)
MeO -- NH2 MeO Et -- 4C-NH [72667-88-0] (11)
MeO -- NMe2 MeO Me -- DONMM [88753-12-2] (7,12)
MeO -- NHAc MeO Me -- DOAA [42203-87-2] (6,1 0,13)
MeO -- N02 MeO Me -- DON (this entry)
Meo -- N02 MeO Me Ac DON-Ac [ 42203-72-5] (10)
MeO -- N02 MeO Et -- 4C-NO [72667-87-9] (11)
(1) MAOI properties were evaluated (Scorza et al., 1997).
(2) Synthesis (Jara et al., 1994).
(3) Patented as a hypotensive agent (Stone, 1963).
(4) The structure of 3-DON was entered in Chemical Abstracts based on an error in a paper (Merahi
et al., 1992), in which DON was identified as 2,5-dimethoxy-3-nitroamphetamine (DOB is simi
larly misnamed 2,5-dimethoxy-3-bromoamphetamine). 3-DON does not currently exist in the
published scientific literature.
(5) 4-Amino-2,5-dimethoxyamphetamine (DONH) was synthesized by the reduction of DON
(Coutts and Malicky, 1973).
(6) The N-acetyl analogue, 4-acetamido-2,5-dimethoxyamphetamine (DONHAc) was synthesized
from 2,5-DMA (Coutts and Malicky, 1973)
(7) Compounds synthesized and assayed for their ability to inhibit MAOA and MAOB. Most were
potent against MAOA; none were appreciably active against MAOB (Gallardo-Godoy et al., 2005).
(9) A large study of psychedelic compounds showed that the lipophilicity of the 4-position substituent
was of primary importance in determining 5-HT2 receptor affinity (Glennon and Seggel, 1989) .
(11) Synthesis and studied in cat behavior (Standridge et al., 1980).
(12) The MAOI properties were evaluated (Scorza et al., 1997).
(13) Neurotoxicity was determined through both in vivo and in vitro studies (Ma et al., 1995).

DON / DOPR
Biochemistry
Part of a series of compounds, whose octanol-water partition coefficient served as predic
tors of human psychedelic potency (Nichols et al., 1977) . Molecular connectivity analysis
gave excellent correlation to serotonin agonist activity in a large number of phenethyl
amines and amphetamines (Kier and Glennon, 1978a). The R-isomer of DON was more
potent than the racemate in binding to the 5-HT2 receptor (Shannon et al., 1 984) . A cor
relation was made between the electron orbital at the 4-position and serotonin receptor
binding (G6mez-Jeria et al., 1 987) . A large study of psychedelic compounds showed that
the lipophilicity of the 4-position substituent was of primary importance in determining
5-HT2 receptor affinity (Glennon and Seggel, 1 989) . The affinity to 5-HT2 receptors was
measured and compared to structurally related compounds (Seggel et al., 1 990); affinity
to cloned human 5-HT2N 5-HT2w and 5-HT2c receptors was measured and similarly com
pared (Nelson et al., 1 999) . A series of psychedelic amphetamines were compared to their
phenethylamine counterparts, as agonists to 5-HT2A and 5-HT2c receptors (Acuna-Castillo
et al., 2002).
Several compounds were synthesized and assayed for their ability to inhibit MAOA and
MAOB . Most were potent against MAOA; none were appreciably active against MAOB
(Gallardo-Godoy et al., 2005). DON did not show any effects on inhibition of MAOA or
MAOB at 100 µM (Scorza et al., 1 997) .
Electrochemical studies of DON were performed (Richter et al., 1988), and on TMA-2,
DOB, DOM, and DON, compared with the 4-unsubstituted 2,5-DMA, (Squella et al., 1992) .
DON neurotoxicity was compared, through both in vitro and in vivo studies, with des
methyl derivatives (dopamine analogues) (Ma et al., 1995) .
Pharmacology
A comparison of serotonin receptor affinity and behavioral properties of racemic and the
R-isomer of DON reported (Glennon et al., 1 982a) . Research evidence was presented for
the involvement of serotonin in the mechanism of action of psychedelic drugs (Glennon et
al., 1984b).
Legal Status
DON is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#62. DOPR
1-(2,5-Dimethoxy-4-propylphenyl)propan-2-amine
1-(2,5-Dimethoxy-4-propylphenyl)-2-aminopropane
2,5-Dimethoxy-4-propylamphetamine
Registry Numbers
CAS #
HCl salt [53581-55-8]
Freebase [63779-88-4]

DOPR
Synthesis
From p-dimethoxybenzene (with propionic acid, polyphosphoric acid) to 2,5-dimethoxy
propiophenone; (with Zn, Hg) to 2,5-dimethoxy-propiobenzene; (with N-methylformani
lide and POCl) to 2,5-dimethoxy-4-propyl-benzaldehyde; (with nitroethane, acetic acid,
and ammonium acetate) to 1-(2,5-dimethoxy-4-propylphenyl)-2-nitropropene; (with LAH)
to DOPR (Shulgin and Dyer, 1975).
Exact Mass: 237. 1 729

m / z: 237. 1 729 (100.0%), 238.1762 (15. 1 % ), 239.1796 ( 1 . 1 % )
HCl salt m.p. 283-284 °C (Aldous et al., 1974) (EtOH / Etp)

HCl salt m.p. 1 82-183 °C (Shulgin and Dyer, 1975) (MeCN)
Biochemistry
Serotonin agonist activity was first reported in sheep umbilical preparations (Shulgin and
Dyer, 1975). Molecular connectivity analysis gave excellent correlation to serotonin ago
nist activity in a large number of phenethylamines and amphetamines (Kier and Glen
non, 1978a) . Serotonin receptor affinities were determined in isolated rat fundus prepara
tion, and studies in rats trained to discriminate 5-MeO-DMT from saline (Glennon et al.,
1 981b) . The 5-HT2 receptor was the preferred site of psychedelic action, as its radiolabeling
marker (tritiated DOB) was preferentially targeted; three controls (appropriately radiola
beled 5-HT 1 N 5-HT 1 81 and 5-HTic) were not as strongly stimulated (Titeler et al., 1 988). A
large study of psychedelic compounds revealed that the lipophilicity of the 4-position sub
Seggel, 1989). Affinity to 5-HT2 receptors was measured and compared to structurally re
lated compounds (Seggel et al., 1 990) . Binding at 5-HTic and 5-HT2 receptor was observed
(Glennon et al., 1992) . Affinity to cloned human 5-HT2N 5-HT281 and 5-HT2c receptors was
measured and compared to structurally related compounds (Nelson et al., 1 999). Binding
at 5-HT2A receptors was compared with the binding affinity of several (:3-carbolines (Glen
non et al., 2000).
Drug-induced disruption of behavior and thermoregulation studied in a series of trypt

amines, and mono- and di-substituted amphetamines; the di-substituted amphetamines
were intermediate in activity with respect to the other two compound groups (Kuhlemeier
et al., 1 977) .
Pharmacology
Rabbit hyperthermia assays were performed with DOPR (Aldous et al., 1 974) . Six com
pounds were assayed for psychedelic activity in trained rats, as determined by disrup
tion of discriminated avoidance responses. Of DOET, DOPR, DOIP, DOTB, DOBU, and
DOAM, DOPR was the most potent (Morin et al., 1975) . Effects on integrated sensory
function, and active startle in male rats (Geyer et al., 1978), as well as further effects on the
behavior of rats has been reported (Geyer et al., 1 979) . Behavioral effects on rats trained
to discriminate 1 .0 mg / kg of (±)-DOM from saline were compared with reported human
psychedelic potency (Glennon et al., 1982b; Shulgin, 1 978) .
Evidence was found for the involvement of serotonin in the mechanism of action of psy
chedelic drugs (Glennon et al., 1984b) . The octanol-water partition coefficient may serve as
a predictor of human psychedelic potency (Nichols et al., 1 977) .

DOPR / DOTFM
DOPR was reported to be orally active in humans at 4 mg (Shulgin and Dyer, 1975), and at
2.5-5.0 mg; duration 20-30 hours (Shulgin and Shulgin, 1991).
Legal Status
DOPR is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#63. DOTFM
1-(2,5-Dimethoxy-4-( trifluoromethyl)phenyl)propan-2-amine
2,5-Dimethoxy-4-trifluoromethylamphetamine
1-(2,5-Dimethoxy-4-( trifluoromethyl)pheny1)-2-aminopropane
Registry Numbers
CAS #
HCl salt [159277-12-0]
Freebase [159277-07-3]

From DOI (with trifluoroacetic anhydride) to 1-(2,5-dimethoxy-4-iodophenyl)-2-trifluoro
acetamido)propane; (with methyl chlorodifluoroacetate, KF, Cul) to 1-(2,5-dimethoxy-4-
trifluoromethylphenyl)-2-trifluoroacetamido)propane; (with KOH) to DOTFM (Nichols et
al., 1994) .

m / z: 263. 1133 (100.0% ), 264.117 (13.0% )
Elemental Analysis: C, 54.75; H, 6. 13; F, 21 .65; N, 5.32; 0, 12.16
HCl salt m.p. 210 °C (Nichols et al., 1994) (EtOH / EtOAc)

2- 3- 4- 5- 6- a- N- Name CAS # Ref
CF3 -- -- -- -- Me -- 2-TFMA [670-03-1] (1)
-- CF3 -- -- -- -- -- 3-TFMPEA [141029-1 7-6] (2)
-- CF3 -- -- -- -- Me 3-TFMMPEA [52516-31-1] (3)
-- CF3 -- -- -- -- Et N-Et-3-TFMPEA [125236-62-6] (4-6)
-- CF3 -- -- -- Me -- 3-TFMA [673-18-7] (1,7-14)
-- -- CF3 -- -- Me -- TFMA [882-00-8] (1,15-18)
MeO -- CF3 -- -- Me -- 2-MTFMA -- (19)
MeO -- CF3 MeO -- Me -- DOTFM (this entry)
MeO -- CF3 -- MeO Me -- DOTFM-6 -- (19)
-- Meo CF3 -- -- Me -- 3-MTFMA -- (19)
(1) Studied as an anorexigenic agent (Holland et al., 1963).
(2) Analogue used to probe structural features contributing to 5-HT28 and 5-HT2c affinity (Setola et
al., 2005).
(3) Improved memory acquisition and retention in rats (Hansl, 1975).
(4) Seen in urine sample of a drug user (Caldwell and Challenger, 1989).
(5) Studied as a serotonin uptake inhibitor (Hansch and Caldwell, 1991).

DOTFM / Escaline
(6) Synthesis (Griffith et al., 1979).

(7) Major metabolite of fenfluramine and possible contributor to its anorectic efficacy (Broekkamp
et al., 1975).
(8) Synonyms: Norfenfluramine, 3-trifluoromethylamphetamine, desethylfenfluramine, JP-92,
NSC-43036.
(9) Derivatization with heptafluorobutyryl-L-proline allowed chiral GC analysis (Srinivas, et al., 1989).
(10) Studies on the release of serotonin and dopamine (McKenna et al., 1991 ).
(11) Norfenfluramine (and m-trifluoromethylhippuric acid) are metabolites of fenfluramine (Bruce
and Maynard, 1968).
(12) Plasma levels determined by GC of the acetyl derivative (Lindley and Sharman, 1977).
(13) Following oral administration of fenfluramine, norfenfluramine ' s maximum concentration was
reached in four hours and remained constant for 24 hours (Campbell, 1971 ).
(14) Resolved to its optical isomers with dibenzoyl tartaric acid (Jacewicz, 1975).
(15) Synonyms: P-1 726, trifluorex, triflutamine.
(16) Studies on inhibition of food intake and growth, and toxic retinopathy in rats and dogs (Delahunt
et al., 1963).
(17) The potency as an inhibitor of phenethanolamine N-methyltransferase was determined (Fuller
et al., 1971 ).
(18) Correlation of chemical structure and phenethanolamine N-methyltransferase reactivity (Han
sch and Glave, 1972).
The three-carbon chain homologue of N-Et-3-TFMPEA is homo-N-Et-3-TFMPEA and has

been synthesized; CAS # [71250-31 -2] (Griffith et al., 1979) .
Biochemistry
Among a series of compounds synthesized to evaluate structural features that confer prefer
ential binding to 5-HT28 or 5-HTzA / zc receptors, and possibly explain adverse cardiopulmo
nary side-effects of norfenfluramine (Setola et al. 2005). Compounds were synthesized and
assayed for their ability to inhibit MAOA and MAOB . Most were potent against MAOA;
none were appreciably active against MAOB (Gallardo-Godoy et al., 2005). DOTFM did
not show any effects on inhibition of MAOA or MAOB at 100 µM (Scorza et al., 1997) .
Pharmacology
DOTFM was shown to be a more potent serotonin agonist than either of the two halo
gen analogues, DOB and DOI (Nichols et al., 1994) . Several phenethylamine / phenyliso
proplyamine "pairs" were evaluated as partial agonists of the phospholipase C-signaling
pathway in cloned rat and human 5-HT2A receptors, expressed in mammalian cell systems
(Parrish et al., 2005).
Threshold oral activity reported in humans at 300 µg (Anon., 2003).
Legal Status
DOTFM is not a scheduled compound under federal drug law, or under District of Colum
# 64. Escaline
2-(4-Ethoxy-3,5-dimethoxypheny l)ethanamine
3,5-Dimethoxy-4-ethoxyphenethylamine
E

Escaline
Registry Numbers
CAS # CAS #
HCI salt [3166-82-3] Sulfate [39477-30-0]
Bisulfate [54110-93-9] Freebase [39201-82-6]
PtC16 salt [40275-08-9]
Synthesis
From 3,5-dimethoxy-4-hydroxybenzyl alcohol (with ethyl iodide, EtONa) to 3,5-dime
thoxy-4-ethoxybenzyl alcohol; (with acid chloride) to 3,5-dimethoxy-4-ethoxybenzylchlo
ride; (with NaCN) to 3,5-dimethoxy-4-ethoxybenzylcyanide; (with catalytic reduction) to
Escaline (Jensch, 1929) .
From 3,5-dimethoxy-4-hydroxybenzaldehyde (with ethyl sulfate) to 3,5-dimethoxy-4-eth

oxybenzaldehyde; (with nitromethane) to 1-(3,5-dimethoxy-4-ethoxyphenyl)-2-nitroeth
ene; (with LAH) to Escaline (Benington et al., 1954a) .
From 3,5-dimethoxy-4-ethoxybenzaldehyde (with nitromethane) to 1-(3,5-dimethoxy-4-

ethoxyphenyl)-2-nitroethene; (with Zn) to Escaline (Leminger, 1972b).
From 3,5-dimethoxy-4-hydroxyphenylacetonitrile (with ethyl iodide) to 3,5-dimethoxy-4-

ethoxyphenylacetonitrile; (with H2, Pd) to Escaline (Nichols and Dyer, 1977) .
From syringaldehyde (3,5-dimethoxy-4-hydroxybenzaldehyde) (with ethyl iodide) to

3,5-dimethoxy-4-ethoxybenzaldehyde; (with nitromethane) to 1 -(3,5-dimethoxy-4-ethoxy
phenyl)-2-nitroethylene; (with LAH) to Escaline (Braun et al., 1978a) .

m / z: 225.1365 (100.0% ), 226.1298 (13.0%)
HCl salt m.p. 165 °C (Jensch, 1929)

HCl salt m.p. 165-166 °C (Benington et al., 1954a) (MeOH / EtOAc)
HCl salt m.p. 166-167 °C (Nichols and Dyer, 1977) (EtzO / IPA)
Picrate m.p. 182-183 °C (Benington et al., 1954a) (EtOH)
Biochemistry
were reported (Clark et al., 1956). The octanol-water partition coefficient may serve as a
predictor of human psychedelic potency (Nichols et al., 1977) . Molecular connectivity anal
ysis gave excellent correlation to serotonin agonist activity in a large number of phenethyl
amines and amphetamines (Kier and Glennon, 1978a) . The calculated electrostatic poten
tial was related to that of serotonin (G6mez-Jeria et al., 1984) .
Pharmacology
The action of mescaline, escaline, and ASB was observed on frogs, cats, and dogs (Grace,
1 934), and it was observed to produce experimental catatonia in cats (Noteboom, 1934) .
Studies on enzymatic oxidative deamination, and effects on cat behavior were performed
(Clark et al., 1964) . escaline was found to be more potent than mescaline in contracting
sheep umbilical artery strips (Nichols and Dyer 1977), and was among several phenethyl
amines and tryptamines that were compared in studies with rats (Kier and Glennon,
1978b) .

Escaline I EDA
Using molecular connectivity analysis of ten psychedelic phenethylamines, importance of

the 2,5-positions of the methoxy groups and the 4-substituent was demonstrated (Glennon
et al., 1979a) . Comparison made of steric properties with animal and human potency of sev
eral phenethylamines, tryptamines, and lysergide derivatives (Nichols, 1986a) . Me0-2C-SF
and Me0-2C-IFLY compared with mescaline and escaline in several tests including a two
lever discrimination assay in rats trained to distinguish LSD from saline (Monte et al., 1997)
Escaline is orally active in humans at 60 mg (Braun et al., 1978a), at 30-60 mg (Jacob and
Shulgin, 1984), and at 40-60 mg; duration 8-12 hours (Shulgin and Shulgin, 1991).
Legal Status
Escaline is not a scheduled compound under federal drug law, or under District of Colum
#65. EDA*
1-(2,3-Dihydrobenzo[b ] [1,4] dioxin-6-yl)propan-2-amine
a-Methyl-1,4-benzodioxan-6-ethylamine
3,4-Ethylenedioxyamphetamine
EDA-6
*In the code name EDA, the E can represent the first letter of either
ethylene or ethylidene. The present compound is the ethylene isomer, and has been called EDA-6 (as
it is a part of a six-membered ring; it is now known as simply EDA), the ethylidene isomer is either
EDA-5 or 7-Me-MDA (see #77).
Registry Numbers
CAS # CAS #
Synthesis
From 6-cyano methylbenzodioxan (with EtOAc, NaOEt) to 6-(a-cyanoacetonyl)benzodi
oxan; (with polyphosphoric acid) to 6-acetonalbenzodioxan; (with formamide, ethanolic
KOH) to EDA (Dauksas et al., 1966).

m / z: 193.1103 (100.0% ), 194.1136 (12.0%)
HCI salt m.p. 1 71-172.5 °C (Dauksas et al., 1966)

HCl salt m.p. 167-1 70 °C (Vallejos et al., 2005)
Freebase b.p. 133-135 C0 / 0. 1 mm (Dauksas et al., 1966)
A number of N-substituted derivatives were synthesized (Dauksas et al., 1966). Analysis of

human urine by LC-MS-MS methods has also been reported (Nordgren et al., 2004).

a- N- N- Name CAS # Ref
-
-- - -- ED PEA [22310-84-5] (1)
-- -CCCC- ED-pyr-PEA [13015-25-3] (1)
-- Me Me ED-N-DMPEA [10554-62-8] (1)

EDA / F
a- N- N- Name CAS # Ref

-- -CCOCC- ED-mor-PEA [ 1 0554-60-6] (1)
Me -- -- EDA (this entry)
Me Me -- EDMA [133787-66-3] (3-6)
Me Me Me ED-ND MA [15057-44-0] (1,2)
Me Et -- EDEA [15033-73-5] (2)
Me -CCOCC- ED-mor-A [15057-45-1 ] (1,2)
Me -CCCC- ED-pyr-A [1547-05-4] (1,2)
(1) Toxicity and hypotensive activity were assayed on mice (Skublickiene, 1968).
(2) Synthesis (Dauksas et al., 1966).
(6) Impurities in the precursors to illicit drugs and the drugs themselves can indicate the synthetic
routes used in their production (Cimeno et al., 2005).
Pharmacology
Toxicity and hypotensive activity were assayed on mice (Skublickiene, 1968). EDA has
been evaluated for MAO inhibition properties (Vallejos et al., 2005).
Threshold oral activity in humans at 150 mg (Shulgin and Shulgin, 1991 ) .
Legal Status
EDA is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#66. F
1 -(5-Methoxy-2,3-dihydrobenzofuran-6-yl)propan-2-amine
2,3-Dihydro-5-methoxy-a-methyl-6-benzofuranethanamine
Semi-fly
�--O-C H 3
Registry Numbers
CAS#
Methanesulfonate [99355-78-9]
Freebase [99355-77-8]
Synthesis
From 5-methoxy-2,3-dihydrobenzofuran (with N-methylformanilide, POCl) to 6-formyl-
5-methoxy-2,3-dihydrobenzofuran; (with nitroethane, acetic acid, and ammonium acetate)
to 5-methoxy-6-(2-nitro-1-propenyl)-2,3-dihydrobenzofuran; (with LAH) to F (Nichols et
al., 1986b).

m / z: 207.1259 (100.0% ), 208.1293 (13.0% )
Methanesulfonate m.p. 141-144 °C (Nichols et al., 1986b) (EtOH / Etp)
Methanesulfonate m.p. 148-151 °C (Nichols et al., 1991) (EtOH / Etp)

F / FEA

2- 3- 4- I 5- 6- Name CAS # Ref
MeO -- -CCO- -- F (this entry)
MeO -- -CCMeO- -- F-2 [85258-13-5] (1-5,6)
MeO -- -CCMe20- -- F-22 [952016-51-2] (1,4,5,7)
--
MeO -- -CMeCMeO- F-23 -- (5)
-
MeO -- -CMeFMeO- -- F-233 - (5)
(2) Synthesis and physical properties (Nichols et al., 1986b).
(3) Discrimination studies (with rats, against LSD) showed a low potency for both F-2 and the un
methylated homologue, F (Nichols et al., 1986b).
(4) Not orally active in humans at 15 mg (Shulgin and Shulgin, 1991 ) .
(5) Synthesis discussed, not attempted. These compounds were designed t o have a dimethyldihy
drobenzofuran ring reflecting the dimethyldihydrobenzopyran ring signature of tetrahydrocan
nabinol (THC) from Cannabis sativa. Two close homologues of F-2 are the 2,3-dimethyl and the
2,3,3-trimethyl compounds, F-23 and F-233. Synthetic approaches were explored but not com
pleted; they are unknown both chemically and pharmacologically (Shulgin and Shulgin, 1991),
although F-23 does have an assigned CAS # .
(6) Drug discrimination studies i n rats trained with LSD (Nichols e t al., 1986b).
(7) A CAS reference number indicates this compound (2,3-dihydro-5-methoxy-a,2,2-trimethyl
benzofuranethanamine) is available on the ARVI Product List, but otherwise is unknown to the
published scientific literature.
Pharmacology
Discrimination studies (with rats, against LSD) showed a low potency for both F and the
2-methyl homologue, F-2 (Nichols et al., 1986b, 1991).
Human activity of F is unknown.
Legal Status
F is not a scheduled compound under federal drug law, or under District of Columbia or
any state laws.
#67. PEA
2-(Furan-2-yl)ethanamine
2-Furylethylamine
2-Furanethanamine
Registry Numbers
CAS # CAS #
HCl salt [86423-58-7] Oxalate [856943-52-7]
cs2 salt [53356-38-0] Freebase [1121-46-6]

From furylproprionic acid (with EtOH, H2S04 ) to ethyl furylproprionate; (with hydrazine)
to the hydrazide; (with methoxybenzaldahyde) to the anisalhydrazide; (with NaN02,
CaO) to PEA (Windaus and Dalmer, 1920) .

FEA
Furfural ethyl chloroacetate, (with NaOEt, NHpH) to the oxime; (with Na, Hg) to FEA
(Asahina and Fujita, 1 922) .
Synthesis from the furylnitroethene precursor b y electrochemical methods (Takamoto, 1928) .
From �-2-furylacrylic acid (with NO) to �-nitro-2-furylethylene; (with Al, Hg) to 2-furylac
etaldoxime; (with Na, Hg) to FEA (Yabuta and Kambe, 1928) .
From 2-nitro-2-furylethene (with LAH) to FEA (Kametani et al., 1954; Kametani et al., 1956) .
From 1 -(2-furyl) 2-nitroethene (with LAH) to FEA (Novitskii et al., 1965).

rn / z: 111.0684 (100.0%), 112.0718 (6.5% )
Pierate rn.p. 129 °C (Windaus and Dalrner, 1920)

Carbarnate rn.p. 87 °C (Asahina and Fujita, 1922)
HCl salt rn.p. 190 °C (Karnetani et al., 1954) (EtOH)
HCl salt rn.p. 207-210 °C (Dornow and Gellrich, 1955) (EtOH / Etp)
Oxalate rn.p. 1 71-172 °C (Karnetani et al., 1956)
Picrolonate rn.p. 204 °C (Windaus and Dalrner, 1920) (Hp)
Picrolonate rn.p. 204-205 °C (Novitskii et al., 1965)

Ring Ring a- Other Name CAS # Ref
furan 2- -- -- FEA (this entry)
furan 2- Me -- a-Me-PEA [ 5 7580-64-0 l (1,2)
furan 2- Me 5-Br 5-Br-a-Me-FEA [ 860003-96-9] (1)
furan 2- -- N-Me N-Me-FEA [14497-54-2] (3)
furan 2- Me N-Me a,N-Me-FEA [ 63825-18-3] (3)
furan 2- Me -- a-Me-3-FEA [860003-93-6] (1,4)
tetrahydrofuran 2- -- -- TH-FEA [98277-97-5] (5-7)
tetrahydrofuran 2- Me -- a-Me-TH-FEA [ 1 00868-39-1 ] (3)
tetrahydrofuran 2- -- N-Me N-Me-TH-FEA [71259-74-0] (3)
tetrahydrofuran 2- Me N-Me a,N-Me-TH-FEA [ 98486-68-1 ] (1)
thiophene 2- Me --
-- ---- � ------- �
a-Me-ThEA [30433-93-3] (1,8-11)
thiophene 2- -- -- ThEA [861 88-24-1 ] (1,9,10,12)
thiophene --
2- -- N-Me N-Me-ThEA [7404-71-9] -�-
thiophene 2- Et -- a-Et-ThEA [5934-00-9] (11)
thiophene 2- Allyl -- a-A-ThEA [1 8620-27-4] (11)
thiophene 2- Me N-Me a,N-Me-ThEA [7464-94-0] (9)
thiophene 2- Me f3-Me a,f3-Me-ThEA [53387-69-2] (11)
thiophene 2- Me 4-Br 4-Br-a-Me-ThEA [ 860003-94-7] (1)
thiophene 2- Me 5-Br
-----··- --------- -· L-__-�-
5-Br-a-Me-ThEA
�-�--�---···
[860003-95-8] (1)

FEA
Ring Ring a- Other Name CAS # Ref

thiophene 2- Me -- 3-Cl-a-Me-ThEA [67482-59-1 ] (13)
thiophene 2- Me -- 4-Cl-a-Me-ThEA [67482-60-4] (13)
thiophene 2- Me -- 5-Cl-a-Me-ThEA [67482-58-0] (13)
thiophene 2- Me 3,4-Cl 3,4-Cl-a-Me-ThEA [67482-61-5] (13)
thiophene 3- -- -- 3-ThEA [ 34843-84-0 l (14)
-
thiophene 3- Me - a-Me-3-ThEA [86188-25-2] (1,14)
thiophene 3- -- N-Me N-Me-3-ThEA [857361 -89-8] (14)
thiophene 3- Me N-Me a,N-Me-3-ThEA [ 857361-90-1] (14)
pyrrole 2- -- -- NEA [ 40808-62-6] (15-18)
pyrrole 2- Me -- a-Me-NEA [ 90000-40-1 ] (19,20)
pyrrole 3- -- -- 3-NEA [73625-10-2] (20,21 )
pyrrole 3- Me -- a-Me-3-NEA [97561 -43-8] (20)
N-Me-pyrrole 2- -- N-Me NMEA [83732-75-6] (18,20)
N-Me-tetrahydropyrrole 2- -- N-Me TH-NMEA [ 422545-96-8] (18,22)
(1) Evaluated as a MAO inhibitor (Vallejos et al., 2005).
(2) Physical properties (Erlenmeyer and Simon, 1941).
(3) Synthesis (McCarthy and Kahl, 1956).
(4) Synthesis (Arnoldi et al., 1990).
(5) Synthesis (Windaus and Dalmer, 1920).
(6) Synthesis by electrochemical methods (Takamoto, 1928).
(7) Produces a strong constricting action on the uterus (Windaus and Dalmer, 1920).
(8) Produces pressor effects similar to amphetamine (Alles and Feigen, 1941).
(9) Synthesis (Blicke and Burckhalter, 1942) .
(10) Synthesis (Gilsdorf and Nord, 1950).
(11) Synthesis and hypoglycemic activity in fasted rats (Grisar et al., 1976).
(12) Synthesis (Suh et al., 1998) .
(13) Synthesis and action on central serotonergic mechanisms (Conde et al., 1978).
(14) Synthesis and physical properties (Campaigne and McCarthy, 1954) .
(15) Observations of histamine activity on the isolated guinea pig ileum (Lee and Jones, 1949).
(16) Effects on the gastric acid secretion of the dog (Grossman et al., 1952).
(17) Synthesis (Herz et al., 1956).
(18) Synthesis (Herz, 1953) (note that the N-Me is attached to the ring nitrogen).
(19) Synthesis (Herz and Toggweiler, 1964).
(20) Synthesis (Hamdan and Wasley, 1985).
(21 ) Synthesis (Osanova and Piskov, 1965).
(22) Synthesis (Rui et al., 2002) as a 5-HT7 receptor ligand. Many references to this material (under
CAS # [51387-90-7]) are patents referring to its use as a synthetic precursor to more complex
compounds.
Pharmacology
FEA produces a strong constricting action on the uterus (Windaus and Dalmer, 1920), and
pressor effects similar to amphetamine (Alles and Feigen, 1 941 ) .
Human psychoactive effects o f FEA are unknown.

FEA / FLY
Legal Status
FEA is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#68. FLY
1-(2,3,6, 7-Tetr ahydrobenzo[ 1,2-b :4,5-b'] difuran-4-y1 )propan-2-amine
1-(2,3,6,7-Tetrahydrobenzo[l,2-b:4,5-b'] difuran-4-yl)-2-aminopropane
2,3, 6, 7-Tetr ahydro-a-methy1-benzo[ 1,2-b: 4,5-b' ] difuran-4-ethanamine
Registry Numbers
CAS #
(±)-HCI salt [178557-11-4]
(±)-Freebase [219986-80-8]
R-(-)-Isomer, HCI salt [332012-16-5]
S-( +)-Isomer, HCI salt [332012-17-6]
S-( +)-Isomer freebase [769911-33-3]

From 4-formyl-2,3,6,7-tetrahydrobenzo [ l,2-b:4,5-b' ] difuran (see # 1 2, B-FLY) (with
nitroethane, acetic acid, and ammonium acetate) to 4-(2-nitro-1-propenyl)-2,3,6,7-
tetrahydrobenzo[l,2-b:4,5-b' ]difuran; (with LAH) to FLY (Monte et al., 1996).
From optically active (R- or 5-) alanine (with CF3 C02Et) to R- (or 5-) N-trifluoroacetylal
anine; (with oxalyl chloride, tetrahydrobenzo[l,2-b;4,5-b' ]difuran and AlCl) to R- (or 5-)
N-trifluoroacetyl-2,3,6,7-tetrahydro-4-alanylbenzo[l,2-b;4,5-b' ]difuran; (with Et3SiH) to R
(or 5-) N-trifluoroacetyl-l -(2,3,6,7-tetrahydrobenzo[l,2-b;4,5-b'] difuran-4-yl)-2-aminopro
pane; (with NaOH) to R- (or S-) FLY (Chambers et al., 2001).

m / z: 219.1259 (100.0% ), 220.1293 (14.1 % )
HCl salt m.p. 267-269 °C (Monte, et al., 1996) (EtOH / EtOAc)

R-(-)-Isomer HCl salt m.p. 275-276 °C [a] � -11 .78 (Chambers et al., 2001) (IPA)(dec.)
S-(+)-Isomer HCl salt m.p. 275-276 °C [a] � + 11.72 (Chambers et al., 2001) (IPA)(dec.)
History
The "FLY" name was inspired by the presence of two dihydrofuran rings that extend from
the opposite sides of the benzene ring. When aromatized (furan rings) they are planar
with the benzene ring leading to the code name "DRAGONFLY." They are listed as DFLY
derivatives.

2- I 3- 4- 5- I 6- a- Name CAS # Ref
-OCC- -- -OCC- -- 2C-FLY [178557-20-5] (1,2)
-OCC- -- -OCC- Me FLY (this entry)
-OCC- Br -OCC- -- 2C-B-FLY [733720-95-1] (2-5)

FLY
2- I 3- 4- 5- I 6- a- Name CAS # Ref

-OCC- I -OCC- -- 2C-I-FLY -- (6)
-OCC- I -OCC- Me I-FLY -- (6)
-OCC- Me -OCC- Me DOM-FLY [178557-22-7] (1,2)
-OCC- CF 3 -OCC- Me TFM-FLY [733730-70-6] (7,8)
-CCO- MeO -OCC- -- Me0-2C-2,6-IFLY [194787-78-5] (9-14)
-OCC- Me -CCO- Me Me-3,5-IFLY [ 497239-34-6] (9,15,16)
-OCCC- -- -OCCC- -- 2C-PLY [ 502924-26-7] (17,18)
-OCCC- -- -OCCC- Me PLY [502924-27-8] (17,18)
-OCCC- Br -OCCC- -- 2C-B-PLY [502659-24-7] (17-19)
-OCCC- Br -OCCC- Me B-PLY [ 502659-23-6] (17-19)
(1) Synthesis (Monte et al., 1996).
(2) Assayed in a drug discrimination paradigm with LSD-trained rats, and for interactions with
various serotonin receptors (Monte et al., 1 996).
(3) Orally active in humans at 2.5-10 mg (Shulgin, 2003).
(4) Synthesis (Monte et al., 1 996).
(5) Mass spectra of 2C-B-FLY, B-FLY and B-DFLY (Reed and Kiddon, 2007).
(8) The optical isomers of TFM-FLY were assayed for their affinity to 5-HT2A and 5-HT2c receptors
(Chambers et al., 2001).
(9) The code IFLY stands for iso-FLY, where the two furan oxygens are meta to one-another. The
2,6- and 3,5-prefixes denote where the furan rings are attached to the benzene ring.
(10) Syntheses described (Monte et al., 1997; Ahrendt et al., 2003; Thalji et al., 2005).
(11) The 4-bromo analogue is currently not in the chemical literature.
(12) Me0-2C-SF and Me0-2C-IFLY were compared with mescaline and escaline in several tests
including a two-lever discrimination assay with rats trained to distinguish LSD from saline
(Monte et al., 1997).
(13) Rapid methods for tricyclic mescaline analogue synthesis (Alberico and Lautens, 2006) .
(14) A norbornene-mediated palladium-catalyzed sequence is described (Alberico et al., 2007).
(15) This ring system, with 4-H, 4-MeO or 4-Br, is not in the published literature, nor are any of the
corresponding 2-C homologues.
(17) Synthesis, serotonin receptor binding affinity, and behavioral assays (Whiteside et al., 2002).
(18) Allowing the "F" in FLY to represent the furyl nature of the fused rings, then the "P" in the PLY
represents the pyryl nature of the fused ring system.
(19) Studied as serotonin agonists and activity on phospholipase systems (Kurrasch-Orbaugh et al.,
2003).
Pharmacology
Five "FLY" compounds (2C-FLY, 2C-B-FLY, FLY, B-FLY, and DOM-FLY) were assayed in a
drug discrimination paradigm with LSD-trained rats, and for their interactions with vari
ous serotonin receptors (Monte et al., 1996) . The optical isomers of each of three "FLY"
compounds (FLY, B-FLY, and TFM-FLY) and their DFLY counterparts (DFLY, B-DFLY, and
TFM-DFLY) were assayed for their affinity to 5-HT2A and 5-HT2c receptors (Chambers
et al., 2001 ) . The potency of several polysubstituted phenethylamine psychedelics was
changed by the relocation of just one substituent (Chambers et al., 2002).
Human activity of FLY has not been reported.

FLY / GEA
Legal Status
FLY is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#69. GEA
4-(2-Aminoethyl)-2-methoxyphenol
4-Hydroxy-3-methoxyphenethylamine
4-(2-Aminoethyl)guaiacol
Guaiacylethylamine
Homovanillylamine
3-0-Methyldopamine
Methoxytyramine
3-Methoxytyramine
Vanillylethylamine
Vanillyl-PEA
4-H0-3-MeO-PEA
MHPEA
3-MT
Registry Numbers
CAS # CAS # CAS #
HCl salt [1477-68-5] (x)-Picrate [129111-14-4] 2,5,6,a,j)-[ d 5 ] [ 83008-35-9]
HBr salt [53799-05-6] Acid salt [100098-95-1 ] a,j3-[ 3H]2 HCI salt [27954-87-6]
HI salt [52532-94-2] Freebase [554-52-9] a,j3-[ 3H]2 Freebase [801201-30-9]
Acetate [97289-40-2] 5-[d] [81587-01-1] [14C]-labeled [131889-58-2]
Monopicrate [94001-17-9] 2,5,6-[d3 ] HCl salt [53587-31-8] NaV04 adduct [892247-47-1 ]
Perchlorate [144576-58-9] a, j)-[ d4 ] Freebase [74719-64-5]
Natural Sources
GEA was present i n the cactus Trichocereus pachanoi (Agurell and Lundstrom, 1 968; Crosby
and McLaughlin, 1 973), T. werdermannianus (as a possible biosynthetic precursor of mesca
line; Agurell, 1 969b), and T. peruvianus (Agurell, 1 969a; Pardanani et al., 1 977) .
The cactus Echinocereus merkeri contained DMPEA, N-Me-DMPEA, N,N-Me-DMPEA, hor

denine, and GEA (Agurell et al., 1969) . The cactus Carnegiea gigantea also contained GEA
(Bruhn and Lundstrom, 1976), as did Opuntia spinosior (Pardanani et al., 1 977), Pachycereus
pecten-aboriginum (Strombom and Bruhn, 1 978a), Pereskia grandifolia, P. corrugata, P. grandi
folia, Pereskiopsis chapistle (Doetsch et al., 1980), and Epithelantha micromeris (Starha, 1995).
Tyramine, 3-methoxytyramine, hordenine, and N-methyltyramine were found in 0. cylin
dropuntia and other Opuntia spp. (Meyer et al., 1980) . GEA and the tetrahydroisoquinoline
lemaireocereine were found in Backebergia militaris (Pummangura and McLaughlin, 1981).
Reported to be present in Acacia berlandieri (Clement et al., 1 997), and A. rigidula (Clem
ent et al., 1998) . GEA was isolated from the undifferentiated tissue of a Nicotiana tabacum
crown gall tumor (Mitchell et al., 1 984) .

From 4-benzyloxy-3-methoxybenzaldehyde (with nitromethane ) to 1 -(4-benzyloxy-3-
methoxy)-2-nitroethene); (with Zn and acetic acid) to 4-benzyloxy-3-methoxyphenylace
toxime; (with Na, Hg) to 4-benzyloxy-3-methoxyphenethylamine; (with cone. HCI) to GEA
(Kobayashi, 1 927) .

GEA
From vanillin (with nitromethane) to 4-hydroxy-3-methoxy-B-phenylnitroethene; (with

LAH) to GEA (Ramirez and Burger, 1950; Kametani et al., 1963) .
The above phenylnitroethene can also be reduced to GEA by Clemensen reagent (Zn,
HgC12) (Sheth and Tolkachev, 1 968), or electrically (Wang et al., 1983) .
Synthesis and spectral characterization o f MBDB, BOB, GEA, and N-Me-a-Et-GEA has
been reported (Kanamori et al., 1 999).

ml z: 167.0946 (100.0% ), 168.0980 (9.7% )
HCl salt m.p. 210-211 °C (Kobayashi, 1927)

HCl salt m.p. 213-214 °C (Ramirez and Burger, 1950) (MeOH / EtOAc)
HCl salt m.p. 203-206 °C (Sheth and Tolkachev, 1968)
Chloroplatinate m.p. 211 °C (Kobayashi, 1927)
Picrate m.p. 194-196 °C (Kobayashi, 1927; Kametani et al., 1963)
Picrate m.p. 198-199 °C (Ramirez and Burger, 1950) (H20)
Freebase m.p. 156-157 °C (Kobayashi, 1927)
Freebase m.p. 153-154 °C (Sheth and Tolkachev, 1968)
Specific ion-exchange chromatography and fluorimetric assays were developed for urinary
GEA (Dalmaz and Peyrin, 1 976) . Mass spectrometric assays were performed for GEA in rat
brain (Galli et al., 1976; Wiesel, 1 976) and the caudate nucleus (Kilts et al., 1977) . Rapid
and simple methods for the determination of picogram levels of 3-methoxytyramine and
GEA in brain tissue used liquid chromatography with electrochemical detection (Ponzio
et al., 1981; Jouve et al., 1 983) . Three catecholamines (dopamine, norepinephrine, and epi
nephrine), and their 3-methyl ethers (GEA, metanorepinephrine, and norephedrine) were
distinguished from one another in single GC / MS runs (Tas et al., 1 984) . GEA in urine was
isolated and fluorometrically determined in tissues (Maruchin and Olesinski, 1 986). Uri
nary normetanephrine, metanephrine and 3-methoxytyramine were measured by high
performance liquid chromatography (Volin, 1992) .
Biochemistry
GEA, DESMETHYL, and 3,4-DESMETHYL found to be biosynthetic precursors of mesca
line in Lophophora williamsii, but HMPEA and 3-DESMETHYL were not. The role of dopa
mine as a precursor was proposed (Rosenberg et al., 1969); this pathway was confirmed in
L. williamsii, with 3-0-methylation of dopamine (to GEA) , then 5-hydroxylation to 3,4-DES
METHYL (Lundstrom, 1971b). Radioactive dopamine fed to Trichocereus pachanoi was also
3-0-methylated to give GEA, leading to both DMPEA and mescaline (Lundstrom, 1970a).
GEA affects alkaline phosphatase activity and pyruvate utilization in rat brain homog
enates (Clark et al., 1 956) . Metabolism of GEA was studied in the rat (Goldstein et al., 1 959),
and agonist and antagonist activity with dopamine B-oxidase was observed (Creveling et
al., 1 962) .
Dopamine and [ 1 4C]-labeled S-adenosylmethionine, incubated in rat liver, formed GEA

and HMPEA but no DMPEA (Kuehl, 1 967) . GEA (3-methoxytyramine, a metabolite of
dopamine) is 5-hydroxylated in rat or rabbit liver hydrogenates to form 3,4-DESMETHYL,
a potential precursor to analogues of mescaline (Benington and Morin, 1 968). About 2%

GEA / HMePEA
of [ 1 4 C]-labeled MDPEA given to a rat is excreted as GEA and dopamine (Schweitzer

et al., 1 978) . MBDB, administered orally to male rats at 20 mg / kg, was excreted in part
unchanged, and as the three metabolites BOB, GEA, and N-Me-GEA (Kanamori et al.,
1998a) .
The GEA level was found unsuitable as an indicator of synaptic dopamine release by some
researchers (Vulto et al., 1 986), in contrast with the results of others (Waldmeier et al.,
1981; Westerink and Spaan, 1 982) . GEA had no effect on isolated human ceruloplasmin
catalyzed serotonin oxidation, in vitro (Barrass and Coult, 1972) . Serotonin receptor agonist
activity was characterized (Glennon et al., 1980b).
GEA levels in human cerebrospinal fluid were determined by GC with electron capture
detection (Ota et al., 1 973); chromatographic methods for the isolation and determination
of 3-methoxytyramine in brain tissue were described (Kehr, 1974) . GEA accumulates in
postmortem tissue in the rat brain (Carlsson et al., 1974); this phenomenon in humans has
been suggested as a forensic tool in the estimation of the time of death (Sparks et al., 1 984) .
Postmortem increase in GEA is linear (up to 55 hours and regardless of the age of the per
son) when used to establish the time of death (Sparks et al., 1 986) .
Voluntary alcohol drinking in trained rats selectively accelerates dopamine release in the
ventral striatum as reflected by 3-methoxytyramine levels (Honkanen et al., 1997) . Uri
nary GEA levels explored as evidence of possible dopamine administration to race horses
(Wynne et al., 2004) .
Pharmacology
GEA produced cataleptic activity in mice (Michaux and Yerly, 1963) . GEA effectiveness
in releasing cardiac norepinephrine was measured (Daly et al., 1 966). DMPEA was not
formed by the action of 0-methyltransferase on dopamine but both monomethyl com
pounds were products (Kuehl et al., 1 964) . GEA was included in a study of relationships
between possible psychedelic activity and electronic configuration (Snyder and Merril,
1965). GEA produced a hypokinetic rigid syndrome in cats (Ernst, 1965a), and pharma
cological effects were observed following i.v. administration of 1 mg to a cat (Talalaenko,
1971). The continuous intrastriatal injection of GEA in awake, freely moving rats produced
motor dysfunction similar to those produced by cholinergic stimulation (Little and Dill,
1969). The medial prefrontal cortex mediates GEA-induced behavioral changes in the rat
(Nakazato, 2002) . The possible role of GEA as the endogenous toxin in psychosis was dis
cussed (Dill and Campbell, 1973) .
Human activity o f GEA i s unknown.
Legal Status
GEA is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
# 70. HMePEA
4-(2-(Methylamino )ethyl)phenol
N-Methyl-2-(4-hydroxyphenyl)ethylamine
4-Hydroxy-N-methylphenethylamine
N-Methyltyramine
NSC 113958

HMePEA
Registry Numbers
CAS # CAS # CAS #
HCl salt [13062-76-5] Hydroxycitrate [923587-27-3] Freebase [370-98-9]
HBr salt [61186-07-0] Oxalate [2419-58-1 ]
Natural Sources
N-Methyltyramine isolated from the roots of barley strains (Kirkwood and Marion, 1 950).
HMePEA is widely distributed in the cacti. It was found in Lophophora williamsii (Lundstrom
and Agurell, 1968a), in Ariocarpus fissuratus and A. lloydii (McLaughlin, 1969), A. retusus (Bra
ga and McLaughlin, 1969), A. kotschoubeyanus (Neal et al., 1971 a), A. scapharostrus (Bruhn,
1 975), and in trace quantities in A. trigonus (Speir et al., 1970) . Found in seven species of
yonii (Keller et al., 1973), and C. (Neobesseya) missouriensis (Pummangura et al., 1981). Found
Coryphantha (Hornemann et al., 1972), C. ramillosa (Sato et al., 1973), C. macromeris var. run
in seven species of the cactus genus Gymnocactus, specifically G. aguirreanus, G. beguinii, G.

horripilus, G. knuthianus, G. mandragora, G. roseanus, G. viereckii (West et al., 1974), and in
other members of the genus Gymnocalycium (Starha, 1996). Found in the cactus Trichocereus
spachianus, and T. candicans (Mata et al., 1976). Identified in Dolichothele surculosa and other
Dolichothele species (Dingerdissen and McLaughlin, 1973), in the cactus Opuntia cylindropun
tia and other Opuntia spp. (Meyer et al., 1980). HMePEA was found in Lobivia backebergii, L.
binghamiana, L. pentlandii, and Pseudolobivia kermesina (Follas et al., 1977), Pilosocereus maxonii
(Pummangura et al., 1977) and Islaya minor Backbg. (Doetsch et al., 1980) . Mescaline, tyra
mine, and HMePEA were isolated from Opuntia ficus-indica (El-Moghazy et al., 1984) .
HMePEA was found i n Desmodium gangeticum (Ghosal and Bhattacharaya, 1 972), the suc
culent Stapelia gigantea (Meyer et al., 1981), and the Central Asian desert tree Haloxylon
salicornicum (El-Shazly et al., 2005) . HMePEA has been isolated from Acacia berlandieri (Ad
ams and Camp, 1 966; Clement et al., 1 997), from A. rigidula (Clement et al., 1998), and, as
a minor component, from A. augustissima (McSweeney et al., 2005). HMePEA has been a
known constituent, and is alleged to contribute to ruminant toxicity in Phalaris aquatica L.
(syn. P. tuberosa) (Culvenor et al., 2005). Recent research disproved this compound's role in
the Phalaris "sudden death" syndrome in sheep (Bourke et al., 2006).
HMePEA is found in beer (Kimura et al., 2000), and in preparations of Citrus aurantium
(bitter orange)(Dai and Xiong, 1 989; Nelson et al., 2007) .

From 4-hydroxyphenylglyoxal (with N-methylbenzylamine and Raney Ni, H2) to 1 -(4-
hydroxyphenyl)-2-(methyl(phenyl)amino)ethanone (HOC6H4COCH2N(CH3 )CH2C6H5 );
(with N-methylamine) to HMePEA (Fodor and Kovacs, 1951).

m l z : 151.0997 (100.0%), 152.1031 (9.7% )
Elemental Analysis: C, 71 .49; H, 8.67; N, 9.26; 0, 1 0.58
HCI salt m.p. 149-150.5 °C (Platanova et al., 1958)

Picrate m.p. 148-148.5 °c (Platanova et al., 1958)
Freebase m.p. 133-134.5 °C (Platanova et al., 1958) (acetone)
Ultraviolet absorption spectra and apparent acidic dissociation constants were determined
(Kappe and Armstrong, 1965).

HMePEA / Hordenine
Biochemistry
Effects were reported on alkaline phosphatase activity and pyruvate utilization in rat brain
homogenates (Clark et al., 1 956). Studies were made of both agonist and antagonist activ
ity with dopamine f3-oxidase (Creveling et al., 1 962) . Action on the CNS of the chicken was
evaluated (Dewhurst and Marley, 1 965). Effectiveness of releasing cardiac norepinephrine
from the mouse heart was measured (Daly et al., 1 966) .
The pressor-activity rating was predicted by pattern recognition of molecular structures

(Zotov and Altymyshev, 1 980).
Pharmacology
The Asian herbal Zhishi (Citrus auriatum L.) contains HMePEA and synephrine, and is fre
quently consumed as a food supplement for weight loss and energy enhancement (Nelson
et al. 2007) . Experiments to study potential in treatment of shock showed this material was
not effective in correcting myocardial abnormalities in rabbits, in contrast with ginsen
oside and clonidine (Chen et al., 1981), although it did have cardiovascular activity in mice
and rats, and increased plasma and myocardial cGMP and cAMP (Yen et al. 1 983) . As a
clinical agent in shock intervention, administration of synthetic synephrine and HMePEA
produced cardiotonic, pressor, and diuretic effects in children and adults, and exhibited
limited side-effects (Dai and Xiong, 1989) . Absorbtion and metabolic profiles of HMePEA
from beer were studied in the rat, and it was shown to be a potent stimulant for gastrin
release (Kimura et al. 2000)
Human central effects from HMePEA are unknown.
Legal Status
HMePEA is not a scheduled compound under federal drug law, or under District of Co
# 71. Hordenine
4-(2-(DimethyI amino )ethyI )phenol
N,N-Dimethyl-4-hydroxyphenethylamine
N,N-Dimethyltyramine
Anhalin
Anhaline
Cactine
Eremursine
Hordenin
Ordenina
Peyocactine
m-Tyramine
Registry Numbers
CAS # CAS #
HCl salt [6027-23-2] Sulfate [622-64-0]
HBr salt [6027-24-3] Sulfate hydrate [ 60411-16-7]
Bisulfate [62493-39-4] Sulfate dihydrate [6202-1 7-1]
Camphorsulfonate [113038-79-2] ( + )-Tartrate [ 6209-35-4]
Phosphate, anhydrous [123830-49-9] ( + )-Bitartrate [17350-73-1 ]
Phosphate, hydrate [ 123830-50-2] Freebase [539-15-1]
Pi crate [5990-96-5]

Hordenine
Natural Sources
Un-sprouted barley contains no hordenine, but it appears following germination. During
the four days immediately after germination, the hordenine content was highest, and de
creased as the embryo grew older, so that after 25 days no hordenine was present (Torquati,
1911). The accumulation of hordenine in the seedlings of Panicum miliaceum continues for
at least eight days (Demaree and Tyler, 1956) . Both hordenine and gramine are biosynthe
sized in barley malt during germination (Mangino and Scanlan, 1 984) . Ten grams of fresh
barley rootlets, upon extraction with dilute sulfuric acid and clean-up, yielded 1 .2 mg of
pure hordenine (Raoul, 1934) . The major source of hordenine consumption in humans is
from beer brewed from barley (Singh et al., 1 992) .
An alkaloid (anhaline) from Lophophora williamsii was shown to be hordenine (Spath, 1919),
and further proven to be identical with hordenine by the comparison of the mixed melting
points of the picrate, the perchlorate, the methiodide, and the 0-acetyl ester hydrochloride
(Spath, 1921 ) . The L. williamsii alkaloid peyocactin was shown to be hordenine (Rao, 1970).
It has also been found in L. williamsii by others (Lundstrom and Agurell, 1968a), and in
Ariocarpus kotschoubeyanus (Neal et al., 1971a), A. fissuratus, vars. fissuratus and lloydii
(McLaughlin, 1969), A. retusus (Braga and McLaughlin, 1969), A. trigonus (Speir et al.,
1970), Echinocereus merkeri (Agurell et al., 1969), Gymnocalycium saglione (Nieto et al., 1982),
Gymnocalycium spp. (Starha, 1996), Cereus aethiops and Gymnocalycium schickendantzii (Ruiz
et al., 1 973), Mammillaria microcarpa (Howe et al., 1977a), Obregonia denegrii (Neal et al.,
1971b), Islaya minor Backbg. (Doetsch et al., 1980), Ariocarpus agavoides and Pelecyphora asel
macromeris var. runyonii (Keller et al., 1973) and C. ( Neobesseya ) missouriensis (Pummangura
liformis (Bruhn and Bruhn, 1973; Neal et al.,1 972), Coryphantha ramillosa (Sato et al., 1973), C.
et al., 1981), seven species of the cactus genus Gymnocactus, specifically G. aguirreanus,
G. beguinii, G. horripilus, G. knuthianus, G. mandragora, G. roseanus, and G. viereckii (West
et al., 1974), Ariocarpus scapharostrus (Bruhn, 1975), Lobivia backebergii, L. binghamiana, L.
pentlandii, and Pseudolobivia kermesina (Follas et al., 1977), Espostoa huanucensis (Mata et al.,
1976), Dolichothele surculosa and other Dolichothele species (Dingerdissen and McLaughlin,
1973), Turbinicarpus species (Starha et al., 1999), seven species of Coryphantha (Hornemann
et al., 1972), and the Opuntia subgenera Cylindropuntia and other Opuntia spp . (Meyer et al.,
1 980). Hordenine was found in Coryphantha greenwoodii, C. bumamma, and three additional
species (Bruhn et al., 1975), and was the sole alkaloid found in Coryphantha vivipara var
arizonica (Howe et al., 1 977b). Hordenine, along with tyramine, 3-methoxytyramine, and
N-methyltyramine were found in Opuntia species (Meyer et al., 1980). Hordenine was iso
lated from Stapelia gigantea (Keller, 1981), and hordenine, its glucoside and its acetate ester,
the quaternary amine candicine, and the flavone luteolin were isolated from the African
cactus S tapelia hirsuta L., commonly known as window sill cactus (Shabana et al., 2006) .
Hordenine, tyramine, and HMePEA were isolated from Acacia berlandieri and Lophophora
williamsii (Adams and Camp, 1966; McLaughlin and Paul, 1 966) .
Extraction of NH40H moistened leaves and twigs of Acacia harpophylla, and similarly
treated tissues of A. holosericea, A. kettlewelliae, A. adunca, and A. harpophylla produced hor
denine (Fitzgerald, 1 964) . Hordenine was reported in A. berlandieri (Clement et al., 1 997),
A. rigidula (Clement et al., 1998), and in fresh trunk bark from A. spirorbis (Poupat and
Sevenet, 1 975) . Hordenine has been isolated from Pancratium maritimum (Sandberg et al.,
1963), and from the roots of Securinega virosa (Iketubosin and Mathieson, 1963) . Hordenine
has been found in the legumes Desmodium gangeticum (Ghosal and Bhattacharaya, 1972),
D. tiliaefolium (Ghosal and Srivastava, 1 973a), in the stem (and to a lesser extent, the root)

Hordenine
of Alhagi pseudalhagi (Ghosal and Srivastava, 1973b), in Desmodium triflorum (Ghosal et al.,
1 973) and D. floribundum G. Don. (Maurya et al., 1 985) . Hordenine was isolated from Sele
nicereus grandiflorus and S. pteranthus (Petershofer-Halbmayer et al., 1 982), from shrubs of
the Rhamnaceae: Sageretia hamosa, S. henryi, S. melliana, and S. thea (Zhong et al., 1 994), and
from Aconitum tanguticum (Wang et al., 2002), Ephedra aphylla (Abdel-Kader et al., 2003),
and Haloxylon salicornicum (El-Shazly et al., 2005) .Hordenine was identified in the dried
leaves of Cannabis sativa (El-Feraly and Turner, 1975) .
Reed canary grass (Phalaris arundinacea) contains both hordenine (Audette et al., 1969) and
several indolealkylamines; meadow voles were used to estimate the toxicity of this grass
as forage material (Goelz et al., 1980). Quantitative analyses were made of P. arundinacea
(Duynisveld et al., 1990; Kalen et al., 1992). Hordenine and 5-MeO-NMT (5-methoxy-N
methyltryptamine) were also isolated from P. arundinaceae (Wilkinson, 1 958; Bourke et al.,
1988) . The acute toxicity of Phalaris aquatica (also known as P. tuberosa, Harding grass) is pur
ported to be due to three alkaloids that are present: gramine, 5-MeO-DMT, and hordenine
(Bourke et al., 1988), though other phenethylamines have also be implicated (Culvenor et
al. 2005; Bourke et al., 2008) .
Hordenine has been also observed in the marine algae Phyllophora nervosa (Guven et al.,
1 969, 1 970), Ahnfeltia paradoxa (Kawauchi and Sasaki, 1978), and the marine red alga Gigar
tina stellata (Barwell and Blunden, 1 981 ) .

From 4-methoxyphenethylamine (with methyl iodide) to N,N-dimethyl-4-methoxy
phenethylamine; (with HI) to hordenine (Rosenmund, 1910).
From phenylethanol (with CHCly PC15 ) to a-chloro-�-phenylethane; (with dimethylamine,

100 °C for several hours) to a-dimethylamino-�-phenylethane; (with HN03 at -10 °C) to a
dimethylamino-�-(p-nitrophenyl)ethane; (with oxalic acid) to a-dimethylamino-�-(p-nitro
phenyl)ethane oxalate; (with EtOH, Sn, HCl; then NaOH, ext. w / Et20) to the "crude amino
compound"; (with H2S04, NaN02) to hordenine (Barger, 1910).
From 4-methoxyphenyl chloromethyl ketone (with dimethylamine) to 4-methoxyphenyl

N,N-dimethylaminomethyl ketone; (with HI) to 4-hydroxyphenyl-N,N-dimethylamino
methyl ketone; (with HI and P under pressure) to hordenine (Voswinckel, 1911).

m / z: 165.1154 (100.0%), 166.1187 (10.8%)
HCl salt m.p. 1 80-1 81 °C (Fitzgerald, 1964)
Methiodide m.p. 229-230 °C (Rosenmund, 1910) (Hp)
Methiodide m.p. 229-230 °C (Barger, 1910) (MeOH)
Methiodide m.p. 228-231 °C (Fitzgerald, 1964)
Picrate m.p. 140 °C (Fitzgerald, 1964)
Picrolonate m.p. 221-224 °C (Fitzgerald, 1964)
Freebase m.p. 119-120 °C (Fitzgerald, 1964)
(Kappe and Armstrong, 1965) . The crystal structure of hordenine sulfate was determined
(Chose and Dattagupta, 1989); two polymorphs of hordenine crystals are known (Parvez
and Malone, 1991).

Hordenine
Analysis of human urine containing hordenine can give false positive tests for several mor
phine-related alkaloids (Singh et al., 1992) .

HO N- Other Name CAS # Ref
2 -- -- 2-HPEA [2039-66-9] (1-4)
2 Me -- N-Me-2-HPEA [154585-1 8-9] (5)
2 Me2 -- N,N-Me-2-HPEA [94-54-2] (6)
2 -- f3-HO [3-H0-2-HPEA [2234-25-5] (1,7)
3 -- -- 3-HPEA [588-05-6] (1,8-14)
3 -- f3-HO [3-H0-3-HPEA [536-21-0] (1,2,12,14,15)
3 Me -- 3-HMPEA [51674-33-0] (16)
3 Me [3-HO [3-HO-N-Me-3-HPEA [54-04-6] (7,12, 14)
3 Me2 -- N,N-Me-3-HPEA [ 60189-30-2] (6)
3 Me3 -- Leptodactyline [13957-33-0] (17)
4 -- f3-Me f3-Me-HPEA [90765-58-5] (2,8,9)
4 -- f3-HO f3-HO-HPEA [104-14-3] (12,18,19)
4 Me f3-HO f3-HO-N-Me-HPEA [1477-63-0] (1,8,20-26)
4 Me f3-Me0 f3-MeO-HMePEA [25006-35-3] (24,27,28)
4 Me 0-Ac AcO-MePEA [99985-96-3] (16)
4 Me2 -- Hordenine (this entry)
4 Me2 [3-HO f3-HO-Hordenine [2039-58-9] (1)
4 Me2 0-Ac Hordenine acetate [857767-21-6] (30-32)
4 Me3 + -- Candicine [ 198821-67-9] (29,32-37)
(1) Ultraviolet absorption spectra and apparent acidic dissociation constants (Kappe and Armstrong,
1965) .
(3) Serotonin agonist evaluation (Glennon et al., 1980b).
(4) Synthesis via electrolytic reduction of the nitrostyrene (Kondo and Tanaka, 1932) .
(7) Effective at releasing cardiac norepinephrine (Daly et al., 1966).
(8) Studies of agonist and antagonist activity with dopamine f3-oxidase (Creveling et al., 1962) .
(9) Also known as octopamine.
(10) Human metabolism of PEA observed by the oral administration of deuterium-labeled PEA. The
major metabolite was phenyl acetic acid, but 3-HPEA and 4-HPEA were detected in significant
amounts along with their respective hydroxylated phenyl acetic acids (Davis and Boulton, 1980).
(11) Involvement in hyperactivity induction by phenethylamine derivatives (Costall et al., 1976).
(12) The pressor-activity rating was predicted by features of molecular structures (Zotov and Alty
myshev, 1980).
(13) The relationship between psychedelic activity and electronic configuration was established
(Snyder and Merril, 1965).
(14) Kinetics of mydriatic action of f3-HO-DHA on the mouse iris (Freundt, 1973).
(15) Several compounds tested at microgram levels as plant growth inhibitors (Mandava et al., 1981).

Hordenine
(17) The effects on the Heobania vermiculata nerve cell firing were studied (Avoli et al., 1978) .
(18) A procedure for extraction and separation of phenethylamine, tyramine, and octopamine from
human plasma (Baker et al., 1980).
(19) In a large number of methoxylated amphetamines, rabbit hyperthermia paralleled human po
tency as psychedelics (Anderson et al., 1978b).
(20) Also known as m-hydroxy-a-[(methylamino)methyl]-benzyl alcohol, Mesatone, Metasympatol,
Mezaton, Oxedrine, Neo-Synephrine, m-Sympathol, m-synephrine, and Visadron.
(21 ) Action on the iris of the cat (Marley, 1962).
et al., 1956).
(23) Isolated from seven species of Coryphantha (Hornemann et al., 1972).
(24) Found in the cactus Coryphantha ramillosa (Sato et al., 1973).
(25) Found in the cactus Coryphantha macromeris var. runyonii (Keller et al., 1973).
(26) Found in Dolichothele surculosa and other Dolichothele species (Dingerdissen and McLaughlin, 1973).
(27) Synonyms: 4-[1-methoxy-2-(methylamino)ethyl]-phenol, [3-0-methylsynephrine.
(28) Found in the cactus Coryphantha greenwoodii (Bruhn et al., 1975) .
(29) Hordenine, the acetate ester, the quaternary amine candicine, and the flavone luteolin were
isolated from the African succulent Stapelia hirsuta L., commonly known as windowsill cactus
(Shabana et al., 2006).
(30) CC characterization (Brooks and Horning, 1964).
(31) LD50 for mice was determined (Aliev et al., 1967).
(32) Found in Trichocereus candicans (Luduena, 1933), Magnolia grandiflora (Nakano, 1954), Lophophora
williamsii (McLaughlin and Paul, 1966), Desmodium gangeticum (Ghosal and Bhattacharya,
1972; Ghosal et al., 1972), Cereus aethiops and Gymnocalycium schickendantzii (Ruiz et al., 1973),
Trichocereus pasacana (Meyer and McLaughlin, 1980), Stapelia gigantea (Meyer et al., 1981), and
Hordeum distichon (Urakawa et al., 1961).
(33) Synthesis (Meyer and McLaughlin, 1980).
(34) Candicine is also known as Maltoxin (Urakawa et al., 1961 ).
(35) Synthesis and physical properties (Barger, 1910).
(36) Found in Desmodium gangeticum (Ghosal and Bhattacharaya, 1972).
(37) Isolated from Stapelia hirsute accompanied by the glucoside ester and the N-acetyl derivative
(Shabana et al., 2006).
Biochemistry
Radiolabeling showed that tyrosine was the biosynthetic precursor to both HMePEA and
hordenine in barley (Leete and Marion, 1 953) .
Action on isolated frog heart was studied (Ellis, 1 949) . LD50 for mice determined (Aliev et
al., 1 967) . Effects on the Heobania vermiculata nerve cell firing studied (Avoli et al., 1 978) .
Pharmacology
Tyramine (HPEA) and N-methyltyramine (HMePEA) were equally effective as pressors and
bronchodilators (at 1 µg / kg). Hordenine is only one tenth as potent, but the quaternary salt
(HMe3PEA) was more potent than all three (Alles, 1 933). Hordenine has sympathacolytic
actions; large doses decreases or inverts the hypertensive action of adrenaline (Raymond
Hamet, 1 936) .
Enzymatic oxidative deamination and behavioral effects on the cat were observed (Clark
et al., 1 964); hordenine was also studied in relationship to the compulsive gnaw syndrome
in the rat (Ernst, 1 965b). Hordenine, in i.v. and oral administration in sheep, induced the
clinical signs of Phalaris toxicity but not the cardiac sudden death syndrome (Bourke et al.,
1 988, 2006).

Hordenine I IM
Hordenine was studied in laboratory animals, along with 32 other ring-substituted

phenethylamines, as protective agents against ionizing radiation (Il'yuchenok et al., 1 976) .
The occasional observation o f hordenine i n the urine of racehorses led t o a pharmacologi

cal study of hordenine administration for performance enhancement (Frank et al., 1 990;
Hapke and Strathmann, 1 995) .
Human psychoactivity of hordenine is unknown.
Legal Status
Hordenine is not a scheduled compound under federal drug law, or under District of Co
# 72. IM
2-(2,3,4-Trimethoxyphenyl)ethanamine
2,3,4-TMPEA
2,3,4-Trimethoxyphenethylamine
Isomescaline
Reciprocal mescaline
2C-TMA-3
TMPEA-3
Registry Numbers
CAS # CAS #
HCI salt [3166-75-4] Acid salt [87059-74-3]
Oxalate [100009-75-4] Freebase [3937-16-4]
Picrate [4668-1 0-4]

From 2,3,4-trimethoxybenzaldehyde (with malonic acid) to 2,3,4-trimethoxycinnamic acid;
(with Na, Hg) to 2,3,4-trimethoxyphenylpropionic acid; (with NH3 ) to 2,3,4-trimethoxy
phenylpropionamide; (with NaOCl) to IM (Slotta and Heller, 1 930) .
From 1-(2,3,4-trimethoxyphenyl)-2-nitroethene (with electrolytic reduction) to IM (Slotta

and Szyszka, 1 933) .
From 2,3,4-trimethoxyphenylbenzaldehyde (with nitromethane) to 1 -(2,3,4-trimethoxy

phenyl)-2-nitroethene; (with LAH) to IM (Erne and Ramirez, 1 950).

m / z: 211. 1208 (100.0% ), 212.1242 (11.9%)
HCl salt m.p. 167 °C (Slotta and Szyszka, 1933)

Pi crate m.p. 137 °C (Slotta and Szyszka, 1933)

2- 3- 4- Name CAS # Ref
MeO MeO Meo IM (this entry)
MeO MeO Mes 4-TIM [78335-87-2] (1,2)

IM

MeO Mes Meo 3-TIM [78335-86-1 ] (1,3)
Mes MeO MeO 2-TIM [75510-74-6] (1,4)
EtO EtO EtO I-TRIS [876486-72-5] (5)
(2) Not orally active in humans (7 subjects) at 160 mg (Jacob and Shulgin, 1981).
(5) Synthesis (Slotta and Szyszka, 1933).
The conformation of the aryl methoxy groups of several psychedelics was established
by [ 13 C] NMR spectrometry (Knittel and Makriyannis, 1981 ) . [ 13 C] NMR spectra for
methoxylated phenethylamines and amphetamines were found to be distinctive, and
suitable for identification (Bailey and Legault, 1983) . Analysis was developed for HPLC,
employing fluorescamine derivatization for fluorescence detection (Shimamine, 1 984) .
IM was part of a study of the fragmentation patterns of some fifty-five phenethylamines,
determined by a variety of mass spectrometry techniques (Kolliker and Oehme, 2004).
Biochemistry
Isomescaline was found to be a stimulant of uterine activity (Kudrin et al., 1 963) . Effects of
ring methoxy groups on oxidative deamination were evaluated (Clark et al., 1 965). Mesca
line and IM were compared for susceptibility to oxidative deamination with in vitro mouse
brain studies (Seiler and Demisch, 1 971 ); in the mouse, mescaline and IM were metabolized
to the corresponding phenylacetic acids (Seiler and Demisch, 1 974) . Regional distribution
of tritium-labeled mescaline and IM was studied in the mouse (Korr and Seiler, 1 976) .
Mescaline produced a four-fold increase o f prolactin i n human serum, whereas I M had no

effect (Demisch and Neubauer, 1 979) . Demethylation of IM in schizophrenic patients was
measured before and after L-methionine loading (Antun and Kurkjian, 1 982) .
Pharmacology
Studies on the enzymatic oxidative deamination and effects on cat behavior were per
formed (Clark et al., 1 964) . The relationship between psychedelic activity and electronic
configuration was established (Snyder and Merril, 1 965) . Effects of IM on mouse behavior
and the activity of the brain enzymes MAO and DOPA decarboxylase were observed (De
Ropp and Kastl, 1970), and the stimulus properties of mescaline and IM were compared in
trained rats, in an early drug discrimination effort (Winter, 1 973) .
Using molecular connectivity analysis of ten psychedelic phenethylamines, the impor

tance of the 2,5-positions of the methoxy groups and the 4-substituent was demonstrated
(Glennon et al., 1 979a).
IM was not orally active in four humans at 400 mg (Jacob and Shulgin, 1 981).
Legal Status
IM is a positional isomer of mescaline, and therefore a Schedule I hallucinogen under fed
eral drug law, and in states where isomers are included in the controlled drug definition.

Lophophine
# 73. Lophophine
2-(7-Methoxybenzo[d] [l,3]dioxol-5-yl)ethanamine
3-Methoxy-4,5-methylenedioxyphenethylamine
7-Methoxy-1,3-benzodioxole-5-ethanamine
5-Methoxy-homopiperonylamine
2C-1
Registry Numbers
CAS # CAS #
HCl salt [77158-52-2] Freebase [23693-38-1 ]
Natural Sources
Lophophine has been used a s a synthetic intermediate i n the preparation o f methoxymethyl
enedioxy tetrahydroisoquinolines. Best known are anhalonine and lophophorine (with the
6-methoxy-7,8-methylenedioxy orientation, found largely in the Gymnocalycium genus of
the Cactaceae) and cotarnoline (the 8-methoxy-6,7-methylenedioxy isomer, from the genus
Papaver). The synthetic intermediate, lophophine, not reported as a natural plant alkaloid
(Shulgin and Perry, 2002).
Synthesis
From �-3-methoxy-4,5-methylenedioxyphenylpropionic acid (with PC15, NH40H) to �-3-
methoxy-4,5-methylenedioxyphenylpropionamide; (with reduction) to lophophine (Sal
way, 1910) .
From myristicinaldehyde (with malonic acid) t o the corresponding cinnamic acid (with
Raney Ni, H2) to the corresponding propionic acid (with conversion to the amide, and reac
tion with Br2 and NaOH) to lophophine (Surrey, 1 948).
From myristicinaldehyde (with nitromethane) to 3-methoxy-4,5-methylendioxy-�-nitro

ethene; (with LAH) to lophophine (Hamlin and Weston, 1 949; Clark et al., 1 996b).

m / z: 195.0895 (100.0%), 196.0929 (10.8%)
Elemental Analysis: C, 61 .53; H, 6.71; N, 7.18; 0, 24.59
HCl salt m.p. 165 °C (Salway, 1910)

HCl salt m.p. 164-164.5 °C (Shulgin and Shulgin, 1991)
Freebase b.p. 132 °C / l mm (Hamlin and Weston, 1949)

3- 4- I 5- Other Name CAS # Ref
Cl -OCO- -- 3-Cl-4,5-MDPEA [29401 -05-6] (1)
MeO -OCO- -- Lophophine (this entry)
Meo -OCO- N-Me N-Me-Lophophine [33543-07-6] (2)
MeO -OCO- a-Et a-Et-Lophophine [172518-54-6] (3)
(1) Synthesized as a potential psychoactive drug (Hellot et al., 1970a).
(3) a-Ethyl homologue of lophophine has been synthesized (Clark et al., 1996b; for the a-Me homo
logue, see MMDA, #97).

Lophophine I 2-MA
Pharmacology
Several phenethylamines and tryptamines were compared in studies with rats (Kier and
Glennon, 1 978b). Using molecular connectivity analysis of ten psychedelic phenethyl
amines, the importance of the 2,5-positions of the methoxy groups, and the 4-substituent
was demonstrated (Glennon et al., 1979a).
Among several compounds tested at microgram levels as plant growth regulators (Man
dava et al., 1981).
Threshold oral activity in humans at 250 mg; duration unknown (Shulgin and Shulgin,
1 991).
Legal Status
Lophophine is not a scheduled compound under federal drug law, or under District of
# 74. 2-MA
1 -(2-Methoxyphenyl)propan-2-amine
2-Methoxyamphetamine
1 -(2-Methoxyphenyl)-2-aminopropane
NSC 1139
Registry Numbers
CAS # CAS # CAS #
HCl salt [72739-03-8] Acid salt [87059-52-7] R-Isomer freebase [11 7772-42-6]
Bioxylate [59291-68-8] Freebase [15402-84-3] S-Isomer freebase [73495-53-1 ]
x-Oxalate [52850-79-0] R-Isomer tartrate [223930-67-4]
Sulfate [ 6461 0-39-5] S-Isomer tartrate [223930-70-9]

From 2-methoxybenzaldehyde (with methyl ethyl ketone, hypohalite) t o 2-methoxy-a
methylcinnamic acid; (with H2) to 2-methoxy-a-methyldihydrocinnamic acid; (with SOC12,
NH3 ) to 2-methoxy-a-methyldihydrocinnamamide; (with Br2, KOH) to 2-MA (Woodruff
and Conger, 1 938) .
Synthesis, TLC and GC chromatographic properties, UV spectra, and other physical

properties reported (Ono et al., 1976) .

m / z: 165. 1154 (100.0% ), 166.1187 (10.8% )
HCl salt m.p. 1 01-103 °C (Woodruff and Conger, 1938) (EtOH / Etp)
HCl salt m.p. 110-112 °C (Squella et al., 1992) (IPA)
Identification of 2-, 3-, and 4-methoxyamphetamines and 2-, 3-, and 4-methylamphetamines
(Bailey et al., 1974b). [ 13 C]-NMR spectra for 2-MA and other methoxyamphetamines were
obtained, intramolecular interactions analyzed (Bailey et al., 1 971 ); distinctive and suitable
for identification (Bailey et al., 1981; Bailey and Legault, 1 983) . Analysis by HPLC employing
fluorescamine derivatization for fluorescence detection (Shimamine, 1 984) . Derivatization
with heptafluorobutyryl-L-proline allowed chiral resolution and GC analysis (Srinivas

2-MA
et al., 1 989) . Optically active form was synthesized from the corresponding ketone by
bacterial culture (Sato et al., 1 990).
Screening methods for substituted amphetamine derivatives by fluorescence polarization

immunoassay developed (Cody and Schwarzhoff, 1 993) . Optical resolution of racemic o-,
m- and p-methoxyamphetamines was achieved by Candida antarctica lipase B (CAL-B, No
vozym 435) catalyzed enantioselective acylation using ethyl acetate as solvent and acyl
donor (Gonzalez-Sabin et al., 2002).

GC with electron capture detection (Midha et al., 1 979a); synthesis and LC / MS analysis
performed (Noggle et al., 1 989d).
Analytical details were presented for distinguishing between 2-MA, 3-MA, and PMA, and
between their synthetic precursors (Dal Cason, 2001 ); 2-MA was among the fragmentation
patterns of some fifty-five phenethylamines, determined by a variety of mass spectrometry
techniques (Kolliker and Oehme, 2004) .

2- a- �- N- Name CAS # Ref
F Me -- -- 2-FA [1716-60-5] (1,2)
Cl Me -- -- 2-CA [21193-23-7] (1-3)
Cl Me -- Me 2-CMA [ 4302-93-6] (4)
-
Cl Me2 -- - 2-Cl-a,a-MePEA [ 10389-72-7] (5,6)
Br Me -- -- 2-BA [861006-36-2] (3)
HO Me -- -- 2-HA [69271-67-6] (7)
HO Me -- Me 2-HMA [61866-77-1] (8,9)
MeO Me -- -- 2-MA (this entry)
MeO Me -- Me 2-MMA [93-30-1 ] (10,11)
MeO Me Me Me �-Me-2-MMA [21900-10-7] (12-14)
MeO Me C=O Me 2-MMA-�k [882302-55-8] (15)
MeO Me -- Me2 N,N-Me-2-MA [71861-16-0] (16-20)
MeO Me -- Et N-Et-2-MA [91553-50-3] (18,21)
Meo Me -- Et2 N,N-Et-2-MA [ 100966-45-8] (19)
MeO Me -- iPr N-iPr-2-MA [22331-67-5] (19)
MeO Me -- Bu N-Bu-2-MA [92330-91-1] (19)
MeO Me -- iBu N-iBu-2-MA [93721-06-3] (19)
MeO Me -- He N-He-2-MA [101425-96-1 ] (19)
MeO Me -- -CC=CC=C- N-fur-2-MA [101104-91-0] (20)
Meo Me -- mor N-mor-2-MA [92322-94-6] (19)
Meo Me -- pip N-pip-2-MA [132912-56-2] (19)
MeO Et - -
-- 4C-2-MPEA [223923-44-2] (21 )
EtO Me -- -- 2-EA [39590-27-7] (22)

2-MA
(1) .. Potency as an inhibitor of phenethanolamine N-methyltransferase determined (Fuller et al., 1971).

(Hansch and Glave, 1972)
(3) Synthesis (Patrick et al., 1946a).
(4) PCA, and several structurally related compounds, lowered rat brain serotonin levels but not the
level of norepinephrine (Fuller et al., 1965).
(5) Analysis by GC (Canfield et al., 1977).
(6) Synonyms: Su-10568, Voranil.
(7) Synthesis (Woodruff and Conger, 1938) .
(8) 2-MMA metabolized to 2-MA, 2-HMA, and 2-HA following oral administration (Niwaguchi and
Inoue, 1978).
(9) HPLC separation techniques for the identification of illicit drugs (Cashman et al., 1973) .
(10) The generic name i s methoxyphenamine (Methoxyphenadrine, Orthoxine, Ortodrinex, Ortox-
ine, Proasura, NSC 65644); it is a commercial bronchodilator.
(11) Synthesis and LC / MS analysis (Noggle et al., 1989d).
(12) Analysis by non-polar GC / MS and comparison to MDMA (Aalberg et al., 2004).
(13) Analysis by LC and ESI-MS-MS and comparison to MDMA (Pihlainen et al., 2005).
(14) Synthesis (Woodruff and Pierson, 1938) .
(15) GC / MS was compared with that of the isomeric compound MDMA (Awad et al., 2006).
(16) Clinically studied as a bronchodilator (Graham and Kuizenga, 1948).
(17) Synthesis and reaction with [ 1 8F] acetyl hypofluorite (Mathis et al., 1986a).
(18) Synthesis (Woodruff et al., 1940).
(19) Synthesis (Horii et al., 1957a) .
(20) Synthesis (Horii et al., 1957b).
(21 ) A correlation between structure and the locomotor activity of mice was made (van der Schoot et
al., 1962).
(22) Among fragmentation patterns of some fifty-five phenethylamines, determined by a variety of
(23) Synthesis and spectral characterization (By et al., 1991).
Biochemistry
2-MA was a metabolite of 2-MMA in humans, found in plasma (Roy et al., 1 984) and urine
(Chundela and Slechtova, 1976) . Action on the uptake and release of serotonin by human
blood platelets was studied (Tseng and Loh, 1 977), who also found it effective in increasing
the release (or blocking the uptake) of serotonin in brain tissue slices (Loh and Tseng, 1 978) .
Serotonin receptor site affinity was determined (Glennon e t al., 1 980a) . 2-MA was effective
as an inhibitor of serotonin oxidation by MAO, using in vitro mouse brain studies (Green
and Hait, 1 980) . Interaction with the liver enzyme CYP2D6 was studied (Wu et. al., 1 997);
metabolism of methoxyphenamine and 2-methoxyamphetamine in P4502D6-transfected
cells and cell preparations was observed (Geertsen et al., 1995) .
Cross-reactivity of several substituted amphetamines was evaluated with the Roche Abu
screen® (Cody, 1 990a), and the Diagnostic Products Corporation (Cody, 1 990b) radioimmuno
assays for amphetamines .
Biotransformation studies with 2-, 3-, and 4-methoxyamphetamines by Cunninghamella

echinulata were reported (Foster et al., 1991).
Pharmacology
2-MA was clinically studied as a bronchodilator (Graham and Kuizenga, 1 948) . A correla
tion was made between structure and the locomotor activity in mice (van der Schoot et
al., 1962), and between the energy of the highest occupied molecular orbital of the drug
and potency in humans (Kang and Green, 1970) . A correlation has been made between

2-MA / 3-MA
the degree of native fluorescence and psychedelic potency of the methoxy derivatives in
humans (Antun et al., 1971). A positive correlation was found with a series of psychedelic
amphetamines, between the stability of molecular complexes (as determined by NMR)
and the threshold active dose in humans (Sung and Parker, 1 972) .
PMA was the most effective o f three mono-methoxy amphetamines tested, i n disrupting
rat behavior (Tseng et al., 1 976), and pharmacological evidence for the central serotonergic
effects of 2-MA was presented (Menon et al., 1 976) . Relationships were drawn between
drug-induced disruption of behavior and thermoregulation (Kuhlemeier et al., 1 977) . Ste
reoselective effects were observed in rats trained to respond to food presentation schedules
(Harris et al., 1978) . In a large number of methoxylated amphetamine, the rabbit hyper
thermia paralleled human potency as psychedelics (Anderson et al., 1978b) .
Rats trained t o discriminate 5-MeO-DMT from saline partially generalized this response
when exposed to 2-MA (Glennon et al., 1 981b). A series of amphetamines were studied for
correlation between 5-HT2 affinity, charge complex stability, rabbit hyperthermia, and hu
man activity (Domelsmith et al., 1981); comparisons between the serotonin receptor affin
ity and behavioral properties reported (Glennon et al., 1 982a, and amphetamnine-trained
rats were used to relate action with discrimination methodology (Glennon et al., 1 985).
While all three mono-methoxylated amphetamines produced positive responses, none
were as potent as amphetamine itself.
Human psychedelic activity of 2-MA is unknown.
Legal Status
2-MA is a positional isomer of PMA, and therefore a Schedule I hallucinogen under federal
drug law, and in states where isomers are included in the controlled drug definition. 2-MA
is also explicitly listed as a Schedule I hallucinogen in South Dakota.
# 75. 3-MA
1 -(3-Methoxyphenyl)propan-2-amine
1-(3-Methoxyphenyl)-2-aminopropane
Registry Numbers
CAS # CAS #
HCI salt [35294-1 0-1] Acid salt [87059-54-9]
Bioxalate [59291-69-9] Freebase [17862-85-0]
x-Oxalate [52850-80-3] R-Isomer freebase [ 66033-00-9]
Sulfate [ 64610-40-8] S-Isomer freebase [66033-04-3]

From 3-methoxybenzaldehyde (with methyl ethyl ketone, hypohalite) to 3-methoxy-a
methylcinnamic acid; (with H2) to 3-methoxy-a-methyldihydrocinnamic acid; (with SOC12,
NH3 ) to 3-methoxy-a-methyldihydrocinnamamide; (with Br2, KOH) to 3-MA (Woodruff
and Conger, 1 938) .
Synthesis, TLC and GC chromatographic properties, UV spectra, and other physical

properties measured (Ono et al., 1 976) .

3-MA

m / z: 165.1154 (100.0% ), 166. 1187 (10.8% )
HCl salt m.p. 112-113 °C (Woodruff and Conger, 1938) (EtOH / Etp)
NMR spectrum of 3-MA was obtained and intramolecular interactions analyzed

(Bailey et al., 1 971 ) . Identification of 2-,3-, and 4-methoxyamphetamines and 2-, 3-,
and 4-methylamphetamines was achieved (Bailey et al., 1974b); [ 13C]-NMR spectra for
methoxyamphetamines were distinctive and suitable for identification (Bailey et al., 1981;
Bailey and Legault, 1 983). Analysis by HPLC was developed, employing fluorescamine
derivatization for fluorescence detection (Shimamine, 1984) . Optical resolution of racemic
o-, m-, and p-methoxyamphetamines was achieved by Candida antarctica lipase B (CAL-B,
Novozym 435) catalyzed enantioselective acylation using ethyl acetate as solvent and acyl
donor (Gonzalez-Sabin et al., 2002). Analytical details were presented for distinguishing
between 2-MA, 3-MA, and PMA, and between their synthetic precursors (Dal Cason, 2001).
Fragmentation patterns of some fifty-five phenethylamines were determined by a variety
of mass spectrometry techniques (Kolliker and Oehme 2004) .

GC with electron capture detection (Midha et al., 1 979a) . Synthesis and LC / MS analysis
was reported (Noggle et al., 1 989d) . Microbial synthesis of this and other chiral amines has
been reported (Iwasaki et al., 2006).

3- a- N- Other Name CAS # Ref
F Me -- -- 3-FA [1626-71-7] (1-3)
F Me Et -- N-Et-3-FA [54982-43-3] (4,5)
Cl Me -- -- 3-CA [32560-59-1 ] (1,3,6)
Cl Me Et -- N-Et-3-CA [54947-20-5] (4,5)
Br Me Et -- N-Et-3-BA [54947-21-6] (4,5)
I Me Et -- N-Et-3-IA [54947-22-7] (4,5)
N02 Me Et -- N-Et-3-N02-A [54947-52-3] (4)
HO Me -- -- 3-HA [1075-61-2] (1,3,7-9)
HO Me Et -- N-Et-3-HA [50623-68-2] (4,5)
HO Me -- [}-HO [3-H0-3-HA [54-49-9] (9-12)
MeO Me -- -- 3-MA (this entry)*
Meo Me Me -- 3-MMA [93675-25-3] (13-18)
Meo Me Me Me [3-Me-3-MMA [827611-28-9] (19-21)
MeO Me Me [3-C=O 3-MMA-f}k [882302-56-9] (22)
MeO Me Me2 -- N,N-Me-3-MA [99540-14-4] (16,17)
Meo Me Et -- N-Et-3-MA [ 50623-66-0 l (4,5, 14,16,17)
MeO Me Et2 -- N,N-Et-3-MA [71250-21-0] (23)

3-MA
3- a- N- Other Name CAS # Ref

-
Meo Me Bu - N-Bu-3-MA [71250-19-6] (23)
EtO Me -- -- 3-EA [ 135014-86-7] (24)
��
EtO Me Me -- N-Me-3-EA [959219-61-5] (25)

*The alkyl chain positional isomer of 3-MA, with the methyl group in the 13 - rather than the a-position,
synthesized (3-methoxy-1)-methylphenethylamine, HCI salt m.p. 124 "C, Woodruff and Pierson, 1938).
(2) Also known as PAL 353.
(3) Correlation of chemical structure and phenethanolamine N-methyltransferase reactivity (Hansch
and Glave, 1972).
(4) Correlation of mouse locomotor activity with 3-substitution (Tessel et al., 1975a) .
(5) Assayed with isolated guinea pig atria (Tessel et al., 1975b).
(6) 3-CA and PCA lead to a long-lasting serotonin reduction in iprindole-treated rats (Fuller and
Baker, 1974).
(7) The 0-demethylated homologue (3-hydroxyamphetamine, 3-HA, [1075-61-2]) was made from
3-MA with HCI; HCI salt m.p. 138 "C (Woodruff and Conger, 1938).
(8) In the dog, monkey, and in humans, urinary metabolites of 3-MA were identified as MHA and
3-HA (Midha et al., 1981).
(9) Effectiveness of releasing cardiac norepinephrine measured (Daly et al., 1966).
(10) Pulmonary circulation effects measured in the dog (Aviado et al., 1957).
(11) Synonyms are: Metaraminol, Metaradrine, Pressonex, 3-hydroxynorephedrine, and a-[1-amino-
ethyl]-3-hydroxybenzyl alcohol.
(12) Effects on the renal blood flow in dogs (Aviado et al., 1958).
(13) The synthesis, infra-red spectra, NMR and GC / MS data were presented (Clark, 1984).
(14) N-Alkylated homologues of 3-MA include the N-methyl compound (3-MMA), the N,N-dimethyl
compound, and the N-ethyl compound (N-Et-3-MA).
(16) 3-MA and these three homologues were evaluated as bronchodilators, with comparison made
to Orthoxine (2-MMA) (Graham and Kuizenga, 1948).
(18) Synthesis and LC / MS analysis (Noggle et al., 1989d).
(19) Analysis by non-polar GC and MS comparison to MDMA (Aalberg et al., 2004).
(20) Analysis by LC and ESI-MS-MS and comparison to MDMA (Pihlainen et al., 2005).
(21) GC / MS characterization (Pihlainen et al., 2005).
(22) GC / MS was compared with that of the isomeric compound MDMA (Awad et al., 2006).
(23) Synthesis (Griffith et al., 1979).
(24) Synthesis and spectral characterization (By et al., 1991).
(25) Analysis reported by GC / MS (Awad et al., 2008), and GC-IRD (Bela! at al., 2009).
Biochemistry
The potency of 3-MA as an inhibitor of phenethanolamine N-methyltransferase was de
termined (Fuller et al., 1 971 ) . Correlation was made between chemical structure and the
phenethanolamine N-methyltransferase reactivity (Hansch and Glave, 1 972) .
Action on the uptake and release of serotonin by human blood platelets was researched
(Tseng and Loh, 1977), as were the effects of 2-MA, 3-MA, and PMA in increasing the
release or blocking the uptake of serotonin by brain tissue slices (Loh and Tseng, 1 978) .
Serotonin receptor site affinity was determined (Glennon e t al., 1 980a) . Effectiveness a s an
inhibitor of serotonin oxidation by MAO in vitro was evaluated with mouse brain (Green
and Hait, 1 980) .

3-MA
3-MA was metabolized in the dog, monkey, and in humans, to form 3-HA and MHA. Non
nitrogenous metabolites were detected, including 3-hydroxyphenylacetone, 3-methoxy
phenylacetone, 3,a-dihydroxyphenylacetone, and several substituted phenyl propanols. In
the dog and monkey, HMA was also seen as a metabolite (Midha et al., 1981). In dog, mon
key, and in humans, urinary metabolites of 3-MA were identified as MHA and 3-HA (Midha
et al., 1981 ) . Interaction with the liver enzyme CYP2D6 was reported (Wu et al., 1 997) .
Biotransformation studies were reported with 2-, 3-, and 4-methoxy-amphetamines by

Cunninghamella echinulata (Foster et al., 1991).
Pharmacology
A correlation was made between the energy of the highest occupied molecular orbital of
the drug and potency in humans (Kang and Green, 1970), and between the degree of native
fluorescence and psychedelic potency of the methoxy derivatives (Antun et al., 1971 ) . A
positive correlation was found with a series of psychedelic amphetamines, between the
stability of molecular complexes (as determined by NMR) and the threshold active dose in
humans (Sung and Parker, 1 972) .
3-MA was evaluated i n rats that had been trained t o discriminate stimulation produced
by d-amphetamine from saline (Huang and Ho, 1 974a) . PMA was the most effective of the
three mono-methoxy amphetamines in disrupting rat behavior (Tseng et al., 1976), and
pharmacological evidence for the central serotonergic effects of 3-MA was studied (Menon
et al., 1976) . Relation between drug-induced disruption of behavior and thermoregulation
in the rat was noted (Kuhlemeier et al., 1 977) . 3-MA effects were observed in rats trained
to respond to food presentation schedules (Harris et al., 1 978) . Rats trained to discrimi
nate 5-MeO-DMT from saline partially generalized this response when exposed to 3-MA
(Glennon et al., 1981b). A comparison of the serotonin receptor affinity and the behavioral
properties in the rat were reported (Glennon and Young, 1982), and trained rats were used
to compare mono-, di- and tri-methoxylated amphetamine activity with amphetamine re
sponses, using drug discrimination methodology (Glennon et al., 1985).
A series of amphetamines were studied for correlation between 5-HT2 affinity, charge com
plex stability, rabbit hyperthermia, and human activity (Domelsmith et al., 1981).
3-MA has a transient pressor effect on humans. The minimal effective dose on oral admin
istration was 25 mg. No tachycardia or sustained elevation of blood pressure (Schelling et
al., 1974) .
No psychedelic activity was detected in humans at 50 mg (2 x 25 mg doses, separated by

three hours) (Shulgin and Shulgin, 1991).
Legal Status
3-MA is a positional isomer of PMA, and therefore a Schedule I hallucinogen under federal
drug law, and in states where isomers are included in the controlled drug definition. 3-MA
is also explicitly listed as a Schedule I hallucinogen in South Dakota.

MBDB
# 76. MBDB
1-(Benzo[d] [l,3]dioxol-5-yl)-N-methylbutan-2-amine
(±)-N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine
2-Methylamino-1-(3,4-methylenedioxyphenyl)butane
a-Ethyl-N-methyl-1,3-benzodioxole-5-ethanamine
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-aminobutane
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butylamine
N-Methyl-1 -(3,4-methylenedioxyphenyl)-2-butanamine
EDEN
MB
MDBD
Methyl-J
Registry Numbers
CAS #
HCl salt [128767-12-4]
Freebase [135795-90-3] CAS #
R-(-)-Isomer HCl salt [103882-49-1] R-(-)-Isomer freebase [1 03882-53-7]
S-(+)-Isomer HCl salt [103882-50-4] S-( +)-Isomer freebase [1 03882-54-8]

From piperonal (with Mg turnings, 1-bromopropane, diethyl ether) to 1-(1,3-benzodioxol-
5-yl)butan-l-ol; (with KHS04, distillation) to 1-(1,3-benzodioxol-5-yl)butene; (with Hp2,
HC02H) to 1-(1,3-benzodioxol-5-yl)butan-2-one; (with Al foil, HgC12, CH3NH2Cl) to
(±)-N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine (Nichols et al., 1 986a) .

ml z : 207. 1259 (100.0% ), 208. 1293 (13.0% )
HCl salt m.p. 156 °C (Nichols et al., 1986b) (IPA)

R-(-)-Isomer HCl salt m.p. 192-193 °C [aJ ;31 -26.04° (Nichols et al., 1986b) (EtOH / Etp)
S-(+)-Isomer HCl salt m.p. 192-193 °C [aJ ;31 +25.89° (Nichols et al., 1986b) (EtOH / Etp)
Several a-ethyl phenethylamines were synthesized and analytically compared with their
amphetamine counterparts (Clark et al., 1 995) . MS analysis of the three isomeric com
pounds MBDB, MOE, and MDDMA, was reported (Clark et al., 1 996). N-Methyl-[ 11 C]
labeled MBDB was synthesized and used to determine the blood-to-brain uptake in rats
(Solbach et al., 1 997b ). Eight structurally related methylenedioxy compounds were dis
tinguished by reversed-phase liquid chromatography and MS of the pentafluoropropion
amide derivatives (DeRuiter et al., 1 998b). Automated online dialysis and liquid chroma
tography reported MBDB in plasma and serum samples with detection limits of 10 ng / ml
(Sadeghipour and Veuthey, 1 998). MBDB also could be identified by FTIR spectral analysis
(Praisler et al., 2000), and analyzed without derivatization by HPLC / MS (Bogusz et al.,
2000) . 2,3- and 3,4-isomers were synthesized and distinguished by GC-MS-MS (Borth et
al., 2000) . Chromatographic and spectroscopic identifications were described (Aalberg et
al., 2003). MBDB was among some fifty-five phenethylamines whose fragmentation pat
terns were determined by a variety of mass spectrometry techniques (Kolliker and Oehme,
2004) .

MBDB
MOE, MDDMA, MBDB, and their 2,3-methylenedioxy positional isomers 2,3-MDE,

2,3-MDDMA, and 2,3-MBDB, all of identical mass and extremely similar mass spectra,
were synthesized, derivatized, and clearly defined by GC / MS (Thigpen et al., 2007) . MBDB
was identified and distinguished from several structurally related compounds in human
urine by capillary electrophoresis and fluorescence spectroscopy (Chung et al., 2001). An
enantiomeric analysis of MBDB and its metabolite BOB was developed for rat urine (Nagai
et al., 2002). A GC / MS screening of a urine sample to differentiate between MOMA, MDA,
MOE, and MBDB following extraction, deconjugation, and derivatization was reported
(Pellegrini et al., 2002). Analytical procedures were developed for MBDB analysis of hair
samples (Junker et al., 2001; Van den Berg et al., 2002; Musshoff et al., 2002). A plasma
screening and quantitative GC / MS analysis has been reported (Peters et al., 2003). Hu
man urine was analyzed by LC-MS-MS methods (Nordgren and Beck, 2004; Nordgren et
al., 2005), and serum was analyzed by extraction, derivatization with trifluoroacetic an
hydride, and GC / MS (Hidvegi et al., 2006). Determination of MOMA, MDA, MOE, and
MBDB in oral fluid was achieved via high performance liquid chromatography with native
fluorescence detection (Concheiro et al., 2005).
Distinction of MBDB from structurally related compounds was achieved by GC / MS

(Clark et al., 1996a) . The nearly identical isomers, MOE and MBDB, were distinguished
from one another by MS (Garofano et al., 1998), and GC / MS, with appropriate derivatiza
tion (Maruyama et al., 1 998) . Synthesis and spectral characterization of MBDB, BOB, GEA,
and N-Me-a-Et-GEA was reported (Kanamori et al., 1999). Chromatographic and GC /
MS techniques were developed for distinguishing the three isomers MDDMA, MOE, and
MBDB (Aalberg et al., 2003) .
Neural network analysis (NN) and neural networks coupled with principal component
analysis (PC-NN) were applied to infrared spectra of stimulant and psychedelic amphet
amines (Gosav et al., 2005).

3- I 4- a- N- Name CAS # Ref
-OCO- Et Me MBDB (this entry)
-OCFp- Et Me --
F2-MBDB [914800-83-2] (1)
(1) Synthesis (Trachsel et al., 2006).
Biochemistry
With MBDB treatment, [ 3 H]-labeled serotonin was released from rat hippocampal slices
and [ 3H]-labeled dopamine, similarly, from rat caudate nucleus slices (Johnson et al.,
1986). Stereochemical aspects of 3,4-methylenedioxymethamphetamine (MOMA) and re
lated amphetamine derivatives' inhibition of uptake of [ 3H] -monoamines into synapto
somes from different regions of rat brain were evaluated (Steele et al., 1987) . With S-MBDB,
telemetric recordings of field potentials from frontal cortex, hippocampus, striatum, and
reticular formation were made on freely moving rats (Dimpfel et al., 1989). The optical
isomers of PMMA, DOM, MBDB, MOMA, and OMA were compared as stimulants in rats
(Rangisetty et al., 2001).
GC / MS analysis of human urine has shown that the methylenedioxy ring of MBDB opens
to give DH-a-Et-MA and MH-a-Et-MA as metabolites (Maurer, 1 996) .

MBDB
MBDB, administered orally to male rats at 20 mg / kg, was excreted in part unchanged, and
as the three metabolites BOB, GEA, and N-Me-GEA (Kanamori et al., 1998a); (Nagai et al.,
2002) also found MBDB and its metabolite BOB in rat urine following oral administration.
Using CC / MS and LC / MS, two major routes to the observed human urinary metabolites
of MBDB were N-dealkylation and demethyleneation to the catechol, and demethylation
and also N-demethylation by CYP1A2 (Maurer et al., 2000) . The conversion of MBDB to
BOB was confirmed in human trials monitoring urine, saliva, and sweat with CC / MS; in
all the biological specimens tested, MBDB was present in higher concentrations than its
metabolite (Kintz, 1997) . Studies were reviewed on screening procedures for detection of
MDA, MOMA, MOE, BOB, and MBDB, and on their metabolism, including cytochrome
P450 isoenzyme dependencies (Maurer and Kraemer, 2002).
and release of monoamines (dopamine, serotonin, and norepinephrine) by rat brain syn
aptosomes (Nagai et al., 2007) .
Pharmacology
3,4-MMA and MMAI were tested for stimulus generalization in two-lever discrimination
tests with rats trained with MOMA or MBDB (Johnson et al., 1991b). BOB, MBDB, and
MMBDB responses were compared to one another in the newly hatched chicken, and
produced behaviors more characteristic of psychedelics than amphetamine (Bronson et al.,
1 995a); the effects of 2C-B, MDA, MBDB, and cathinone were similarly compared (Bronson
et al., 1995b). MTA, MBDB, and MMAI were compared as serotonin releasers in rats (Li et
al., 1996) .
Biochemical and behavioral studies with MOMA and MBDB gave results similar to one
another, but distinct from stimulants (amphetamine) or psychedelics (DOM, LSD); this
prompted the creation of a new class name, "entactogens" (Nichols, 1986b ). MBDB partially
generalized for LSD in rat discrimination studies (Nichols et al., 1986a), and produced
MOMA-like behaviors (Oberlender and Nichols, 1990); rats trained to discriminate
between MBDB and saline, substituted MDA, MOMA, MDAI, and MDMAI completely,
but not mescaline, DOM, or LSD. The term "entactogen" was further discussed for those
compounds that substituted completely (Oberlender and Nichols, 1990) . In establishing
the definitions of entactogen, hallucinogen, and stimulant, drug discrimination-trained
rats (MOMA versus (+)-amphetamine), had been used to evaluate the optical isomers of
MDA, MOMA, MBDB, amphetamine, LSD, and DOM (Oberlender and Nichols, 1 988) .
Possible neurotoxic effects of MBDB in rats were evaluated (Johnson and Nichols, 1989) .
Ten suspected drug offenders (in Sweden) showed the presence of MBDB in urine at levels
ranging from 0.10 to 24 µg / ml. All specimens also contained the metabolite BOB, with
qualitative and quantitative CC / MS analysis of trifluoroacetic anhydride derivatives of
MBDB, BOB, MOMA, MDA, and MOE (Kronstrand, 1996) . Several homologues of MDA
appeared in the illicit drug market in Italy (Furnari et al., 1998). The appearance of MBDB
in France required careful analysis to distinguish it from its illegal, structurally close ana
logues and isomers (Baudot et al., 1999) . GC / FTIR analysis showed that 2C-B, MOMMA,
and MBDB had appeared for sale in Belgium (Dirinck et al., 2000). Employing HPLC-PDA,
HPLC-MS, TLC, and NMR, a library of 35 illegal drugs was assembled and used to identify
street samples (Nakashima et al., 2005). Analysis by CC / MS and LC-ESI-MS also found
MBDB to be present in street drugs in Japan (Kikura-Hanajiri et al., 2005). In Japan, homo
MDMA was sold on the street under the recognized name MBDB (Matsumoto et al., 2006).

MBDB / MDA
Syntheses and analytical methods for MBDB and its analogues, including BDB, MDA,
MDE, MDMA, and methylone, were developed to support forensic investigations (Sanuki
et al., 2006). An thorough review article highlighted the distinction of MBDB (analytically
and pharmacologically) from its close analogues and homologues (Van Aerts et al., 2000).
Two deaths were established as having been caused by MBDB (Carter et al., 2000) .
MBDB' s S-( +)-isomer is orally active in humans at 125 mg, the racemate is active at 150-210
mg (Nichols et al., 1986a); the racemate was active at 180-210 mg; duration 4-6 hours
Legal Status
MBDB is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
MBDB has been regulated in Japan by their Narcotics and Psychotropics Control Law since
April 22, 2006 (Sanuki et al., 2006).
# 77. MDA
1-(Benzo[ d ] [ 1,3] dioxol-5-yl)propan-2-amine
1-(3,4-Methylenedioxyphenyl)-2-aminopropane
a-Methyl-1,3-benzodioxole-5-ethanamine
a-Methyl-3,4-(methylenedioxy)phenethylamine
5-(2-Aminopropyl)-l,3-benzodioxole
3,4-Methy lenedioxyphenylisopropylamine
3,4-Methylenedioxyamphetamine
Amphedoxamine
Tenamfetamine
EA-1298
NSC 9978
NSC 271 06
SKF-5
Registry Numbers
CAS # DEA CAS # CAS #
HCl salt [6292-91-7] 7400 Sulfate [64610-47-5] S-Isomer HCl salt [70745-97-0]
HBr salt [590346-12-6] Tartrate [95172-73-9] R-Isomer Sulfate [61614-61-7]
Bisulfate [91012-27-0] Freebase [4764-1 7-4] R-(-)-Isomer freebase [61614-60-6]
Carbonate [56440-59-6] R-Isomer HCl salt [70745-96-9] S-( +)-Isomer freebase [65620-66-8]
x-Oxalate [65955-47-7]
History
A detailed report of the use of MDA in psychotherapy was presented (Di Leo, 1981). A later
review of the history of MDA and MDMA suggested this class of compounds can be used
safely and effectively in psychotherapy (Pentney, 2001).

From 3,4-methylenedioxyphenylacetone (with hydroxylamine) to 3,4-methylenedioxy
phenylacetone oxime; (with NaH or Na, Hg) to MDA (Mannich and Jacobsohn, 1910).

MDA
From isosafrole (with formic acid, hydrogen peroxide) to methylenedioxybenzyl methyl

ketone; (with formamide, HPz) to MOA (Fujisawa et al., 1956) .
From safrole (with HgClz, AcOH and HBr) to 1-(3,4-methylenedioxyphenyl)-2-bromo

propane; (with NH3, Cup) to MOA (Muszynski, 1961).
From piperonal (with nitroethane, acetic acid, and ammonium acetate) to 1 -(3,4-methyl
enedioxyphenyl)-2-nitropropene; (with LAH) to MOA (Ho et al., 1970a) .
From piperonal (with nitroethane, acetic acid, and ammonium acetate) to 1-(3,4-methyl
enedioxyphenyl)-2-nitropropene; (with sodium bis(2-methoxyethoxy)aluminum dihy
dride) to MOA (Butterick and Unrau, 1974) .
From piperonal (with nitroethane, acetic acid, and ammonium acetate) to 1-(3,4-methyl
enedioxyphenyl)-2-nitropropene; (with Pd / C, Hz) to MOA (Ohshita and Ando, 1992) .
Optical isomers: From piperonylacetone (with R-(-) (or S-(+)-) a-methylbenzylamine,

Raney Ni) to R,R- (or S,S-) N-a-methylbenzyl-MOA; (with Hz, Pd) to R-(-)- (or S-(+)-) MOA
(Anderson et al., 1978a) .
Exact Mass: 1 79.0946

Molecular Weight: 1 79.22
m / z: 1 79.0946 (100.0% ), 180.0980 (10.8% )
HCl salt m.p. 180-181 °C (Mannich and Jacobsohn, 1910)

HCl salt m.p. 1 88 °C (Bruckner and Kramli, 1935)(EtOH)
HCl salt m.p. 183-185 °C (Merck, 1912)
HCl salt m.p. 181-1 82 °C (Ho et al., 1970a)
Freebase b.p. 157 °C / 22 mm (Mannich and Jacobsohn, 1910)
Freebase b.p. 122-127 °C / 5 mm (Fujisawa et al., 1956)
R-(-)-Isomer HCl salt m.p. 200-202 °C [a]0 -25.70°(c 2.0) (Nichols et al., 1986a) (EtOH / Etp)
S-(+)-Isomer HCl salt m.p. 200-202 °C [a]0 +26.52°(c 2.0) (Nichols et al., 1986a) (EtOH / Etp)
S-(+)-Isomer HCl salt m.p. 198 °C [a] �0 +26.6°(c 1 .40) (Effenberger and Jager, 1997)
R-(-)-Isomer [aJ ;31 -24.7° (Anderson et al., 1978a)
S-( +)-Isomer [aJ ;31 +25.3° (Anderson et al., 1978a)
MOA was also synthesized by reductive amination of 3,4-methylendioxyphenylacetone

(Noggle et al., 1 987b). Several a-ethyl phenethylamines were synthesized and analytically
compared with their amphetamine counterparts (Clark et al., 1995); MBOB and its an
alogues, including BOB, MOA, MOE, MOMA, and methylone were synthesized and
analyzed by IR, GC / MS, HPLC, and NMR (Sanuki et al., 2006). A warning that a possible
incorrect synthesis could arise from the use of the term "piperonylacetone" being applied to
chemically different commercial products (piperonylacetone and piperonylbenzylacetone;
Shulgin and Jacob, 1982a,b) . 3,4-Methylenedioxybenzonitrile was isolated in 5.6% yield
during the synthesis of 1-(3,4-methylenedioxyphenyl)-2-nitropropene from piperonal and
nitroethane in the presence of glacial acetic acid and ammonium acetate (Guy et al., 2008).
Chromatographic methods for MOA were reported for TLC (Bussey and Backer, 1974),
HPLC (Chan et al., 1974; Helmlin and Brenneisen, 1992), and GC (Ono et al., 1976; Canfield

MDA
et al., 1977) . MDA was included in TLC (O'Brien et al., 1982) and color tests (DeMayo et al.,
1 972) developed for the identification of substituted amphetamines. NMR spectroscopy of
MDA (Avolio and Rothchild, 1985), and spectrophotometric, mass spectral, and chromato
graphic methods for identification of MDA, MOMA, MOE were presented (Noggle et al.,
1 986; Noggle et al., 1988) . Synthesis and analytical properties by TLC, UV, IR, HPLC, GC /
MS, and NMR were reported (Shimamine et al., 1990; Kanamori et al., 1 998b; Hays, 2005).
Identification of impurities in illegally synthesized MDA tablets has been used to char
acterize the origin (Bohn et al., 1993) . HPLC analysis of whole blood for MDA reported a
sensitivity of 1 ng / ml (Michel et al., 1993), and a single HPLC-UV analysis of human urine
could detect amphetamine (and its metabolite PHA), MOMA (and its metabolite MDA),
2C-B, and MTA (Soares et al., 2004).
MDA was differentiated from MBDB by GC / MS (Clark et al., 1996a) . HPTLC-UV / FTIR
was used to determine MOE and its two metabolites, MHEA and MDA, in urine (Kovar
and Pisternick, 1996; Pisternick et al., 1997) . Identification by FTIR spectral analysis was re
ported (Praisler et al., 2000) . Quantitative methods for determination of MDA and MOMA
in hair samples by GC / MS (Rohrich and Kauert, 1997; Kintz and Cirimele, 1 997; Junker et
al., 2001), and HPLC with fluorescence detection (Tagliaro et al., 1999) were presented. The
impact of pigmentation on hair analysis for MDA was determined in pigmented hairy rat
experiments (Kikura et al., 1 997) .
Proton and [ 13C]-NMR spectra were reported, with proton assignments (Dal Cason et al.,
1997a) . Automated online dialysis and liquid chromatography of MDA in plasma and se
rum samples was described (Sadeghipour and Veuthey, 1998). MDA was identified by a
rapid HPTLC screening method (Pater et al., 1998), and in a urine screening procedure by
GC / MS (Battu et al., 1998) . HPLC separations for the identification of illicit drugs com
pared adsorption, gradient elution, and ion-exchange methods (Cashman et al., 1973) .
MDA levels were determined in biological fluids by LC / MS (Clark et al., 1990a; Valaer et
al., 1990), and it was among a number of amphetamine-related drugs identified by LC /
MS and LC-MS-MS (Noggle et al., 1986, 1987a,b, 1988; DeRuiter et al., 1998b; Bogusz et
al., 2000; Mortier et al., 2002; Nordgren and Beck, 2004; Nordgren et al., 2005). Analysis by
HPLC employing fluorescence detection was described (Shimamine, 1984; Clauwaert et
al., 2000; da Costa and da Matta, 2004), and this method was used to evaluate sample sta
bility in biological fluids stored at different temperatures (Clauwaert et al., 2001). MOMA,
MDA, MOE, and MBDB were measured in oral fluid using high performance liquid chro
matography and native fluorescence detection (Concheiro et al., 2005). Amphetamine,
methamphetamine, MDA, MOE, and MOMA were detected in urine by online solid-phase
extraction, ion-pairing liquid chromatography and electrospray tandem mass spectrom
etry (Wu and Fuh, 2005).
MS data were presented for the detection of metabolites of MDA and MOMA (Verweij,
in urine by heads pace I solid phase micro-extraction and GC I MS was described (Centini
1996) . Qualititative and quantitative analysis of MOMA, MOE, MA and amphetamine
et al., 1 996) . Quantitative GC / MS methods were described for the analysis of the optical
isomers of MOMA (and the three major metabolites MDA, MHMA, and MHA) in hu
man plasma and urine after trifluoroacetylation (Pizarro et al., 2002a,b, 2003, 2004) . Mea
surement of MDA by GC / MS has been reported (Mariani et al., 1 999; Peters et al., 2003;
Scheidweiler and Huestis, 2006), with derivatization with trifluoroacetic anhydride (Hid
vegi et al., 2006), and by GC with electron capture detection, as the pentafluorobenzamide

MDA
derivatives (Midha et al., 1979a) . Extraction, deconjugation and derivatization permitted

GC / MS screening of urine samples for MOMA, MOA, MOE, and MBOB (Pellegrini et al.,
2002). MOA was included among fifty-five phenethylamines whose mass spectra were
presented (Kolliker and Oehme, 2004) . A negative-ion chemical ionization GC / MS assay
for enantioselective measurement of the designer drugs MOE, MOMA, and MOA was
validated for analysis of blood (Peters et al., 2005). Rapid simultaneous determination of
amphetamine, methamphetamine, MOA, MOMA, and MOE in urine by fast GC / MS was
described (Klette et al., 2005). Sensitive GC / MS methods for simultaneous measurement
of MOE, MOMA, and metabolites MHA, MOA, and MHMA in human urine were de
scribed (Pirnay et al., 2006).
MOA was identified and distinguished from several structurally related compounds in
forensic seizures by capillary electrophoresis (CE) with UV detection (Trenerry et al., 1 995;
Esseiva et al., 1997), in human urine by CE with fluorescence spectroscopy (Chung et al.,
2001), and in whole blood by CE with photodiode array detection (Boatto et al., 2002). Ra
cemic MOA and metabolites were resolved with optically active electrophoresis (Lanz et
al., 1 997); the S-isomer of MOMA, and the main metabolites S-MHMA and S-OHMA, were
also prepared and analyzed by CE (Pizarro et al., 2002b ) .
Three commercial amphetamine immunoassays for detection o f MOA, MOMA, and MOE
in urine were evaluated for cross-reactivity (Ruangyuttikarn and Moody, 1 988); cross-reac
tivity of several substituted amphetamines with the Diagnostic Products Corporation radio
immunoassay for amphetamines was also evaluated (Cody, 1990b). Substituted amphet
amine derivatives were screened by fluorescence polarization immunoassay (Cody and
Schwarzhoff, 1993) .
MOA, and three analogues with a chloro-, bromo- or a nitro-group in the 6-position, were
experimentally oxidized by differential pulse voltammetry (Squella et al., 1 993) .
Resolution of optical isomers of MOA and determination in whole blood was reported
(Fitzgerald et al., 1989a). Optical isomers of MOA were obtained by fractional crystalli
zation (Buchlera et al., 2000). A method for simultaneous determination of the ratio of
enantiomers of amphetamine, methamphetamine, MOA, MOMA, and MOE in urine by
GC / MS was presented (Hensley and Cody, 1999), and for the latter three in human whole
blood samples (Rasmussen et al., 2006) .
Neural network analysis (NN) and neural networks coupled with principal component
analysis (PC-NN) were applied to infrared spectra of stimulant and psychedelic amphet
amines (Gosav et al., 2005) .

a- N- Other Name CAS # Ref
Me -- -- MDA (this entry)
Me -- j)-HO j)-HO-MDA [61555-32-6] (1)
Me -- 8-F2 F2-MDA [91 0393-51-0] (2)
Me Me 6-Me MADAM-6 [ 207740-46-3] (3,4)
Me Me,Et -- MDMEA [129819-63-2] (5) ·-
Me Me,Pr --
�--
MDMPA [129819-65-4] (5) ·-

MDA
a- N- Other Name CAS # Ref

Me Me,iPr -- MDMIPA [129819-64-3] (5)
!---·�-�
--
Me Etz -- MDDEA ------
[74698-51-4]
-·-----
(6)
Me HOCC- -- MDHOET [74341-74-5] (6,7)
Me MeOCC- -- MDMEOET [74341-80-3] (6,8)
Me -CCN -- MDCM [74698-42-3] (6)
Me iPr -- MDIP [74698-37-6] (6,8-12)
--�
Me Ally! -- MDAL [74341-75-6] (6,8)

Me PR -- MDPL [74341-81-4] (6,8)
Me Bu -- MDBU [74341-86-9] (6,7,10,13)
Me iBu -- MDIB [74341-85-8] (6,10)
Me sBu -- MDSB [113527-37-0] (10)
-
Me tBu - MDTB -- (14)
Me tBuNH -- MDBA [74698-49-0] (15)
Me cPrM -- MDCPM [74341-84-7] (6) --
Me Pentyl -- MDAM [74698-40-1 ] (6)

Me Hexyl -- MDHE [74698-41-2] (6)
Me Octyl -- MDOC [25070-60-4] (6,16)
Me Benzyl -- MDBZ [2980-08-7] (8, 1 7,18)
Me MeO -- MDMEO [74698-48-9] (6,8, 1 8,19)
Me2 -- -- MDPH [39235-63-7] (20-28)
Me2 Me -- MDMP [81262-69-3] (22)
Me,Et -- -- a-Et-MDA [ 627876-91-9] (29)
Et Me2 -- MMBDB [167394-40-3] (30-33)
-
Et Et - EBDB (ETHYL-J) [167394-39-0] (30,32)
Et Pr -- PBDB [337464-40-1 ] (30)
Et iPr -- IPBDB [337464-41-2] (30)
Et HO -- HOBDB [167394-41 -4] (32,34)
Pr -- -- K [220491-69-0] (29,35,36)
Pr Me -- METHYL-K -- (37)
Pr Et -- ETHYL-K -- (38)
iPr -- -- a-iPr-MDPEA [ 627876-89-5] (29)
Bu -- -- L -- (39)
-
Bu Me - METHYL-L -- (40)
(1) Synthesis (Ohshita and Ando, 1992) .
(2) Synthesis (Trachsel et al., 2006) .
(3) Also known as 2,N-dimethyl-4,5-methylenedioxyamphetamine.
(4) Synthesis and bio-distribution studies of MADAM-6 (Patt et al., 1999) .
(5) Reversed-phase chromatography and mass spectral analysis (Clark et al., 1990a) .
(6) Studies of motor activity, tail flick, stretch reflex, and analgesia in mice (Braun et al., 1980) .

MDA
(7) Threshold oral activity in humans at 40 mg (Shulgin and Shulgin, 1991).

(8) Threshold oral activity in humans at 160 mg (Braun et al., 1980).
(9) Proton and [ 1 3C]-NMR spectra recorded, with proton assignments (Dal Cason et al., 1997a) .
(10) Synthesis, identification, and acute toxicity of N-alkyl derivatives of MDA (Noggle et al., 1987b).
(11) Liquid chromatographic and mass spectral analysis for N-substituted analogues of 3,4-methyl-
enedioxyamphetamine (Noggle et al., 1988).
(12) Liquid chromatographic and mass spectral analysis of N-substituted analogues of MDA (Noggle
et al., 1988).
(13) Analysis and identification by color tests, TLC, GC, GC / MS, UV, IR (Kanamori et al., 1998b).
(14) Synthesis (Shulgin and Shulgin, 1991 ), no physical data, animal or human tests; otherwise not
in the published literature.
(15) Syntheses described; b.p. of freebase 95-105 °C / O.l mm, m.p. HCl salt 220-222 °C (dee.) (Braun
et al., 1980; Shulgin and Shulgin, 1991 ). No animal or human tests; otherwise not in the published
literature.
(16) Patented as an insecticide synergist (Aries, 1968).
(17) Synthesis (Muszynski, 1965).
(18) Not orally active in humans at 150 mg (Shulgin and Shulgin, 1991).
(19) Responses observed in rats trained to discriminate DOM from saline (Glennon et al., 1982c).
(20) Analysis by non-polar GC / MS, and comparison to MOMA (Aalberg et al., 2004).
(21 ) Analysis by LC and ESI-MS-MS and comparison to MOMA (Pihlainen et al., 2005).
(22) Effect on release of serotonin from rat synaptosomes (Nichols et al., 1982).
(23) Distinguished from MOMA by GC / MS analysis of the pentafluoropropionamides (Liu, 2005).
(24) Chromatographic and spectroscopic identification (Aalberg et al., 2003, 2004) .
(25) Also known as: a,a-Me-MDPEA, 3,4-methylenedioxyphentermine , and a,a-dimethyl-3,4-
methylenedioxyphenethylamine.
(26) Synthesis (Suh, 1977).
(27) The identification of MOMA and nine isomers by GC / MS (Aalberg et al., 2000, 2004) and by
LC-ESI-MS-MS (Pihlainen et al., 2005).
(29) Chromatographic and spectroscopic identification (Aalberg et al., 2003).
(30) Synthesis and GC / MS spectral distinction between 2,3- and 3,4-isomers (Borth et al., 2000) .
(31) BDB, MBDB, and MMBDB compared in the newly hatched chick (Bronson et al., 1995a) .
(32) Several a-ethyl phenethylamines synthesized and analytically compared with their amphet-
amine counterparts (Clark et al., 1995).
(33) Among several homologues of MDA in illicit drug market in Italy (Furnari et al., 1998).
(34) Thermally unstable, degrading to BOB under GC conditions (Clark et al., 1995) .
(35) Neurotransmitter releaser in rat (Yoneda et al., 2001 ).
(36) Synthesis and GC / MS characterization (Aalberg et al., 2003) .
(37) Threshold oral activity in humans at 100 mg (Shulgin and Shulgin, 1991); otherwise not in the
published literature.
(38) Threshold oral activity in humans at 40 mg; m.p. HCI salt 157-158 °C (Shulgin and Shulgin,
1991); otherwise not in the published literature.
(39) No human studies; m.p. HCI salt 202-203 °C (Shulgin and Shulgin, 1991); otherwise not in the
(40) No human studies; m.p. HCl salt 139-141 °C (Shulgin and Shulgin, 1991); otherwise not in the
Derivatives of the 2,3-Methylenedioxy Isomer

-
-- - 2,3-MDPEA [ 33542-90-4] (1-3)
Me -- 2,3-MDA [86029-48-3] (1,3-10)
Me2 -- a,a-Me-2,3-MDPEA [301642-50-2] (11-13)
-- Me 2,3-MDMPEA [33543-05-4] (3,5)

MDA

-- Me2 N,N-Me-2,3-MDPEA [301642-48-8] (11-13)
-- Et N-Et-2,3-MDPEA -
[301642-49-9] (12,13)
Me Me 2,3-MDMA [168967-99-5] (8,11,12,13-17)
Me Me2 2,3-MDDMA [168968-03-4] (8, 14,18,19)
Me Et 2,3-MDE [ 1 68968-00-1 ] (8,10,14,19)
Et -- 2,3-BDB [337464-36-5] (3,10-14,16,18)
Et Me 2,3-MBDB [337464-37-6] (3,10,14,19)
Et Me2 2,3-MMBDB [337464-39-8] (14)
Et Et 2,3-EBDB [337464-38-7] (14)
(1) Synthesis (Dallacker et al., 1971).
(2) Synthesis described; b.p. 98-100 °C / 1 mm (Govindachari et al., 1958).
(4) Generalizes to MDA response in animal drug discrimination studies (Glennon et al., 1984c).
(5) Orally 50 mg leads to wakefulness but no MDA-like action (Shulgin and Shulgin, 1 991) .
(6) Included i n study o f structural requirements for psychedelic activity (Shulgin e t al., 1969) .
(7) 2,3-MDA is a positional isomer of MDA, and thus a Schedule I compound under federal drug
laws. See Legal Status for this entry.
(8) Synthesis and characterization of several 2,3-methylenedioxy isomers of psychoactive amphet
amines (Casale et al., 1995).
(9) Urine and plasma samples were analyzed as the pentafluorobenzamide derivatives by GC-ECD
(Midha et al., 1979a).
(10) Eight structurally related methylenedioxy compounds were distinguished by reversed-phase
chromatographic analysis (DeRuiter et al., 1998c) .
(11) Analysis by non-polar GC / MS, comparison to MDMA (Aalberg et al., 2004).
(12) Analysis by LC-ESI-MS-MS, comparison to MDMA (Pihlainen et al., 2005).
(13) The identification of MDMA and nine isomers by GC / MS (Aalberg et al., 2000, 2004) and by
(14) Synthesis and GC / MS spectral distinction between 2,3- and 3,4-isomers (Borth et al., 2000).
(15) A positional isomer of MDMA (FR, 1970), and therefore automatically a Schedule I drug.
(16) Identified and distinguished from several structurally related compounds in human urine
(Chung et al., 2001 ).
(17) Synthesis and analysis of MBDB and its analogues (Sanuki et al., 2006).
(18) Synthesis and GC / MS differentiation between 2,3- and 3,4-isomers (Thigpen et al., 2007).
(19) MDE, MBDB, MDDMA, and their 2,3-methylenedioxy positional isomers 2,3-MDE, 2,3-MBDB
and 2,3-MDDMA, all with identical mass and extremely similar mass spectra, were synthesized,
derivatized, and clearly defined by GC / MS. (Thigpen et al., 2007).
Ring Configuration Isomers *

I
--·- ---�·-
5- 4- 3- 2- a- N- Name CAS # Ref

-OCO- --
�----·-- - · --�---
-C-
- ·-- -------- -
--
-
5,6-MDAI
----,____ -- -�----
[ 155344-90-4] (1-6)
-OCO- -- -C- Me 5,6-MDMAI [132741-82-3] (2,4)
-OCO- -- -CC- -- 6,7-MDAT [101625-35-8] (3,4,7)
-----
-OCO- -- -CC- Me 6,7-MDMAT [34620-52-5] (4,8)

-- -OCO- -- I Me -- MDA (this entry)
-- -OCO- -C- -- 4,5-MDAI [182634-37-3] (3,4,7)

MDA
I I
-�,.......- ----
5- 4- 3- 2- a- N- Name CAS # Ref

-- -OCO- -C- Me 4,5-MDMAI [ 1 82634-38-4] (4)
-- -OCO- -CC- -- 5,6-MDAT [124399-99-1 ] (3,4,7)
*These compounds have fusion of the a-methyl group directly, or with the inclusion of an additional
carbon atom, to the "2-" position of the aromatic ring. For the purposes of this table only, the methy
lenedioxy structure of MDA is shown at the 4,5-position, to illustrate the relationship of this group
to the "2-a" linkage in the indanes and tetralines. The actual numbering schemes for these new ring
systems (as seen in their code names) are those used by Nichols et al., 1 990.
(1) The role of dopamine in the neurotoxicity of serotonin following MDAI has been studied (Johnson
et al., 1991c).
(2) Rats trained to discriminate between MBDB and saline, substituted MDA, MDMA, MDAI, and
MDMAI completely, but not mescaline, DOM, or LSD. The term "entactogen" was proposed for
those compounds that substituted completely (Nichols, 1986b; Oberlender and Nichols, 1990).
(3) Rats trained to discriminate between LSD and saline, or between MDMA and saline, were tested
with MDAI, MDAT, 4,5-MDAI, 5,6-MDAT, DOMAI, and DOMAT (Nichols et al., 1990).
(4) Synthesis, and animal behavior (Malmusi et al., 1996).
(5) Rats trained to discriminate between amphetamine and saline only produced saline-appropriate
responses when challenged with MDAI (Oberlender and Nichols, 1991).
(6) Several psychedelic amphetamines were compared with their 2-aminoindan or their
2-aminotetralin analogues as serotonin uptake inhibitors in rats trained to discriminate between
MDMA and MBDB (Johnson et al., 1991a).
(7) Synthetic intermediate (Clark et al., 1986).
(8) Synthesis, and pharmacological screening (Violland et al., 1971).
MDA Homologues and Analogues with Changes Involving the

Methylenedioxy Ring or Substitutions on the Aromatic Ring
3- I 4- Other Name CAS # Ref
-OCO- -- MDA (this entry)
-OCO- 2-Me 2-Me-MDA [204916-87-0] (1)
-OCO- 5-Me 5-Me-MDA [204916-89-2] (1)
-OCO- 6-Me 6-Me-MDA [204916-90-5] (1)
-OCMeO- -- 7-Me-MDA [71203-56-0] (2-5)
-OCMeiCO- -- IDA [71203-59-3] (6-9)
-OCC- -- BF6AP [152623-93-3] (10)
-COC- -- IBF5AP [201407-57-0] (11)
-COC- N-Me IBF5MAP [201407-56-9] (11)
-COC- 6-Br,N-Me 6-B-IBF5AP [201407-53-6] (11,12)
-COC- 6-Cl,N-Me 6-C-IBF5AP [201407-55-8] (11,12)
-COC- 6-N02,N-Me 6-N02-IBF5AP [201407-54-7] (11,12)
-CCO- -- BF5AP [152624-03-8] (10)
(1) Synthesis and pharmacological evaluation (Parker et al., 1998b).
(2) Less active than MDA by a factor of three in LSD- and MDMA-trained rats (Nichols et al., 1989).
(3) Behavioral studies comparing 7-Me-MDA with MDA in mice (Nichols and Kostuba, 1979).
(4) Threshold oral effects in humans at 150 mg (Shulgin and Shulgin, 1991).
(5) In the code name EDA, the E can represent the first letter of ethylene or ethylidene. This is the
ethylidene isomer and has been called EDA-5, as it is a part of a five-membered ring. It is now
known as 7-Me-MDA, the ethylene isomer is either EDA-6, or just EDA (see #65).

MDA
(6) Synthesis (Nichols and Kostuba, 1979).

(7) With LSD and MDA trained rates, IDA has near half the activity of MDA (Nichols et al., 1989).
(8) Behavioral studies comparing IDA with MDA in mice (Nichols and Kostuba, 1979) .
(9) Human activity unknown.
(10) Evaluated in rats for discriminative stimulus effects (Monte et al., 1993).
(11) MAOI properties were evaluated (Scorza et al., 1997).
(12) The 6-position is the correct location if the compound is viewed as a substituted isobenzofuran,
but the -COC- ring should be numbered 1- and 3-; as an amphetamine, based on the MDA
model, the 6-substituent is properly at the 2-position, and the ring is bonded to the 4,5-positions.
Biochemistry
MOA affected the oxidation of tyramine by amine oxidase (Fellows and Bernheim, 1950) .
Two metabolites of MOA, 3,4-methylenedioxyphenylacetone and 3,4-methylenedioxyben
zyl methyl ketoxime, were identified by GC / MS in guinea pig and rabbit liver prepara
tions incubated with MOA (Midha, 1 974) . The catalytic conversion of MOA to OHA by rat
liver microsomes may have involved the NAOPH-dependent cytochrome P450 hydroxy
lase (Marquardt and DiStefano, 1974) . In the dog and monkey, MOA is metabolized to
3-0-methyl-a-methyldopamine (MHA), excreted in part as the j)-glucuronide or sulfate
conjugates (Midha et al., 1977) . Using [ 1 4C]-labeled MOA in the rat, urine contained the
conjugates of MHA and OHA. No unchanged MOA was excreted (Schweitzer et al., 1978) .
MOA metabolites in the dog and monkey included a-methyldopamine and 3,4-dihydroxy
phenylacetone; the monkey' s urine also contained 3,4-methylenedioxyphenylacetone, and
conjugated 3,4-methylenedioxybenzoic acid, and the dog's urine contained 3-methoxy-4-
hydroxybenzoic acid (Midha et al., 1 978) . Following i.p. injection of [ 3H]-labeled MOA
to rats, unchanged MOA was the major component in brain and liver, but after 24 hours,
OHA and MHA were the major metabolites seen (Marquardt et al., 1978c) .
S-MOA and R-MOA affected the release of serotonin from rat synaptosomes (Nichols et
al., 1982) . Incubation of MOA and MOMA with rat hepatic microsomes generated a spec
trally observable inhibitory complex with cytochrome P450 (Brady et al., 1986). MOA is
a metabolite of MOMA in the rat (Lim and Foltz, 1988), and in humans (Lim and Foltz,
1989) . Stereochemistry of the metabolism of MOMA to MOA was evaluated (Fitzgerald et
al., 1989b). MOA is a metabolite of MOOH; blood plasma isolation was described (Clark et
al., 1990b). MOMA was metabolized by the rat to give MOA, MHMA, MHA, HMMA, and
OHA. MOA was also seen in plasma (Yousif et al., 1990) . With i.v. administration of (+)-,
and separately (-)-MOMA to male rats, the dextrorotatory isomer produced three times the
quantity of MOA than from the levoisomer (Cho et al., 1990) .
The chemistry of the P450 demethylenation of MOA and MOMA was investigated (Fu
kuto et al., 1991). Rat liver produced hydroxylated metabolites of both MOA and MOMA,
at all three of the available aromatic positions (2-, 5-, and 6-) . Only the 6-hydroxylated
regioisomer (6-MOOH and 6-MOMOH) was found in the brain or plasma, and neither of
these was found in the urine (Lim and Foltz, 199la). There were indications that MOA was
converted to MOOH by cytochrome P450 (Kumagai et al., 1992; Lin et al., 1992) . 3-Methyl-
6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline was detected as a new metabolite in rat
urine (Nakagawa et al., 1993) . Interaction with the liver enzyme CYP206 was studied (Wu
et al., 1997) .
MOA is a human metabolite of MOE, and is visible in the urine for up to 36 hours after
MOE ingestion (Ensslin et al., 1996a) . In humans, 3% of administered MOE is excreted as
MOA (Ensslin et al., 1996b). GC / MS analysis of human urine has shown that the methyl-

MDA
enedioxy ring of MDA opens to give DHA and MHA as metabolites (Maurer, 1996), and a
major urinary metabolite of MDA is the demethyleneated catechol (Maurer et al., 2000). In
humans, the peak plasma level of MDA (following MOMA ingestion) was 15 µg I mL at six
hours (Helmlin et al., 1996) . Human cytochrome P450 was further shown to be involved in
the oxidative metabolism of MOMA-related drugs, and MDA was metabolized to DHA in
human liver microsomes containing CYP206 (Kreth et al., 2000) .
The blood and urine of human volunteers were analyzed for the optical isomers of MOMA
and its metabolite MDA, after the volunteers had been orally dosed with racemic MOMA
(Fallon et al., 1999). A review of studies on MDA metabolism included cytochrome P450
isoenzyme dependency, and screening procedures for detection of MDA, MOMA, MOE,
BOB, and MBDB (Maurer and Kraemer, 2002). Five N-hydroxylated derivatives of MOMA,
and its metabolite MDA, were identified in the urine of the horse; these were DHMAOH,
MHAOH, MHMAOH, MDOH, and FLEA (Dumasia, 2003). In the metabolism of MOMA
in humans, the S-isomer was more rapidly consumed, to give MDA, DHMA, and MHMA
(Pizarro et al., 2004) .
The action on isolated frog heart was studied (Ellis, 1949) . MDA was found effective in
releasing cardiac norepinephrine in the mouse (Daly et al., 1966) . MDA affected sponta
neous brain electrical activity in the cat (Fairchild et al., 1967), inhibited uptake of meta
raminol and efflux of noradrenaline by rabbit atria (Paton, 1975), and inhibited uptake of
labeled norepinephrine (Marquardt et al., 1978a) . The synthesis and tissue distribution of
radioiodine-labeled psychoactive drugs was motivated by a need for brain imaging agents
(Ghaffari et al., 1997) . MOMA, MDA, and MOE affected blood pressure, heart rate, loco
motor activity, and body temperature in the rat; these responses were shown to involve
a-adrenoceptors (Bexis and Docherty, 2006).
The octanol-water partition coefficients, steric bulk, and in vitro activity served as predic
tors of human psychedelic potency (Nichols et al., 1977) . Using calculated energy interac
tions between several amphetamines and a model compound (3-methylindole), a recep
tor model for psychedelics was developed (DiPaolo et al., 1978) . Stereochemical effects
of 3,4-methylenedioxymethamphetamine (MOMA) and related amphetamine derivatives
were noted, on inhibition of uptake of [ 3H]monoamines into synaptosomes from different
regions of rat brain (Steele et al., 1987) . Tolerance and cross-tolerance between MOMA,
MDA, and methamphetamine was studied in the rat (Zacny et al., 1990).
Serotonin receptor site affinity was determined (Glennon et al., 1978; Glennon et al.,
1980a) . The acute and long-term neurochemical effects of MDA, MOMA, and MOE were
examined in the serotonergic system of the rat brain (Schmidt, 1987b). 5-HT2 receptors
were the preferred site of psychedelic action as its radiolabeling marker (tritiated DOB)
was preferentially targeted; three controls (appropriately radiolabeled 5-HT 1 N 5-HT 1 w and
5-HT 1 c were not as strongly stimulated (Titeler et al., 1988) . Interactions between several
phenethylamines, phenylisopropylamines, and LSD with isolated rat and human brain
cortex 5-HT2 receptors were studied (Sadzot et al., 1989) . The binding affinities of MDA,
MOMA, and MOE were determined at nine neurotransmitter binding sites in human cor
tex (Pierce and Peroutka, 1989) .
Release of serotonin and dopamine by synaptosomes was evaluated (McKenna et al.,

1991). MHA and DHA, the major metabolites of MDA, did not produce serotonin deple
tion when injected into the brains of rats (McCann and Ricaurte, 1991a). The effects on

MDA
rats injected s.c. with 10 mg / kg of MDA on serotonin and 5-HIAA levels were observed
and recorded (Yeh and Hsu, 1991). The binding of a large number of phenethylamines,
phenylisopropylamines to 5-HT 1 c and 5-HT2 receptors was evaluated, and the affinities
were found to be less than an order of magnitude different across the compounds studied,
leading the authors to conclude that binding to these receptors was relatively non-specific
(Glennon et al., 1992) .
Mutagenic activity was not detected for MDA in Salmonella typhimurium (White et al.,
1977) . Toxicological studies of MDA and HMDA, and MOMA and HMDMA, in mice were
reported (Davis and Borne, 1984) . Racemic MDA was tested for acute intravenous lethality
in mongrel dogs (Waters et al., 1986) . Neurotoxic potential of MDA, MOMA, and MOE was
compared in rats (Stone et al., 1986, 1987a) .
Synthesis, identification, and acute toxicity of some N-alkyl derivatives of MDA was stud
ied (Noggle et al., 1987b). The toxicity of MDA and MOMA were compared in five animal
species (Davis et al., 1987) . Serotonin neurotoxicity of MDA was potentiated by inhibition
of y-glutamyl transpeptidase (Bai et al., 2001 ) .
Pharmacology
Synthesis and pharmacological evaluation was performed in cats (Benington et al., 1958a) .
A correlation was noted between structure and the locomotor activity of mice was made
(van der Schoot et al., 1962) . MDA was evaluated for toxicity, effects on barbiturate sleep
ing time, and ability to disrupt mouse behavior (Ho et al., 1970a), and was compared phar
macologically with mescaline, DMPEA, MDPEA, TMA, OMA, BOB, and MOMA in five
animal species (Hardman et al., 1973) . In a large number of methoxylated amphetamines,
the rabbit hyperthermia response was shown to parallel human psychedelic potency (An
derson et al., 1978b).
MDA was found to inhibit food intake in the dog (Vaupel et al., 1979) . Gross behavioral
and physiological effects of MDA and other psychedelics were evaluated in conscious,
restrained monkeys (Wilson et al., 1981). Amphetamine, and several psychedelics (PMA,
MDA, DOM, DOB, and 4C-M) protected rats from electroshock seizure (Davis et al., 1982) .
MDA produced a long-lasting reduction of serotonin levels, numbers of serotonin uptake
sites, and the concentration of 5-indoleacetic acid in the rat brain (Ricaurte et al., 1985) .
MDA released [ 3H]-labeled serotonin from rat hippocampal slices, and [ 3H]-labeled do
pamine from rat caudate nucleus slices (Johnson et al., 1986). MDA and MOMA caused
marked reductions in both tryptophan hydroxylase activity and concentrations of sero
tonin and 5-hydroxyindoleacetic acid in several serotonergic nerve terminal regions of the
rat (Stone et al., 1986).
Effects of an i.v. lethal dose of 3,4-methylenedioxyamphetamine (MDA) in the dog, and

antagonism by chlorpromazine was described (Davis et al., 1986) . Effects of MOMA, S
MDMA, MDA, and S-MDA were compared with respect to stereotyped behavior in rats
(Hiramatsu et al., 1989) . MDA was assessed in pigeons trained with a food presentation
paradigm (Nader et al., 1989); their responses were compared with the effects of 2C-B,
MBDB, and cathinone in newly hatched chickens (Bronson et al., 1995b). Comparisons of
the spontaneous behavior of rats were made with PMA, MOMA, MDA, and MOE (Hega
doren et al., 1995) . Effects of morphine, MOMA, MDA, and 2C-B were observed on condi
tioned place preference of newly hatched chickens (Bronson et al., 1996) .

MDA
MDA affected behavior in rats trained to respond to food presentation schedules (Har
ris et al., 1978) . Rats trained to discriminate between d-amphetamine and saline did not
respond to either MDA or DOM (Shannon, 1980) . Discriminative stimulus properties were
observed in rats trained to discriminate DOM from saline (Glennon et al., 1982c). Drug dis
crimination tests were utilized in rats to demonstrate that MDA produced stimulant effects
similar to those produced by OMA, LSD, and cocaine; properties of the optical isomers
were also evaluated (Glennon and Young, 1984a,b).
(±)-MDA and (±)-MOMA evaluated in monkeys trained to discriminate (+)-amphetamine

from saline (Kamien et al., 1986) . Discriminative stimulus properties of MDA and MOMA
studied in pigeons (Evans and Johanson, 1986) . About a dozen psychedelics were com
pared to stimulants by evaluation in rats trained in a conditioned avoidance paradigm
(Davis and Hatoum, 1987) .
MDA, MOMA, BOB, and MBDB were compared in a two-lever drug discrimination study,
with rats trained to distinguish saline from LSD (Nichols et al., 1986a). In establishing
definitions of entactogen, hallucinogen, and stimulant, drug discrimination-trained rats
(e.g. : MOMA versus (+)-amphetamine), the optical isomers of MDA, MOMA, MBDB, am
phetamine, LSD, and DOM were tested (Oberlender and Nichols, 1988). Rats trained to
discriminate between MBDB and saline substituted MDA, MOMA, MDAI, and MDMAI
completely, but not mescaline, DOM, or LSD. The term "entactogen" was proposed for
those compounds that substituted completely, and this line of evidence supported a func
tional distinction between these classes of psychoactives (Oberlender and Nichols, 1990) .
Four analogues of MDA involving the methylenedioxy ring (BF5AP, BF6AP, IAP, and TAP)
were further evaluated in rats for discriminative stimulus effects (Monte et al., 1993).
Racemic and R-MDA caused apparent psychedelic-like responses in mice: the S-MDA iso
mer was more effective in producing amphetamine-like behavior (Marquardt et al., 1978b).
tive phenylisopropylamines including the S- and R-isomer of MDA (Glennon et al., 1981b).
The separate effects of the optical isomers of MDA and MOMA were studied on central
serotonergic, dopaminergic and nigral neurotensin systems of the rat (Johnson et al., 1988),
and three-lever operant procedures differentiated the stimulus effects of R-(-)-MDA from
S-(+)-MDA (Young and Glennon, 1996) . MDA and MOMA optical isomers were assessed
in a stimulant-psychedelic discrimination evaluation (Baker and Taylor, 1997) .
The first human studies of MDA were directed toward possible therapeutic relief for Par
kinson's disease, but it proved to be detrimental (Loman et al., 1941 ). MDA was found oral
ly active in humans in the range of 80 to 140 mg, with some blood pressure rise, eye dila
tion, and visual effects noted (Alles, 1959); it was patented as an anorexogenic drug (Cook
and Fellows, 1961) and though clinically equivalent to amphetamine for this application, at
higher levels (120 mg / day) the stimulant properties were found to be objectionable.
Human potency was affected by changes in substitution patterns (Shulgin et al., 1969).
A positive correlation was found, in a series of psychedelic amphetamines, between the
stability of molecular complexes (as determined by NMR) and the threshold active dose in
humans (Sung and Parker, 1972); compounds with greater potency had lower ionization
potential as measured by photoelectron spectroscopy (Domelsmith and Houk, 1978) .
Pharmacological activity was studied in several animal and human assays (Braun et al.,
1980) . Many of the N-substituted homologues were screened for motor activity and analge-

MDA / homo-MDA
sia in mice. A series of amphetamines were studied for correlation between 5-HT2 receptor
affinity, charge complex stability, rabbit hyperthermia, and human activity (Domelsmith
et al., 1981).
The symptoms of MDA intoxication exhibited by a man prior to death closely mimicked
those of acute amphetamine poisoning: profuse sweating, violent and irrational behavior,
and stereotypically compulsive behaviors. Ingestion of a divided dose of 850 mg (2 hours,
15 minutes apart) caused death in four hours (Poklis et al., 1979). MDA was indicated in
the death of a 35-year-old male; the concentration found in blood and urine were within
the range of previously reported fatal MDA levels (Lukaszewski, 1979) .
Postmortem distribution studies were reported in MDA, MDMA, and MDE fatalities (Cox
and Williams, 1996), MDA and MDMA in a fatal overdose (De Letter et al., 2002a), and in
a fatal case following the insufflation of MDMA, cocaine, and heroin (Moore et al., 1996) .
Five patients died while hospitalized for MDMA intoxication; antemortem and postmor
tem samples were analyzed and compared for MDMA levels and the major metabolite,
MDA (Elliott, 2005).
Clinical trials in psychotherapy were explored with a fixed dose of 75 mg of the R-(-)-iso
mer (Turek et al., 1974); human trials were reported with oral doses between 40 and 200 mg
of the R-(-)-isomer (Yensen et al., 1976). Pharmacologically equivalent doses of the optical
isomers and the racemate in humans are: the R-(-)-isomer 70 mg, the racemic mixture 125
mg, and the S-( +)-isomer, 225 mg, the last with a considerable stimulant component (Mar
quardt, 1977) . Plasma samples (of six volunteers with 140 mg (±)-MDE HCl) were assayed
by chiral HPLC for unchanged MDA and the metabolites MDA and MHEA (Brunnenberg
and Kovar, 2001 ) .
Doses o f between 4 0 and 1 5 0 mg were evaluated a s an adjunct t o psychotherapy (Naranjo

et al., 1967) . MDA has been reported to be orally active in humans at 60-120 mg (Braun
et al., 1980), at 80-160 mg; duration 3-5 hours (Erowid and Erowid, 2001), and 8-12 hours
Analogues of MDA have appeared in the illicit drug market in Italy (Furnari et al., 1998).
Legal Status
MDA is a Schedule I hallucinogen under federal drug law (FR, 1970), and under District of
Columbia and all state laws except for Utah, and Vermont.
# 78. homo-MDA
4-(Benzo[d] [ l,3] dioxol-5-yl)butan-2-amine
1-(3,4-Methylenedioxylphenyl)-3-isobutylamine
a-Methyl-y-(3,4-methylenedioxyphenyl)propylamine
�------�
HMDA
CH3
Registry Numbers
CAS #
HCl salt [53581-65-0]
Freebase [40742-32-3]
R-Isomer HCl salt [103664-98-8]

homo-MDA
Synthesis
From methylenedioxybenzene (with methyl vinyl ketone, BF3 ) to 1-(3,4-methylenedioxy
phenyl)-3-butanone; (with NHzOH) to 1 -(3,4-methylenedioxyphenyl)-3-butanone oxime;
(with LAH) to homo-MDA (Aldous et al., 1974) .
From piperonal (with acetone, KOH) to 3,4-methylenedioxybenzilidineacetone; (with Pd,

H2) to 3,4-methylenedioxybenzylacetone; (with ammonia, Al, Hg) to homo-MD A (Shulgin
and Jacob, 1982a) .
From the hydrogenolysis of a 3-methylisoxazolone precursor over Raney Ni in MeOH

(Batra et al., 1992) .

m / z: 193. 1103 (100.0% ), 194.1136 (12.0%)
HCl salt m.p. 122-123 °C (Aldous et al., 1974) (acetone / MeOH)
The term "piperonyl acetone" has been applied to two commercially available products.
One of these, 3,4-methylenedioxyphenylacetone, when reductively aminated, gives rise
to MDA. The other, 3,4-methylenedioxybenzylacetone, gives rise to homo-MDA (Shulgin
and Jacob, 1982a, 1982b), which may give rise to unexpected toxicity in the illegal drug
market (Shulgin and Jacob, 1982b; cf: Davis and Borne, 1984); there is very little pharmaco
logical data on the latter material.
Synthesis and UV spectra, HPLC separation, and MS analysis were presented (Noggle et
al., 1989a) . homo-MDA was evaluated along with several a-ethyl phenethylamines synthe
sized and analytically compared with their amphetamine counterparts (Clark et al., 1995) .
Homologues and Analogues*

- -
- - homo-MDPEA [33543-11-2] (1)
Me -- homo-MDA (this entry)
Me Me2 homo-MDDMA [125559-67-3] (2,3)
Me Et homo-MDE [125559-68-4] (2-5)
Me Pr homo-MDPR [125559-69-5] (2,4)
Me iPr homo-MDIP [ 125583-22-4] (2,4)
Me HO homo-MDOH [167394-42-5] (3,6)
*Several homologues and analogues of homo-MDA were synthesized. These compounds all share
the 3,4-methylenedioxy substitution, and are named with parent molecule preceded by "homo" to
indicate the side chain has an additional carbon.
(2) Synthesis, UV spectra, HPLC separation, and MS analysis (Noggle et al., 1989a).
(3) Several a-ethyl phenethylamines were synthesized and analytically compared with their am-
phetamine counterparts (Clark et al., 1995).
(4) Synthesis (Noggle et al., 1989b).
(5) Also known as HMDE.
(6) Synthesis (Clark et al., 1995).
1 78 The Shulgin Index - Psychedelic Plzenethylamines and Related Compounds

homo-MDA / MDBP
Pharmacology
Behavioral effects in rats were compared with those produced by LSD, mescaline, and
amphetamine (Buxton, 1972) . When compared with MDA in mice, homo-MDA was found
to be more toxic and faster acting (Davis and Borne, 1984) .
Human activity o f homo-MDA has not been reported.
Legal Status
homo-MDA is not a scheduled compound under federal drug law, or under District of
# 79. MDBP
1 -(Benzo[d] [l,3]dioxol-5-ylmethyl)piperazine
1 -(3,4-Methylenedioxybenzyl)piperazine
1-(Benzo[ l,3] dioxol-5-yl-methyl)piperazine
1-( 1,3-Benzodioxy1-5-y1-methyI )piper azine
1 -(Benzodioxyl-5-y1-methyl)piperazine
1-( 4-Piperonyl)piperazine
N-Piperonylpiperazine
MBDZP
Registry Numbers
CAS #
di HCI salt [38063-96-6]
diacid salt [130313-17-6]
Freebase [32231-06-4]

From piperonyl chloride (with 1 : 1 mixture of piperazine dihydrochloride and piperazine
hexahydrate in methanol) to MDBP (Graizon et al., 1962) .
From piperonal (with piperazine) to the hemiaminal; (with Pd / C, H2) to MDBP (Gorins,
2001 ) .

m / z: 220.1212 (100.0% ), 221 . 1 245 (13.1 % )
d i HCl salt m.p. 232-236 °C (Graizon et al., 1962)
A plasma screening and quantitative GC / MS analysis was reported (Peters et al., 2003).

Ar-sub N- Name CAS # Ref
3,4-0CO- -CCNCC- MDBP (this entry)
4-Br-2,5-MeO -CCNCC- 2C-B-BZP -- (1,2)
(1) 1 00-200 mg range, 2C-B-BZP produces stimulant effects that last 3-6 hours, said by several sourc
es that it increases the effects of other compounds when combined (Wikipedia, 2007d).

MDBP / MDDMA
Biochemistry
The administration of serotonin uptake inhibitors including a,N-DMMDBA and MDBP
decrease the effectiveness of MOMA in the rat brain (Hashimoto and Goromaru, 1992;
Hashimoto et al., 1992a), and in mice (Hashimoto et al., 1993). Pretreatment in animals
with MDBP interfered with the metabolism of MOMA (Hashimoto et al., 1993). MDBP is
metabolized in the rat, first by demethylenation and then by methylation to 1 -(4-hydroxy-
3-methoxyphenyl)piperazine [443694-35-7], which forms a glucuronide or a sulfate conju
gate. MDBP is also metabolized by dealkylation of the piperazine ring to give N-(3,4-meth
ylenedioxybenzyl)ethylenediamine, and finally 3,4-methylenedioxy-benzylamine (Staack
and Maurer 2004; Staack et al., 2004b).
Pharmacology
The neurotoxicity of MOMA in rat brain was attenuated by the co-administration of MDBP,
as well as by N02-BP and Cl-BP (Hashimoto et al., 1992a) . MDBP inhibits MOMA-induced
neurotoxicity by effects other than serotonin uptake inhibition (Hashimoto et al., 1992b).
Acute effects of MOMA in the rat brain are reversed by MDBP (Hashimoto and Goromaru,
1992; Hashimoto, 1993) .
MDBP is a mild stimulant, and does not produce euphoria, empathogenic, or psychedelic
effects (Wikipedia, 2007a) .
Legal Status
MBDP is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
# 80. MDDMA
1-(Benzo[ d ] [1,3 ] dioxol-5-yl)-N,N-dimethylpropan-2-amine
N,N-Dimethyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N,N-dimethylamphetamine
N,N-Dimethyl-MDA
MOMMA
Registry Numbers
CAS # CAS #
HCI salt [74341-79-0] R-Isomer [872679-98-6] --- -- ----
Freebase [74698-50-3] S-Isomer [872679-99-7]

From piperonyl acetone (with dimethylamine, sodium cyanoborohydride) to MDDMA
(Braun et al., 1980) .
Synthesis by reductive amination of methylendioxyphenylacetone (Noggle et al., 1987b) .

m / z: 207. 1259 (100.0%), 208.1 293 (13.0%)
HCI salt m.p. 1 77-1 78 °C (Braun et al., 1980)

Freebase b.p. 85-88 °C / 0.15 mm (Braun et al., 1980)

MDDMA / MDE
Structural homologues were separated by liquid chromatography (Noggle et al., 1 987a)

and LC / MS (Noggle et al., 1988) . Substituted amphetamine derivatives were screened by
fluorescence polarization immunoassay (Cody and Schwarzhoff, 1 993) . Several a-ethyl
phenethylamines were synthesized and analytically compared with their amphetamine
counterparts (Clark et al., 1995). Proton and [ 13C]-NMR spectra recorded, with proton as
signments (Dal Cason et al., 1 997a) . Liquid chromatographic and mass spectral analysis
for N-substituted analogues of MDA presented (Noggle et al., 1988). Gas chromatograph
ic identification was performed as the heptafluorobutyl derivative (Lillsunde and Korte,
1 991 ) . Gas chromatographic and GC / MS techniques used to distinguish the three isomers
MDDMA, MOE and MBDB (Aalberg et al., 2003).
Reversed-phase (LC) chromatography and mass spectral analysis (Clark et al., 1 990a), and
mass spectral studies of the three isomeric compounds: MBDB, MOE and MDDMA, were
performed (Clark et al., 1 996a). Cross-reactivity of several substituted amphetamines were
studied with the Roche Abuscreen® (Cody, 1 990a), and with the Diagnostic Products Corpora
tion (Cody, 1 990b) radioimmunoassays for amphetamines. Analysis of human urine by
LC-MS-MS was reported (Nordgren and Beck, 2004; Nordgren et al., 2005). A connection
between impurities in the precursors to illicit drugs and the drugs themselves can indicate
the synthetic routes used in their production (Cimeno et al., 2005). The distinction between
MOE and MDDMA was apparent when using a quadrupole-orthogonal acceleration TOF
mass spectrometer, coupled to an LC separation system (Casteele et al., 2005) .
MOE, MDDMA, MBDB, and their 2,3-methylenedioxy positional isomers 2,3-MDE,

2,3-MDDMA, and 2,3-MBDB, all of identical mass and extremely similar mass spectra,
were synthesized, derivatized, and clearly defined by GC / MS (Thigpen et al., 2007) .
Pharmacology
Studies of motor activity, tail flick, stretch reflex, and analgesia in mice were performed
(Braun et al., 1 980) . Synthesis and tissue distribution of radioiodine-labeled psychoactive
drugs was studied, motivated by a need for brain-imaging materials (Ghaffari et al., 1 997) .
GC / FIR analysis showed that 2C-B, MOMMA, and MBDB had appeared for sale in Bel
gium (Dirinck et al., 2000) .
MDDMA was not orally active in humans at 160 mg (Braun et al., 1 980) .
Legal Status
MDDMA is not a scheduled compound under federal drug law, or under District of Co
# 81. MOE
1-(Benzo[ d] [ 1,3 ] dioxol-5-yl)-N-ethy lpropan-2-amine
N-Ethyl-3,4-methylenedioxyamphetamine
EMDA
Eve
MDEA

MDE
Registry Numbers
CAS # DEA# CAS #
HCl salt [74341-78-9] 5-(+)-Isomer HCl salt [ 197787-15-8]
Freebase [82801-81-8] 7404 R-Isomer freebase [114612-27-0]
R-(-)-Isomer HCl salt [328529-93-7] 5-Isomer freebase [114612-26-9]

From piperonyl acetone (with ethylamine, sodium cyanoborohydride) to MOE (Braun et
al., 1 980) .
From MDA (with acetic anhydride in pyridine) to N-Ac-MDA; (with LAH) to MOE (Braun
et al., 1 980) .
Synthesis by reductive amination of methylendioxyphenyl acetone (Noggle et. al., 1 987b).

Additional syntheses of MOE and its analogues were reported (Noggle et al., 1 986; Sanuki
et al., 2006).

m/ z : 207. 1259 (100.0% ), 208.1293 (13.0% )
HCl salt m.p. 201-202 °C (Braun et al., 1980)

TLC methods and color tests were defined for identification of substituted amphetamines
(O'Brien et al., 1 982) . Separation from structural homologues was achieved by LC (Noggle
et al., 1 987a) and LC / MS (Noggle et al., 1 988) . Three commercial amphetamine immunoas
says were compared for detection of MDA, MOMA, and MOE in urine (Ruangyuttikarn
and Moody, 1 988) . Cross-reactivity of several substituted amphetamines was evaluated
with the Roche Abuscreen® (Cody, 1 990a), and the Diagnostic Products Corporation (Cody,
1 990b) radioimmunoassays for amphetamines. GC identification utilized heptafluorobutyl
derivatives (Lillsunde and Korte, 1991). HPLC was developed for quantification of MOE in
urine samples (Helmlin and Brenneisen, 1992), and in whole blood, with linearity between
1 ng / ml and at least 1 µ g / ml, utilizing electrochemical detection (Michel et al., 1 993) .
Synthesis and chromatographic characterization were presented (Shimamine et al., 1 993a) .

Screening of substituted amphetamines was explored with fluorescence polarization im
munoassay (Cody and Schwarzhoff, 1 993) . Several a-ethyl phenethylamines were synthe
sized and analytically compared with their amphetamine counterparts (Clark et al., 1 995);
the N-hydroxy analogue, HOT-MOE, [167394-41 -4] was also synthesized. MBDB was dis
tinguished from the isomeric MOE by GC / MS (Clark et al., 1 996a; Garofano et al., 1 998),
and (again with GC / MS) the three isomeric compounds MBDB, MOE, and MDDMA were
MOE, MA, and amphetamine in urine by headspace I solid phase micro-extraction and
separately identified (Clark et al., 1 996a) . Quantitative and qualitative analysis of MOMA,
GC / MS reported (Centini et al., 1 996).
HPTLC-UV / FTIR was used to determine MOE and its two metabolites, MHEA and MDA,
in urine (Kovar and Pisternick, 1 996; Pisternick et al., 1 997) . Identification and quantifi
cation by capillary electrophoresis was described (Esseiva et al., 1 997) . Proton and [ 13 C]
NMR spectra were presented, with proton assignments (Dal Cason et al., 1 997a) . Rapid
planar chromatographic screening methods identified MOE (Fater et al., 1 998). Automated

MDE
online dialysis and LC of MDE in plasma and serum samples was achieved (Sadeghipour
and Veuthey, 1 998) . Urine screening procedures by GC / MS were described (Battu et al.,
1998) . Identification by color tests, TLC, GC, GC / MS, UV, and IR, was reported (Kanamo
ri et al., 1998b). Eight structurally related methylenedioxy drugs were distinguished by
reversed-phase liquid chromatography (DeRuiter et al., 1998c). A method was described
for the simultaneous determination of the ratio of d- and l- enantiomers of amphetamine,
titation in biological fluids was achieved with chemical ionization GC I MS (Mariani et

methamphetamine, MDA, MDMA, and MDE in urine (Hensley and Cody, 1 999). Quan
al., 1 999) . MDA, MDMA, and MDE analyses were developed, using HPLC and fluores
cence detection, for whole blood, serum, vitreous humor, and urine (Clauwaert et al.,
2000). Optical isomers of MDE were obtained by fractional crystallization (Buchlera et al.,
2000). Synthesis and GC / MS spectral distinction between the 2,3- and 3,4-isomers was
elucidated (Borth et al., 2000). GC / MS screening of urine samples to differentiate between
MDMA, MDA, MDE, and MBDB followed extraction, deconjugation and derivatization
(Pellegrini et al., 2002). Whole blood analyses were developed utilizing capillary electro
phoresis with diode-array detection (Boatto et al., 2002); plasma analyses by GC / MS were
reported (Peters et al., 2003). MDMA, MDE, and MDA were analyzed in urine by HPLC
with fluorescence detection (da Costa and da Matta, 2004), and enantiomeric separation
and quantitation of (±)-amphetamine, (±)-methamphetamine, (±)-MDA, (±)-MDMA, and
(±)-MDE in urine specimens by GC-EI-MS after derivatization with (R)-(-)- or (S)-(+)-a
methoxy-a-(trifluoromethy)phenylacetyl chloride (MTPA; Paul et al., 2004) . Blood testing
was validated for negative-ion chemical ionization GC / MS and enantioselective measure
ment of MDE, MDMA, and MDA (Peters et al., 2005). Chiral analysis of MDA, MDMA,
and MDE (as well as of amphetamine and methamphetamine) was performed on human
whole blood samples (Rasmussen et al., 2006).
The effectiveness of hair analysis for MDE was determined with pigmented hairy rat
experiments (Kikura et al., 1 997) . Procedures were developed for hair analysis of MDA,
MDMA, and MDE (Rohrich and Kauert, 1997; Tagliaro et al., 1 999), and MDE (Junker et al.,
2001; Van Den Berg et al., 2002). Detection of methamphetamine, MDMA, and MDE in hu
man hair was achieved by ion mobility spectrometry (Keller et al., 1 998). The ORAL•screen
saliva drug test was evaluated for the screening of methamphetamine, MDMA, and MDE
incorporated in hair (Miki et al., 2004) .
Analysis without derivatization by LC / MS was reported (Bogusz et al., 2000), and GC /

MS techniques for distinguishing the three isomers MDDMA, MDE, and MBDB were re
ported (Aalberg et al., 2003). A stability study of MDA, MDMA, and MDE in water, serum,
whole blood, and urine under various storage temperatures was performed (Clauwaert et
al., 2001 ) . MDE was among the fragmentation patterns of some fifty-five phenethylamines
determined by a variety of mass spectrometry techniques (Kolliker and Oehme, 2004).
Analysis of human urine by LC-MS-MS was reported (Nordgren and Beck, 2004; Nordgren
et al., 2005) . MDE and MDDMA were distinguished from one another using a quadru
pole orthogonal-acceleration time-of-flight mass spectrometer, coupled to an LC system
(Casteele et al., 2005). Amphetamine, methamphetamine, MDA, MDE, and MDMA were
analyzed in urine by online solid-phase extraction, and ion-pairing liquid chromatography
with detection by electrospray tandem mass spectrometry (Wu and Fuh, 2005). MDMA,
MDA, MDE, and MBDB were analyzed in oral fluids using HPLC with native fluorescence
detection (Concheiro et al., 2005). Fast GC / MS techniques were used for determination of
amphetamine, methamphetamine, MDA, MDMA, and MDE in urine, in under 3.5 minutes
(Klette et al., 2005).

MOE
Identification from IR spectra, with neural network processing, and with neural networks
coupled with principal component analysis was presented (Gosav et al., 2005) . A sensitive
GC / MS method for simultaneous measurement of MOE, MOMA, and metabolites MHA,
titation for the target compounds of 25 ng I ml. Analysis of serum by extraction, derivatiza
MOA, and MHMA in human urine was reported (Pirnay et al., 2006), with limits of quan
tion with trifluoroacetic anhydride, and GC / MS was described (Hidvegi et al., 2006). Oral
fluids were analyzed by GC / MS, for MOMA, MOE, and their metabolites (Scheidweiler
and Huestis, 2006). MOE, MOOMA, MBOB, and their 2,3-methylenedioxy positional iso
mers 2,3-MOE, 2,3-MOOMA, and 2,3-MBOB, all of identical mass and extremely similar
mass spectra were synthesized, derivatized, and clearly defined by GC / MS (Thigpen et
al., 2007) .

3- I4- a- j)- N- Name CAS # Ref
-OCO- Me -- Et MDE (this entry)
- OCFp- Me - - Et F2-MDE [914800-82-1] (1)
Biochemistry
Enantiomers of MOE and its metabolite MOA were detected in the rat brain (Tucker, 1 996) .
GC / MS analysis of human urine showed that the methylenedioxy ring of MOE opens to
give OHEA as a metabolite (Maurer, 1996). In human studies MOE and its metabolites OHEA
and MOA were detectable in urine for up to three days. MHEA could be seen a week after
ingestion. Trace metabolites OHA, MHA, piperonylacetone, 3,4-dihydroxyphenylacetone,
and 3-methoxy-4-hydroxyphenylacetone were detectable for only a few hours (Ensslin et
al., 1 996a) . In humans, after 32 hours, 31 .6% of the ingested MOE is excreted as MHEA,
19% as unchanged MOE, and 2.8% as MOA (Ensslin et al., 1996b). 3,4-Methylenedioxyhip
puric acid and hydromethoxyhippuric acid were human metabolites of MOE (Ensslin et al.,
1996b). Clinical studies with 14 volunteers given oral doses between 1 00 and 140 mg MOE
provided a quantitative urinary excretion range of unmetabolized MOE and the metabo
lites MOA and MHEA (Brunnenberg et al., 1998) . Two major routes to the observed urinary
metabolites of MOE were N-dealkylation, and demethyleneation to the catechol (Maurer et
al., 2000). The human cytochrome P450 involved in the oxidative metabolism of MOMA
related drugs was identified (Kreth et al., 2000). Plasma samples (of six volunteers given 140
mg dl-MOE HCl) were assayed by chiral HPLC for unchanged MOE and the metabolites
MOA and MHEA (Brunnenberg and Kovar, 2001). A review of studies on MOE metabolism
included cytochrome P450 isoenzyme dependencies, and screening procedures for detec
tion of MOA, MOMA, MOE, BOB, and MBOB (Maurer and Kraemer, 2002).
Synthesis, identification, and acute toxicity of some N-alkyl derivatives of MOA has been
reported (Noggle et al., 1987b). Studies on the release of serotonin and dopamine were
performed, with discussion of structural features that might give rise to neurotoxicity
(McKenna et al., 1991). Immunocytochemical evidence was given for serotonergic
neurotoxicity of MOE (Series and Molliver, 1 994) . MOMA and MOE were compared as to
pharmacology, biochemistry, and toxicity in the rat (Colado et al., 1999). MOE purportedly
produced long-lasting depletion of serotonin in the rat brain (Ricaurte et al., 1987). Effects
of MOE on central serotonergic and dopaminergic systems of the rat were described
(Johnson et al., 1 987a) . Acute and long-term neurochemical effects of MOA, MOMA,
and MOE were examined in the serotonergic system of rat brain (Schmidt, 1 987b). Acute

MDE
MOE action on the central serotonergic system of the rat was characterized (Johnson et
al., 1 989a) . The neurotoxic potentials of MDA, MOMA, and MOE were compared in rats
(Stone et al., 1986, 1987a) . Binding affinities of MDA, MOMA, and MOE were determined
at nine neurotransmitter binding sites in human cortex (Pierce and Peroutka, 1 989) . Sleep
EEG effects of MOE were monitored in healthy volunteers (Gouzoulis et al., 1992).
Pharmacology
MOE effects on motor activity, tail flick, stretch reflex and analgesia reported in mice; initial
human trials were also described (Braun et al., 1 980) . Behavioral effects of MOE described
in male rats, with suggestion of possible serotonergic and dopaminergic mediation of the
MOE discriminative stimulus (Boja, 1 988; Boja and Schechter, 1987, 1991 ) . Locomotor and
investigative behavioral responses were profiled in rats for MOMA and MOE (Gold et
al., 1988) . Effects of MOE assessed in pigeons trained with a food presentation paradigm
(Nader et al., 1 989) . Pre-pulse inhibition of the acoustic startle response of the rat was dis
rupted by MOE (Mansbach et al., 1989). Spontaneous behavior of rats was compared with
PMA, MOMA, MDA, and MOE (Hegadoren et al., 1 995) . Baboons trained to self-inject co
caine were switched to MOE, MDOH, DIMETH, and 2C-B, and changes in behavior were
noted (Sannerud et al., 1 996) . MOE produced serotonergic deficits and impaired passive
avoidance learning in rats (Barrionuevo et al., 2000). MOMA, MDA, and MOE effects on
blood pressure, heart rate, locomotor activity, and body temperature in the rat shown to
involve a-adrenoceptors (Bexis and Docherty, 2006).
Discriminative stimulus properties of the R- and 5-isomers of MOE were observed in

rats trained to discriminate DOM from saline (Glennon et al., 1 982c). MOMA, MOE,
and MDOH were evaluated in rats that were trained to distinguish amphetamine from
DOM (Glennon et al., 1 988d), and MOE and MDOH were evaluated with rats trained to
discriminate MOMA from saline (Glennon and Misenheimer, 1989) .
Oral activity in humans was first reported at 140-200 mg (Braun et al., 1 980) . Psychological
effects of 140 mg of MOE were recorded for 14 human subjects (Hermle et al., 1993) . In dou
ble-blind human studies, it was found that MOE exerted similar mental effects in humans
as MOMA, and was also less toxic in animal studies (Gouzoulis et al., 1 992) . Cranial meta
bolic activity was localized with PET scanning following administration of MOE, psilocy
bin or d-methamphetamine to eight healthy subjects (Gouzoulis-Mayfrank et al., 1999b);
psychological, neuroendocrine, and autonomic effects of administration of the same suite of
drugs were observed in 32 healthy volunteers, with similar controls (Gouzoulis-Mayfrank
et al., 1999a) . The authors noted MOE created a calming, empathetic psychological state ac
companied by physiological activation. At oral doses of 70 mg of the HCl salt in humans,
the 5-isomer gave the subjects an elevated mood and cognitive impairment (Spitzer et al.,
2001 ); the R-isomer produced depression and enhanced visual effects. The authors con
cluded that the 5-isomer was responsible for the entactogenic effects, and the R-isomer was
responsible for neurotoxicity. Neuropsychopharmacology and toxicology of MOE reviewed
(Freudenmann and Spitzer, 2004).
A number of toxic overdoses cases have been seen with this drug. Five deaths due to, or
associated with, the combined use of MOMA and MOE were reported (Dowling et al.,
1 987) . A patient was admitted with hyperthermia, muscle rigidity, rhabdomyolysis (rapid
breakdown of skeletal muscle) and disseminated intravascular coagulation; blood analysis
revealed the presence of MOE (Tehan et al., 1993) . A toxic psychosis case was attributed
to MOE (Gouzoulis et al., 1 993a), and psychiatric disorders were reported after a single
combined MOE and cannabis use (Assion and Heinemann, 1 996) .

MDE / MDMA
The first observation of lethal recreational use of MOMA and MOE in Italy was reported,
together with extensive toxicological and histopathological documentation (Fineschi and
Masti, 1996). A case of oral ingestion of large doses of both MOE and heroin was reported;
despite high serum levels of both drugs, the patient did not present with the classic signs
and symptoms normally seen during intoxication with either (Jorens et al., 1 996).
Autopsy records were given for seven young adults who had used either MOMA or MOE,
which indicated myocardial events were involved (Milroy et al., 1996). Postmortem blood
levels were reported in MDA, MOMA, and MOE fatalities (Cox and Williams, 1 996) . In a
report of an MOE-related death in Greece, blood MOE was 3.1 µ g / ml, and MOE concen
trations in liver, lung, and kidney were 4.8, 5.2, and 4.8 µ g / g, respectively (Tsatsakis et al.,
1997) . An intentional overdose and death with MOE was reported (Arimany et al., 1 998),
and an analytical autopsy was reported in an MOE overdose fatality (Weinmann and Boh
nert, 1998). Three fatal cases of MOMA / MOE misuse were examined. The subjects were
white males between 19 and 20 years of age, in which post-mortem toxicology showed the
presence of MOMA in one case, MOE in another case, and both in the third case (Fineschi
et al., 1999).
MOE, MOMA, and MDA were found in the urine of Ecstasy users at raves, in a study that
compared detectability by GC / MS and HPLC-DAD with several commercially available
immunoassay kits (Zhao et al., 2001).
Following its appearance in Japan, MOE was declared illegal (Ohshita et al., 1995; Katagi et
al., 2002). In Canada, pills sold as "Ecstasy" were found to contain largely MOE (Dawson et
al., 1997).
MOE is orally active at 1 00-200 mg; duration 3-5 hours (Shulgin and Shulgin, 1991).
Legal Status
MOE is a Schedule I hallucinogen under federal drug law, and under all state laws except
for California, Delaware, Kentucky, Maryland, Massachusetts, Michigan, Minnesota,
Nebraska, New Jersey, New Mexico, Oklahoma, Rhode Island, South Carolina, Tennessee,
Vermont, and Washington.
# 82. MOMA
1 -(Benzo[ d] [1,3 ] dioxol-5-yl)-N-methylpropan-2-amine
3,4-Methylenedioxymethamphetamine
a,N-Dimethyl-1,3-benzodioxole-5-ethanamine
a,N-Dimethyl-3,4-methylenedioxy)phenethylamine
N-Methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane
Methylsafrylamin
Adam
E
Ecstasy
Love Drug
XTC
Yaoto-wang (Japan)
NSC-168383

MDMA
Registry Numbers
CAS # DEA# CAS #
HCI salt [64057-70-1 ] 7405 5-( +)-Isomer freebase [66142-89-0]
Freebase [ 42542-10-9] [d5 ]-MDMA [ 136765-43-0 l
R-(-)-Isomer HCI salt [ 69558-31 -2] N-CH2-[ 3H]-labeled [128671-19-2]
5-( +)-Isomer HCI salt [ 69558-32-3] N-[ 11 C]-Me [153506-20-8]
R-(-)-Isomer freebase [81262-70-6] R-Isomer N-[ 11 C]-Me [165172-59-8]

From safrole (with aqueous HBr) to 5-(2-bromopropyl)benzo-1,3-dioxole; (with methyl
amine in EtOH) to MOMA (Merck, 1912; Bineicki and Krajewski, 1960) .
From 3,4-methylenedioxyphenylacetone (aka: piperonylacetone; with methylamine,

sodium cyanoborohydride) to MOMA (Braun et al., 1980) .
From MOA (with formic acid or ethyl formate) to N-formyl-3,4-methylenedioxy

amphetamine; (with LAH) to MOMA (Shulgin and Shulgin, 1991)
From isosafrole (with formic acid, H202) to 3,4-methylenedioxyphenylacetone; (with Al,

HgC12, CH3NH2) to MOMA (Shulgin and Shulgin, 1991).
(For the optical isomers) from piperonylacetone (with R-(-)- (or 5-(+)-) a-methylbenzyl
amine, Raney Ni) to R,R- (or 5,5) N-a-methylbenzyl-MOA; (with Pd, H2) to R-(-)- (or 5-(+)-)
MOA; (with methyl formate) to R-(+)- (or 5-(-) N-formamido-MOA; (with LAH) to R-(-)
(or 5-(+)-) MOMA (Anderson et al., 1978a) .

m / z: 193.1103 (100.0% ), 194.1136 (12.0% )
HCl salt m.p. 148-150 °C (Merck, 1912)

HCl salt m.p. 148-149 °C (Biniecki and Krajewski, 1960)
HCl salt m.p. 152-153 °C (Braun et al., 1980)
HCI salt m.p. 149.85-151 .85 °C (Morimoto e tal., 1998) (Etp / IPA)
R-(-)-Isomer HCI salt m.p. 181-183 °C [a] � -18.2° (Anderson et al., 1978a)
5-( +)-Isomer HCl salt m.p. 1 84-1 85 °C [a] � + 1 7.2° (Anderson et al., 1978a)
R-(-)-Isomer HCI salt m.p. 192-193 °C [a] � -17.54° (Nichols et al., 1986a)
5-( +)-Isomer HCI salt m.p. 192-193 °C [a] � + 1 7.43° (Nichols et al., 1986a)
5-( +)-Isomer HCl salt m.p. 187 °C [a] � + 1 7.9° (Effenberger and Jager, 1997)
MOMA is unique among the psychedelic amphetamines both in its mode of action, its
relatively late rediscovery, and the breadth of research devoted to it. The chemistry sec
tion is consequently more involved than for virtually all other compounds covered in this
volume, and has been roughly broken into papers dealing with general chemical and spec
troscopic characterization, alternate synthetic routes and forensic analysis, detailed ana
lytical methods suitable for studies of physiological effects or metabolic fate, and screening
methods that address rapid identification or preliminary analysis of samples such as drug
seizures, hair, oral fluids, and other samples of opportunity. Research is largely arranged
chronologically within these areas.

MDMA
Spectrophotometric and chromatographic methods for identification of MDA, MOMA,

MOE were reported (Noggle et al., 1 986). In support of preliminary toxicological exami
nations, MOMA and related compounds were synthesized by reductive amination of
3,4-methylenedioxyphenylacetone; the series was characterized by UV and LC (Noggle
et al., 1 987a,b) . Structural homologues were separated and characterized by liquid chro
LC / MS (Clark et al., 1990a; DeRuiter et al., l998b ). Resolution of optical isomers of MOMA
matography (Noggle et al., 1987a, 1988), LC / MS (Noggle et al., 1988), and reversed-phase
was achieved (Fitzgerald et al.,1989a) . Synthesis and analytical properties for TLC, UV, IR,
HPLC, GC / MS, and NMR were described (Shimamine et al., 1 990). MOMA could be dis
tinguished from BOB (Noggle et al., 1991 c), and from MBDB (Clark et al., 1 996a) by GC /
MS, through careful analysis of their spectra. MOMA was among several methylenedioxy
propanamines and butanamines synthesized and analytically compared by LC, UV, FTIR,
and GC / MS (Clark et al., 1995).
Proton and [ 13 C]-NMR spectra were reported, with proton assignments (Dal Cason et al.,
1 997a) . Analysis and identification by color tests, TLC, GC, GC / MS, UV and IR spectro
metry was reported (Kanamori et al., 1 998b). The crystal structure of MDMAHCl was
determined by x-ray diffraction (Morimoto et al., 1998) . The actual form of the final salt
is highly dependent on the temperature and concentration conditions at the moment of
crystallization, and several forms were observed, only some of which have sharp melting
points (Shulgin and Shulgin, 1 991 ) . MOMA was identified by FTIR spectral analysis (Praisler
et al., 2000), and by IR spectroscopy, with neural network analysis, and neural networks
coupled with principal component analysis (Gosav et al., 2005). An NMR procedure was
described for the identification of substituted amphetamines and related compounds (Hays,
2005). In a study of synthesis and analysis of MBDB and its analogues, 2,3-methylendioxy
variants could be distinguished from the more common 3,4-methylenedioxy compounds
by IR and NMR spectroscopy (Sanuki et al., 2006).
Alternative synthetic routes to MOMA and other related compounds that might be
encountered in clandestine laboratories were described (Dal Cason, 1990) . Analysis of the
contaminants in street MOMA indicated that reductive amination and the Leuckart reaction
were preferred synthesis methods employed (Verweij, 1 991 ) . Identification of impurities in
illegally synthesized MOMA tablets, by a variety of techniques, was used to characterize
their origin (Bohn et al., 1993) . If crude sassafras oil is used instead of safrole, the natural
contaminating allylbenzenes give rise to impurities such as DMMA and MHMA (Noggle
et al., 1991a). Other intermediates and byproducts from different syntheses of MOMA were
identified and characterized, and can be used to establish the synthesis routes employed
(Renton et al., 1993; Cimeno et al., 2002; Swist et al., 2005a,b) . Analysis of seized tablets
for isotopic composition and impurities generates a "fingerprint" to define a common
source (Carter et al., 2002). Employing HPLC-PDA, LC / MS, TLC, and NMR, a library
of 35 illegal drugs was assembled and used to identify street samples (Nakashima et al.,
2005). Techniques were explored for the LC / MS analysis of street drugs without the use of
primary reference standards (Laks et al., 2004) . Fragmentation patterns of some fifty-five
and Oehme, 2004).
MDA and MOMA enantiomers were determined in whole blood (Fitzgerald et al., 1 989a) .
Heptafluorobutyl derivatives of MOMA were identified by GC (Lillsunde and Korte,
1991). HPLC analysis of whole blood for MOMA had a detection limit of 1 ng / ml (Mi
chel et al., 1993) . Automated online dialysis and liquid chromatography of MOMA was

MDMA
developed for plasma and serum samples (Sadeghipour and Veuthey, 1 998). A CC / ni
trogen-phosphorous detector method was descried for MOMA and its metabolites, for
analysis of human urine samples (Ortuno et al., 1999) . Levels were determined in biologi
cal fluids by chemical ionization GC / MS (Mariani et al., 1999) . A method was described
for the simultaneous determination of the ratio of d- and 1-enantiomers of amphetamine,
methamphetamine, MOA, MOMA, and MOE in urine by GC / MS following formation of
trifluoroacetyl-l-prolyl derivitives; the technique was used to evaluate stereospecific me
tabolism of the parent drugs (Hensley and Cody, 1999) . Analysis of serum was possible
following solid-phase extraction, and LC / MS with atmospheric pressure chemical ioniza
tion using deuterated analogues as internal standards (Bogusz et al., 2000). MOA, MOMA,
and MOE were detected with HPLC and fluorescence detection in whole blood, serum,
vitreous humor, and urine (Clauwaert et al., 2000). A study of MOA, MOMA, and MOE
in water, serum, whole blood, and urine examined stability at various storage tempera
tures (Clauwaert et al., 2001 ) . A quantitative GC / MS method was described for the optical
isomers of MOMA (and its three major metabolites MOA, MHMA, and MHA) in human
plasma and urine, derivatized as the trifluoroacetates (Pizarro et al., 2002b, 2003).
Enantiomeric separation and quantitation of (±)-amphetamine, (±)-methamphetamine,

(±)-MOA, (±)-MOMA, and (±)-MOE in urine specimens by GC-EI-MS was achieved af
ter derivatization with R-(-)- or S-( + )-a-methoxy-a-(trifluoromethyl)phenylacetyl chloride
(MTPA; Paul et al., 2004) . Chiral GC analysis of MOA, MOMA, and MOE (as well as of
amphetamine and methamphetamine) was performed on human whole blood samples
(Rasmussen et al., 2006). Sensitive GC / MS methods were described for simultaneous mea
surement of MOE, MOMA, MBOB, and metabolites MHA, MOA, and MHMA in human
urine with quantitation limits of 5-10 ng / ml (Pellegrini et al., 2002) and 25 ng / ml (Pirnay
et al., 2006). MOMA, isomers, and related compounds were identified by GC / MS (Aalberg
et al., 2000, 2004; Klette et al., 2005), by high performance liquid chromatography with flu
orescence detection (da Costa and da Matta, 2004), by LC / MS with sonic-spray ionization
(Mortier et al., 2002), and by electrospray ionization LC / MS (Pihlainen et al., 2005) . Blood
determination was validated for a negative-ion chemical ionization gas chromatographic
mass spectrometric assay for enantioselective measurement of MOE, MOMA, and MOA
(Peters et al., 2005). Analysis of human urine by LC-MS-MS methods was reported (Nor
dgren and Beck, 2004; Nordgren et al., 2005). Amphetamine, methamphetamine, MOA,
MOE, and MOMA were analyzed in urine by online solid-phase extraction and ion-pairing
liquid chromatography with detection by electrospray tandem mass spectrometry (Wu
and Fuh, 2005). Serum samples were analyzed by extraction, derivatization with trifluoro
acetic anhydride, and GC / MS (Hidvegi et al., 2006).
Analysis by capillary electrophoresis was reported (Trenerry et al., 1995; Esseiva et al.,
1997) . MOMA could be identified and distinguished from several structurally related com
pounds in human urine by capillary electrophoresis with fluorescence detection (Chung et
al., 2001). Blood analyses were developed with capillary electrophoresis coupled to photo
diode array detectors (Boatto et al., 2002) . The S-isomer of MOMA, and the main metabo
lites S-MHMA and S-OHMA were also prepared and analyzed by capillary electrophoresis
(Pizarro et al., 2002a, b).
TLC and color tests were defined for the rapid identification of substituted amphetamines
(O'Brien et al., 1982) . Three commercial amphetamine immunoassays were compared for
detection of MOA, MOMA, and MOE in urine (Ruangyuttikarn and Moody, 1988) . Cross
reactivity of several substituted amphetamines with the Roche Abuscreen® (Cody, 1990a),

MOMA
and the Diagnostic Products Corporation (Cody, 1990b) radioimmunoassays was evaluated.
Substituted amphetamine derivatives were also screened by fluorescence polarization im
munoassays (Cody and Schwarzhoff, 1993) . Quantitative and qualitative analysis was de
veloped for MDMA, MDE, MA, and amphetamine in urine by headspace / solid phase mi
cro-extraction and CC / MS (Centini et al., 1 996) . MDMA was identified by a rapid planar
chromatographic screening method (Fater et al., 1998), and a urine screening procedure
by CC / MS was reported (Battu et al., 1998) . A plasma screening and quantitative CC /
MS analysis was reported (Peters et al., 2003). A single HPLC-UV analysis of human urine
could detect amphetamine (and its metabolite PHA), MDMA (and its metabolite MDA),
2C-B and MTA (Soares et al., 2004) . MDMA, MDA, MDE, and MBDB were determined in
oral fluid using high performance liquid chromatography with native fluorescence detec
tion (Concheiro et al., 2005). Oral fluids were analyzed by CC / MS, for MDMA, MDE, and
their metabolites (Scheidweiler and Huestis, 2006).
CC / MS procedures were reported for detection of amphetamine, MDA, MDMA, and

MDE in hair (Rohrich and Kauert, 1 997), and MDA and MDMA in hair samples (Kintz and
Cirimele, 1997) . Concentrations in hair samples from 20 amphetamine and MDMA users
were described, along with self-reported use histories from the subjects (Rothe et al., 1 997);
scalp hair from several MDMA users also showed both MDMA and MDA by CC / MS (Ki
kura et al., 1997) . The effectiveness of hair analysis for MDMA (and its metabolites MDA,
MHA, and MHMA), and hair pigment influence was determined with pigmented hairy
rat experiments. Disposition of MDMA in hair roots was also studied in the rat (Nakahara
and Kikura, 1997) . Methamphetamine, MDMA, and MDE were detected in human hair
by means of ion mobility spectrometry (Keller et al., 1 998) . Procedures were developed
for MDMA analysis in hair samples by HPLC with fluorescence detection (Tagliaro et al.,
1 999), CC / MS (Junker et al., 2001 ), and CC with triple-quad MS-MS techniques (Van Den
Berg et al., 2002). The ORAL•screen saliva drug test (currently of Craig Medical Distribution,
Inc.) was applied to the screening of methamphetamine, MDMA, and MDE incorporated
in hair (Miki et al., 2004). Segmental hair analysis was shown to accurately reflect past us
age history (Pichini et al., 2006) .
unteers administered known doses of MDMA (Pacifici et al., 2001 ) . ( AurnoRs' NoTE: This
Skin testing was performed with DrugWipe (Integrity Detection Systems, LLC) with vol
vendor claims their "lab-on-a-stick" is "capable of detecting target drug residues on any
surface, whether a user has recently been present or not," and is "ideal" for testing in the
workplace or at schools) . A detailed study compared this skin monitoring approach with a
second skin-patch monitor, following the administration of MDMA to human volunteers;
the target drug could be detected in sweat in 1 .5 hours and peaked at 24 hours. Concentra
tions varied 30 fold from subject to subject; only traces of MDA were detected; measure
ments were corroborated with CC / MS (Pichini et al., 2003). Plasma, oral fluid, and sweat
wipe MDMA concentrations were compared in controlled and "real life" conditions (Sa
myn et al., 2002).
History
Many papers state incorrectly that the original synthesis of MDMA was for use as an ap
petite suppressant. It was patented as a precursor in a new synthesis for haemostatic sub
stances (Merck, 1912). The new pathway was patented in order to evade an existing patent
by a local competitor. A history of MDMA from 1912 to 1988 referred to patents, notebooks
from the period, and internal Merck databases (Freudenmann et al., 2006). Toxicological
and behavioral studies in animals on MDMA and several related compounds were funded

MDMA
by the Army Chemical Center in the early 1950s. These were declassified in 1969, and first
published in 1973 (Hardman et al., 1 973) .
The first mention w e have located o n MDMA i n forensic exhibits reports a second encoun
ter with the material (Anon., 1972); a subsequent report described color reactions, melting
points, GC retention times, and IR data from samples analyzed by the Chicago Regional
Laboratory of the Bureau of Narcotics and Dangerous Drugs (Gaston and Rasmussen,
1972) . The modern "rediscovery" and report on the psychological effects of MDMA is gen
erally traced to the seminal paper of Shulgin and Nichols (1978), after which interest in
this compound spread rapidly. The Drug Enforcement Administration placed MDMA in
an emergency Schedule I status of the Controlled Substances Act in 1986 (FR, 1986; note
that MDMA was deleted, then replaced into Schedule I status in 1 988. cf: FR, 1988a,b). In
an issue of the Journal of Psychoactive Drugs (Seymour et al., 1986) devoted to papers from
a conference addressing the use of MDMA (at the Health Education Center of the Mer
ritt Peralta Medical Center, Oakland, CA, May 1 7-18, 1986), numerous aspects of MDMA
were discussed, including historical background and chemistry of MDMA (Shulgin, 1986),
differences between the action of MDMA and classic psychedelics (in which the term "en
tactogen" was discussed; Nichols, 1986b), composition of "Ecstacy" tablets and capsules
(Renfroe, 1986), and side-effects encountered in the emergency room setting (Hayner and
McKinney, 1986), among others. A later review of the history of MDA and MDMA ad
dressed the potential of these materials to be used safely as psychotherapeutic tools (Pent
ney, 2001 ) .
Despite the declaration o f illegality, popular use o f MDMA worldwide has dramatically
expanded, resulting in a concurrent rise of interest in its pharmacology and potential for
toxicity through misuse. Recent reviews have drawn from the growing literature investi
gating the mode of action and unique pharmacological properties of MDMA (Green, 2003),
and have pointed to the importance of MDMA action on monoamine transporters, the trig
gering of serotonin release, and the inhibition of reuptake of neuronal monamines. MDMA
popularity also ignited intense debate on its actual potential for harm, as a contributor to
neurotoxicy or psychiatric disorders. This led to a symposium at the Annual Meeting of the
Society for Neuroscience (San Diego, CA, October 23-27, 2004) reported in a special issue
of Psychopharmacology (cf: De La Garza and Miczek, 2007) . Notably in this issue, the fol
lowing statement summarized findings in the realm of psychiatric effects: " .. .longitudinal
studies have failed to show an increase in psychiatric symptoms in Ecstasy users, and the
bulk of the evidence has indicated that psychiatric symptoms or vulnerabilities tend to
precede Ecstasy use." (Guillot and Berman, 2007) . Clearly we can expect further growth in
this research area.

2- 3- 4- 5- N- Name CAS # Ref
-- -OCO- -- Me MOMA (this entry)
HO -OCO- -- Me 2-MDMOH [138556-75-9] (1)
HO -- -OCO- -- 6-MDOH [145284-65-7] (1,2)
HO -- -OCO- Me 6-MDMOH [ 138808-79-4] (2,3)
-- HO -OCO- Me 5-MDMOH [138537-66-3] (1)
-- -- -OCFp- -- F2-MDMA [914800-81-0] (4)
-- -- -OCCO- -- EDMA [133787-66-3] (5-8)

MDMA
(1) MS characterization of hydroxylated MOMA metabolites in the rat (Lim and Foltz, 1 991a).
(2) Metabolite evaluated for contribution to MOMA neurotoxicity (Elayan, et al. 1992).
(3) Synthesis and neurotoxicological evaluation (Zhao et al., 1992).
(5) Synthesis (Shulgin and Shulgin, 1991 ).
(7) Orally active in humans at 200-250 mg; duration 3-5 hours (Shulgin and Shulgin, 1 991).
(8) Impurities in the precursors to illicit drugs and the drugs themselves can indicate the synthetic
routes used in their production (Cimeno et al., 2005) .
Removal of one methylene from the amphetamine chain gives rise to a,N-OMMOBA (see
#45); addition of one methylene group to the amphetamine chain gives rise to OMOMA
(see #83, under homo-MOA).
Biochemistry
Incubation of MOA and MOMA with rat hepatic microsomes generated a spectrally observ
able inhibitory complex with cytochrome P450, which interfered with normal oxidation of
a variety of compounds (Brady et al., 1986) . MOMA and three known urinary metabolites,
MOA, MHMA, and MHA, were synthesized, separated by TLC, and characterized by IR
and mass spectrometry (Tanaka et al., 1988) .
Four paths of metabolism were shown for MOMA: N-demethylation, 0-dealkylation,

deamination, and conjugation; all four were found to occur in the rat. In urine there
were MHMA (both free and conjugated), HMMA (free and conjugated), 3,4-methylene
dioxyphenylacetone, 3-methoxy-4-hydroxyphenylacetone, 3,4-dihydroxyphenylacetone,
and MOA; OHMA was generated in vitro in either liver or brain supernatants (Lim and
Foltz, 1988). Stereochemistry of the metabolism of MOMA to MOA was evaluated in the
rat (Fitzgerald et al., 1989b). MOMA was metabolized by the rat the give MOA, MHMA,
MHA, HMMA, and OHA; MOA was also seen in plasma (Yousif et al., 1990). With i.v. ad
ministration of ( + )-, and separately (-)-MOMA, to male rats, the dextrorotatory isomer pro
duced three times the quantity of MOA than from the levoisomer (Cho et al., 1990). Using
in vitro studies, both optical isomers of MOMA were converted to OHMA by cytochrome
P450, and further oxidized by superoxide dismutase to reactive species that, in turn, were
proposed responsible for toxic effects on serotonergic neurons (Hiramatsu et al., 1990). In
rat liver, both MOA and MOMA were hydroxylated at all three of the available aromatic
positions (2-, 5-, and 6-); only the 6-hydroxylated regioisomer (6-MOOH and 6-MOMOH)
was found in the brain or plasma, and neither of them was found in the urine (Lim and
Foltz, 1991a). Oemethylenation of MOA and MOMA was investigated with isolated rabbit
liver cytochrome P450IIB4, utilizing deuterium isotope effects (Fukuto et al., 1991); meta
bolic demethylenation of MOA and MOMA in the rat also appeared to be mediated by cy
tochrome P450 (Lin et al., 1992) . MOMA was excreted unchanged in the rat (353) and the
mouse (723) largely within 24 hours; the primary rat and mouse metabolites of MOMA
were MHMA and MHA, both excreted (>853) as the glucuronide and sulfate conjugates
(Lim et al., 1992) .
The administration of serotonin uptake inhibitors including a,N-OMMOBA and MOBP,

and the 5-HT2 antagonist ketanserin each decreased the apparent neurotoxicity of MOMA
in the rat brain (Hashimoto and Goromaru, 1992; Hashimoto et al., 1992b), and in mice,
(Hashimoto et al., 1993), although the mechanism of the protective effect remained unclear.
The chiral metabolic profile of MOMA in rats and mice was examined, following derivativ
ization of extracts of the urine and brain with N-heptafluorobutyryl-5-prolyl chloride prior
to GC / MS (Lim et al., 1993). The methylenedioxy ring of MOMA was demethylenated

MOMA
to give DHMA with 5accharomyces cerevisiae microsomal preparations expressing human

debrisoquine hydroxylase (CYP2D6; Tucker et al., 1994) . MS data were presented for the
detection of metabolites of MDA and MDMA (Verweij, 1996). Bio-distribution studies in
the rat compared the blood-brain ratios of MDMA with MADAM-6, and were performed
with [ 11 C]-labeled material (Patt et al., 1999). Five N-hydroxylated derivatives of MDMA
and its metabolite MDA were identified in the urine of a horse; these were DHMAOH,
MHAOH, MHMAOH, MDOH, and FLEA (Dumasia, 2003). A comparative study on the
acute and long-term effects of MDMA and DHMA on brain monoamine levels in mice was
reported (Escobedo et al., 2005).
Human metabolites of MDMA were MHMA, HMMA, MDA, MHA, DHA, and the two
ketones, piperonylacetone and 3-methoxy-4-hydroxyphenylacetone (Lim and Foltz, 1989;
in this paper urine that tested positive for MDMA was obtained from a motorcyclist in
volved in a fatal crash, and no data was available on the amount ingested); the three re
ported phenolic human urinary metabolites (MHMA, MHA, and DHA), and the newly
identified DHMA, were excreted mainly as the glucuronides. In a separate study, peak
plasma levels of MDMA (300 ng / ml), and of MDA (15 ng / ml), were at two and six hours,
respectively after dosing; urine levels of MDMA were up to 30 µg / ml (Helmlin et al., 1996).
GC / MS analysis of human urine showed that the methylenedioxy ring of MDMA opens
to give DHMA and MHMA as metabolites (Maurer, 1996) . Interactions with human liver
CYP2D6 suggested active metabolites of MDMA were inhibitory to this enzyme (Wu et al.,
1997) . MDOH was observed as a metabolite of MDMA in humans (de Boer et al., 1997) .
With optically active electrophoresis, racemic MDMA, and its major metabolites MHMA
and MDA, were resolved in human urine; subjects showed a preferential excretion of the
R-isomer over the 5-isomer for un-metabolized racemic MDMA (4: 1 ) . Quantitative levels
of the asymmetric metabolites were given (Lanz et al., 1997) . Blood and urine of human
volunteers were analyzed for the optical isomers of MDMA and its metabolite MDA, after
receiving oral doses of racemic MDMA (Fallon et al., 1999) . In the human metabolism of
MDMA, producing MDA, DHMA, and MHMA, the 5-isomer was more rapidly consumed
(Pizarro et al., 2004). An unknown TLC spot in the urine of an MDMA user was tentatively
identified as 6-chloro-MDMA (Maresova et al., 2005).
The human cytochrome P450 enzymes involved in the oxidative metabolism of MDMA
related drugs were identified (Kreth et al., 2000). The two major routes to the observed
urinary metabolites of MDMA were N-dealkylation and demethyleneation to the catechol,
in both the rat and humans (Maurer et al., 2000) . In human urine samples recovered over
24 hours following MDMA administration, plasma levels of DHMA were equal to the
MDMA levels, and urinary DHMA accounted for 1 7.7% of the administered dose (Segura
et al., 2001). A review of studies on the metabolism including cytochrome P450 isoenzyme
dependency, and on screening procedures for detection of MDA, MDMA, MDE, BDB, and
MBDB has been presented (Maurer and Kraemer, 2002) .
Effects of R-MDMA and 5-MDMA on the release of serotonin from rat synaptosomes were
reported (Nichols et al., 1982) . When administered acutely to rats in high doses, MDMA
caused a selective and dramatic decrease in brain concentrations of serotonin. The deple
tion persisted for up to at least one week after a single injection of MDMA at approximately
four to five times the acute dose reported for humans (Schmidt et al., 1986) . Evidence was
given for specific MDMA binding sites in the rat brain (Gehlert et al., 1985). MDA, MDMA,
and their optical isomers were assayed for affinities at radiolabeled, isolated rat brain se
rotonin (5-HT 1 , 5-HT2) and dopamine (D2) binding sites (Lyon et al., 1986a), and the sug-

MOMA
gestion was made that MOMA effects, unlike those of other psychoactive phenethylamines
and amphetamines, might be primarily mediated by serotonin receptors. Acute and long
term neurochemical effects of MOA, MOMA, and MOE were examined in the serotonergic
system of the rat brain (Schmidt, 1987b). MOMA produced long-term reductions in brain
serotonin in rats (Mokler et al., 1987b), and interacted with human brain 5-HT2 receptors
(Sadzot et al., 1989).
MOMA-induced hyperthermia and neurotoxicity were shown to be independently me

diated by 5-HT2 receptors (Schmidt et al., 1990) . The release of serotonin and dopamine
was evaluated (McKenna et al., 1991). The substituted amphetamines MOMA, metham
phetamine, PCA, and fenfluramine induced synaptosomal serotonin release, which was
compared using a novel microassay system (Berger et al., 1992) . The disposition of MOMA
and three metabolites (MOA, OHMA, and 6-MOMOH) in rat brain may explain observed
serotonin depletion (Chu et al., 1996). MOMA and three of its metabolites (MHMA, OHA,
and OHMA) had effects on hormone release from isolated rat hypothalamus (Forsling et
al., 2002) . Stereochemical effects of MOMA and related amphetamine derivatives on inhi
bition of uptake of [ 3H]-labeled monoamines into synaptosomes from different regions of
rat brain were reported (Steele et al., 1987) .
Release of [ 3H]-labeled serotonin from rat hippocampal slices and [ 3H]-labeled dopamine
was observed from rat caudate nucleus slices (Johnson et al., 1986). Tritiated MOMA bind
ing to both rat brain membrane preparations and glass fiber filter papers was observed
(Wang et al., 1987) . In vitro and in vivo neurochemical effects of MOMA on striatal mono
aminergic systems were observed in the rat brain (Schmidt et al., 1987) . Acute effects of
MOMA on dopamine release were monitored in the awake-behaving rat (Yamamoto and
Spanos, 1988) . Pharmacologic profiles of MOMA at various brain recognition sites showed
comparable activity between MOMA and serotonin uptake sites, a2-adrenoceptors and
5-HT2 receptors (Battaglia et al., 1988). MOMA had impacts on local cerebral glucose uti
lization in the rat (Wilkerson and London, 1989), reduced in vivo binding of [ 3H]-labeled
paroxetine in mouse brain (Hashimoto and Goromaru, 1990), and affected the release of
monoamines from rat brain slices (Fitzgerald and Reid, 1990). The effects in rats injected
s.c. with 10 mg / kg of MOMA on serotonin and 5-hydroxyindoleacetic acid levels were ob
served (Yeh and Hsu, 1991), as were MOMA effects on brain function of the rhesus monkey
(Frederick et al., 1995). Repeated exposure to MOMA in rats altered nucleus accumbens
neuronal responses to dopamine and serotonin (Obradovic et al., 1998). Cardiovascular
effects of MOMA and PMA were compared at different doses in rats (Irvine et al., 2001).
In the isolated rat hypothalamus, MOMA and five of its metabolites were studied for their
ability to release arginine vasopressin; MHMA was the most potent (Fallon et al., 2002). Ba
clofen prevented MOMA-induced rise in core body temperature in rats (Bexis et al., 2004).
Structure-activity relationships of MOMA-like substances were addressed (Nichols and

Oberlender, 1989). Binding affinities of MOA, MOMA, and MOE were determined at nine
neurotransmitter binding sites in the human cortex (Pierce and Peroutka, 1989). Prelimi
nary observations were reported on the presence of aminergic metabolites in cerebrospinal
fluid of humans previously exposed to MOMA (Ricaurte et al., 1990). Urinary retention
followed MOMA use in humans (Bryden et al., 1995), cardiovascular autonomic dysregu
lation was noted in users of MOMA (Brody et al., 1998), and facial rashes and pimples
(Wollina et al., 1998) were reported following use of MOMA in humans. Cardiovascular
effects of MOMA (Lester et al., 2000), and thermoregulatory effects (Freedman et al., 2005)
of MOMA were also reported in human volunteers.

MOMA
Pharmacology
The pharmacology and toxic properties of mescaline, DMPEA, MDPEA, TMA, MDA, OMA,
BOB, and MOMA were compared in five animal species (Hardman et al., 1973), in a report
of research performed at the Army Edgewood Arsenal in the early 1950s. Studies of motor
activity in mice were reported (Braun et al., 1980), and included monitoring of tail flick,
stretch reflex and analgesia. Toxicological comparisons between MDA and homo-MDA,
and MOMA and homo-MOMA in mice were reported (Davis and Borne, 1984) . Biochemi
cal and behavioral studies with MOMA and MBDB gave results that were similar to one
another, but differed from responses to stimulants (amphetamine) or psychedelics (DOM,
LSD). This prompted the creation of a new class name, "entactogens" (Nichols, 1 986b).
Drug self-administration in experimental animals has been used as a model to predict the
likelihood of a reward-seeking dependence potential in humans (Nichols, 2004). Early re
ports suggested MOMA was a positive re-enforcer for rhesus monkeys, which suggested
a potential for recreational use of MOMA by humans (Beardsley et al., 1 986; Lamb and
Griffiths, 1987) . However, these results were later challenged; unlike other classic depen
dence-producing psychostimulants, MOMA and its stereoisomers did not reliably rein
force self-administration in rhesus monkeys (Fantegrossi et al., 2002; Fantegrossi, 2007) .
MOMA and MOE had impacts on the locomotory and investigatory behavior profiles in
rats (Gold et al., 1988). Effects of the separate optical isomers of MDA and MOMA were
studied on central serotonergic, dopaminergic, and nigral neurotensin systems of the rat
(Johnson et al., 1988) . The relative effects of R-(-)-MDMA, S-(+)-MDMA, and S-(+)-MDA
were compared to stereotypic behaviors in rats induced by p-chloroamphetamine (Hira
matsu et al., 1989); the S-enatiomers of both methylendioxy compounds were more po
tent, and S-(+)-MDA was more potent than S-(+)-MDMA. Monkeys were considered more
sensitive than rats to the serotonin-depleting effects of MOMA (Ricaurte, 1989). Effects of
MOMA were assessed in pigeons trained to respond to food presentation schedules (Nad
er et al., 1989). With S-MDMA, field potentials were recorded with telemetric equipment,
from frontal cortex, hippocampus, striatum, and reticular formation of freely moving rats
(Dimpfel et al., 1989) . Tolerance and cross-tolerance to MOMA, MDA, and methamphet
amine was evaluated in the rat (Zacny et al., 1990). Behavioral and neurochemical effects
of prenatal MOMA exposure in rats (St. Omer et al., 1991), and effects on rat locomotor ac
tivity from s.c. administration of MOMA were presented (Yeh and Hsu, 1 991). Impacts on
the memory performance of pigeons as a consequence of MOMA exposure were described
(LeSage et al., 1993) .
MOMA enhanced associative and non-associative learning in the rabbit (Romano and Har
vey, 1994) . MOMA effects were evaluated on the chicken embryo and the one-day-old
chicken (Bronson et al., 1994b), and effects of morphine, MOMA, MDA, and 2C-B were
observed on conditioned place preference of newly hatched chickens (Bronson et al., 1996).
Acute effects of MOMA on brain serotonin synthesis in the dog were studied by positron
emission tomography (Nishisawa et al., 1999) . a-Lipoic acid prevented MOMA-induced
neurotoxicity in the rat (Aguirre et al., 1999). The rat was used to compare MOMA and
MOE pharmacology, biochemistry, and toxicity (Colado et al., 1999). Effects of MOMA
on anxiety in mice were tested using a light-dark box startling methodology (Maldonado
and Navarro, 2000), and MOE was compared with MOMA in production of serotonergic
deficits and impaired passive-avoidance learning in rats (Barrionuevo et al., 2000). MOMA
increased social interaction in rats (Morley and McGregor, 2000) . The optical isomers of
PMMA, DOM, MBDB, MOMA, and OMA were compared as stimulants in rats (Rangi-

MOMA
setty et al., 2001 ) . MDMA, MDA, and MDE effects on blood pressure, heart rate, locomotor
activity, and body temperature in the rat were shown to involve a-adrenoceptors (Bexis
and Docherty, 2006). Adrenergic receptors have also been found to mediate the locomotor
response to MDMA in rats (Selken and Nichols, 2007) .
Drug discrimination methods were used by several people to distinguish the effects of the
"entactogen" class of drugs from stimulants and classic psychedelics. Discriminative stim
ulus properties of the R- and 5-isomer were first observed in rats trained to discriminate
DOM from saline (Glennon et al., 1982c). In two studies of discriminative stimulus proper
ties of MDA and MDMA in pigeons (Evans and Johanson, 1986), and in rhesus monkeys
trained to discriminate (+)-amphetamine from saline, MDMA substituted completely for
amphetamine, and MDA partially generalized for amphetamine (Kamien et al., 1986), sug
gesting both had significant similarity to stimulants. MDA, MDMA, BDB, and MBDB were
compared in a two-lever drug discrimination study to distinguish saline from LSD, and
none produced responses that generalized for the training compound, suggesting their
action might be mediated by other pathways (Nichols et al., 1986a) . Male rats trained with
racemic MDMA in food-motivated discrimination studies were used to evaluate the dose
dependent responses to the R-(-)- and 5-(+ )-isomers, and found that the latter was twice as
effective in substituting for the racemic drug (Schechter, 1987) . Drug discrimination stud
ies with MDMA, MBDB, and amphetamine complicated the picture; MDMA-trained rats
partially responded to the stimulants, and did not generalize to LSD or DOM, suggesting
that while the methylenedioxy materials shared some stimulant character, they were also
distinct from the formal psychedelics (Oberlender and Nichols, 1988). MDMA, MDE, and
MDOH were evaluated in rats trained to distinguish amphetamine from DOM (Glennon et
al., 1988d; Glennon and Misenheimer, 1989). Rats trained to discriminate between MBDB
and saline, substituted MDA, MDMA, MDAI, and MDMAI completely, but not mescaline,
DOM, or LSD. The term "entactogen" was proposed for those compounds that substituted
completely (Oberlender and Nichols, 1990). 3,4-MMA and MMAI were tested for stimulus
generalization in rats trained for two-lever discrimination with MDMA or MBDB (Johnson
et al., 1991b) . N-MMDPEA and HMDMA were compared to MDMA, regarding behav
ioral effects (utilizing drug discrimination methods), and developmental effects (examin
ing drug-exposed chick embryos; Bronson et al., 1994a). MDA and MDMA optical isomers
were further compared with classical stimulants and psychedelics in drug discrimination
evaluations (Baker and Taylor, 1997) .
Both MDA and MDMA caused marked reductions in both tryptophan hydroxylase activ
ity and concentrations of serotonin and 5-hydroxyindoleacetic acid in several serotonergic
nerve terminal regions (Stone et al., 1986) . The toxicities of MDA and MDMA were com
pared in five animal species (Davis et al., 1987), and that of MDMA was evaluated in the
dog and the rat (Frith et al., 1987) . Biochemical and histological evidence that MDMA is
toxic to neurons in the rat brain was presented (Commins et al., 1987), and neurotoxicity of
MDA, MDMA, and MDE in rats was investigated (Stone et al., 1986, 1987a) . Toxic effects
of MDMA on central serotonergic neurons were studied in squirrel monkeys, using doses
approximately two- to five-times the level generally consumed by humans, with discus
sion of the importance of route and frequency of drug administration (Ricaurte et al., 1988) .
Selective reduction of striatal type II glucocorticoid receptors was produced by MDMA
in rats (Lowy et al., 1989); glucocorticoids were also implicated in MDMA-induced neu
rotoxicity in high-dose experiments (Johnson et al., 1989b). MDMA selectively destroyed
brain serotonin terminals in rhesus monkeys, again using experimental doses that were
substantially higher than humans could tolerate (Insel et al., 1989). Both intra-gastric and

MOMA
subcutaneous administration of MOMA produced serotonin neurotoxicity in rhesus mon

keys (Kleven et al., 1989). Rat studies suggested that the MOMA metabolite DHMA was
not responsible for the neurotoxicity of MOMA (Steele et al., 1991); neurotoxicity of PMA
and PMMA was compared to that of MOMA in subcutaneous injections into rats, again in
high-dose experiments (Steele et al., 1992) . A neurotoxicological evaluation of metabolites
of MOMA was reported (Zhao et al., 1992) .
CNS effects of two hydroxy metabolites of MOMA (DHMA and THMA-2) on serotonin
and dopamine were investigated in the rat as possible neurotoxic agents (Johnson et al.,
1992); in related experiments, THA, THMA, and DHA were evaluated for effects on other
enzyme systems in the rat, with both in vivo and in vitro experiments (Elayan et al., 1993).
Comparisons of spontaneous behaviors of rats were made with PMA, MOMA, MDA, and
MOE (Hegadoren et al., 1995). The effects of MOMA and several MAO inhibitors were
studied with respect to PCA-induced neurotoxicity in the rat (Sprague et al., 1996). A major
metabolite of MOMA, DHMA, was discussed as possibly responsible for a described toxic
syndrome (Segura et al., 2001 ) . Serotonin neurotoxicity of MOMA was potentiated by inhi
bition of y-glutamyl transpeptidase, and thioether metabolic products were implicated in
MDMA neurotoxicity (Bai et al., 2001 ) . The pharmacology of acute hyperthermic responses
that follow administration of MOMA to rats was evaluated (Meehan et al., 2002). Post-mor
tem redistribution of MOMA in the rabbit was described (De Letter et al., 2002a,b ). Primary
cultures of rat and human renal proximal tubular cells were used to investigate cytotoxic
ity induced by MOMA and its metabolites (Carvalho et al., 2002). Glutathione conjugates
of MOMA or MDA were implicated in serotonin nerve terminal degeneration since neither
parent compound was neurotoxic when injected directly into the brain (Easton et al., 2003).
Subjective reports of the effects of MOMA in human volunteers were produced from trials
in controlled clinical settings (Greer and Tolbert, 1986; Downing, 1986). Intoxicative ef
fects associated with recreational MOMA use, composition of street samples, and general
remarks on patterns of non-medical use were investigated (Siegel, 1986; Peroutka et al.,
1988b). Human sexual function of people under MOMA was reported (Buffum and Moser,
1986). Incidence of recreational use of MOMA on an undergraduate campus was described
(Peroutka, 1987) . MOMA has been used as an adjunct to spiritual pursuits (Watson and
Beck, 1991 ) . Phenomenology and sequelae of MOMA use was remembered by twenty
psychiatrists who had experienced it (Liester et al., 1992) . In double-blind studies, MOE
exerted similar psychoactive effects in humans as MOMA, and was less toxic to animals
(Gouzoulis et al., 1992) . Chronic MOMA use in humans may have lasting effects on mood
and neuropsychological function (Krystal et al., 1992) . In a blind study with volunteers, the
psychological effects of MOE were compared with those of MOMA (Hermle et al., 1 993).
Psychobiologic effects of MOMA in humans were observed, with commentary on method
ological considerations (Grob et al., 1996) . Self-reported psychological and physiological
effects resulting from recreational MOMA use were reported (Davison and Parrott, 1 997) .
Psychotherapeutic sessions with MOMA were described (Greer and Tolbert, 1998). A pos
sible role for MOMA in psychotherapy was evaluated (Sessa, 2007) .
A double-blind study with 1 . 7 mg / kg MOMA in na'ive volunteers helped further define

the term "entactogen" (Vollenweider et al., 1998) . Opposite effects were noted of MOMA
on sensorimotor gating in rats versus healthy humans (Vollenweider et al., 1999b). A con
trolled study of cognitive performance under MOMA in human subjects was performed
(McCann et al., 1999). Cardiovascular and neuroendocrine effects and pharmacokinetics
of MOMA were assessed in a double-blind, randomized, crossover, and controlled clinical

MOMA
trial with placebos and amphetamine as an active control (Mas et al., 1999). Human clinical
studies on healthy volunteers measured the physical parameters of the intoxicated state
(De La Torre et al., 2000), psychomotor performance and subjective effects (Cami et al.,
2000), mood state, and brain electric activity (Gamma et al., 2000), and memory disturbanc
es, correlated with altered brain serotonin neurotransmission (Reneman et al., 2000). Cog
nitive performance amongst recreational users of MOMA and cannabis was compared in
a controlled human study (Rodgers, 2000) . Long-lasting effects of (±)-MOMA on serotonin
cal effects of MOMA were monitored in healthy humans, after pretreatment with the 5-HT 2
system function in humans were studied (Gerra et al., 2000). Psychological and physiologi
antagonist ketanserin (Liechti et al., 2000), after a dopamine 02 antagonist (haloperidol)

pretreatment (Liechti and Vollenweider, 2000), and on pre-pulse inhibition and habituation
of startle in humans after pretreatment with citalopram, haloperidol, or ketanserin (Liechti
et al., 2001 a). Tooth-grinding as a side-effect of MOMA in humans has been reported (Red
fearn et al., 1998; Murray and Wilson, 1998; Milosevic et al., 1999).
Gender differences were noted in the subjective effects of MOMA in humans (Liechti et al.,
2001b), and were the subject of a retrospective review (Allott and Redman, 2007) . Subjec
tive effects of MOMA on human sexual function (Zemishlany et al., 2001), and hormonal
status (Harris et al., 2002) were reported. There was evidence of gender differences in sub
acute effects of MOMA on mood (Verheyden et al., 2002). Acute psychological and neu
rophysiological effects of MOMA in humans were described (Vollenweider et al., 2002).
MOMA has been proposed to mimic the post-orgasmic state: impairment of sexual drive
and function during acute MOMA-effects were attributed to increased prolactin secretion
(Passie et al., 2005). MOMA and alcohol effects were studied in humans; psychomotor per
formance attributable to alcohol intake was unaffected by MOMA, but alcohol increased
MOMA blood levels and prolonged the euphoric state; the results were discussed with
regard to drug use and vehicular safety (Hernandez-Lopez et al., 2002).
Specific neurotoxicity of chronic use of MOMA was described (Obrocki et al., 2002). Hu
man pharmacology studies of MOMA addressed pharmacokinetics, metabolism, and dis
position (De La Torre et al., 2004), and the pharmacological effects and pharmacokinetics
of repeated dosing (Farre et al., 2004) . Pain tolerance was increased, and mood measures
were significantly lower in regular MOMA users; serotonergic mechanisms were suggest
ed in discussion of these data (O'Regan and Clow, 2004) . MOMA had measurable effects
on processing of facial expressions (Hoshi et al., 2004), and produced both error-rate de
pendent and independent aspects of decision-making in a two-choice prediction task in
humans (Vollenweider et al., 2005). Memory performance in MOMA users who continued
or discontinued MOMA use remained unchanged (Gouzoulis-Mayfrank et al., 2005). Psy
chiatric and cognitive long-term effects of MOMA were described (Hoiseth et al., 2006).
Human effects of MOMA without or with a simultaneous dose of caffeine were described
(Camarasa et al., 2006); caffeine induced a profound and persistent tachycardia in response
to MOMA co-administration (McNamara et al., 2007) . Technical aspects, conceptual issues,
and future prospects of neuroimaging findings with MOMA were addressed (Reneman et
al., 2006). The variety of subjective experiences of MOMA, and their implications, were dis
cussed (Sumnall et al., 2006). L-tyrosine was shown to contribute to (+)-MOMA-induced
serotonin depletions (Breier et al., 2006), and acute doses of MOMA (75 mg) impaired spa
tial memory for location but left contextual processing of visuospatial information unaf
fected (Kuypers and Ramaekers, 2007) .

MDMA
Toxic outcomes of MOMA exposure have increased as usage has grown. Multiple severe
complications from recreational ingestion of MOMA were outlined (Brown and Oster
loh, 1987) . Deaths due to, or associated with, the use of MOMA and MOE were reported
(Dowling et al., 1987; Chadwick et al., 1991). Toxic (but not lethal) effects of MOMA with
phenelzine (N-amino-phenethylamine, an anxiolytic) were described in a human patient
(Smilkstein et al., 1987) . MOMA and PCA were both shown to cause brain serotonin levels
to decrease in two temporal phases; an acute reversible phase and a later irreversible phase
(Schmidt, 1987a) . MOMA was implicated in a sudden cardiac death (Suarez and Riemers
ma, 1988) . L-Tryptophan induced a rise in the serum prolactin concentration in controls,
but not in MOMA users (Price et al., 1989) . Two human fatalities reportedly followed mod
est MOMA exposures (Henry et al., 1992) . Tissue distribution was studied following two
deaths associated with MOMA use (Rohrig and Prouty, 1992) . Acute renal failure was at
tributed to MOMA use (Fahal et al., 1992) . A 13-month-old boy ingested one capsule of
MOMA, and had neurological and cardiovascular side-effects, which responded well to
treatment with a chlormethiazole infusion (a sedative and hypnotic, widely used in treat
ment of acute alcohol withdrawal and anxiety; Bedford Russell et al., 1 992) . Severe MOMA
poisoning was described in a 1 7-month-old baby (Duffy and Swart, 2006). Human hyper
thermia following MOMA ingestion produced a peak temperature of 42 °C (Logan et al.,
1993; cf. Nimmo et al., 1993) . An 18-year-old female who had regularly taken 1-2 tablets
of MOMA every weekend developed acute liver failure (de Man et al., 1993). A massive
overdose (18 tablets), yet not lethal consumption of MOMA was described (Roberts and
Wright, 1994) . Acute hepatitis was associated with MOMA ingestion (Huarte Muniesa and
Pueyo Royo, 1995). Postmortem blood levels and clinical signs were reported in MDA,
MOMA, and MOE fatalities (Cox and Williams, 1996; De Letter et al., 2002a; Ben-Abraham
et al., 2003; Finsterer et al., 2003; De Letter et al., 2004; Elliott, 2005). Autopsy records are
given for seven young adults who had used either MOMA or MOE (Milroy et al., 1 996) .
The distribution of MOMA and its metabolite MDA was reported in a fatal case following
the insufflation of MOMA, cocaine, and heroin (Moore et al., 1996). Cerebral edema was
described after ingestion of MOMA and unrestricted intake of water (Matthai et al., 1996) .
The first observation of lethal recreational use of MOMA and MOE in Italy was reported,
together with extensive toxicological and histopathological documentation (Fineschi and
Masti, 1996) . A case was reported of a toddler who presented with an apparent febrile con
vulsion after accidental ingestion of MOMA (Cooper and Egleston, 1997) . MOMA has been
associated with hypoglycemia (Montgomery and Myerson, 1997), severe acute hepatotox
icity (Andreu et al., 1998), and memory impairment in abstinent users (Bolla et al., 1 998) .
MOMA-induced rhabdomyolysis was described in humans, and its role in the develop
ment of acute renal failure was discussed (Cunningham, 1997). Survival after a massive
overdose of MOMA was described (50 tablets, in combination with oxazepam and alcohol;
Ramcharan et al., 1998). Three fatal cases of MOMA / MOE misuse were examined, involv
ing white males between 19 and 20 years of age, in which post-mortem toxicology showed
the presence of MOMA in one case, MOE in another case, and both in the third case (Fines
chi et al., 1999). Hyperpyrexia and rhabdomyolysis were associated with MOMA overdose
(Kunitz et al., 2003). MOMA-induced brain death and acute hepatocellular failure com
plicated multiorgan donor and liver transplantation (Caballero et al., 2002). Four deaths
followed the ingestion of MOMA and moclobemide, a MAO inhibitor antidepressant, sold
as Aurorix or Manerix (Vuori et al., 2003).
Hyponatremia and seizures after MOMA use in humans was reported (Kessel, 1994; Hol
mes et al., 1999; Traub et al., 2002). In human subjects, MOMA caused a significant rise in
arginine vasopressin, which may account for hyponatremia observed (Fallon et al., 2002).

MOMA
A young woman died of water intoxication after taking one tablet of MDMA, emphasizing
the need for vigilance and education in dealing with drug use amongst the young (Braback
and Humble, 2001 ) .
Reported psychiatric outcomes have included chronic atypical psychosis (Schifano, 1991),
psychiatric illness (Benazzi and Mazzoli, 1991), chronic paranoid psychosis (McGuire and
Fahy, 1991), lasting neuropsychiatric sequelae (McCann and Ricaurte, 199lb), and panic
disorders (McCann and Ricaurte, 1992; Pallanti and Mazzi, 1992). Flashbacks and recur
rent psychoses were experienced by MDMA users (Creighton et al., 1991; McGuire and
Fahy, 1991). A prolonged psychosis followed brief recreational use of MDMA (Williams et
al., 1993). A controlled study in humans described serotonin neurotoxicity after MDMA
use (McCann et al., 1994) . Attention deficit hyperactivity disorder, was associated with use
of MDMA or LSD in humans (Durst and Rebaudengo-Rosca, 1997), and a pure amnestic
syndrome was reported after MDMA ingestion (Spatt et al., 1997) . Regular MDMA use was
associated with chronic psychiatric symptoms, which persisted after cessation of use (Mc
Guire, 2000), even after a single ingestion of MDMA (Van Kampen and Katz, 2001). Long
term effects of MDMA on the human brain were studied by FDG PET (Buchert et al., 2001 ) .
Acute and long-term effects o f MDMA o n human cerebral dopamine biochemistry and
function were described (Colado et al., 2004), and currently accepted models of MDMA ac
tion on monamine transporters and neurotransmitter release were reviewed (Green et al.,
2003). Recent studies have compared the interaction of MDMA, its metabolites HMA and
HMMA, and related compounds on several transporter systems, in cell cultures expressing
animal and human transporters (Montgomery et al., 2007; Verrico et al., 2007) .
Human PET scan evidence for toxic effects of MDMA on brain serotonin receptors was
presented (McCann et al., 1998) . While the PET images in this paper revealed localized
binding of PET-active compounds to show brain regions affected by MDMA exposure, the
images were misleadingly promoted to the public as evidence of necrotic brain damage on
The Oprah Winfrey Show, and elsewhere.
MDMA was reported to be highly toxic in primates (Ricaurte et al., 2002); however this
paper was formally retracted, as the material administered turned out to be methamphet
amine mislabeled as MDMA (Ricaurte et al., 2003). Several comments later addressed this
error (Holden, 2003; Knight, 2003; Pincock, 2003); the controversy generated discussion
regarding reliability of government-sponsored research on psychoactive drugs (Bartlett,
2004). The possible negative effect of the MDMA neurotoxicity controversy on the ap
proval of future research studies with new psychoactive drugs was addressed (Grob et al.,
1 992) . Diverse views from several sources converged on the topic of MDMA neurotoxicity
(Turner and Parrott, 2000); cognitive and behavioral indices of change have also been ad
dressed (Parrott, 2000) .
MDMA appeared as a street drug in New Zealand (Laverty and Logan, 1989; Ellis and
Schimmel, 1989), in Spain (Prat et al., 1991), Australia (Solowij et al., 1992; Topp et al., 1999),
Ireland (Cregg and Tracey, 1993), Japan (Katagi et al. 2002), Brazil (de Almeida and Silva,
2003), and in South Africa (Pliiddemann et al., 2004) .
In Canada, pills sold as "Ecstasy" were found to contain largely MDE (Dawson et al., 1997).
The term "candyflipping" was a reported street term for the co-administration of LSD and
MDMA (Schechter, 1998). In Switzerland, "Ecstasy" tablets were found that contained only
2C-B (Giroud et al., 1999; de Boer et al., 1999b). Analysis of MDMA tablets revealed wide
variation of composition, including samples completely devoid of MDMA (Sherlock et al.,

MOMA / homo-MOMA
1 999), and pills that contained dextromethorphan (Baggott et al., 2000) . Tablets containing
PMA and PMMA were misrepresented as MOMA (Dal Cason, 2001 ) . MOMA tablets seized
in Japan were found to also contain MDA, ephedrine, caffeine, ketamine, and methamphet
amine (Makino et al., 2003). A survey over 30 years of the content of Ecstasy tablets sold on
the street has been presented (Parrott, 2004). Many street samples of MOMA were assayed
for major contaminants; MDA, caffeine, methamphetamine, and pseudoephedrine were
the most common (Tanner-Smith, 2005). Analysis of MOMA tablets in Taiwan showed the
presence of caffeine, methamphetamine, MOE, amphetamine, MDA, ketamine, ephedrine,
and diazepam (Teng et al., 2006). Mercury and arsenic were recently detected in Ecstasy
tablets by electrochemical methods (Fierro et al., 2006).
An analysis of 64 individuals' urines from a rave party showed that 88% of the samples
contained MOMA and I or MDA alone or in combination with other amphetamine deriva
tives such as amphetamine, methamphetamine, or MOE (Zhao et al., 2001).
Orally active doses of MOMA in humans were described by several people; early reports
have suggested 75-150 mg (Shulgin and Nichols, 1978), 100-160 mg (Braun et al., 1980),
and 130 mg (Lemaire et al., 1985) . The 5-isomer is orally active in humans at 80-120 mg,
slightly more potent than the racemate, and some three times more potent than the R-iso
mer (Anderson et al., 1978a) . MOMA was orally active in humans at 80-1 50 mg; duration
4-6 hours (Shulgin and Shulgin, 1991 ) .
Legal Status
MOMA is a Schedule I hallucinogen under federal drug law, and under District of Columbia
and all state laws except for California, New Jersey, Utah, and Vermont.
# 83. homo-MOMA
4-(Benzo[d] [ l,3] dioxol-5-yl)-N-methylbutan-2-amine
N-Methyl-1-(3,4-methylenedioxypheny1)-3-isobutylamine
a,N-Dimethyl-3-(3,4-methylenedioxyphenyl)propylamine
a,N-Dimethyl-1,3-benzodioxole-5-propylanamine
N, 1-Dimethy1-3-(3,4-methylenedioxyphenyl )propylamine
HMO MA
MDP-3-MB
Registry Numbers
CAS #
HCI salt [92279-85-1]
Freebase [108248-08-4]
------ -- -. -· ·- · --------�

From 4-(3,4-methylenedioxyphenyl)-2-butanone (with reductive amination) to homo
MDMA (Noggle, et al., 1989a) .

ml z : 207. 1259 (100.0% ), 208.1293 (13.0%)
HCL salt m.p. 128.5-130.5 °C (Shulgin and Daley, unpublished data)

homo-MOMA / MDOH
Synthesis, UV spectra, and analysis by LC / MS (Noggle et al., 1989a) . Several a-ethyl

phenethylamines were synthesized and analytically compared with their amphetamine
counterparts (Clark et al., 1995) . Distinction from MBDB was shown by GC / MS (Clark et
al., 1996a) .
Biochemistry
Release of serotonin and dopamine was studied (McKenna et al., 1991 ) . Effects on the
chicken embryo and the one-day-old chicken were observed (Bronson et al., 1994b). Toxi
cological studies between MDA and homo-MDA, and MOMA and homo-MOMA were
reported in mice (Davis and Borne, 1 984) .
Pharmacology
homo-MOMA partially substituted for MOMA in MOMA-trained rats; at high levels, it
evoked seizure (Bronson et al., 1994a) .
homo-MOMA has been sold on the street in Japan under the recognized name MBDB
(Matsumoto et al., 2006).
Human activity of homo-MOMA has not been reported in the scientific literature.
Legal Status
homo-MOMA is not a scheduled compound under federal drug law, or under District of
# 84. MDOH
N-(1-(Benzo[ d] [ l,3 ]dioxol-5-yl)propan-2-yl)hydroxylamine
N-Hydroxy-3,4-methylenedioxyamphetamine
N-Hydroxy-a-methyl-1,3-benzodioxole-5-ethanamine
N-Hydroxy-1 -(3,4-methylenedioxyphenyl)-2-aminopropane
N-Hydroxy MDA
NOHMOA
Registry Numbers
CAS# DEA# CAS #
HCl salt [74341-83-6] R-Isomer [198017-93-5]
Freebase [74698-47-8] 7402 S-Isomer [19801 7-94-6]

From piperonylacetone (with hydroxylamine and sodium cyanoborohydride) to MDOH
as a solid residue; (with warm IPA, HCl) to MDOH (Braun et al., 1980) .

m/ z : 195.0895 (100.0% ), 196.0929 (10.8% )
HCl salt 149-150 °C (Braun et al., 1980) (IPA)
MDOH is thermally unstable; at elevated temperatures it decomposes into MDA and the
oxime of piperonylacetone, and cannot be analyzed by gas chromatography without de
rivatization (Noggle et al., 1 988) . This decomposition occurs at a temperature of 1 00 °C, so
distillation of the freebase is also not possible (Shulgin and Shulgin, 1991).

MDOH
Liquid chromatographic and mass spectral analysis were described for N-substituted ana
logues of MDA included MDOH (Noggle et al., 1988) . The effects of changes of condi
tions in reversed-phase liquid chromatography of MDOH and the unhydroxylated MDA
were noted (Valaer et al., 1990). Cross-reactivity of several substituted amphetamines with
the Roche Abuscreen® (Cody, 1990a) and the Diagnostic Products Corporation (Cody, 1990b)
radioimmunoassays for amphetamines was evaluated. Substituted amphetamine deriva
tives could be screened by immunoassay and fluorescence polarization (Cody and Schwar
zhoff, 1993) . Additional syntheses and chromatographic characterization were reported
(Shimamine et al., 1993a) . Several a-ethyl phenethylamines were synthesized and ana
lytically compared with their amphetamine counterparts (Clark et al., 1995) . MDOH was
identified by a rapid planar chromatographic screening method (Fater et al., 1998), and by
FTIR (Praisler et al., 2000) .

3- I 4- N- N- Name CAS # Ref
-OCO- OH - - MDOH (this entry)
-OCO- OH Me FLEA [214414-88-7] (1--4)
(1) A metabolite of MOMA in the horse (Dumasia, 2003).
(2) Interaction with the cytochrome P450 enzyme system (Keizers et al., 2004) .
(3) Orally active in humans at 1 00-160 mg; duration 4-8 hours (Shulgin and Shulgin, 1991).
(4) Also called N-hydroxy-MDMA.
Biochemistry
MDA is a metabolite of MDOH, plasma isolation was described (Clark et al., 1990b);
MDOH was rapidly metabolized to MDA in both in vitro rat liver slices and in the intact
rat (Ravis et al., 1994) . There are also indications that MDA is converted to MDOH by P450
(Kumagai et al., 1992), MDOH has been observed as a metabolite of MDMA in humans (de
Boer et al., 1997) .
Pharmacology
Pharmacological activity in several animal and human assays, including studies of motor
activity, tail flick, stretch reflex, and analgesia was reported in mice (Braun et al., 1 980) .
With rats trained to distinguish amphetamine or DOM from saline, MDMA, MDE, and
MDOH only partially generalized for the training drug responses, indicating their ac
tion might be attributed to other mechanisms (Glennon et al., 1988d). Effects of MDE and
MDOH were observed with rats trained to discriminate MOMA or amphetamine from
saline (Glennon and Misenheimer, 1989), who concluded that while MDMA produces ef
fects other than that of amphetamine, MDE and MDOH produce even less of this response.
Baboons trained to self-inject cocaine were switched to MDA, MDOH, DIMETH, and 2C-B,
and changes in behavior were noted (Sannerud et al., 1996) .
MDOH was reported orally active in humans at 80-120 mg (Braun et al., 1980), and at
100-1 60 mg; duration 3-6 hours (Shulgin and Shulgin, 1991).
Legal Status
MDOH is a Schedule I hallucinogen under federal drug law (FR, 1989), and under all
state laws except for California, Delaware, Kentucky, Maine, Maryland, Massachusetts,
Michigan, Minnesota, Nebraska, New Jersey, New Mexico, Oklahoma, Rhode Island,
South Carolina, Tennessee, Vermont, and Washington.

MDPEA
# 85. MDPEA
2-(Benzo[d] [l,3] dioxol-5-yl)ethanamine
3,4-Methylenedioxyphenethylamine
2-(Benzodioxol-5-yl)ethylamine
5-(2-Aminoethyl)-1,3-benzodioxole
2-(3,4-Methylenedioxyphenyl)ethylamine
Homopiperonylamine
Registry Numbers
CAS # CAS #
HCl salt [ 1653-64-1 ] Sulfate [6461 0-36-2]
HBr salt [849186-61-4] p-Toluenesulfonate [8491 86-62-5]
Bioxalate [58738-59-3] Freebase [1484-85-1 ]
Homopiperonylacetate [36406-68-5] a-[d] Freebase [152089-67-3]
Homopiperonyldithio-carbamate [859932-61-9] a,a-[d2]* Freebase [152089-68-4]
Picrate [109442-31-1] a, f3-[ d2] Freebase [152089-63-9]
*The structure has been incorrectly drawn in Chemical Abstracts as the a,a,f3-[d 3 ] analogue.

From piperonal (with nitromethane) to the nitroethene; (with electrolytic reduction) to
MDPEA (Tanaka and Midzuno, 1929).
From 3,4-methylenedioxybenzaldehyde (with malonic acid) to 3,4-methylenedioxycin

namic acid; (with Na, Hg) to 3,4-methylenedioxypropionic acid; (with NH3 ) to 3,4-methyl
enedioxypropionamide; (with NaOCl) to MDPEA (Slotta and Heller, 1930).
From 3,4-methylenedioxyhydrocinnamamide (Kindler, 1931).
From piperonal (with nitromethane) to the nitroethene; (with Pd, H2) to MDPEA (Schales,
1935a; Maurer and Schiedt, 1935) .
Synthesis by catalytic hydrogenation of homopiperonyloximine (Schales 1935b).
From piperonal (with nitromethane) to the nitroethene; (with LAH) to MDPEA (Erne and
Ramirez, 1950; Dallacker et al., 1971 ) .
From piperonal (with nitromethane) t o the nitroethene; (with Raney Ni, o r Raney Co, H2)
to MDPEA (Reeve and Eareckson, 1950) .
From piperonal (with malonic acid) to 3,4-methylenedioxycinnamic acid; (with Pd, H2) to
3,4-methylenedioxyphenylpropionic acid; (with SOCL2, NH3 ) to 3,4-methylenedioxyphen
ylpropionamide; (with aq. KOCI ) to MDPEA (Habermehl and Khalique, 1 967) .
Synthesis by reduction of the 2-nitrophenylethane with Fe powder in ethanol in the

presence of ammonium chloride (Ran et al., 2000).

m / z: 165.0790 (100.0% ), 166.0823 (9.7% )
HCI salt m.p. 208 °C (Tanaka and Midzuno, 1929)
Oxalate m.p. 218-219 °C (Tanaka and Midzuno, 1929) (dee.)
Picrate m.p. 160 °C (Semmler and Bartelt, 1908)

MDPEA
Pi crate m.p. 1 75 °C (Tanaka and Midzuno, 1929)

Freebase b.p. 146-148 °C / l0 mm (Semmler and Bartelt, 1908)
Freebase b.p. 150 °C / 20 mm (Schales, 1935a)
Freebase b.p. 148 °C / l 8 mm (Schales, 1935b)
Note: nitrogen-substituted homologues of MDPEA are listed under MDA ( # 77) .
MDPEA reacts with sodium and ammonia to give tyramine (Tomita and Takano, 1 959).
The NMR spectrum was reported (Bagli et al., 1976) . Synthesis, TLC and GC chromato
graphic properties, UV spectra, and other physical properties were reported (Ono et al.,
1976) . Analysis by HPLC employing fluorescamine derivatization and fluorescence detec
tion was reported (Shimamine, 1984) . Deuterated analytes were prepared in the study of
6-[ 1 8F]-dopamine (Ding et al., 1993) . Identification was accomplished with LC / MS (Mortier
et al., 2002). Fragmentation patterns of some fifty-five phenethylamines were determined
by a variety of mass spectrometry techniques (Ki:illiker and Oehme, 2004).

N- Other Name CAS# Ref
-- -- MDPEA (this entry)
-- f3-Me f3-Me-MDPEA [56311-97-8] (1,2)
-- 7-F2 F2-MDPEA [278183-65-6] (3)
Me -- N-Me-MDPEA [451-77-4] (4-9)
Me f3-Me f3,N-Me-MDPEA [83329-26-4] (1)
Me2 -- N,N-Me-MDPEA [65953-87-9] (10-1 7)
Me,Et -- N-Me-N-Et-MDPEA [ 627876-88-4] (17)
Et -- N-Et-MDPEA [133011-30-0] (10,11,16,17)
Pr -- N-Pr-MDPEA [ 627876-90-8] (17)
-
iPr - N-iPr-MDPEA [106310-52-5] (17)
(1) Discriminative stimulus properties observed in rats trained to discriminate DOM from saline
(Glennon et al., 1982c) .
(2) The S-isomer is CAS # [83329-25-3], the R-isomer is [83329-23-1 ] .
(3) Synthesis (Trachsel e t al., 2006).
(5) N-Me-MDPEA and N,N-Me-MDPEA are effective as antitussives at 30 mg (Brown, 1958).
(6) N-Me-MDPEA is also called homarylamine and MDMIEA.
(8) Synthesis and animal behavior studies (Malmusi et al., 1996) .
(9) Behavioral and developmental effects of N-Me-MDPEA and HMDMA compared to those of
MDMA (Bronson et al., 1994a) .
(10) Analysis by non-polar GC, and MS comparison to MDMA (Aalberg et al., 2004).
(11) Analysis by LC with ESI-MS-MS, and comparison to MDMA (Pihlainen et al., 2005).
(12) Isolated as a minor alkaloid from the cactus Trichocereus lobivioides (Shulgin, 2002).
(13) Synthesis and tissue distribution of radioiodine labeled psychoactive drugs (Ghaffari et al., 1997).
(14) Also known as N,N-Me-MDPEA, N,N-dimethyl-3,4-methylenedioxyphenethylamine, and lo-
bivine.
(15) Distinguished from MDMA by GC / MS of the pentafluoropropionamide (Liu, 2005).
(16) The identification of MDMA and nine isomers by GC / MS (Aalberg et al., 2000, 2004) and by
(17) Chromatographic and spectroscopic identification (Aalberg et al., 2003) .

MDPEA / MDPR
Biochemistry
Studied as a striatal dopamine stimulant in rats (Costall et al., 1974) . About 2% of [ 1 4 C]
labeled MDPEA given to a rat is excreted as GEA and dopamine (Schweitzer et al., 1978) .
The synthesis and tissue distribution o f a radioiodine labeled derivative was studied for
application as a brain imaging material (Ghaffari et al., 1997) .
Serotonin receptor site affinity was determined (Glennon et al., 1980a) . Adrenergic and
5-HT2 serotonergic effects on the rat thoracic aorta were compared (Saez et al., 1994) .
Pharmacology
The first relationships between toxicology and pharmacology of MDPEA were reported
(Epstein et al., 1932) . Synthesis and pharmacological evaluation of MDPEA was performed
in cats (Benington et al., 1958a) . Mescaline, DMPEA, MDPEA, TMA, MDA, OMA, BOB,
and MOMA were compared pharmacologically in five animal species (Hardman et al.,
1973) . Discriminative stimulus properties were observed in rats trained to discriminate
DOM from saline (Glennon et al., 1982c); other effects of MDPEA on animal behavior were
reported (Malmusi et al., 1996) .
MDPEA was included in a molecular connectivity analysis of ten psychedelic phenethyl

amines, which identified the importance of the 2,5-positions of the methoxy groups, and
the 4-substituent (Glennon et al., 1979a) .
MDPEA has no oral activity in humans at 200 mg (Alles, 1959), none was detected at greater
than 400 mg (Lemaire et al., 1 985), nor at 300 mg (Shulgin and Shulgin, 199 1 ) .
Legal Status
MDPEA is not a scheduled compound under federal drug law, or under District of
# 86. MDPR
N-(1-(Benzo[d] [1,3] dioxol-5-yl)propan-2-yl)propan-1-amine
3,4-Methylenedioxy-N-propylamphetamine
a-Methyl-N-(propyl)-1,3-benzodioxole-5-ethanamine
MDPA
Registry Numbers
CAS #
HCl salt [74341-77-8]
Freebase [74698-36-5]
S-Isomer freebase [150200-07-0]

From piperonyl acetone (with propylamine, NaBH3CN) to MDPR (Braun et al., 1980) .

m / z: 221 .1416 (100.0%), 222.1449 (14. 1 % )
HCI salt m.p. 194-195 °C (Braun et al., 1980)


MDPR / MEM
Liquid chromatographic and mass spectral analysis of several N-substituted analogues of

MDA has been performed (Noggle et al., 1988) . Proton and [ 13 C]-NMR spectrum reported,
with proton assignments (Dal Cason et al., 1997a) . Analysis and identification by color tests,
TLC, GC, GC/ MS, UV, and IR spectroscopy (Kanamori et al., 1998b). Analysis automated
by online dialysis and liquid chromatography of MDPR in plasma and serum samples
(Sadeghipour and Veuthey, 1998), and analysis of human urine by LC-MS-MS (Nordgren
and Beck, 2004; Nordgren et al., 2005). MDPR has been isolated as a side-product during
the preparation of its cyclopropane counterpart (Effenberger and Jager, 1997) .
Biochemistry
Differences in regioselectivity and stereoselectivity in the oxidative metabolism of MDPR
2
and derivatives by both wild-type and the Phe 1 0Ala mutant of CYP2D6 were studied
(Keizers et al., 2004) .
Pharmacology
Studies of motor activity, tail flick, stretch reflex, and analgesia in mice (Braun et al., 1980).
Synthesis, identification, and acute toxicity of some N-alkyl derivatives of MDA was re
ported (Noggle et al., 1987b).
MDPR is not orally active in humans at 160 mg (Braun et al., 1980) .
Legal Status
MDPR is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
# 87. MEM
1-(4-Ethoxy-2,5-dimethoxyphenyl)propan-2-amine
2,5-Dimethoxy-4-ethoxyamphetamine
1-(2,5-Dimethoxy-4-ethoxyphenyl)-2-aminopropane
DMEA
Registry Numbers
CAS #
HCI salt [17231-80-0]
Freebase [16128-88-4]
R-Isomer [67313-99-9]

From 2,5-dimethoxybenzaldehyde (with Hp2) to 2,5-dimethoxyphenol; (with ethyl io
dide) to 2,5-dimethoxy-1-ethoxybenzene; (with N-methylformanilide, POC1 3 ) to 1,4-dime
thoxy-2-ethoxybenzaldehyde; (with nitroethane, acetic acid, and ammonium acetate) to
1 -(2,5-dimethoxy-4-ethoxyphenyl)-2-nitropropene; (with LAH) to MEM (Shulgin, 1 968).
From 3-ethoxy-4-hydroxybenzaldehyde (bourbonal) (with methyl iodide) to 3-ethoxy-4-

methoxybenzaldehyde; (with peracetic acid, HOAc) to 3-ethoxy-4-methoxyphenyl for
mate; (with NaOH) to 3-methoxy-4-ethoxyphenol; (with KOH, methyl iodide) to 1,4-dime
thoxy-2-ethoxybenzene; (with N-methylformanilide, POCI) to 2,5-dimethoxy-4-ethoxy
benzaldehyde; (with nitroethane, acetic acid, and ammonium acetate) to 1-(2,5-dimethoxy-
4-ethoxyphenyl)-2-nitropropene; (with LAH) to MEM (Shulgin and Shulgin, 1991).

MEM

m / z: 239. 1521 (100.0% ), 240.1555 (14. 1 % )
HCl salt m.p. 1 72 °C (Shulgin, 1968)

HCl salt m.p. 1 71-172.5 °C (Shulgin and Shulgin, 1991)
Identification of the 4-position substituent by NMR analysis (Dawson and Avdovich, 1987) .
2
Synthesis by two routes, with UV, IR, [ H] and [ 13C]-NMR, and GC / MS data (By et al., 1990) .
Biochemistry
Four psychedelic amphetamines were incubated with the filamentous fungus Cunning
hamella echinulata: TMA-2 and MEM were poorly metabolized, MPM was acetylated and
0-dealkylated, and ALEPH was oxidized to the sulfoxide (Foster et al., 1992) .
Studies compared mouse behavior and the activity of the brain enzymes MAO and DOPA
decarboxylase (De Ropp and Kastl, 1970) . Evidence was presented for the involvement of
serotonin in the mechanism of the action of psychedelic drugs (Glennon et al., 1984b ). Sero
tonin agonist activity and psychedelic potency of MEM, EMM, and MME did not correlate
with rat stomach fundus assay predictions (Nichols et al., 1984) . Studies of the relative
5-HT 1 and 5-HT2 binding properties were reported (Shannon et al., 1984). The 5-HT2 recep
tor was shown to be the preferred site of psychedelic action, as its radiolabeling marker
(tritiated DOB) was preferentially targeted; three controls (appropriately radiolabeled
5-HT 1 N 5-HT 1 w and 5-HT 1 c receptors) were not as strongly stimulated (Titeler et al., 1988).
Affinity to 5-HT2 receptors was measured and compared to structurally related compounds
(Seggel et al., 1990) . Binding at 5-HTic and 5-HT2 receptors has been studied (Glennon et
al., 1992); affinity to cloned human 5-HT2N 5-HT2w and 5-HT2c receptors was measured
and compared with structurally related compounds (Nelson et al., 1999) . A large study of
psychedelic compounds showed that the lipophilicity of the 4-position substituent was of
primary importance in determining 5-HT2 receptor affinity (Glennon and Seggel, 1989),
and the electron withdrawing or donating nature of the 4-position substituent was corre
lated with the human potency of the compound (Neuvonen et al., 2006).
Pharmacology
Human potency is affected by changes in substitution patterns (Shulgin et al., 1969) . Rats
trained to discriminate 5-MeO-DMT from saline were tested with several psychoactive
phenylisopropylamines (Glennon et al., 1981a). A comparison of the serotonin receptor
affinity and the behavioral properties of MEM was reported (Glennon et al., 1982a) . Dis
criminative properties of TMA, MEM and ALEPH were determined with rats trained to
discriminate amphetamine from saline (Corrigall et al., 1992a) .
The positional isomer (with the ethoxy group at the 5-position), MME [23693-32-5] showed
threshold or greater oral activity in humans at 40 mg, but was not studied at higher doses
(Shulgin and Shulgin, 1991 ) .
MEM i s orally active a t 20-50 mg; duration 1 0-14 hours (Shulgin and Shulgin, 1991).
Legal Status
MEM is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.

MeOPP
# 88. MeOPP
1-(4-Methoxyphenyl)piperazine
4-MeOPP
1-(p-Anisy l)piperazine
Paraperazine
Registry Numbers
CAS #
HCl salt [84145-43-7] CAS # CAS #
di-HCl salt [38869-47-5] HBr salt [11 7208-67-0] Succinate [154306-45-3]
x-HCl salt [70849-64-8] Oxalate [876132-12-6] Freebase [38212-30-5]

From p-anisidine (with f3,j)'-NH(CH2CH2Br)2) to 1-(4-methoxyphenyl)piperazine (Prelog
and Blazek, 1934) .
Synthesis of related piperazines, and evaluation of MeOPP and others as f3-blocking agents
(Phillips et al., 1992) .

m/ z: 192. 1263 (100.0% ), 193.1296 (11 .9% )
HBr salt m.p. 219 °C (Prelog and Blazek, 1934)
Identification and analysis was performed by HPLC-UV (de Boer et al., 200 1 ) . A plasma
screening and quantitative GC / MS analysis was reported (Peters et al., 2003). Employing
HPLC-PDA, HPLC-MS, TLC, and NMR, a library of 35 illegal drugs was assembled and
used to identify street samples (Nakashima et al., 2005).

Substituent Name CAS# Ref
H pp [92-54-6] (1,2)
4-0H HOPP [ 56621-48-8] (3)
2-0CH3 2-MeOPP [35386-24-4] (4-6)
3-0CH3 3-MeOPP [16015-71-7] (7)
4-0CH3 MeOPP (this entry)
(1) Hypocholesterolemic activity observed in rats (Cascio et al., 1985).
(2) Various serotonin receptor-mediated effects were noted for the action of PP (Fuller, 1986) .
(3) A metabolite of MeOPP in the rat. Also a metabolite of the commercial antitussive dropropizine
(Staack and Maurer, 2003a).
(4) A hypotensive in the dog (Page et al., 1959).
(5) Used as a derivatization reagent for determination of total isocyanate pollution in air (Molander
et al., 2000).
(6) Pharmacological evaluation, with focus on role of 5-HT A receptors (Khatri et al., 2009) .
1
(7) Synthesis (Sriram et al., 2006) .
Biochemistry
MeOPP is metabolized in the rat by 0-demethylation (HOPP) and there is some degra
dation of the piperazine ring (Staack and Maurer, 2003a; Staack et al., 2004b ). A series of

MeOPP I N-MePEA
arylpiperazines was synthesized in an effort to incorporate class II ([3-receptor blocking)

and class III antiarrythmic properties in a single molecule; canine Purkinje fiber responses
were used as the bioassay (Phillips et al., 1992) .
and release of monoamines (dopamine, serotonin, and norepinephrine) using rat brain
Pharmacology
MeOPP was reported as a component of street drugs sold in Japan (Nishioka et al., 2007) .
MeOPP is reportedly consumed at 100-200 mg orally, but in and of itself is not psychedelic
unless taken with other stimulants, such as BZP (Wikipedia, 2007c).
Legal Status
MeOPP is not a scheduled compound under federal drug law, or under District of Colum
# 89. N-MePEA
N-Methyl-2-phenylethanamine
N-Methylphenethylamine
NSC 113957
Registry Numbers
CAS # CAS #
Natural Sources
Extraction of the leaves and stems of Acacia kettlewelliae yielded 0.9% N-MePEA as a na
tive alkaloid, and the dried leaves of A. adunca gave 2.4% N-MePEA (Fitzgerald, 1964) .
Reported to be present in Acacia berlandieri (Clement et al., 1997), and A. rigidula (Clement
et al., 1998) . Found in the stem and (to a lesser extent) the root of Alhagi pseudalhagi (Ghosal
and Srivastava, 1973b). Isolated from Haloxylon salicornicum (El-Shazly et al., 2005).
N-MePEA was found in Dolichothele surculosa and other Dolichothele species (Dingerdissen
and McLaughlin, 1973), and in seven species of the cactus genus Gymnocactus, including
Gymnocactus aguirreanus, G. beguinii, G. horripilus, G. knuthianus, G. mandragora, G. roseanus,
G. viereckii (West et al., 1974) .

From 2-phenylacetonitrile (with methyl iodide) to trimethylphenylethylammonium io
dide; (with naphthyl cyanate) to 1 -phenyl-2-a-naphthylurea; (with benzenesulphone chlo
ride, NaOH, methyl iodide) to benzenesulphone methylphenethylamine; (with HCI, heat)
to N-methylphenethylamine (Johnson and Guest, 1910).

ml z: 135. 1 048 (100.0%), 136.1082 (9.7% )
HCI salt m.p. 152-154 °C (Johnson and Guest, 1910)

Chloroplatinate m.p. 212 °C (Johnson and Guest, 1910)

N-MePEA / MEPEA
Picrate m.p. 141 °C (Johnson and Guest, 1910)

Picrolonate m.p. 218-21 8 °C (Johnson and Guest, 1910)
Acid oxalate m.p. 183-1 84 °C (Johnson and Guest, 1910)
Biochemistry
N-MePEA was effective at releasing cardiac norepinephrine from mouse heart (Daly et al.,
1 966) . Spasmolytic activity on isolated rabbit small intestine was studied (Stolyarchuk et
al., 1 975) .
Pharmacology
A correlation was made between chemical structure and the locomotor activity of mice
(van der Schoot et al., 1 962), and pulmonary circulation effects were measured in the dog
(Aviado et al., 1 957) .
Human activity of N-MePEA is unknown.
Legal Status
N-MePEA is not a scheduled compound under federal drug law, or under District of Co
# 90. MEPEA
2-(4-Ethoxy-3-methoxyphenyl)ethanamine
4-E thoxy-3-methoxyphenethylamine
3-Methoxy-4-ethoxyphenethy!amine
Registry Numbers
CAS # CAS#
Chloroplatinate [39697-37-5] Sulfate [39201-83-7]
Picrate [109035-92-9] Freebase [36377-59-0]
Synthesis
From 3-methoxy-4-ethoxybenzaldehyde (with nitromethane) to 3-methoxy-4-ethoxy-[3-
nitroethene; (with Zn) to MEPEA (Leminger, 1 972a) .
From 3-methoxy-4-ethoxybenzaldehyde (with nitromethane) to 3-methoxy-4-ethoxy-[3-

nitroethene; (with LAH) to MEPEA (Shulgin and Shulgin, 1 991).

m / z: 195.1259 (100.0% ), 196.1293 (11.9%)
Freebase HCI 162 °C (Ide and Buck, 1937)

3- 4- Name CAS # Ref
MeO EtO ME PEA (this entry)
Meo AllylO MAPEA [39201-81-5] (1,2)
(2) Orally active in humans at 1 00-300 mg (Leminger, personal communication).

MEPEA / Mescaline
Pharmacology
Orally active in humans at 1 00-300 mg (Leminger, personal communication), and at great
er than 300 mg; duration "very short" (Shulgin and Shulgin 1 991).
Legal Status
MEPEA is not a scheduled compound under federal drug law, or under District of Colum
# 91. Mescaline
3,4,5-Trimethoxy-[3-phenethylamine
2-(3,4,5-Trimethoxyphenyl)ethylamine
Mezcaline
Mescalin
M
2C-TMA
TMPEA
NSC 30419
Registry Numbers
CAS # CAS # DEA#
HCl salt [832-92-8] Acid salt [87059-78-7]
HBr salt [ 41 885-48-7] Freebase [54-04-6] 7381
HI salt [51749-33-8] a,a-[ d2 ] Isomer freebase [87096-79-5]
4-Aminobutyrate [856823-11-5] a,f3-[d2 ] Isomer HCI salt [27954-94-5]
Bisulfate salt [5967-42-0] f3,f3-[d2] Isomer HCI salt (f3-D)*
Picrate [5967-44-2] 4-Methyl-[d3 ] HCI salt (4-D)*
x-Picrate [13338-64-2] (C[ d3]0) 3 Isomer [152477-93-5]
x-Sulfate salt [1152-76-7] 2,6-[ 3H] 2 Isomer HCI salt [27954-95-6]
Sulfate salt [642-73-9] a,f3-[ 3H] 2 Isomer HCI salt [28008-37-9]
Sulfate hydrate [51 749-34-9] a-[ 1 4C] Isomer [ 94600-00-7]
Sulfate salt tetrahydrate [6043-76-1]
*Not in Chemical Abstracts, and therefore no CAS numbers have been registered; the human pharma
cology of each is indistinguishable from the deuterium-free prototypes.
Natural Sources
Mescaline is widely encountered in all three tribes of the Cactaceae: the Pereskieae, Opun
tieae, and the Cacteae (Schultes and Hofmann, 1973; Trout, 1997) . Mescaline, anhalonidine,
lophophorine, and possibly pellotine were first isolated in pure form by Arthur Heffter
from the cactus Lophophora williamsii (Lemaire) Coulter, commonly known as peyote, from
the Nahuatl word peyotl; also known as Anhalonium lewinii, and by several other binomi
als (Heffter, 1894, 1 896, 1 898). (Although there is solid conjecture that the pellotine Heffter
isolated probably came from the plant now known as L. diffusa.) Through self-experimen
tation, Heffter identified the predominant role of mescaline in the psychological proper
ties of the peyote plant. At that time, mescaline was the first chemically pure psychedelic,
although the structure of mescaline remained unknown until its successful synthesis some
twenty years later by Ernst Spath (Spath, 1919); in the same paper Spath also showed that
another minor peyote alkaloid, anhaline, was identical to hordenine. Anhalamine (Kauder,
1899), anhalinine, anhalidine (Spath and Becke, 1935a,b), and many other alkaloids were

Mescaline
found over the years (for a chronology, see Trout, 1999; pp 115-11 7) . Extensive summaries of
the early history of cultural, ethnopharmacological, and botanical research on peyote were
presented (Bruhn and Holmstedt, 1974; LaBarre, 1975), which illustrate the vast develop
ment of literature on peyote. This plant is explicitly listed as a Schedule I hallucinogen on
the federal level, and has been assigned an Administrative Controlled Substances Code
Number: 7415 (see discussion on state laws regarding peyote in Legal Status, below) . The
natural range of this plant and closely related species is from central Mexico, north to the
Rio Grande Valley; in much of this region L. williamsii is rare to endangered.
known as Echinopsis ) where it was found in T. terscheckii (Reti and Castrill6n, 1951) in the
Mescaline has been repeatedly identified in the South American genus Trichocereus (now
first instance of mescaline identification apart from peyote; it was later isolated from the
cactus T. pachanoi (Crosby and McLaughlin, 1 973), also known as aguacolla, gigant6n, hua
chuma, or San Pedro, and indigenous to Ecuador and Peru (Poisson, 1960). Mescaline was
found in T. peruvianus (Pardanani et al., 1977), and T. strigosus (Nieto et al., 1 982) . A com
ponent was obtained by the extraction of T. peruvianus with chloroform, that proved to be
2-chloromescaline, a contaminant formed by reaction with the extraction solvent (Pardan
ani et al., 1 977) . Re-extraction of the original plant with ethanol gave no 2-chloromescaline.
The mescaline-containing cactus T. werdermannianus also contained HPEA, GEA, DMPEA,
and DESMETHYL; the mescaline-containing T. pachanoi contained these alkaloids, as well
as the tetrahydroisoquinoline, anhalonidine (Agurell, 1969b). GEA and 3,4-DESMETH
YL were shown to have a role in the biosynthesis of mescaline and the isoquinolines in
Lophophora williamsii (Lundstrom, 1 971a).
Mescaline was later confirmed in Lophophora williamsii varieties (Lundstrom and Agurell,
1968a; Fujita et al., 1972), and identified in the cactus Pelecyphora aselliformis (Neal et al.,
1 972), as well as the cactus Opuntia, subgenus Cylindropuntia (cholla) and other Opuntia
spp. (Meyer et al., 1980), Opuntia spinosior (Pardanani et al., 1 978), and in the cacti Isla
ya minor, Pereskia corrugata, P. tampicana, and Pereskiopsis scandens (Doetsch et al., 1 980) .
Mescaline, tyramine, and HMePEA were isolated from the cactus Opuntia ficus-indica (El
Moghazy et al., 1 984).
Mescaline was present as the major alkaloid, albeit in much lower concentrations, in the
cacti Opuntia acanthocarpa, 0. basilaria, 0. echinocarpa, Polaskia chende, S tenocereus stellatus
and S. treleasei. It was present as a minor alkaloid in the cacti Pterocereus gaumeri and S teno
cereus beneckei, with a concentration level (dry weight) of < 0.01 % . It was not present in the
echinocarpa, 0. ramosissima, Pterocereus Joetidus and S tenocereus eruca above a detection limit
cacti Escontria chiotilla, Melocactus maxonii, Neoraimondia arequipensis, Opuntia bigelovii, 0.
(dry weight) of 0.001% (Ma, et al., 1 986) . HPLC analysis with photodiode-array detection
of the cactus Trichocereus pachanoi for mescaline gave values that varied between 1 .09 and
23.75 µg / mg (Helmlin and Brenneisen, 1 992) . Mescaline was present in Gymnocactus be
guinii, Echinocactus polycephalus, Coriphantha radians, C. scolymoides, C. palmeri, Lophophora
williamsii, and Trichocereus pachanoi; the average amounts of mescaline found in L. williamsii
and T. pachanoi were, respectively 2.55 mg and 3.10 mg / g of fresh cactus (Gennaro et al.,
1 996) . Mescaline was found in the South American cactus genus Gymnocalycium (Starha,
1 996), and in Turbinicarpus species (Starha et al., 1 999) .
Mescaline was reported to be present in Acacia berlandieri (Clement et al., 1 997), and A.
rigidula (Clement et al., 1 998) .

Mescaline

From 3,4,5-trihydroxybenzoic acid (gallic acid; with dimethyl sulfate, NaOH) to 3,4,5-tri
methoxybenzoic acid; (with PCl5 ) to 3,4,5-trimethoxybenzoyl chloride; (with Pd, BaS04,
H2) to 3,4,5-trimethoxybenzaldehyde; (with nitromethane ) to 1 -(3,4,5-trimethoxy)nitro
ethene; (with Zn, HOAc) to an oxime; (with Na, Hg; Spath, 1919), or (with LAH; Bening
ton and Morin, 1951; Ono et al., 1 973a), or (with Pd / C, H2; Ohshita and Ando, 1 992) to
mescaline.
From 3,4,5 methoxybenzaldehyde (with malonic acid) to 3,4,5-trimethoxycinnamic acid;

(with Na, Hg) to 3,4,5-trimethoxypropionic acid; (with NH3 ) to 3,4,5-trimethoxypropion
amide; (with NaOCl) to mescaline (Slotta and Heller, 1930) .
From Et-3,4,5-trimethoxybenzoylacetate (with reduction) to Et-3,4,5-trimethoxyhydrocy

namate and its acid amide; (with the Hofmann degradation) to mescaline (Frisch and
Waldmann, 1931 ) .
From 3,4,5-trimethoxynitroethene (with electrolytic reduction) t o mescaline (Slotta and

Szyszka, 1933) .
From 3,4,5-trimethoxybenzaldehyde (with nitromethane) to 3,4,5-trimethoxynitroethene;

(with LAH) to mescaline (Erne and Ramirez, 1950; Shulgin, 1 963) .
From trimethoxybenzoic acid (with methyl sulfate) t o methyltrimethoxy-benzoate; (with

LAH) to trimethoxybenzyl alcohol; (with cone. HCl) to trimethoxybenzyl chloride; (with
KCN) to trimethoxybenzylcyanide (also known as 3,4,5-trimethoxyphenylacetonitrile);
(with LAH) to mescaline (Tsao, 1 951).
From 3,4,5-trimethoxybenzoyl chloride (with diazomethane) to 2-diazo-3,4,5-trimethoxy

acetophenone; (with NH3 ) to 3,4,5-trimethoxyphenylacetamide; (with LAH) to mescaline
(Banholzer et al., 1952) .
The 3,4,5-trimethoxybenzaldehyde needed for this synthesis was produced by the isolation
of syringaldehyde, obtained by the oxidation (with nitrobenzene and alkali) of sawdust
from one of several Eucalyptus species, and its conversion to above aldehyde by methylation
(Amos, 1964) .

m / z: 211 . 1208 (100.0% ), 212.1242 (11.9%)
HCl salt m.p. 205 °C (Reti and Castrill6n, 1951) (EtOH)

HCI salt m.p. 1 80-1 81 °C (Shulgin, 1963)
Benzoate m.p. 120-121 °C (Spath, 1919)
Chloroaurate m.p. 140-141 °C (Spath, 1919) (with 1 Hp)
Chloroaurate m.p. 136-139 °C (Reti and Castrill6n, 1951) (dee.)
Chloroplatinate m.p. 187-188 °C (Spath, 1919)
Chlorop latinate m.p. 1 84-1 85 °C (Tsao, 1951)
Chloroplatinate m.p. 1 87-1 88 °C (Reti and Castrill6n, 1951)
Methiodide m.p. 226-228 °C (Reti and Castrill6n, 1951)
m-Nitrobenzoate m.p. 161-162 °C (Spath, 1919)
Picrate m.p. 216-218 °C (Spath, 1919)
Picrate m.p. 216-218 °C (Reti and Castrill6n, 1951) (acetone)

Mescaline
Picrate m.p. 216 °C (Banholzer et al., 1952)

Picrate m.p. 214-216 °C (Shulgin, 1963)
Picrolonate m.p. 166 °C (Reti and Castrill6n, 1951) (EtOH / acetone)
Quaternary (M3+) salt m.p. 165 °C (Reti and Castrill6n, 1951) (Hp)
2:1 Sulfate dihydrate m.p. 1 83-186 °C (Spath, 1919)
Freebase b.p. 120-130 °C / 0.05 mm (Banholzer et al., 1952)
A number of salts and derivatives were described for identification purposes. (Jansen,
1931). Reductive cleavage with Na and NH3 formed DESMETHYL (Tomita and Takano,
1959). Mescaline was radiolabeled with [ 3H] or [ 1 4C] for biosynthesis studies (Lundstrom
and Agurell, 1971 ) . A quantitative colorimetric urine screening assay was described (Rut
ter, 1 972) . Thin-layer electrophoretic behavior was characterized (Cavallaro and Elli, 1 972) .
Picogram levels o f mescaline were measured b y GC / MS analysis o f the isothiocyanate
derivatives (Brandenberger and Schnyder, 1972) . Analysis by TLC (Bussey and Backer,
1 974), and by HPLC (Chan et al., 1974; Cashman et al., 1 973) has been reported. Synthesis,
TLC, and GC methods, and the UV spectrum were reported (Ono et al., 1 976) . Analyses by
packed-column GC compared mescaline with several other drugs (Canfield et al., 1 977) .
A GC / MS technique was applied to detection of mescaline and a series of other abusable
drugs in physiological fluids (Foltz, 1 978) . The conformation of the aryl methoxy groups
was established by [ 13C]-NMR spectral analysis (Knittel and Makriyannis, 1 981 ) . TLC and
color visualization tests were defined for the identification of substituted amphetamines
(O'Brien et al., 1982) . The [ 13C]-NMR spectra for methoxylated phenethylamines and am
phetamines were shown to be distinctive and suitable for identification (Bailey and Le
gault, 1 983) . HPLC employing fluorescamine derivatization for fluorescence detection was
reported (Shimamine, 1984) . Rapid forensic identification of illicit phenethylamines was
described, using TLC in six different solvent systems, and five color reactions for specific
visualizations (Neuninger, 1 987) . Cross-reactivity of several substituted amphetamines
was evaluated with the Roche Abuscreen® (Cody, 1 990a), and the Diagnostic Products Corpo
ration (Cody, 1 990b) radioimmunoassays for amphetamines. Screening methods for sub
stituted amphetamine derivatives by fluorescence polarization immunoassay were also
developed (Cody and Schwarzhoff, 1 993) . A synthesis was described with emphasis on
reductions that might increase yield (Liu and Cui, 2002) . Quantitative determination of
human plasma was achieved by GC / MS analysis of the heptafluorobutyrate amides (Hab
rdova et al., 2005). Mescaline was found in samples of street drugs in Japan, with confirma
tional analysis by GC / MS and LC-ESI-MS (Kikura-Hanajiri et al., 2005)
History
Peyote has been dubbed the prototypical Western hemisphere psychedelic, being the first
to be observed in use, as the Conquistadores invaded Mexico in 1519 (Schultes and Hof
mann, 1 973) . Recent [ 14 C] analyses of museum specimens of peyote (El-Seedi et al., 2005),
and peyote-containing artifacts collected in West Texas and Mexico (Terry et al., 2006) have
clearly established prehistoric use of this plant as early as 6,000 years ago. Through their
use of peyote the Huichol, Tarahumara, Cora, and neighboring cultures of Southwest Mex
ico have had relationships with mescaline that reach into antiquity (Benzi, 1 969; Pares,
1 969; Schaefer, 1 996) . Despite centuries of civil and ecclesiastical repression during the
Spanish conquest, peyote use in Mexico has survived to the present (Schultes and Hof
mann, 1973) . The introduction of peyote to more northerly Native American peoples is
attributed to the Commanche leader Quanah Parker in the 1 880s, who was treated with
peyote by a Mexican curandera. A Caddo religious figure, John Wilson, was also influen
tial in the early spread of peyote use, and he is thought to have been responsible for the

Mescaline
incorporation of Christian influences and motifs into peyote religion. Their adoption and
promotion of peyote as a religious sacrament overlapped the climax of the Ghost Dance
movement, and gave rise to the second great Native American syncretic religion of the
North, the Native American Church (LaBarre, 1975; Stewart, 1 987) . Since that time the Na
tive American Church has spread throughout the United States and Canada, and may have
over 200,000 practitioners.
The San Pedro cactus, Trichocereus pachanoi, and related species also have ancient history of
religious veneration and medical use in Peru (Sharon, 1 972; De Rios, 1977) .
Positional Isomers*
2- 3- 4- 5- 6- Name Entry
Meo MeO MeO -- -- IM #72
Meo Meo -- MeO -- TMPEA-4 see # 120
MeO MeO -- -- MeO TMPEA-5 see #121
MeO -- MeO Meo -- TMPEA-2 see #124
Meo -- MeO -- MeO TMPEA-6 see #122
-
-- MeO MeO Meo - M (this entry)
*Note that all entnes m this table are Schedule I compounds (see Legal Status, this entry), and are
covered in separate entries.

Cl Meo MeO a-Me 3-Cl-4,5-DMA [27164-30-3] (1)
Br Meo Br -- 3,5-Br-4-MPEA [99180-14-0] (2)
Me Meo Me -- 3,5-Me-4-MPEA [52670-14-1] (2)
Me Meo Me a-Me 3,5-Me-PMA [24973-30-6] (3-6)
MeO Meo Meo -- M (this entry)
Meo Meo MeO N-Me3 T-Mel [6308-78-7] (7)
Meo Meo MeO N-CCCl N-CCCl-M [15257-73-5] (8)
MeO MeO Meo N-Pr N-Pr-M [ 62028-43-7] (9)
Meo MeO MeO N-Allyl N-AL-M [ 62028-46-0 l (9)
MeO Meo Meo N-CC=CC-N N,N-Butenyl-M [ 62028-47-1 ] (9)
Meo MeO MeO N-CCC N-CPM-M [ 62028-44-8] (9)
Meo Meo MeO f3-HO f3-HOM [13079-18-0] (1,10,11-13)
Meo MeO MeO f3-HO,N-Me f3-HO-M-M [91554-99-3] (14)
MeO MeO Meo f3-C=0 M-f3k [13079-19-1] (11)
Meo EtO MeS -- 3-TE [90132-38-0] (15-17)
MeO iPrO MeO -- IP [61367-70-2] (18-22)
MeO PRO Meo -- PROPYNYL [95201 7-05-9] (23)
Meo cPrCO MeO -- CPM [207740-23-6] (24,25)
Meo BuO MeO -- B [ 64778-75-2] (25-28)

Mescaline
�--�

MeO iBuO Meo -- IB [501 700-05-6] (29)
MeO MeAllylO Meo -- MAL [207740-41-8] (30,31)
Meo BzO MeO -- BZ [2176-16-1 ] (20,26)
Meo PhEtO MeO -- PE [207740-42-9] (32)
Meo Mes MeO -- TM [71539-35-0] (15,33-35)
MeO Mes EtO -- 4-TME [90109-47-0] (36,37)
MeO EtS MeO -- TE [90109-50-5] (36,38)
Meo Bus MeO -- TB [90109-57-2] (36,39)
EtO MeO Meo -- ME [90132-31-3] (36,40,41)
EtO MeO EtO -- SB [90109-62-9] (42,43)
EtO MeO Mes -- 5-TME [90132-40-4] (15,44)
EtO EtO EtO -- TRIS [90109-63-0] (45,46)
EtO Mes EtO -- 4-TSB [90109-46-9] (37,48)
EtO EtS MeO -- 4-TASB [90109-52-7] (36,37)
EtO EtS EtO -- 4-T-TRIS [90109-53-8] (36,49)
PrO MeO MeO -- MP [90132-33-5] (42,50,51)
Mes Meo Meo -- 3-TM [78335-85-0] (50-52)
Mes EtO EtO -- 5-TASB [90132-48-2] (15, 1 7)
EtS Meo MeO -- 3-TME [90132-35-7] (15,17,53)
EtS MeO EtO -- 3-TSB [90132-52-8] (15,44)
EtS EtO MeO -- 3-TASB [90132-49-3] (15,54)
EtS EtO EtO -- 3-T-TRIS [90123-54-0] (15,55)
(1) Pharmacokinetics in rat brain, liver, and plasma (Cohen et al., 1974) .
(2) Synthesis and pharmacological evaluation i n cats (Benington e t al., 1958a).
(3) Studies of injection into the rat optic nerve and cat sciatic nerve (Paulson and McClure, 1973).
(4) Pharmacology evaluated for toxicity, barbiturate sleeping time, and disruption of mouse
behavior (Ho et al., 1970a).
(5) Synthesis (Butterick and Unrau, 1974).
(6) Synthesis (Ho et al., 1970a) .
(7) Compounds tested at the microgram levels as plant growth inhibitors (Mandava et al., 1981 ).
(8) Synthesis (Cooper, 1973).
(9) Synthesis and disruption of swimming of mice (DeSantis and Nieforth, 1976).
(12) The cactus Pereskia grandiflora contains j)-HOM (Doetsch et al., 1980).
(13) Physiological responses in the rat brain, liver, and plasma (Cohen et al., 1974) .
(14) Synthesis (Friedman at al., 1963)
(15) Synthesis from the acetonitrile (Jacob and Shulgin, 1984).
(16) Orally active in humans at 60-80; duration 8-12 hours (Shulgin and Shulgin, 1991).
(17) Orally active in humans at 30-60 mg (Jacob and Shulgin, 1984).
(18) Synthesis (Nichols et al., 1977).
(19) Molecular connectivity analysis gave excellent correlation to serotonin agonist activity in a large
number of phenethylamines and amphetamines (Kier and Glennon, 1978a).

Mescaline
(20) The octanol-water partition coefficient served as a predictor of human psychedelic potency
(21 ) IP is more potent than mescaline in contracting sheep umbilical artery strips (Nichols and Dyer,
1997).
(22) A comparison of steric properties with animal and human potency of several phenethylamines,
tryptamines, and lysergamide derivatives was made (Nichols, 1986a).
(23) Synthesis described; threshold oral activity in humans at 80 mg; duration 8-12 hours (Shulgin
and Shulgin, 1991)
(25) Orally active in humans at 60-80 mg; duration 12-1 8 hours (Shulgin and Shulgin, 1991 ).
(26) B and Bz are more potent than mescaline in contracting sheep umbilical artery strips (Nichols
and Dyer, 1997). Note that the code BZ is also applied to 3-quinuclidinyl benzilate, a synthetic
tropane deleriant developed as a military incapacitating agent.
(27) Syntheses described (Nichols and Dyer, 1977; Jacob and Shulgin, 1984).
(28) Indications of body toxicity in humans at 150 mg orally (Shulgin and Shulgin, 1991 ).
(31 ) Orally active in humans at 40-65 mg; duration 12-16 hours (Shulgin and Shulgin, 1991 ).
(32) Synthesis described; threshold oral activity in humans at 150 mg; duration unknown (Shulgin
and Shulgin, 1991).
(33) Using molecular connectivity analysis of ten psychedelic phenethylamines, importance of the
2,5-positions of the methoxy groups, and the 4-substituent, was demonstrated (Glennon et al.,
1979a).
(34) Reported orally active in humans (nine subjects) at 16-40 mg (Jacob and Shulgin, 1981), and at
30 mg (Braun et al., 1978), and at 12-24 mg (Jacob and Shulgin, 1984), and at 20-40 mg; duration
1 0-15 hours (Shulgin and Shulgin, 1991).
(35) Also called 4-thiomescaline, 4-TM.
(37) Orally active in humans at 50-100 mg (Jacob and Shulgin, 1984), and at 60-100 mg; duration
10-15 hours (Shulgin and Shulgin, 1991 ).
(38) Reported orally active in humans at 10-20 mg (Jacob and Shulgin, 1984), and at 20-30 mg;
(39) Orally active in humans at 60-120 mg (Jacob and Shulgin, 1984), and at 60-120 mg; duration
about eight hours (Shulgin and Shulgin, 1991).
(40) Production of experimental catatonia in cats (Noteboom, 1934).
(41 ) Orally active in humans at 200-400 mg (Jacob and Shulgin, 1984), and at 200-350 mg; duration
8-12 hours (Shulgin and Shulgin 1991).
(43) Synthesis from the acetonitrile (Jacob and Shulgin, 1984) .
(44) Not orally active (Jacob and Shulgin, 1984), not active at 200 mg (Shulgin and Shulgin, 1991).
(45) Studies on oxidative deamination and effects on cat behavior (Clark et al., 1964) .
(46) Syntheses described (Slotta and Szyszka, 1933; Jacob and Shulgin, 1984) .
(48) Not orally active in humans at 240 mg (Shulgin and Shulgin, 1991 ).
(50) Several phenethylamines and tryptamines were compared in studies with rats (Kier and Glen
non, 1978b).
(51 ) Synthesis (Jacob and Shulgin, 1981 ).
(52) Synthesis from the nitroethene; orally active in humans at 30-60 mg (Jacob and Shulgin, 1984),
and at 60-100 mg; duration 8-12 hours (Shulgin and Shulgin, 1991 ).
(54) Orally active in humans at about 160 mg; duration 10-1 8 hours (Shulgin and Shulgin, 1991).
(55) Orally active in humans at 1 00-200 mg (Jacob and Shulgin, 1984).

Mescaline
Homologues with 3-Carbon Chains

Ar- a- Name CAS # Ref
3,4,5-MeO -- homo-Mescaline [3166-94-7] (1,2)
2,4,5-MeO Me homo-TMA-2 [38910-36-0] (3,4)
2,3,4-MeO Me homo-TMA-3 [38910-35-9] (3,4)
2,4,6-MeO Me homo-TMA-6 [38910-37-1] (3,4)
(1) Studies on enzymatic oxidative deamination and effects on cat behavior (Clark et al., 1964) .
(2) The effects on rat brain enzymes have been observed (Clark et al., 1956) .
(3) Synthesis and activity assessment through rabbit hyperthrmia, cat EEG, and rat behavioral tests
(Aldous et al., 1974).
(4) The behavioral effects in rats were compared with those produced by LSD, mescaline, and am
phetamine (Buxton, 1972).
Biochemistry
The biosynthesis of mescaline has been vigorously investigated since the late 1 960s. With
[ 1 4 C]-labeled tyrosine, mescaline biosynthesis in peyote was outlined (Agurell et al., 1 967;
Lundstrom and Agurell, 1 968b); phenylalanine, dopa, and dopamine were precursors in
Lophophora williamsii (Rosenberg et al., 1 967) . Radioactive dopamine was 3-0-methylated
to give GEA in Trichocereus pachanoi, which led to both DMPEA and mescaline (Lundstrom,
1 970a) . Hydroxylated and methoxylated biosynthetic intermediates of mescaline and re
lated isoquinolines were detected in T. pachanoi, T. werdermannianus, and L. williamsii, and
supported the proposal that biosynthesis proceeded by ring hydroxylation and 0-meth
ylation (Agurell and Lundstrom, 1 968; Agurell 1969b; Basmadjian and Paul, 1 971; Khanna
et al., 1 969; Lundstrom and Agurell, 1969; Lundstrom, 1970a, 1 971b; Paul et al., 1 969, 1970;
Rosenberg et al., 1969) . Injection of a-[ 1 4 C]-3,4,5-DESMETHYL into L. williamsii led to the
biosynthesis of mescaline, whereas the injection of a-[ 1 4 C]-dopamine gave a higher yield,
suggesting that DMPEA might be an intermediate (Paul et al., 1 969) . GEA, DESMETHYL,
and 3,4-DESMETHYL were found to be biosynthetic precursors of mescaline in L. william
sii, but HMPEA and 3-DESMETHYL were not; the role of dopamine as a precursor was
proposed (Rosenberg et al., 1 969) . The principle biosynthetic pathway for mescaline in
Lophophora williamsii was therefore proposed to be from dopamine, with 3-0-methylation
to GEA, followed by 5-hydroxylation to 3,4-DESMETHYL (Lundstrom, 1971a) . The effi
ciency of incorporation of several possible bio-precursors of mescaline and related peyote
tetrahydroisoquinolines was measured (Paul, 1 973) .
DESMETHYL and 3-DESMETHYL were metabolites o f mescaline i n humans (Ratcliffe and

Smith, 1959). Effects of ring methoxy groups on oxidative deamination were studied (Clark
et al., 1 965) . The metabolism of mescaline and DMPEA was compared in human subjects
(Friedhoff and Hollister, 1966; Charalampous, 1971 ) . Urinary catecholamine excretion was
monitored after mescaline exposure in humans (Hollister and Moore, 1 968) . Susceptibility
of mescaline and isomescaline to oxidative deamination was compared with in vitro mouse
brain preparations (Seiler and Demisch, 1971 ) . Tissue levels of mescaline were reported
following chronic treatment of rats (Sethy and Winter, 1 973) . Mescaline pharmacokinetics
were monitored in rat brain, liver, and plasma (Cohen et al., 1 974) . The metabolism of mes
caline and isomescaline to the corresponding phenylacetic acids was studied in the mouse
(Seiler and Demisch, 1 974) . A radioimmunoassay specific for mescaline (sensitive in the
picomole range) showed that an i.v. administered dose to rabbits rapidly disappeared from
circulation. The major metabolite in serum and urine was 3,4,5-trimethoxyphenylacetic
acid (Riceberg et al., 1 974) .

Mescaline
Mescaline was metabolized (by in vitro preparations from mouse tissues, including CNS
fractions) to 3,4,5-trimethoxybenzoic acid (Demisch and Seiler, 1975), yet the distribution
of [ 1 4 C]-labeled mescaline in the rat showed 3,4,5-trimethoxyphenylacetic acid to be a ma
jor metabolite in the rat (Shah et al., 1975) . Mescaline demethylase could remove either the
3-methoxy or the 4-methoxy methyl group (Datta and Ghosh, 1 977) . 3,4,5-Trimethoxyben
zoic acid was found to be a low-level metabolite of mescaline in human subjects (Demisch
et al., 1 978) . While a number of substituted phenethylamines and amphetamines were
competitive inhibitors of the liver cytochrome P450 complex enzyme CYP2D6, mescaline
did not interact with this enzyme (Wu et al., 1997) .
Effects on alkaline phosphatase activity and pyruvate utilization were studied in rat brain
homogenates and supernatants (Clark et al., 1956) . In studies of mescalinoids with mono
amine oxidase, only those compounds which either were unreactive with MAO, or inhib
ited its action, were psychedelic in humans (Hellot et al., 1970b ). Rat liver supernatant was
capable of biosynthsis of [ 1 4 C]-labeled mescaline from DESMETHYL, with [ 1 4 C]-methyl
adenosylmethionine (Friedhoff et al., 1 972) . Immunological studies produced antibodies
to mescaline in rabbits, and followed behavioral effects in rats treated with those antibod
ies; the conclusion was that vaccination against a psychedelic with low potency, such as
mescaline, was likely to be ineffective in preventing psychological effects since very large
amounts of antibody would have to be present to bind the target compound (Utzinger,
1 975) . No mutagenic activity of mescaline was detected in tests with Salmonella typhimuri
um (White et al., 1977) .
Effects on the sensitivity of acetylcholine-reactive receptors in peripheral vascular sys

tems were observed (Matthies, 1 957) . Effects were noted when mescaline was applied to
the dog peroneal tibialis anticus nerve muscle (Schopp and Walsh, 1 964); mescaline, LSD,
and DOM effects on rat brain serotonin metabolism were reported (Freedman et al., 1 970) .
There was no interaction of mescaline with ceruloplasmin-catalyzed serotonin oxidation
(Barrass and Coult, 1972) . Action of mescaline on the salivary gland of the adult blowfly
was compared with the action of serotonin (Berridge and Prince, 1 973) . Mescaline interact
ed with serotonin turnover in rat brain and spinal cord (Anden et al., 1 974), and had effects
on isolated rat atria (Siegel and Orzechowski, 1977) . Binding to dopamine neuroreceptors
was measured (Whitaker and Seeman, 1977) . Molecular connectivity analysis gave excel
lent correlation to serotonin agonist activity in a large number of phenethylamines and
amphetamines (Kier and Glennon, 1 978a); receptor binding was studied (Glennon et al.,
1978), and serotonin receptor site affinity was determined (Glennon et al., 1 978; Glennon
et al., 1980a) . Increases of serotonin level in both dorsal and median raphe neurons were
observed (Geyer, 1 980) . The calculated electrostatic potential of mescaline was related to
that of serotonin (G6mez-Jeria et al., 1 984) . Human platelet shape changes were induced
by mescaline, reflecting 5-HT2 agonism (McClue et al., 1989) . Functional selectivity of sero
tonin receptor subtypes for DOM and a series of substituted phenylisopropylamines and
phenethylamines was studied in hamster ovary cells expressing cloned human receptors,
and through behavioral tests with rats (Moya et al., 2007) .
Mescaline was found to stimulate uterine activity (Kudrin et al., 1963), and was effective
in releasing norepinephrine from the mouse heart (Daly et al., 1966), and affected cardiac
function in the cat and the dog (Ellis, 1965) . Effects of mescaline on the stability of brain
cortex ribosomes were reported (Datta and Ghosh, 1970a,b, 1971 ). Mescaline effects were
measured on single cortical neurons in the cat (Bradshaw et al., 1971), and on the RNA

Mescaline
and protein content of cortical neurons and their glial cell-satellites in cats (Tencheva and
Pevzner, 1973). Physiological response in the rat brain, liver, and plasma were recorded
(Cohen et al., 1974). The distribution of tritiated mescaline was studied in the brain of the
mouse and the marmoset (Korr, 1976). Serotonin mediated the action of mescaline, DMPEA,
and DOM on plasma prolactin levels of rats (Meltzer et al., 1 978), and produced a four-fold
increase of prolactin in human serum, whereas isomescaline had no effect (Demisch and
Neubauer, 1 979) . Effects on dorsal and median raphe neurons were monitored (Geyer and
Mandell, 1 979). Synaptosomal neurotransmitter uptake was inhibited by several psyche
delics (Whipple et al., 1 983) . DOM, mescaline, and d-amphetamine effects on the rat dorsal
raphe neurons were compared (Penington and Reiffenstein, 1 986a) .
Pharmacology
The action of mescaline, escaline, and ASB was observed on frogs, cats, and dogs (Grace,
1934). DMPEA (100 mg), but not mescaline, caused a 20% rise in arterial blood pressure in
the cat (Geesink and Jager, 1939). Alternative synthesis methods, pharmacological evalua
tion in cats (Benington et al., 1 958a), and studies on oxidative deamination and effects on cat
behavior were presented (Clark et al., 1964). Mescaline effects on spider web building was
compared with effects of psilocybin (Christiansen et al., 1962) . Mescaline produced catalep
sy in mice (Michaux and Yerly, 1 963); intracerebral administration in the cat produced cata
tonia (Michaux and Cession-Fossion, 1 964), and generated a hypokinetic rigid syndrome in
cats (Ernst, 1965a) . Rabbits with brain transections at various levels showed electroencepha
lographic arousal when mescaline was administered (Takeo and Himwich, 1 965).
Mescaline, MCPA, and tranylcypromine were compared with LSD effects on motor be
havior in mice (Walters and Cooper, 1 968) . Continuous intrastriatal injection of mescaline
in awake, freely moving rats produced motor dysfunction similar to that produced by
cholinergic stimulation (Little and Dill, 1 969) . Relative effectiveness of several psychedel
ics was compared in disrupting maze performance by rats (Uyeno and Mitoma, 1 969), and
on action on single midbrain raphe neurons (Aghajanian et al., 1 970) . The pharmacology
of mescaline was evaluated for toxicity, effects on barbiturate sleeping time, and ability
to disrupt mouse behaviors (Ho et al., 1 970a; Schneider and Chenoweth, 1 970) . 2C-D pro
longed phenobarbital sleeping time in mice, while mescaline shortened it (Ho and Huang,
1 970) . Behavioral and neurochemical effects of psychedelics were evaluated in neonate
chicks (Wallach et al., 1 972a). Mescaline was compared to MCPA in rat hyperactivity assays
(Cooper and Walters, 1 972) . Mescaline, LSD, and amphetamine were used as rat behavior
disruption standards for studies of several psychedelic drugs (Buxton, 1 972).
Mescaline, DMPEA, MDPEA, TMA, MDA, OMA, BOB, and MOMA were compared phar
macologically in five animal species (Hardman et al., 1 973) Mescaline, DOM, DOET, and
DOIP induced a dose-dependent scratching response in mice, in increasing potency; DOTB
was inactive (Kulkarni, 1973) . Studies were made of mescaline injection into the rat optic
nerve and the cat sciatic nerve (Paulson and McClure, 1 973) . DOM behavioral effects were
compared with those of mescaline and methamphetamine in rats and mice (Yamamoto
and Ueki, 1975) . Mescaline had measurable effects on learning rate and dopamine me
tabolism in goldfish, Carassius auratus (Zeller et al., 1 976), and on operant behavior in the
pigeon (Hadorn et al., 1 976) .
Several psychedelic drugs were compared i n effects o n cat behavior (Jacobs e t al., 1 977) .
Mescaline and several other psychedelics depressed the response rate of rats trained to

Mescaline
respond to food presentation schedules (Harris et al., 1 978) . Effects were observed on inte
grated sensory functions, and active startle in male rats (Geyer et al., 1 978) . Acute toxicol
ogy and gross behavioral effects were observed in rodents, dogs, and monkeys (Davis et
al., 1 978). Mescaline had effects on investigatory behaviors of the rat (Geyer et al., 1 979),
and inhibited food intake in the dog in a dose-dependent manner, but not to the degree of
d-amphetamine (Vaupel et al., 1 979) . Behavioral effects of intracerebroventricular admin
istration of LSD, DOM, mescaline, or the non-psychedelic LSD analogue lisuride, were
compared (Mokler and Rech, 1 984) . Chronic administration of mescaline altered dynamic
operant conditioned behavioral responses in the rat (Fundaro et al., 1 986), and several psy
chedelic drugs elicited myoclonic jumping behavior in the guinea pig (Carvey et al., 1989).
Relationships between serotonin level and sexual behavior were explored in the rat (Everitt
and Fuxe, 1 977) . A role of central serotonergic mechanisms was proposed to explain head
twitch and backward locomotion induced by psychedelics (Yamamoto and Ueki, 1 981 ) .
Mescaline elicited behavioral effects i n cats b y action a t both serotonin and dopamine re
ceptors (Trulson et al., 1 983); activity of serotonin-containing neurons in the nucleus cen
tralis superior and nucleus raphe pallidus were studied in freely moving cats (Trulson et
al., 1 984) . 5-HT2 receptors were shown to mediate acute behavioral effects of mescaline and
other psychedelics in rats (Wing et al., 1 990) .
In a series of mono-, di-, tri- tetra- and penta-methoxylated phenethylamines tested on rats
trained with various avoidance programs, only PPEA, TPEA, and mescaline showed activ
ity; potency increased with the degree of ring substitution (Smythies et al., 1 967a). Tests
with rats trained to discriminate either mescaline or isomescaline from saline did not sup
port the hypothesis that the psychedelic (mescaline), and non-psychedelic (IM) could be
discriminated by these animals, shedding some doubt on the utility of the discrimination
paradigm (Winter, 1 973) . However, supporting the paradigm, 3,4-dimethoxyphenethyl
amine did not generalize to the responses of rats trained with mescaline as a discriminative
stimulus (Winter, 1 974) . Mescaline was evaluated in rats that had been trained to respond
to stimulation produced by d-amphetamine (Huang and Ho, 1 974a) . In rats trained to dis
tinguish mescaline from saline, following intraventricular administration neither the N
methyl nor the N,N-dimethyl homologue (M-M, trichocereine) evoked activity (Browne
et al., 1 974) . DOM, DOET, cocaine, and amphetamine responses were compared in rats
trained to discriminate mescaline from saline (Winter, 1 975) .
Mescaline and DMPEA were compared a s facilitators and disruptors o f shock avoidance in
trained rats (Gorelick and Bridger, 1977) . Several phenethylamines and tryptamines were
evaluated by molecular connectivity analysis, and compared in discriminative stimulus
studies with rats (Kier and Glennon, 1 978b). Mescaline activity was evaluated in rats
trained to distinguish DOM from saline (Silverman and Ho, 1 978); similarly trained ani
mals reacted positively to DOET and mescaline (Silverman and Ho, 1980). About a doz
en psychedelics were compared to stimulants, in rats trained in a conditioned avoidance
study (Davis and Hatoum, 1987) . Rats trained to discriminate between MBDB and saline
substituted MDA, MOMA, MDAI, and MDMAI completely, but not mescaline, DOM or
LSD. The term "entactogen" was proposed for those compounds that substituted com
pletely (Oberlender and Nichols, 1 990). Me0-2C-SF and Me0-2C-IFLY were compared
with mescaline and escaline in several tests including a two-lever discrimination assay in
rats trained to distinguish LSD from saline (Monte et p.l., 1997) .

Mescaline
In addition to the known psychological effects, mescaline produced vasodilation of the face
and mydriasis (Chaumerliac, 1 948) . In humans, tolerance to mescaline was rapidly built
up, and there was cross-tolerance observed with LSD exposure (Balestrieri and Fontanari,
1 959). Human subjects treated chronically with mescaline became tolerant to both the sub
jective effects and physical changes (mydriasis, blood pressure), and were cross-tolerant to
LSD (Wolbach et al., 1962) . Subjects were tested for their ability to distinguish colors and
size of objects under the influence of mescaline (Hartman and Hollister, 1963). In human
subjects, DMPEA showed no psychoactivity at doses that were active for mescaline; this
was ascribed to its relatively complete conversion to an acid by oxidative deamination
(Hollister and Friedhoff, 1966) . LSD and mescaline were shown to be cross-tolerant in both
the rat and humans (Appel and Freedman, 1968) . TMPEA-2 potentiated mescaline effects
in a self-experiment, but was not psychoactive itself (Dittrich, 1 971 ) . All possible ethyl
homologues and all of their possible monothio analogues were synthesized and pharma
cologically evaluated in humans (Jacob and Shulgin, 1984) .

correlations were made between psychedelic potency and electronic configuration (Snyder
and Merril 1965), mouse behavioral responses (Corne and Pickering, 1 967), changes in
substitution patterns (Shulgin et al., 1969), and the combined use of partition coefficients,
steric bulk, and in vitro activity (Nichols et al., 1977) . Using molecular connectivity analysis
of ten psychedelic phenethylamines, the importance of the 2,5-positions of the methoxy
groups, and the 4-substituent was demonstrated (Glennon et al., 1 979a) . A comparison
of steric properties with animal and human potency of several phenethylamines, trypt
amines, and lysergamide derivatives was made (Nichols, 1 986a) .
Blood, liver, and urine levels were determined by TLC and GC in the fatality of an indi
vidual under the influence of mescaline. Blood level was 9.7 µg / ml, urine was 1 . 16 mg /
ml, liver was 70.8 µg / g, and bile was 2.9 µ g / ml; 167 mg (total) were estimated remaining
as gastric contents (Reynolds and Jindrich, 1985) .
Right hemisphere involvement in a mescaline-induced psychosis was described (Oepen et

al., 1989). The mescaline-induced "psychotic" state in normal human volunteers could be
used as a tool in psychiatric research (Hermie et al., 1992) . Long-term use of peyote by the
Navajo was evaluated from a psychiatric perspective (Bergman, 1 971; see also Wadsworth,
1 972) . Later, long-term peyote use by members of the Navajo Native American Church was
not associated with negative psychological or cognitive effects, in a study that compared
peyote users with non-substance using controls, and alcoholics (Halpern et al., 2005).
Deception took place in street sales in New York and other East Coast cities, with DOM
being sold as mescaline, at doses of approximately 4 mg (Cheek et al., 1 970) .
Mescaline was orally active in humans at about 400 mg (Lemaire et al., 1 985), and at 200-
400 mg; duration 10-12 hours (Shulgin and Shulgin, 1991).
Legal Status
Mescaline is a Schedule I hallucinogen under federal drug law, and under District of Co
lumbia and all state laws. However, special consideration has been given in federal law,
and in several states, to practicing members of the Native American Church (N.A.C.), and

Mescaline
others, allowing them to possess and consume peyote for spiritual purposes. The exemp
tion in the Controlled Substances act states (adapted with permission, from The Entheogen
Law Reporter, Richard Glen Boire, Esq.):
"The Federal Exemption (2 1 cfr 1307.31 (1 993)) The listing of peyote as a con trolled
substance in Schedule I does not apply to the nondrug use of peyote in bona fide religious
ceremonies of the Native American Church, and members of the Native American Church
so using peyote are exempt from registration. Any person who manufactures peyote for
or distributes to the Native American Church, however, is required to obtain registration
annually and to comply with all other requirements of the law. "
Most states follow the federal guidelines laid out by the Uniform Controlled Substances
Act of 1990 for a religious exemption, but a few states with noticeable N.A.C. activity felt
it was necessary to specifically outline requirements for the use of peyote. Perhaps this is
because this act does not contain an express exemption for the religious use of peyote or
any other controlled substance. The drafters of the Uniform Act only included a "com
ment" admonishing:
"Although peyote is listed as a Schedule I controlled substance in the act and under
Schedule I of the federal act, a separate federal regulation (2 1 cfr 1 307.31 (April 1, 1 989))
exempts the nondrug use of peyote in bona fide religious ceremonies of the Native Ameri
can Church. In light of Employment Division v. Smith 494 U. S. 872, 1 08 L. Ed.2d 876,
1 1 0 S.Ct 1 595 (1 990), states should consider including in Schedule I an exemption simil
iar to that found in 21 cfr 1 307.31 (Uniform Controlled Substances Act (1 990) (U.L.A.)
sec, 204 "commen t "). "
As laws evolved and court cases further shifted peyote's legal position, the prospects
for non-Native American peyote based organizations arose. In Arizona, The Peyote Way
Church can operate because the exemption from prosecution is based on religious sincerity,
not on race, denomination, or physical boundaries. Oregon has a similar statute with the
stipulation of that it is specifically not applicable to the residents of correctional facilities.
Four other states have slightly more stringent requirements. Peyotists in Nevada, New
Mexico, Colorado, and Minnesota must be members of a bona fide religious organization,
for example, the N.A.C. or the American Indian Church (Minnesota) . Some states' statutes
could legally permit a non-Native American to attend a peyote meeting if it was run by the
N.A.C. Others require actual N.A.C. membership, some, even of Native Americans. Texas,
the native habitat of the peyote cactus, has the strictest requirements for exemption from
prosecution. Texas exceeds the federal guidelines by requiring that a person be not only a
member of the N.A.C., but also be of at least 25% Native American descent.
Peyote's religious exemptions do not insure freedom from prosecution, as the burden of
proof still rests with the defendant. Evidence of a spiritual practice is often called for in a
court of law. The table below summarizes the specific exemptions known to exist in state
laws, as of 2006. States not appearing below had no explicit legislative exemption concern
ing peyote possession or consumption for spiritual use.

Mescaline / METHCATH
With a Native
Sincere Within NAC On Incarcerated
bonafide American
religious NAC membership reservation persons
religious descent
intent ceremony required only not exempt
State organization required
AZ •
co •
ID • • •
IA •
�.
KS • • •
MN •
NV •
NM •
OK •
OR •
SD •
TX • •
•
WI
1
WY •
1 In Wisconsin, state law declares both peyote and mescaline legal for use within Native American
Church ceremonies.
# 92. METHCATH
2-(Methylamino)-1-phenylpropan-1-one
Methcathinone
2-Methy laminopropiophenone
�-Ketomethamphetamine
CAT
Ephedrone
Jeff
Rakefet
AL-422 (racemate)
AL-463 (d-isomer)
AL-464 (Z-isomer)
UR 1431
Registry Numbers
CAS # CAS #
HCl salt [49656-78-2] Picrate [860409-50-3]
Mandelate [107778-20-1 ] Freebase (racemic) [5650-44-2]
Mercaptosuccinate [92502-36-8] R-Isomer HCl salt [152610-69-0]

METHCATH
CAS # DEA#
S-Isomer HCl salt [66514-93-0]
S-Isomer freebase [112117-24-5]
S-Isomer aspartate [871228-33-0] 1237
S-Isomer benzoate [871228-34-1 ] 1237
S-Isomer (R,R)-diacetyl tartrate [869277-04-3]
S-Isomer (R,R)-dibenzoyl tartrate [869277-00-9]
S-Isomer lactate [871228-35-2] 1237
S-Isomer phthalate [871228-31-8] 1237
S-Isomer (R,R)-tartrate [ 625454-70-8]
R-C[3HkMethcath (N-Me tritiated) [21 7635-05-7]
f)-[ 14 C]-Methcath HCl salt [58623-25-9]

From propiophenone (with Br2, HOAc) to 2-bromo-1 -phenylpropan-1 -one; (with methyl
amine) to 2-(methylamino)-1 -phenylpropan-l -one (Hyde et al., 1 928) .
From (-)-norephedrine (phenylpropanolamine)(with chromic acid) to methcathinone


m / z: 163.0997 (100.0% ), 164.1031 (10.8% )
HCl salt m.p. 176-177 °C (Hyde et al., 1928)
The oxidation of lR,25-ephedrine and 1 5,25-pseudoephedrine yields 5-methcathinone

and the oxidation of the 1 5,2R- and 1R,2R-isomers yields R-methcathinone with mainte
nance of optical integrity (DeRuiter et al., 1 994) .
Synthesis, stereochemical analysis and analytical properties of methcathinone were de

scribed (Zhingel et al., 1991), and synthesis of the optical isomers was described (Dal Cason
et al., 1 997b). Chiral separation of methcathinone enantiomers isolated from clandestine
tablets and urine was achieved with capillary electrophoresis (Liau et al., 2003).

-- -- Me Me METHCATH (this entry)
Cl -- Me t-Bu Bupropion [34911-55-2] (1-3)
Br -- Me Me 3-BMAP [ 486459-02-3] (4)
TFM -- Me Me2 3-TFMDMAP [74626-42-9] (5)
-- F Me Me 4-F-MCAT [447-40-5] (6,7)
-- Br Me Me 4-BMAP [ 486459-03-4] (4)
-
-- Me Me Me 4-Me-MCAT - (8)
-- Me Me -CCCC- MPPP [28117-80-8] (9-12)
-- Me Bu -CCCC- MPHP [34138-58-4] (13)

METHCATH

-
- MeO Me -CCCC- MeOPPP [478243-09-3] (12,14-16)
HO MeO Me Me MHMC [91819-04-4] (17,18)
MeO HO Me Me HMMC [9161 77-15-6] (18)
*All of these homologues and analogues have a carbonyl group on the benzylic (f)) carbon atom.
(1) Human metabolites were identified by mass spectral fragmentation (Pokrafac et al., 1991).
(2) Unusual decomposition occurred with GC analysis on KOH coated columns (Beckett and Stano-
jcic, 1983) .
(3) Also known as Amfebutamone.
(4) Synthesis and behavioral testing in rats as potential antidepressants (Foley and Cozzi, 2003).
(5) The anorexigenic activity was determined in rats and the spontaneous motor activity in mice
(Sanchez et al., 1979).
(6) Synthesis (Kraft and Dengel, 1952) .
(7) Characterization by GC / MS and [ 1 3 C] NMR, in seizures of "plant feeders," suspected as being
used as recreational drugs (Archer, 2009).
(8) Not in the published scientific literature as of late 2009 (though press reports exist from the U.K.,
referring to this compound as mephedrone; scientific reports are anticipated) . Active in humans
at 120-160 mg i.m., and orally active at about 200 mg (Igor, 2006) .
(9) Metabolism and toxicology (Springer et al., 2002).
(10) Metabolism and toxicology (Springer et al., 2003c).
(11) Oxidative enzyme identification (Springer et al., 2003c).
(12) MPPP, MeOPPP, and MDPPP appeared in the German street drug market , now scheduled in the
German Controlled Substances Act (Roesner et al., 1999; Springer et al., 2002).
(13) MPHP is metabolized in the rat by oxidation of the 4-methyl group to a carboxylic acid group,
hydroxylation of the side chain, reduction of the carbonyl group, or conversion of the pyrrolidi
nyl ring to a lactam (Springer et al., 2003e).
(14) Metabolism and toxicology (Springer et al., 2003b).
(15) Oxidative enzyme identification (Springer et al., 2003b).
(16) A note of caution: the literature uses MOPPP for this drug. The MeOPPP term is more descriptive
but must not be confused with MeOPP. Several N-substituted homologues and analogues of
methylone are reported in the initial patent.
(17) Utilized in analysis of the configuration of a-methyldopamine (Beckett et al., 1965).
(18) A metabolite of methylone in humans (Kamata et al., 2006).
Biochemistry
S-(-)-Methcathinone is a very potent CNS stimulant, which appears to produce its effect, at
least in part, via a dopaminergic mechanism (Young and Glennon, 1998). Methcathinone is
a substrate for the serotonin uptake transporter (Cozzi and Foley, 2003).
Pharmacology
A correlation between structure and the locomotor activity of mice has been made (van
der Schoot et al., 1962) . In rats trained to discriminate amphetamine from saline, meth
cathinone generalizes to amphetamine, and is more potent than cathinone (Glennon et
al., 1 987b). Enantiomeric potency of (S)-(-)-methcathinone is twice that of (S)-(+)-amphet
amine and up to five times more potent then (R)-(+)-methcathinone (Glennon et al., 1 995);
neurotoxicity and neurochemical effects of methcathinone were shown to be mediated by
dopamine (Gygi, 1996) . Neurotoxic and pharmacologic properties of the (R)-(+) and (S)-(-)
enantiomers of methcathinone were described, noting presence in the street drug market,
primarily in the (S)-(-) form (Sparago et al., 1996) .
Multiple doses of 30 mg / kg methcathinone caused dramatic decreases in neurochemical

parameters associated with both dopaminergic and serotonergic systems in the striatum;

METHCATH / Methylone
corresponding decreases also occurred in serotonergic parameters in hippocampus and

frontal cortex of the rat (Gygi et al., 1996) .
Methcathinone first reported as a street drug in Russia (Emerson and Cisek, 1993). The
symptomatology of four hospitalized overdose cases discussed in detail (Emerson and
Cisek, 1 993).
A wide range of doses of this compound have been reported, and tolerant users may con
sume many hundreds of milligrams in 24 hour periods, like the patterns encountered for
amphetamines (Zingel et al., 1991). Stimulant effects with strong euphoria in humans at
50-100 mg (Cozzi, 201 0).
Legal Status
Methcathinone is a Schedule I stimulant under federal drug law (FR, 1993b), and under all
state laws except for Alabama, Alaska, California, Maryland, Massachusetts, New Jersey,
New Mexico, Rhode Island, South Carolina, Vermont, and Washington.
# 93. Methylone
1-(Benzo[ d] [l,3]dioxol-5-yl)-2-(methylamino )propan-1-one
2-Methylamino-1-(3,4-methylenedioxyphenyl)propan-1 -one
1 -(1,3-Benzodioxol-5-yl)-2-(methylamino)-l -propanone
B-Keto-N-methyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxymethcathinone
0
EASE
EMM (street name)*
Explosion (street name in the Netherlands)
Bk-MOMA
MDMC
MDMCAT
MeONE
*The code EMM properly applies to the compound 4,5-dimethoxy-2-ethoxyamphetamine, see #118.
Registry Numbers
CAS # CAS # CAS #
HCl salt [1 86028-80-8] Freebase [1 86028-79-5] 5-Isomer freebase [191916-41-3]

From methylenedioxybenzene (with propionic anhydride) to 3,4-methylenedioxypropio
phenone; (with CuBr2) to 2-bromo-3',4' -methylenedioxy-propiophenone; (with MeNH2) to
methylone (Jacob and Shulgin, 1996).
Another synthesis also starts from the 2-bromopropiophenone but the exact route in the
CAS abstract is unclear (Iwao et al., 1954).

m I z : 207.0895 (100.03 ), 208.0929 (11.9%)
HCl salt m.p. 225-227 °C (Iwao et al., 1954) (MeOH / EtOH) (dee.)
Freebase b.p. 140-145 °C / 0. 1 mm (Jacob and Shulgin, 1996)

Methylone
sembled and used to identify street samples (Nakashima et al., 2005). Further syntheses
described, and analytical data on MBDB and its analogues presented (Sanuki et al., 2006).

Me -- ONE [80535-73-5] (1,2)
Me Me Methyl one (this entry)
Me Me2 DMONE [191916-43-5] (3,4)
Me Et EtONE [191916-42-4] (1,2)
Me Et2 DEONE [191916-44-6) (3)
Me Pr PrONE [201474-93-3) (5)
Me iPr iPrONE [186028-81-9] (6)
Me cPr cPrONE [186028-87-5] (6)
Me Ally! ALONE [ 1 86028-85-3) (6)
Me propargyl PRONE [ 186028-86-4) (6)
Me Bu Bu ONE -- (11)
Me iBu iBuONE [ 1 86028-82-0 l (6)
Me sBu sBuONE [1 86028-83-1 ] (6)
Me tBu tBuONE [1 86028-84-2] (6)
Me -CCCC- MDPPP [24698-57-5) (7-9)
Et Me MDMBP [ 1 7762-90-2] (10-12)
Et Me2 MDDMBP [17763-12-1] (10)
Et Et MDEBP [17764-18-0) (10)
Et Et2 MDDEBP [1 7837-90-0) (10)
Et Pr MDPBP [1 7762-91-3] (10)
Et iPr MDIPBP [1 7762-92-4) (10)
Pr Me MDMVP [1 7763-01-8) (10)
Pr Me2 MDDMVP [1 7763-13-2] (10)
Pr Et MDEVP [ 17763-02-9) (10)
Pr Et2 MDDEVP [1 7763-15-4] (10)
Pr Pr MDPVP [1 7764-20-4] (10)
Pr iPr MDIPVP [ 17763-03-0 l (10)
Pr Bu MDBVP [1 7763-10-9] (10)
Pr sBu MDSBVP [ 17763-05-2] (10)
Bu Me2 MDDMHP [1 7763-16-5] (10)
Bu Et2 MDDEHP [1 7763-1 7-6] (10)
*All of these homologues and analogues have a carbonyl group on the benzylic carbon atom and a
3,4-methylendioxy ring.
(1) The resolved optical isomer has been studied (Dal Cason, 1997).

Methylone I MHA
(2) Animal studies were used to compare the S-isomer of several active amphetamine analogues
with their f)-keto counterparts (Dal Cason et al., 1997b).
(3) Synthesis (Dal Cason, 1997).
(4) Synthesis (Iwao et al., 1954) .
(5) The optical isomer has been made (Dal Cason et al., 1997b).
(7) Metabolism and toxicology (Springer et al., 2003a) .
(8) The synthesis of this compound and several alpha homologues were described in patents (Koppe
et al., 1969).
(9) MPPP, MeOPPP, and MDPPP appeared in the German street drug market, and are now sched
uled in the German Controlled Substances Act (Springer et al., 2002).
(10) Synthesis (Koppe et al., 1967).
(11) The N-butyl compound is not in Chemical Abstracts, however a compound called "butylone"
is mentioned in Wikipedia and several Chinese chemical companies; they refer to a CAS # for
MDMBP.
(12) Also known as butyrophenone and MBDB-f)k; Wikipedia and various Chinese chemical compa
nies refer to this CAS #, but they use the name "butylone."
Biochemistry
Methylone and methcathinone were tested for neurotransmitter uptake inhibition in vi
tro (Cozzi et al., 1999) . A reproducible, simple, and small-scale method for detecting the
uptake and release of monoamines (dopamine, serotonin, and norepinephrine) using rat
brain synaptosomes was developed (Nagai et al., 2007) .
Pharmacology
A series of t)-ketoamphetamines and their amphetamine counterparts were compared
pharmacologically in rats trained to distinguish between cathinone and amphetamine (Dal
Cason et al., 1 997b). Direct pharmacological comparisons of methcathinone and methylone
were based on animal neurotransmitter studies (Cozzi et al., 1 999).
In 2004, a compound called "Explosion" appeared in head shops in Amsterdam in tab

lets of 180 mg. Two independent GC / MS analyses showed it to be methylone (Murple,
2005; Bossong et al., 2005). Methylone has appeared in New Zealand as "EASE," a drug in
clinical trials with the action of MOMA (Murple, 2006). Methylone was reported as a com
ponent of street drugs sold in Japan (Nishioka et al., 2007), where a street sample called
methylone actually contained both methylone (120 mg, 60% ) and 5-methoxy-N-methyl
isopropyltryptamine (76 mg, 40% ). Mislabeling and mixtures appeared more frequent in
street sales (Shimizu et al., 2007) .
Legal Status
Methylone is not a scheduled compound under federal drug law, or under District of Co
# 94. MHA
4-(2-Aminopropy1)-2-methoxyphenol
3-Methoxy-4-hydroxyamphetamine
4-Hydroxy-3-methoxy-a-methylphenethylamine
4-Hydroxy-3-methoxyamphetamine
3-0-Methyl-a-methyldopamine
HMA*
NSC-172191

MHA
*This code has been used occasionally in the literature to represent MHA. The accepted pattern is
to apply the aromatic ring substitution alphabetically in the 3,4-order, so HMA is the usual code for
3-hydroxy-4-methoxyamphetamine.
Registry Numbers
CAS # CAS #
HCl salt [13062-61-8] S-Isomer freebase [150200-03-6]
Synthesis
From vanillin (with nitroethane, acetic acid, and ammonium acetate ) to 1 -(4-hydroxy-3-
methoxyphenyl)-2-nitropropene; (with LAH) to MHA (Fennoy, 1 961).

m / z: 181. 1103 (100.0% ), 1 82.1136 (10.9% )
HCl salt m.p. 259-260.5 °c (Glennon et al., 1980b)
MDMA and three urinary metabolites, MDA, MHMA, and MHA, were synthesized and
separated by TLC. They were identified by IR and mass spectral measurements (Tana
ka et al., 1988) . The effectiveness of hair analysis for MDA and its metabolites was deter
mined with pigmented hairy rat experiments (Kikura et al., 1 997) . A quantitative GC / MS
method was described for the optical isomers of MDMA (and its three major metabolites
MDA, MHMA, and MHA) in human plasma and urine, derivatized as the trifluoroacetates
(Pizarro et al., 2002b, 2003). The S-isomer of MDMA, and the main metabolites S-MHMA
2002a). Sensitive GC I MS methods were described for simultaneous measurement of MDE,

and S-DHMA were prepared and analyzed by capillary electrophoresis (Pizarro et al.,
MDMA, and metabolites MHA, MDA, and MHMA in human urine (Pirnay et al., 2006).

N- Name CAS # Ref
H MHA (this entry)
Me MHMA [117652-28-5] (1-10)
Et MHEA [69389-97-5] (11-20)
(1) Synthesis (Lim and Foltz, 1988).
(2) OHMA and MHMA shown by GC / MS to be metabolites of MOMA in humans (Maurer, 1996).
(3) MHMA and MHA are shown to be metabolites of MOMA in humans (de Boer et al., 1997).
(4) Three reported phenolic human urinary metabolites (MHMA, MHA, and OHA) and a new one,
OHMA, were excreted mainly as the glucuronides (Helmlin et al., 1996).
(5) Quantitative GC / MS analysis of the optical isomers of MOMA (and its three major metabolites
MOA, MHMA, and MHA) in human plasma and urine, derivatized as the trifluoroacetates
(Pizarro et al. 2002b, 2003).
(6) In the metabolism of MOMA in humans, to give MOA, OHMA, and MHMA; the S-isomer is
more rapidly consumed (Pizarro et al., 2004).
(7) The effects of MOMA and three of its metabolites (MHMA, OHA, and OHMA) on hormone
release from the isolated rat hypothalamus were measured (Forsling et al., 2002).
(8) Found with several other drugs in the urine of Ecstasy users at raves (Zhao et al., 2001).
(9) Sensitive GC / MS method for simultaneous measurement of MOE, MOMA, and metabolites
MHA, MOA, and MHMA in human urine (Pirnay et al., 2006).

MHA
(10) This code is occasionally found in the literature, as HMMA. The usual convention is to use the
initial of the 3-position, then the 4-position. HMMA is, thus, 3-hydroxy-4-methoxymethamphet
amine (see #33).
(11) Note that some authors use an alternative code (HME) for MHEA; this conflicts with another
code used in this book (for f),3-dihydroxy-4-methoxyphenethylamine, see #49).
(12) Impact of N-alkyl chain length on metabolic fate of the aromatic ring (Coutts et al., 1978).
(13) Toxicological detection of MDE and metabolites by GC / MS and fluorescence polarization
immunoassay (Ensslin et al., 1996a).
(14) HPTLC with UV I FTIR combined detection for MDE and its metabolites (Kovar and Pisternick,
1996).
(15) Metabolic and toxicological analysis of the fate of methylenedioxyalkylamine drugs by GC / MS
(Maurer, 1996).
(16) Comparison of HPTLC and HPLC for analysis of MDE and metabolites in urine (Pisternick et
al., 1997) .
(17) Quantitation of MDE and metabolites by HPLC with fluorescence detection (Brunnenberg et al.
1998).
(18) Tentatively identified (by GC / MS) as a urinary metabolite following oral adminstration of
racemic ethylamphetamine to the rat (Matsushima et al. 1998).
(19) Quantitation of drug metabolites from plasma and urine with automated solid-phase extraction,
and HPLC with electrochemical detection (Kramer and Kovar, 1999).
(20) Chiral syntheses of MDE and its metabolites (Buchler et al., 2000).
Biochemistry
MHA effectiveness in releasing cardiac norepinephrine was measured (Daly et al., 1 966); it
was shown to be a serotonin receptor agonist (Glennon et al., 1980b).
In hypertensive and normal human subjects, MHA and DHA were found as urinary me
tabolites of [ 1 4 C]-labeled L-a-methyl-DOPA (Au et al., 1972) . Dogs and monkeys metabo
lized MDA to MHA, and excreted it, in part, as the j3-glucuronide or sulfate conjugate
(Midha et al., 1977). Later, DHA, MHA and 3,4-dihydroxyphenylacetone were found, and
3,4-methylenedioxybenzoate was present as a conjugate, in the same animals (Midha et al.,
1978) . MHA was also shown to be the primary metabolite of OMA (Midha et al., 1979b),
of MDA in the rat (Schweitzer et al., 1978), a urinary metabolite of MDA and PMA in the
dog and monkey (Hubbard et al., 1 981), and of 3-MA in the dog, monkey, and in humans
(Midha et al., 1981 ) . Following i.p. injection of [ 3H]-labeled MDA to rats, unchanged MDA
was the major component in brain and liver, but after 24 hours, DHA and MHA were the
remaining major metabolites (Marquardt et al., 1978c) . MHA was reported as a urinary me
tabolite of MOMA in the rat (Yousif et al., 1990) . MHA and MHMA are urinary metabolites
of PMMA in the rat (Staack et al., 2003a) .
MHA and MHMA are primary metabolites of MOMA in the rat and mouse, and are ex
creted (>85% ) as the glucuronide and sulfate conjugates (Lim et al., 1992). They are also
metabolites of MOMA in humans (Lim and Foltz, 1989; de Boer et al., 1997) . MHA and
DHA (as well as the ketones piperonylacetone, 3-methoxy-4-hydroxyphenylacetone and
3,4-dihydroxyphenylacetone) are trace metabolites of MOE in humans, and are detectable
for a few hours after ingestion (Ensslin et al., 1996a,b). They were shown by GC / MS to be
metabolites of MDA in humans (Maurer, 1996); the three reported phenolic human urinary
metabolites (MHMA, MHA, and DHA) and a new one, DHMA, were excreted mainly as
the glucuronides. The peak plasma levels of MOMA (331 ng / ml) and of MDA (15 ng / ml)
were at two hours and six hours, respectively. Urine levels of MOMA peaked at 28 µg / ml
at 22 hours; MDA (to 2.3 µg / ml), HMMA (to 35. 1 µg / ml), and HMA (to 2.1 µg / ml) were
measured between 16 and 22 hours (Helmlin et al., 1996).

MHA / M-M
The effects on rats injected s.c. with 1 0 mg / kg of MHA on serotonin and 5-HIAA levels
were observed and recorded (Yeh and Hsu, 1 991 ) . MHA and DHA, the major metabolites
of MDA, did not produce serotonin depletion when injected into the brains of rats (Mc
Cann and Ricaurte, 1991a).
Pharmacology
MHA was found with several other drugs in the urine of Ecstasy users at raves (Zhao et al.,
2001 ).
Human activity of MHA is unknown.
Legal Status
MHA is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
��,
# 95. M-M
N-Methyl-2-(3,4,5-trimethoxyphenyl)ethanamine
�-------�
N-Methylmescaline
N-Methyl-3,4,5-trimethoxyphenethylamine
H 3 co
I
CH3
Registry Numbers
CAS # CAS #
H 3 co �
OCH3
Natural Sources
Identified in Lophophora williamsii (Spath and Bruck, 1 937; Lundstrom and Agurell, 1968a) .
Reported to be a natural alkaloid in the North American cacti Pelecyphora aselliformis (Neal
et al., 1972), in the South American cactus genus Gymnocalycium (Starha, 1 996), and in
Turbinicarpus species (Starha et al., 1999) .
Present in the stem (and to a lesser extent, the root) of Alhagi pseudalhagi (Ghosal and
Srivastava, 1973b) . Reported to be present in Acacia berlandieri (Clement et al., 1997) and A.
rigidula (Clement et al., 1998).

From mescaline (with benzaldehyde) to the benzylidine derivative; (with methyl iodide)
to the methyl quaternary salt; (with dilute acid) to M-M (Spath and Bruck, 1 937) .

acetophenone; (with methylamine) to N-methyl-3,4,5-trimethoxyphenylacetamide; (with
LAH) to M-M (Banholzer et al., 1 952) .
From mescaline (with ethyl chloroformate) to ethyl N-[f)-(3,4,5-trimethoxyphenyl)]ethyl

carbamate; (with LAH) to N-Methyl-3,4,5-trimethoxyphenethylamine (Lee et al., 1 969).
From mescaline (with ethyl formate) to N-formylmescaline; (with LAH) to N-methyl

mescaline (Shulgin and Shulgin, 1 991 ) .

m / z: 225.1365 (100.0% ), 226.1398 (13.0% )

M-M I 3,4-MMA
HCl salt m.p. 201-202 °C (Spath and Bruck, 1937)

Picrate m.p. 1 77.5-178 °C (Spath and Bruck, 1937)
Picrate m.p. 1 78 °C (Banholzer et al., 1952)
Trinitro-m-cresolate m.p. 1 89.5-190.5 °C (Spath and Bruck, 1937)
Biochemistry
Effects observed on alkaline phosphatase activity and pyruvate utilization in rat brain ho
mogenates (Clark et al., 1956). Serotonin receptor affinity was determined (Glennon et al.,
1 980a) .
Pharmacology
In rats trained to distinguish mescaline from saline, following intraventricular administra
tion neither the N-methyl nor the N,N-dimethyl homologue (M-M, trichocereine) evoked
activity (Browne et al., 1 974).
M-M was not orally active in humans at 25 mg (Shulgin and Shulgin, 1991).
Legal Status
M-M is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
# 96. 3,4-MMA
1 -(3-Methoxy-4-methylphenyl)propan-2-amine
3-Methoxy-4-methylamphetamine
Registry Numbers
CAS #
HCl salt [25068-95-5]
Freebase [24160-29-0] CAS #
R-Isomer HCl salt [133097-26-4] R-Isomer freebase [133097-29-7]
S-Isomer HCl salt [133097-27-5] S-Isomer freebase [133097-28-6]

From 3-methoxy-4-methylphenylacetonitrile (with ethyl acetate, acid) to 3-methoxy-4-
methylphenylacetone; (with ammonium salt, base hydrolysis) to 3,4-MMA (Valenta and
Protiva, 1977).
From 3-methoxy-4-methylbenzaldehyde (with nitroethane, acetic acid, and ammonium

acetate) to 1-(3-methoxy-4-methylphenyl)-2-nitropropene; (with LAH) to MMA (Aldous et
al., 1974; Johnson et al., 1991b) .

m/ z: 1 79.1310 (100.0%), 1 80.134 4(11 .9% )
HCl salt m.p. 159-160 °C (Aldous et al., 1974) (acetone)

HCl salt m.p. 1 82-1 83 °C (Ho et al., 1970a) ( MeOH / Etp)
HCl salt m.p. 181 °C (Johnson et al., 1991b) (EtOH / Etp)
HCl salt m.p. 181 .5-183.5 °C (Valenta and Protiva, 1977)
R-(-)-Isomer HCl salt m.p. 163 °C [aJ ;'j1 -23.42° (Johnson et al., 1991b) (EtOH / Etp)
5-( +)-Isomer HCl salt m.p. 163 °C [aJ ;'j1 +23.30° (Johnson et al., 1991b) (EtOH / Etp)

3,4-MMA / MMDA

3- 4- 6- a- Other Name CAS # Ref
HO Me -- Me - - 3,4-HMeA [ 64829-34-1 ] (1,2)
HO Me -- Et -- HM-a-EPEA [221 73-84-8] (2)
Meo Me -- Me -- 3,4-MMA (this entry)
MeO Me -- Me N-Me N-Me-3,4-MMA -- (3,4)
MeO Me -C- -- MMAI [136468-19-4] (5)
MeO Me -CC- 7,6-MMAT [32828-83-4] (6)
(1) Synthesis from 3,4-MMA (Valenta and Protiva, 1977).
(2) Action on release and inhibition of labeled serotonin in mice (Hwang and Van Woert, 1980).
(4) Not orally active in humans at 1 00 mg (Anon., 2006).
(5) Several psychedelic amphetamines were compared with their 2-aminoindan or their 2-ami
notetralin analogues as serotonin uptake inhibitors, and in rats trained to discriminate between
MDMA and MBDB Oohnson et al., 1991b).
(6) Synthesis and pharmacological screening (Violland et. al., 1971 ).
The optical isomers have also been synthesized and characterized (Johnson et al., 1 99lb).
Biochemistry
Several psychedelic amphetamines were compared with their 2-aminoindan or 2-aminot
etralin analogues (3,4-MMA and MMAI) as serotonin uptake inhibitors, and in rats trained
to discriminate between MOMA and MBDB (Johnson et al., 1991a, 1991b).
Pharmacology
A correlation was made between structure and the locomotor activity of mice (van der
Schoot et al., 1962). The 2-0-desmethyl and 5-0-desmethyl analogues of DOM (2,4-MMA
and 3,4-MMA) were pharmacologically compared to DOM (Eckler et al., 2003). A correla
tion was made between the degree of native fluorescence and psychedelic potency of the
methoxy derivatives in humans (Antun et al., 1971 ) .
MMA appeared i n the Italian street drug market i n capsules containing 1 4 0 m g o f white
powder, although the orally active dose of 3,4-MMDA is said to be 40-60 mg (de Zorzi and
Cavalli, 1974).
Orally active in humans at 40-60 mg; duration "long, and potentially quite dysphoric"
Legal Status
3,4-MMA is not a scheduled compound under federal drug law, or under District of Co
# 97. MMDA
1-(7-Methoxybenzo[d] [ l,3]dioxol-5-yl)propan-2-amine
3-Methoxy-4,5-methylenedioxyamphetamine
4-Methoxy-a-methyl-1,3-benzodioxole-6-ethanamine

MMDA
Registry Numbers
CAS # CAS # DEA
HCI salt [60676-84-8] Freebase [13674-05-0] 7401
Acid salt [62319-20-4] R-Isomer freebase [67225-70-1]

From 3-methoxy-4,5-methylenedioxyallylbenzene (myristicin, from oil of nutmeg) (with
KOH) to 3-methoxy-4,5-methylenedioxypropenylbenzene (isomyristicin); (with tetrani
tromethane) to l-(3-methoxy-4,5-methylenedioxyphenyl)-2-nitropropene; (with LAH) to
MMDA (Shulgin, 1964b).
From protocatechualdehyde (3,4-dihydroxybenzaldehyde) (with bromine) to 3-bromo-

4,5-dihydroxybenzaldehyde; (with CH212) to 3-bromo-4,5-methylenedioxybenzaldehyde;
(with cyclohexylamine) to 3-bromo-4,5-methylenedioxybenzilidine-N-cyclohexylamine;
(with BuLi, HCl) to 3-hydroxy-4,5-methylenedioxybenzaldehyde; (with methyliodide)
to 3-methoxy-4,5-methylenedioxybenzaldehyde (myristicinaldehyde); (with nitroethane,
acetic acid, and ammonium acetate) to 1-(3-methoxy-4,5-methylenedioxyphenyl)-2-nitro
propene; (with LAH) to MMDA (Shulgin and Shulgin, 1991).

m / z: 209.1052 (100.0% ), 210.1085 (12.0% )
HCl salt m.p. 190-191 °c (Shulgin and Shulgin, 1991 )
An HPLC method was developed for the quantification of this compound in urine samples
(Helmlin and Brenneisen, 1992). Synthesis from myristicin and analysis by reversed-phase
HPLC and mass spectrometry was described (Clark et al., 1996b). Synthesis and analysis
by TLC, UV, IR, HPLC, GC / MS, and NMR was reported (Shimamine et al., 1 990). The
effectiveness in hair analysis for MMDA was determined in pigmented hairy rat experi
ments (Kikura et al., 1997) . Levels were determined in biological fluids using chemical
ionization GC / MS (Mariani et al., 1999).
Positional Isomers*
2- 3- 4- 5- 6- N- Name CAS # Ref
-OCO- MeO -- -- -- MMDA-3b [23693-20-1 ] (1-8)
-OCO- -- MeO -- -- MMDA-4 [23693-21-2] (9)
-OCO- -- -- MeO -- MMDA-5 [23693-22-3] (1,10)
MeO -OCO- -- -- -- MMDA-3a [33298-29-2] (11)
- -
-OCO- MeO -- -- MMDA (this entry)
-- -OCO- -- MeO -- MMDA-2 [23693-22-3] (12)
(1) Human potency as affected by changes in substitution patterns (Shulgin et al., 1969).
(2) Threshold oral activity in humans at 80 mg; duration unknown (Shulgin and Shulgin, 1991 ).
(4) Studies were made comparing mouse behavior and the activity of the brain enzymes MAO and
DOPA decarboxylase (De Ropp and Kastl, 1970).
(5) Placed in Schedule I (FR, 1970).

MMDA
(6) Inhibition of serotonin binding to rat brain membranes (De Jong et al., 1982).
(7) Interaction with imidazolium chloride has been studied (Makriyannis et al., 1993).
(8) Calculated energy interactions between several amphetamines and a model compound (3-me-
thylindole) allowed the development of a receptor model for psychedelics (DiPaolo et al., 1978).
(9) MMDA-4 has yet to be synthesized (Shulgin and Shulgin, 1991), but is a Schedule I drug.
(11) See #99.
(12) See #98.

3- 4- I 5- 6- N- Name CAS # Ref
Br -OCCO- -- -- BEDA [ 860003-91 -4] (1)
- --
MeO -OCO- - MMDA (this entry)
MeO -OCO- -- Me MMDMA [172518-52-4] (2)
MeO -OCCO- -- -- MEDA [ 23693-25-6] (3-5)
-
MeO -OCCCO- -- - MPDA [910414-20-9] (6)
(1) Evaluated as a MAO inhibitor (Vallejos et al., 2005).
(2) Synthesis (Clark et al., 1996b).
(3) Synthesis (Shulgin, 1964b; Shulgin and Shulgin, 1991 ).
(6) Found in the Rare Chemicals Catalog, Rare Chemicals GmbH, Schauenburgerstrasse 116, Kiel,
24118, Germany, http: / / www.rarechem.de; otherwise not in the scientific literature.
Biochemistry
Effects on spontaneous brain electrical activity measured in the cat (Fairchild et al., 1967).
Mutagenic activity was not detected in Salmonella typhimurium assays (White et al., 1 977) .
Calculated energy interactions between several amphetamines and a model compound

(3-methylindole) allowed the development of a receptor model for psychedelics (DiPaolo
et al., 1978). Inhibition of serotonin binding to rat brain membranes noted (De Jong et al.,
1 982) . MMDA induced release of serotonin and dopamine from synaptosomes (McKenna
et al., 1991). Interaction with imidazolium chloride was studied (Makriyannis et al., 1993).
Interaction with the liver enzyme CYP2D6, part of the cytochrome P450 mixed-function
oxidase system, was described (Wu et al., 1997). The synthesis and tissue distribution of
radioiodine-labeled psychoactive drugs was evaluated (Ghaffari et al., 1997) .
Pharmacology
Human potency was affected by changes in substitution patterns (Shulgin et al., 1 969). In
the dog, MMDA effects were compared with LSD (Nozaki et al., 1 978). This drug has been
evaluated in extensive QSAR studies (Clare, 1998; Beuerle et al., 1997) .
MMDA is orally active in humans at 120-150 mg; duration moderate; at 250 mg, marked
nystagmus was observed that could produce active vomiting (Shulgin et al., 1973; Shulgin
and Shulgin, 1991).
Legal Status
MMDA is a Schedule I hallucinogen under federal drug law (FR, 1970), and under District
of Columbia and all state laws except for Montana.

MMDA-2
#98. MMDA-2
l -(6-Methoxybenzo[d] [ l,3] dioxol-5-yl)propan-2-amine
6-Methoxy-a-methyl-1,3-benzodioxole-5-ethanamine
Registry Numbers
CAS # CAS# CAS #
HC l salt [ 64778-82-1 ] Freebase [23693-1 8-7] R-lsomer [67225-69-8]

From sesamol (with methyliodide) to 3,4-methylenedioxyanisole; (with POC13 and N
methylformanilide) to 2-methoxy-4,5-methylenedioxybenzaldehyde; (with nitroethane,
acetic acid, and ammonium acetate) to 1 -(2-methoxy-4,5-methylenedioxyphenyl)-2-nitro
propene; (with LAH) to MMDA-2 (Shulgin and Shulgin, 1991).
From sesamol (with allylbromide) to methylenedioxyphenyl allyl ether; (with heat) to 2-al
lyl-4,5-methylenedioxyphenol; (with methyliodide) to 2-methoxy-4,5-methylenedioxyal
lylbenzene; (with KOH) to 2-methoxy-4,5-methylenedioxy-propenylbenzene; (with tetra
nitromethane) to 1-(2-methoxy-4,5-methylenedioxyphenyl)-2-nitropropene; (with LAH) to
MMDA-2 (Shulgin, 1964a) .

m / z: 209.1052 (100.0% ), 210.1085 (12.0%)
HCl salt m.p. 1 87 °C (Shulgin, 1964a)
TLC and color tests were defined for the identification of substituted amphetamines
(O'Brien et al., 1982).

2- a- Other N- Name CAS # Ref
! Sp Me -- -- 2-[18F]-4,5-MDA [153506-1 8-4] (1)
Cl Me -- -- 2-Cl-4,5-MDA [27164-29-0] (2,3)
Cl Me -- Me 2-Cl-4,5-MDMA [319920-71-3] (4,5)
Br Me -- -- 2-Br-4,5-MDA [151920-03-5] (3,6,7)
I -- -- Me2 2-1 -4,5-MDPEA [188852-35-9] (8)
I Me -- -- 2- 1-4,5-MDA [188852-25-7] (8)
I Me -- Me 2-1 -4,5-MDMA [188852-27-9] (8)
I Me -- --- Me2
--· ---
2- 1-4,5-MDDMA [188852-29-1 ] (8)
N02 Me -- Me 2-N02-4,5-MDA [151920-04-6] (3,9)
MeO -- -- -- 2C-2 [13062-96-9] (10)
Meo -- j)-Me -- j)-Me-2C-2 [83329-24-2] (11)
MeO Me -- -- MMDA-2-- (this entry)
--·--------- �--�
MeO Me -- Me N-Me-MMDA-2 [108925-34-4] (12,13)

MMDA-2
2- a- Other N- Name CAS # Ref

MeO Me 4-thio -- 4T-MMDA-2 [133787-69-6] (14)
-
MeO Et -- -- 4C-2 - (15)
(1) [ 1 8F]-labeled material synthesized and its distribution and binding studied in mice and rats. The
unlabeled compound (i.e., with stable [ 1 9F]) not in the scientific literature (Shiue et al., 1993).
(2) Synthesized as a potential psychedelic drug (Hellot et al., 1970a).
(3) MDA, and three analogues with a chloro, bromo, or a nitro group in the 6-position, were experi-
mentally oxidized by differential pulse voltammetry (Squella et al., 1993).
(4) Reported as being present in an MDMA user (Maresova et al., 2005).
(5) Found as a contaminant in MDMA pills (Lewis et al., 2000).
(6) Synthesis described. Orally active in humans at about 400 mg, with an amphetamine-like action
(Sepulveda et al., 1972).
(8) Synthesis, and tissue distribution of radioiodine-labeled psychoactive drugs (Ghaffari et al., 1997).
(10) Effective at releasing cardiac norepinephrine (Daly et al., 1966).
(11) Discriminative stimulus properties of MDA analogues (Glennon et al., 1982c).
(13) Orally active at greater than 70 mg; duration unknown (Shulgin and Shulgin, 1991).
Biochemistry
MMDA-2 inhibited uptake of labeled norepinephrine (Marquardt et al., 1978a) . Using cal
culated energy interactions between several amphetamines and a model compound (3-me
thylindole), a receptor model for psychedelics was developed (DiPaolo et al., 1978). Sero
tonin receptor site affinity was determined (Glennon et al., 1980a). MMDA-2 was shown
to induce release of serotonin and dopamine from synaptosomes (McKenna et al., 1991).
Interactions with imidazolium chloride were studied (Makriyannis et al., 1993), as were
interactions with the liver enzyme CYP2D6, part of the cytochrome P450 mixed-function
oxidase system (Wu et al., 1997) .
Pharmacology
tive phenylisopropylamines (Glennon et al., 1981b) . Positive responses were observed in
rats trained to respond to DOM (Glennon et al., 1982c), and in rats trained with LSD (Nich
ols et al., 1986b). MMDA-2 was assayed in rats trained to discriminate amphetamine from
saline, but did not show a general amphetamine response (Glennon et al., 1 987b). About
a dozen psychedelics were compared to stimulants in rats trained in a conditioned avoid
ance study (Davis and Hatoum, 1987) .
Human potency was affected by changes in substitution patterns (Shulgin et al., 1969).
This drug was included in an extensive QSAR study (Clare, 1998) .
MMDA-2 is orally active in humans at 25-50 mg; duration 8-12 hours (Shulgin and Shul
gin, 1991 ) .
Legal Status
MMDA-2 is a positional isomer of MMDA, and therefore a Schedule I hallucinogen under

MMDA-3a
# 99. MMDA-3a
1-(4-Methoxybenzo[ d] [1,3]dioxol-5-yl)propan-2-amine
4-Methoxy-a-methy1-1,3-benzodioxole-5-ethanamine
Registry Numbers
CAS # CAS #
HCl salt [33298-29-2] R-Isomer [67225-68-7]
Freebase [23693-19-8]

From 2,3-dihydroxyanisole (with CH212) to 3,4-methylenedioxyanisole; (with POC13, N
methylformanilide) to 2-methoxy-3,4-methylenedioxybenzaldehyde and 4-methoxy-
2,3-methylenedioxybenzaldehyde; from 2-methoxy-3,4-methylenedioxybenzaldehyde
(with nitroethane, acetic acid, and ammonium acetate) to 1-(2-methoxy-3,4-
methylenedioxyphenyl)-2-nitropropene; (with LAH) to MMDA-3a (Shulgin, 1 964a) .

m / z: 209.1052 (100.0% ), 210.1085 (12.0% )
HCI salt m.p. 154-155 °C (Shulgin and Shulgin, 1991)
Urine and plasma samples were analyzed as the pentafluorobenzamide derivatives, by GC

with electron capture detection (Midha et al., 1979a). The conformation of the aryl methoxy
groups of several psychedelics has been established by [ 13C]-NMR spectral analysis (Knit
tel and Makriyannis, 1981).

2- 3- I 4- Other Name CAS # Ref
MeO -OCO- -- 2C-3a [2220-19-1 ] (1-4)
MeO -OCO- N-Me N-Me-2C-3a [33543-06-5] (3)
MeO -OCO- a-Me MMDA-3a (this entry)
MeO -OCO- a-Et 4C-3a --
[ 23693-39-2] (5)
MeS -OCO- -- 2T-MMDA-3a -- (6,7)
-OCO- I MeO -- 2C-3b [104958-31-8] (8)
(1) Several phenethylamines and tryptamines were compared with rats trained to discriminate
DOM from saline (Kier and Glennon, 1978b).
(2) Using molecular connectivity analysis of ten psychedelic phenethylamines, the importance of
the 2,5-positions of the methoxy groups and the 4-substituent was demonstrated (Glennon et al.,
1979a).
(3) Synthesis (Dallacker et al., 1971).
(4) The conformation of the aryl methoxy groups of several psychedelics has been established by
[ 1 3C]-NMR spectral analysis (Knittel and Makriyannis, 1981 ).
(5) Human potency was affected by changes in substitution patterns (Shulgin et al., 1969).
(8) Synthesis (Vinogradova et al., 1993).

MMDA-3a / 2-MPEA
Biochemistry
MMDA-3a affected mouse behavior and the activity of the brain enzymes MAO and DOPA
decarboxylase (De Ropp and Kastl, 1970) . Using calculated energy interactions between
several amphetamines and a model compound (3-methylindole), a receptor model for psy
chedelics was developed (DiPaolo et al., 1978) .
Pharmacology
Human potency is affected by changes in substitution patterns (Shulgin et al., 1969). This
drug was included in an extensive QSAR study (Beuerle et al., 1997) .
MMDA-3a is orally active a t 20-80 mg; duration 10-16 hours (Shulgin and Shulgin, 1 99 1 ) .
Legal Status
MMDA-3a is a positional isomer of MMDA, and therefore a Schedule I hallucinogen un
der federal drug law, and in states where isomers are included in the controlled drug
definition.
#100. 2-MPEA
2-(2-Methoxyphenyl)ethanamine
2-Methoxyphenethylamine
o-Methoxyphenethy lamine
Registry Numbers
CAS # CAS #
Bicarbonate [856822-73-6] Freebase [2045-79-6]
Mono-lithium salt [288864-48-2] a,j3-[d2] Isomer [147702-21-4]
Sulfate [64610-28-2]

From 2-methoxybenzaldehyde (with malonic acid) to 2-methoxycinnamic acid; (with Na,
Hg) to 2-methoxypropionic acid; (with NH3 ) to 2-methoxypropionamide; (with NaOCl) to
2-MPEA (Slotta and Heller, 1930; Buck, 1932) .
From 2-methoxybenzaldehyde (with nitromethane) to 2-methoxy-�-nitroethene; (with

electrolytic reduction) to 2-MPEA (Kondo and Tanaka, 1932; Goe�nitzer and Punkenhofer,
2003).
Synthesis via the Schiff bases (Woodruff et al., 1940) .
From 2-nitrophenylethane (with Fe powder, EtOH, NH3Cl) to 2-MPEA (Ran et al., 2000) .

m / z: 151.0997 (100.0%), 152.1031 (9.7% )
HCl salt m.p. 143 °C (Slotta and Heller, 1930)

Sulfate m.p. 230 °C (Slotta and Heller, 1930)

2-MPEA

2- j)- N- Name CAS # Ref
Br -- -- 2-BPEA [69587-09-3] (1)
Cl -- -- 2-Cl-PEA [13078-80-3] (2,3)
NH2 HO -- j)-H0-2-APEA [13078-83-6] (2)
NH2 C=O -- 2-APEA-j)k [13078-85-8] (2)
Me -- -- 2-MePEA [55755-1 8-5] (2,4-6)
--
MeO -- 2-MPEA (this entry)
MeO Me -- j)-Me-2-MPEA [5411-16-5] (7)
MeO Me Me j),N-Me-2-MPEA [5414-92-6] (1)
Meo -- Me N-Me-2-MPEA [ 1 04338-26-3] (8-10)
MeO -- Me2 N,N-Me-2-MPEA [861007-85-4] (11)
EtO -- Me N-Me-2-EPEA [21629-16-3] (9,12)
EtO -- Me2 N,N-Me-2-EPEA [861006-97-5] (12)
(3) Release and inhibition of labeled serotonin in mice (Hwang and Van Woert, 1980).
(4) Studies on the oxidative deamination and effects on cat behavior (Clark et al., 1964)
(6) Synthesis and pharmacological evaluation in the cat (Benington et al., 1 958a) .
(7) Synthesis (Woodruff and Pierson, 1938).
(8) Correlation between structure and the locomotor activity of mice (van der Schoot et al., 1962) .
(10) Synthesis (Buck, 1932; Kondo and Tanaka, 1932).
(11) Synthesis (Buck et al., 1938) .
(12) Synthesis (Ide and Buck, 1937).
UV absorption spectra and apparent acidic dissociation constants for 2-MPEA were report
ed (Kappe and Armstrong, 1965) . Synthesis, UV spectra, TLC and Gas chromatographic
properties, and other physical properties were reported (Ono et al., 1976) . The conforma
tion of the aryl methoxy groups of 2-MPEA was established by [ 13 C]-NMR spectral analy
sis (Knittel and Makriyannis, 1981). [ 13 C]-NMR spectra for methoxylated phenethylamines
and amphetamines were shown to be distinctive and suitable for identification (Bailey and
Legault, 1983). HPLC analysis was demonstrated, employing fluorescamine derivatization
for fluorescence detection (Shimamine, 1984) . Fragmentation patterns of some fifty-five
and Oehme, 2004) .
Biochemistry
Oxidative deamination in rabbit liver was reported (Clark et al., 1965) . Spasmolytic activity
was monitored on isolated rabbit small intestine (Stolyarchuk et al., 1975), and serotonin
receptor site affinity was later determined (Glennon et al., 1 980a) . 2-MPEA inhibited the
release of labeled serotonin in mice (Hwang and Van Woert, 1980) .
Pharmacology
Studies on the oxidative deamination and effects on cat behavior were reported (Clark
et al., 1964) . Effects on cardiac function were observed in the cat and dog (Ellis, 1965).

2-MPEA I 3-MPEA
Relationships between psychedelic activity and electronic configuration were established

(Snyder and Merril, 1965) .
Psychedelic activity for this compound has not been reported in humans.
Legal Status
2-MPEA is not a scheduled compound under federal drug law, or under District of Colum
#101. 3-MPEA
2-(3-Methoxyphenyl)ethanamine
EA-1302 (Edgewood Arsenal)
NSC 124706
Registry Numbers
CAS # CAS # CAS #
HCl salt [2039-54-5] Sulfate salt [64610-29-3] a,a-[d2] [108089-01 -6]
HBr salt [60189-29-9] Acid salt [87059-66-3] a,f3-[d2] [147702-22-5]
Bioxalate [855395-37-8] Freebase [2039-67-0] (C[d3 ]0) 3 [484024-84-2]

From 3-methoxybenzaldehyde (with malonic acid) to 3-methoxycinnamic acid; (with
Na,Hg) to 3-methoxypropionic acid; (with NH) to 3-methoxypropionamide; (with NaO
Cl) to 3-MPEA (Slotta and Heller, 1930; Buck, 1932) .
From 3-methoxybenzylcyanide (with Raney Ni, Hz) to 3-MPEA (Semonsky and Zikan, 1953).
From 3-methoxybenzaldehyde (with Raney Ni, H2 or LAH) to 3-methoxybenzyl alcohol;

(with SOClz) to 3-methoxybenzylchloride; (with NaCN) to 3-methoxybenzyl cyanide;
(with LAH) to 3-MPEA (Jirkovsky and Protiva, 1964) .
From 3-methoxybenzaldehyde (with nitromethane) to 3-methoxyphenyl-�-nitroethene;

(with reduction) to 3-MPEA (Liu and Cui, 2002).
Small scale synthesis for rapid generation of compound libraries, using BH3-THF or Red
Al and brief methanolysis (Dubowchik et al., 2004) .

m / z: 151.0997 (100.0% ), 152. 1031 (9.7% )
HCl salt m.p. 145-146 °C (Semonsky and Zikan, 1953)

Hexachloroplatinate m.p. 204-205 °C (Semonsky and Zikan, 1953) (dee.)
Freebase b.p. 128 °C / 12 mm (Slotta and Heller, 1930)
(Kappe and Armstrong, 1965); as were UV spectra, synthesis, TLC and Gas chromato
graphic properties, and other physical properties (Ono et al., 1976) . Analysis by HPLC
employing fluorescamine derivatization for fluorescence detection was performed (Shi
mamine, 1984) . [ 13 C]-NMR spectra for methoxylated phenethylamines and amphetamines
were shown to be distinctive and suitable for identification (Bailey and Legault, 1983).

3-MPEA

3- j)- N- Other Name CAS # Ref
Cl -- -
- -
- 3-Cl-PEA [ 13078-79-0 l (1)
Me -- -- -- 3-MePEA [5470-40-6] (2--4)
Meo -- -- -- 3-MPEA (this entry)
Meo Me -- -- j)-Me-3-MPEA [5090-33-5] (1,5)
-
MeO - Me -- N-Me-3-MPEA [33543-62-3] (6,7)
-
MeO -- Me2 - N,N-Me-3-MPEA [60189-31-3] (8,9)
Meo -- Et -- N-Et-3-MPEA [727732-11-8] (9)
-
MeO - Et2 -- N,N-Et-3-MPEA -- (10)
MeO -- -- a-Et 4C-3-MPEA [35149-78-1 ] (11)
MeO Me Me2 -- j),N,N-Me-3-MPEA [1 77339-29-6] (12)
MeO MeO -- -- B03M [24566-01-6] (13)
Meo MeO Me -- B03MM [23582-55-0] (13)
Meo MeO -- a-Me B03MA [24578-46-9] (13)
Meo MeO Me2 -- B03MDM [24550-1 8-3] (13)
MeO MeO iPr -- B03MIP [24550-16-1] (13)
MeO Meo Bu -- B03MB [24550-17-2] (13)
MeO EtO -- -- B03ME [23582-49-2] (13)
MeO EtO -- a-Me B03MEA [24550-20-7] (13)
EtO -- Me -- N-Me-3-EPEA [21581-46-4] (6)
EtO -- Me2 -- N,N-Me-3-EPEA [861006-98-5] (8)
EtO MeO -- -- B03E [23582-50-5] (13)
EtO EtO -- -- B03EE [23642-63-9] (13)
PrO Meo -- -- B03P [24550-24-1 ] (13)
AllylO MeO -- -- B03A [24550-23-0] (13)
(1) Effective in releasing cardiac norepinephrine (Daly et al., 1966).
(2) Studies on the oxidative deamination and effects on cat behavior (Clark et al., 1 964).
(4) Synthesis and pharmacological evaluation in the cat (Benington et al., 1958a).
(5) The structural isomer of 3-MA, with the methyl group in the j)- rather than the a-position, was
synthesized (3-methoxy-j)-methylphenethylamine, HCl salt m.p. 124 °C; Woodruff and Pierson,
1938).
(6) Pulmonary circulation effects measured in the dog (Aviado et al., 1957) .
(9) Efficient small-scale synthesis (Dubowchik et al., 2004) .
(11) Fragmentation patterns of some fifty-five phenethylamines determined by a variety of mass
spectrometry techniques (Kolliker and Oehme, 2004).
(13) A number of analogues of B03M were studied for their hypotensive effects (Howe et al., 1966).

3-MPEA I 4-MPEA
The positional isomer of 3-MA, with the methyl group in the [3- rather than the a-position,
was synthesized (3-methoxy-[3-methylphenethylamine, HCl salt m.p. 124; Woodruff and
Pierson, 1 938). The three-carbon chain homologue of N-Et-3-MPEA is homo-N-Et-3-MPEA
(CAS # 71250-30-1 ), and the three-carbon chain homologue of N,N-Et-3-MPEA is homo
N,N-Et-3-MPEA (CAS # 71250-28-7; Griffith et al., 1979) .
Biochemistry
Action on oxidative and hydrolytic enzymes in the rat brain (Clark et al., 1 956) and in rab
bit liver (Clark et al., 1965) has been reported, with emphasis on effects of ring methoxy
groups on oxidative deamination. Effects on cardiac function were observed in the cat and
dog (Ellis, 1965), and on the CNS of the chicken (Dewhurst and Marley, 1965) .
Serotonin receptor site affinity was determined (Glennon et al., 1980a) .
Pharmacology
Relationships between toxicology and pharmacology were studied (Epstein et al., 1932) .
Enzymatic oxidative deamination, effects on behavior, and pharmacological studies were
performed in the cat (Clark et al., 1964), and a hypokinetic rigidity syndrome was demon
strated in cats (Ernst, 1965a) . Several phenethylamines and tryptamines were compared in
studies with rats (Kier and Glennon, 1978b) .
The relationship between psychedelic activity and electronic configuration was established
(Snyder and Merril, 1965) .
Human activity of 3-MPEA is unknown.
Legal Status
#102. 4-MPEA
2-(4-Methoxypheny l)ethanamine
Paramethoxyphenethylamine
2-(4-Methoxyphenyl)ethylamine
2-(p-Methoxyphenyl)ethylamine
4-Methoxybenzeneethanamine
4-Methoxyphenethy lamine
4-Methoxyphenylethylamine
Homoanisylamine
0-Methyltyramine
p-Methoxyphenethylamine
Methyltyramine
Tyramine methyl ether
MPEA
PM PEA
NSC 43687
Registry Numbers
CAS # CAS # CAS #
HCl salt [645-58-9] Bicarbonate [855388-60-2] Dihydrate [330795-83-0]
Acetate [97289-45-7] Bioxalate [856822-70-3] L-Glutamate [ 61035-86-7]

4-MPEA
CAS # CAS #
Hydrate [330795-82-9] j)-[ dz] HCl salt [95864-31-6]
Pierate [ 855388-59-9] 4-C[ dz]H Freebase [ 484024-82-0]
Sulfate [ 64610-30-6] 4-C[d3 ] Freebase [484024-83-1]
Tetrahydrate [330795-85-2] a,a-[ d2] Freebase [884329-98-0]
Tetraiodoplumbate [301650-55-5] j),j)-[ dz] Freebase [757899-75-5]
Trihydrate [330795-84-1 ] a-[ 14C] HCl salt [855632-40-5]
Acid salt [87059-67-4] a-( 14C] Freebase [ 118828-79-8]
Freebase [55-81-2] j)-[ 1 4C] Freebase [136476-77-2]
Natural Sources
Found to be in the urine of schizophrenic patients, but not in normal subjects. (Sen and
McGeer, 1964)
Found in the cacti Lophophora williamsii (Lundstrom and Agurell, 1968a), the closely related
Obregonia denegrii (Neal et al., 1971b), in Coryphantha spp. (Hornemann et al., 1972), in Gym
nocalycium saglione, Cereus validus, and Trichocereus strigosus (Nieto et al., 1 982), and in cacti
of the Turbinicarpus genus (Starha et al., 1999) .
4-MPEA was found in Erica lusitanica (White, 1970) .

From 4-bromoanisole (with Mg, ethylene oxide) to 4-methoxyphenylethanol; (with HBr)
to 4-methoxyphenylethyl bromide; (with phthalimide, hydrazine) to 4-MPEA (Slotta and
Heller, 1930) .
From 4-methoxyhydrocinnamamide (with H2, pressure) to 4-MPEA (Kindler, 1931).
From anisole (with ethyleneimine, AlC13 ) to 4-MPEA (Braz, 1952) .
From anisaldehyde (with nitromethane) to 1-(4-methoxy) nitroethene; (with LAH) to

4-MPEA (Moed et al., 1955) .
From p-anisylalcohol (with cone. HCl, NaCN) to p-methoxyphenylacetonitrile (with Al CL,,

LAH) to 4-MPEA (Kiefer, 1972) .
From 2-nitrophenylethane (with F e powder, EtOH, NH4 Cl) t o 4-MPEA (Ran e t al., 2000) .

ml z : 151.0997 (100.0% ), 152.1 031 (9.7% )
HCl salt m.p. 210 °C (Slotta and Heller, 1930)
HCl salt m.p. 212-214 °C (Kiefer, 1972)
HCl salt m.p. 211-213 °C (Glennon et al., 1980a)
Freebase b.p. 132-136 °C / 12 mm (Moed et al., 1955)
Several salts and derivatives were described for identification purposes (Jansen, 1 931 ) .
4-MPEA is among compounds studied during development o f HPLC separation tech
niques for the identification of illicit drugs (Cashman et al., 1973) . Synthesis, TLC, and
gas chromatographic properties, UV spectra, and other physical properties were reported
(Ono et al., 1976), as was HPLC employing fluorescamine derivatization for fluorescence
detection (Shimamine, 1984) . [ 13C]-NMR spectra for methoxylated phenethylamines and

4-MPEA
amphetamines was shown to be distinctive and suitable for identification (Bailey and Le
gault, 1983) . Fragmentation patterns of some fifty-five phenethylamines were determined
4- j)- N- Name CAS # Ref
F -- -- 4-FPEA [ 1583-88-6] (1-3)
Cl -- -- 4-Cl-PEA [156-41-2] (1-10)
Cl Me -- j)-Me-4-Cl-PEA [4806-79-5] (1)
Cl -- iPr N-iPr-4-Cl-PEA [2275-69-6] (5)
Br -- -- 4-Br-PEA [73918-56-6] (1,2)
I -- -- 4-I-PEA [73918-57-7] (1,2)
NH2 -- -- PAPEA [13078-82-5] (11)
NMe2 -- -- 4-N,N-MePEA [52632-05-0] (12)
--
Me -- 4-MePEA [3261-62-9] (1,2,13-14)
Et -- -- 4-EtPEA [3166-88-9] (2,13,15)
Pr -- -- 4-PrPEA [3166-99-2] (13)
iPr -- -- 4-iPrPEA [61035-87-8] (2)
Bu -- -- 4-BuPEA [3166-76-5] (13)
tBu -- -- 4-tBuPEA [91552-82-8] (2)
He -- -- 4-HePEA [100874-90-6] (2)
MeO -- -- 4-MPEA (this entry)
Meo HO -- j)-H0-4-MPEA [55275-61-1] (16-18)
MeO Me -- j)-Me-4-MPEA [ 13062-93-6] (11,19
MeO Me Me j),N-Me-4-MPEA [725735-35-3] (20,21)
Meo Me Me2 j),N,N-Me-4-MPEA [133302-86-0] (20)
MeO Me Et j)-Me-N-E t-4-MPEA [861007-58-1 ] (20)
MeO Meo -- j),4-DMPEA [31367-42-7] (22)
-
MeO - Me N-Me-4-MPEA [ 4091-50-3] (11,17,23-26)
MeO -- Me2 N,N-Me-4-MPEA [50822-98-5] (27-29)
EtO -- -- 4-EPEA [ 62885-82-9] (12,30)
EtO -- Me N-Me-4-EPEA [21581-35-1] (31,32)
EtO -- Me2 N,N-Me-4-EPEA [777-86-6] (27)
Pro -- -- 4-PPEA [57224-67-6] (30)
-
BuO -- - 4-BPEA [ 65423-11-2] (30)
Amo -- -- 4-APEA [57224-68-7] (30)
HeO -- -- 4-HePEA [ 80938-34-7] (30)
Seo -- -- 4-SPEA [57224-69-8] (30)
OcO -- -- 4-0PEA [861007-75-2] (30)
NoO -- -- 4-NPEA [861007-76-3] (30)

4-MPEA
(1) Action on release and inhibition of labeled serotonin in mice (Hwang and Van Woert, 1980).
(2) Synthesis and pharmacological evaluation in the cat (Benington et al., 1958a).
(3) Of the 21 compounds tested, only 4-Cl-PEA, 4-MPEA, DMPEA, and 4-EPEA were synergistic
with a subliminal dose of 4-MPEA in inducing male-to-male mounting behavior in sexually
nai've rats (Segal et al., 1977) .
(4) The administration of p-chlorophenylalanine to the rat leads to an accumulation of 4-Cl-PEA in
the brain (Baker et al., 1982).
(5) PCA, and several structurally related compounds, lowers rat brain serotonin levels but does not
lower the level of norepinepherine (Fuller et al., 1965).
(6) Brain depletion of serotonin resulting from the administration of 4-chlorophenylalanine may be
due to the metabolite 4-chlorophenylpyruvic acid rather than 4-Cl-PEA (Koe and Weissman, 1966).
(7) 4-Chlorophenylalanine, co-administered with a MAO inhibitor to rats, created pharmacologically
active brain levels of 4-Cl-PEA (Edwards and Blau, 1972) .
(8) The sexual stimulation associated with 4-chlorophenylalanine might be due to the metabolite
4-Cl-PEA (Wilson and Hunter, 1985).
(9) 4-Cl-PEA has been reported as the metabolite of 4-chlorophenylalanine responsible for the en
hanced sexual activity in rats (Sloviter et al., 1978).
(10) Synthesis achieved by the reduction of the 2-nitrophenylethane with Fe powder in ethanol and
ammonium chloride (Ran et al., 2000).
(11) Effective in releasing cardiac norepinephrine (Daly et al., 1966).
(12) Spasmolytic activity on isolated rabbit small intestine (Stolyarchuk et al., 1 975) .
( 1 3 ) Oxidative deamination and effects o n cat behavior (Clark e t al., 1964).
(14) The 4-methyl homologue (4-MePEA) was assayed for its serotonin receptor site activity (Glen
non et al., 1980a).
(15) Synthesis (Braz, 1952).
(16) The cacti Pereskia grandiflora, P. grandifolia, and Pereskiopsis chapistle, contain f3-hydroxy-4-me
thoxyphenethylamine (Doetsch et al., 1980).
(17) Isolated from Coryphantha spp. (Hornemann et al., 1972).
(18) In entering Hornemann et al., 1972, Chemical Abstracts incorrectly identified this compound as
having the hydroxyl group on the a-carbon atom (that carries the amine group), and assigned
the CAS number [35085-82-6] .
(21 ) GC / MS characterization (Pihlainen et al., 2005).
(22) The f3-methoxy analogue (f3,4-DMPEA) produces experimental catatonia in cats (Noteboom, 1934).
(23) Found in the cactus Coryphantha ramillosa (Sato et al., 1973).
(24) Found in the cactus Coryphantha macromeris var. runyonii (Keller et al., 1 973).
(25) Found in the cactus Coryphantha bumamma (Bruhn et al., 1975).
(26) Synthesis (Kiefer, 1972).
(28) LD50 for mice determined (Aliev et al., 1967).
(29) Isolated from Tee/ea simplicifolia (Rutaceae) (Badger et al., 1963).
(30) Synthesis and studies of the inhibition of smooth muscle contraction (Broom and Wayne, 1946) .
(31 ) The pulmonary circulation effects were measured in the dog (Aviado et al., 1 957).
Biochemistry
[ 1 4 C]-labeled 4-MPEA was used to explore the biosynthesis of mescaline in Lophophora
williamsii (Lundstrom and Agurell, 1968b). Cell cultures of Catharanthus roseus metabolized
4-MPEA by demethylation, and cultures of S trobilanthes dyerianus metabolized 4-MPEA to
2-(p-methoxyphenyl)ethyl-�-D-glucopyranoside (Hiraoka and Carew, 1981 ) .
The effects o f ring methoxy groups o n oxidative deamination was evaluated (Clark e t al.,
1965) . P450 effectively removes the 0-methyl group from 4-MPEA, which is followed by
ring oxidation to dopamine (Guengerich et al., 2002).

4-MPEA
Studies were made of both agonist and antagonist activity with dopamine [3-oxidase (Crev
eling et al., 1962) . Effects on the dog peroneal tibialis anticus nerve muscle were studied
(Schopp and Walsh, 1964) . 4-MPEA was investigated as a monoamine oxidase inhibitor
in the rat liver (Takagi and Gomi, 1966) . 4-MPEA was also effective in releasing cardiac
norepinephrine in the mouse (Daly et al., 1966) . 4-MPEA affected monosynaptic reflex
transmission in the cat (Walker et al., 1970) . Depression by 4-MPEA of sympathetic reflex
firing elicited by stimulation of the carotid sinus nerve or pelvic nerve in the cat was dem
onstrated (De Groat and Lalley, 1973). Treatment with competitive · inhibitors revealed the
role of monoamine oxidase in terminating the reflex effects of 4-MPEA on the cat spinal
cord (Willis et al., 1973) . 4-MPEA was shown to affect serotonin turnover in rat brain and
spinal cord (Anden et al., 1974) . Spasmolytic activity induced in isolated rabbit small intes
tine was noted (Stolyarchuk et al., 1 975) . Analysis of the effects of 4-MPEA on spinal cord
neurons has been conducted (Jordan and McCrea 1976) . Serotonin receptor site affinity
was determined, utilizing the rat fundus model (Glennon et al., 1980a) . 4-MPEA's effects
on chronic stress-induced hypertension in the rat were evaluated (Segal, 1979) . 4-MPEA
was a specific substrate for type B monoamine oxidase (MAO) in rat brain mitochondria,
whereas inhibition by DMPEA was common to both types of MAO (Suzuki et al., 1980) .
Pharmacology
The relationships between toxicology and pharmacology for 4-MPEA were studied (Ep
stein et al., 1932) . Pulmonary circulation effects were measured in the dog (Aviado et al.,
1 957), cataleptic activity was observed in mice (Michaux and Yerly, 1963), and 4-MPEA
was shown to be an indirect sympathomimetic amine in the rat (Cession-Fossion, 1963).
4-MPEA was studied in relationship to the compulsive gnaw syndrome in the rat (Ernst,
1965b). Tyramine and 4-MPEA each affected conditioned behavior of the rat (Xhenseval,
1965) . Serotonin was involved in the jumping contest changes resulting from the s.c. injec
tion of 4-MPEA and DMPEA into rats (Hallasmoeller et al., 1973). Some behavioral obser
vations in rats were made with 4-MPEA (Cannon et al., 1977), and in a study of 21 com
pounds, only 4-Cl-PEA, 4-MPEA, DMPEA, and 4-EPEA were synergistic with a subliminal
dose of 4-MPEA in inducing male-to-male mounting behavior in sexually naive rats (Segal
et al., 1977) . Behavioral and biochemical effects of 4-MPEA were studied in the mouse,
including release and inhibition of labeled serotonin (Hwang and Van Woert, 1979, 1980) .
Several phenethylamines and tryptamines were compared in structure-activity studies
with rats trained to discriminate DOM from saline (Kier and Glennon, 1978b) .
Pharmacological studies were performed i n the cat (Clark e t al., 1 964) . Intracerebral ad
ministration of 4-MPEA produced catatonia in the cat (Michaux and Cession-Fossion,
1964), and a hypokinetic rigidity syndrome in cats (Ernst, 1965a) .
The relationship between psychedelic activity and electronic configuration was established
(Snyder and Merril, 1965) . 4-MPEA was not active in humans at 400 mg (Brown et al.,
1968), although this compound was considered in a study of human potency, as affected by
changes in substitution patterns (Shulgin et al., 1969) . Using molecular connectivity analy
sis of ten psychedelic phenethylamines, the importance of the 2,5-substitution pattern of
the methoxy groups, and the 4-substituent was demonstrated (Glennon et al., 1979a) .
Legal Status

MTA
#103. MTA
1-(4-(Methylthio )phenyl)propan-2-amine
4-Methylthioamphetamine
a-Methyl-4-methylthiophenethylamine
p-Methy lthioamphetamine
Flatliners
Golden Eagles
4-MTA
PMTA
p 1882
Registry Numbers
CAS # CAS #
HCI salt [94784-92-6] (+)-Isomer freebase [765898-09-7]
Trifluoroacetate [557768-72-6] (-)-Isomer freebase [756816-57-6]
Freebase [14116-06-4] S-Isomer HCI salt [943744-15-8]
(+)-Isomer HCI salt [634607-22-0] S-Isomer freebase [943816-61-3]
(-)-Isomer HCI salt [634607-23-1]

From 4-methylthiobenzaldehyde (with nitroethane, acetic acid, and ammonium acetate) to
1 -(4-methylthiophenyl)-2-nitropropene; (with LAH) to MTA (Holland et al., 1963).

m / z: 181.0925 (100.0%), 1 82.0959 (10.8%), 1 83.0883 (4.5% )
Elemental Analysis: C, 66.25; H, 8.34; N, 7.73; S, 1 7.69
HCI salt m.p. 190-191 °C (Holland et al., 1963)

4- 3- 2- a- Other N- Name CAS # Ref
-- -- MeS -- -- -- 2-MTPEA [69587-07-1 ] (1)
-- -- Mes Me -- -- 2-MTA [92286-71-0] (2)
-
- MeS -- Me -- -- 3-MTA [91330-07-3] (2)
MeS -- -- Me -- -- MTA (this entry)
MeS -- -- Me -- Me MMTA [91341-37-6] (2)
MeS -- -- Me -- Me MTMA [547736-90-3] (3,4)
MeS -- -- Me f3-HO -- MTC [138889-33-5] (5)
Mes -- -- Me -- Me2 MTDMA [ 634607-13-9] (6)
MeS -- -- Me -- Et MTEA [376580-97-1 ] (6)
MeS -- -- Me -- Et2 MTDEA [ 634607-15-1] (6)
MeS -- -- Me -- Pr MTPA [634607-16-2] (6)
MeS -- -- Me -- Pr2 MTDPA [634607-1 7-3] (6)
MeS -- -- Me -- Ally! MTALA [ 634607-19-5] (6)
MeS -- -- Me -- Allyl2 MTDALA [634607-20-8] (6)
-
MeS -- - Et -- -- a-EMTPEA [634607-21-9] (6)

MTA
4- 3- 2- a- Other N- Name CAS # Ref

MeS -- -C- -- -- MTAI [73536-80-8] (7)
-
EtS -- - Me -- -- ETA [201407-47-8] (5,6,8,9)
iPrS -- -- Me -- -- IPTA [201407-50-3] (2,9)
(1) In a large number of methoxylated amphetamines, rabbit hyperthermia paralleled human psy
chedelic potency (Anderson et al., 1978b).
(2) Proposed as an anorexigenic agent (Holland et al., 1963) .
(3) MTMA produces PMMA-like, but not amphetamine-like responses in trained rats (Dukat et al.,
2002).
(4) Studies of stimulus generalization of 2C-T-7, MTA, and MTMA in rats trained with DOM, cocaine
and MOMA (Khorana et al., 2004).
(5) MTC (4-methylthiocathine) is a metabolite of MTA in the mouse (Carma et al., 2002) .
(6) Synthesis described; MAO-inhibition properties less than those of MTA (Hurtado-Guzman et al.,
2003).
(7) Patented as an inhibitor of phenylethanolamine N-methyltransferase, to limit production of epi
nephrine in vitro (Bondinell and Pendleton, 1980).
(8) MAO-inhibitor activity determined (Scorza et al., 1997) .
(9) Several compounds were synthesized and assayed for their ability t o inhibit MAOA and MAOB.
Most were potent against MAOA; none were appreciably active against MAOB (Gallardo-Godoy
et al., 2005).
The UV, IR, and NMR spectra were shown, as well as spot-test results and GC / MS data
(Poortman and Lock, 1999) . MTA was resolved into its two optical isomers (Hurtado-Guz
man et al., 2003). Plasma screening and quantitative GC / MS analysis was reported (Peters
et al., 2003). A single HPLC-UV analysis of human urine detected amphetamine (and its
metabolite PHA), MOMA (and its metabolite MDA), 2C-B, and MTA (Soares et al., 2004) .
Biochemistry
The sulfoxide was observed as a metabolite of MTA in humans (Elliot, 200 1 ) . In the mouse,
PTA (in addition to being excreted unchanged) was metabolized to the (R,S)- and (S,S)
isomers of the [)-hydroxy analogue MTC (methylthiocathine), to 4-methylthiobenzoic acid,
and to a hydroxylated methylthiobenzoic acid of undetermined structure (Carma et al.,
2002). The major metabolite of MTA with hepatocytes from humans and several animal
species was shown to be 4-methylthiobenzoic acid (Carma et al., 2004a) .
MTA is an inhibitor of MAOA (Li et al., 1996; Scorza et al., 1997) . Several compounds were
synthesized and assayed for their ability to inhibit MAOA and MAOB. Most were potent
against MAOA; none were appreciably active against MAOB (Gallardo-Godoy et al., 2005).
Pharmacology
MTA released serotonin and inhibited its reuptake in the rat, in studies that also included
drug-discrimination trials (Huang et al., 1992) . MTA, MBDB, and MMAI were compared
as serotonin releasers in rats (Li et al., 1996); MTA was a potent MAOA inhibitor in the
rat (Elliott, 2001), and produced hyperthermia in mice (Carma et al., 2003). The MAO
inhibitory potencies of the optical isomers of MTA were determined; the (+)-isomer is 1 8
times more potent than the (-)-isomer (Hurtado-Guzman e t al., 2003).
MTA produced PMMA-like, but not amphetamine-like responses in trained rats Dukat et
al., 2002) . Studies of stimulus generalization of 2C-T-7, MTA, and MTMA in rats trained
with DOM, cocaine, and MOMA were made (Khorana et al., 2004) .

MTA I Proscaline
The first published synthesis of MTA was in 1963, and the drug was introduced as be
ing "Ecstasy" in Holland and in England in the 1990s. An analysis of an English sample
revealed the major component to be MTA (138 mg per tablet), accompanied by 1 00 mg
of caffeine (Groombridge, 1 998) . Two sulfur-containing street drugs (2C-T-2 and MTA)
prompted a GC / MS identification study (Bosman et al., 2000) . MTA was among several
psychedelic drugs verified in the Japanese street drug scene (Katagi et al., 2002), where a
typical individual dose was reported as 125 mg.
An intoxicated patient who had ingested "herbal stimulant" tablets called "S-5" was found
to have MTA in blood analysis (de Boer et al., 1999a) . There have been six deaths associ
ated with the human use of MTA (EMCDDA, 1999) . In one human fatality, blood levels
postmortem were 4.6 µ g / ml, postmortem urine, 87 µg / ml, with no other drugs observed
(Elliott, 2000) . Human plasma levels were observed from 0.13 to 0.76 µ g / ml (Elliott, 2001 ) .
One fatal and seven non-fatal overdoses o f MTA were described (De Letter e t al., 2001 ) . A
lethal overdose showed levels of 5.2 µg I ml in blood, 95 µg I ml in urine, 1 .3 µg I ml in vitre
ous humor, 36 µg / ml in bile, 3 µg / ml in liver, and 4.1 µg / kg in the spleen (Decaestecker
et al., 2001 ) .
Human dose requirements for psychedelic activity and duration o f effects have not been
reported from controlled studies with known material.
Legal Status
MTA is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws except for Wisconsin, where it is a Schedule I drug.
The World Health Organization Expert Committee on Drug Dependence has recommended
international control of MTA (World Health Organization, 2001).
#104. Proscaline
2-(3,5-Dimethoxy-4-propoxyphenyl)ethanamine
3,5-Dimethoxy-4-propoxyphenethylamine
p
Registry Numbers
CAS #
HCl salt [61367-69-9]
Hexachloroplatinate [ 40275-09-0]
Sulfate [39201-79-1]
Freebase [39201-78-0]

From 4-propoxy-3,5-dimethoxybenzaldehyde (with nitromethane) to 4-propoxy-3,5-dime
thoxy)nitroethene; (with Zn; Leminger, 1972b), or (with LAH; Braun et al., 1978a), to P.
From 3,5-dimethoxy-4-hydroxyphenylacetonitrile (with propyl iodide) to 3,5-dimethoxy-

4-propoxyphenylacetonitrile; (with H2, Pd) to P (Nichols and Dyer, 1977) .

m / z: 239. 1521 (100.0% ), 240. 1555 (14. 1 % )
HCI salt m.p. 1 70-1 72 °C (Nichols and Dyer, 1977)

Proscaline I PAT
Biochemistry
Molecular connectivity analysis gave excellent correlation to serotonin agonist activity in a
large number of phenethylamines and amphetamines (Kier and Glennon, 1978a) . P was more
potent than mescaline in contracting sheep umbilical artery strips (Nichols and Dyer, 1997).
Pharmacology
Several phenethylamines and tryptamines were compared in studies with rats (Kier and
Glennon ,1978b ). Using molecular connectivity analysis of ten psychedelic phenethylamines,
the importance of the 2,5-positions of the methoxy groups, and the 4-substituent was dem
onstrated (Glennon et al., 1979a) .
The octanol-water partition coefficient may serve as a predictor of human psychedelic po
tency (Nichols and Dyer, 1977); a comparison was made of other steric properties, with
rivatives (Nichols, l 986b ).

animal and human potency of several phenethylamines, tryptamines and lysergide de
Orally active in humans at 30-60 mg (Braun et al., 1978; Shulgin and Shulgin, 1991); dura
tion 8-12 hours (Shulgin and Shulgin, 1991).
Legal Status
P is not a scheduled compound under federal drug law, or under District of Columbia or
any state laws.
# 105. PAT
H
7-(Dipropylamino )-5,6,7,8-tetrahydronaphthalen-1-ol
7-(Dipropylamino )-5,6,7,8-tetrahydro-1-naphthalenol
OH ? '
2-(N,N-Dipropyl)amino-8-hydroxytetralin
8-Hydroxy-2-(dipropylamino)tetralin
OO:N �CH3
PPAT
8-HO-DPAT
Registry Numbers 7
CAS #
HCI salt [141215-27-2] 6
HBr salt [76135-31-4] 5 4
x-Tartrate [134331-05-8]
Freebase [78950-78-4]
R-Isomer HCI salt [119273-42-6] 7-[ 3H] Isomer HCl salt [ 136696-23-6]
5-Isomer HCI salt [119273-43-7] 7-[ 3H] Isomer freebase [737729-40-7]
R-Isomer HBr salt [78095-19-9] R-Isomer 7-[ 3H] HC! salt [136779-03-8]
5-Isomer HBr salt [78095-20-2] 5-Isomer 7-[ 3H] HC! salt [136779-04-9]
R-Isomer freebase [80300-09-0] R-Isomer 7-[ 3H] freebase [762209-19-8]
5-Isomer freebase [80300-10-3] 5-Isomer 7-[ 3H] freebase [736109-11-8]
R-Isomer, N-(N-benzylcarbonyl)glycyl-L-proline salt [149097-87-0]
5-Isomer, N-(N-benzylcarbonyl)glycyl-L-proline salt [149097-88-1 ]

From 8-methoxy-2-dipropylaminotetralin (with 48% HBr) to PAT (Arvidsson et al., 1981 ).
The optical isomers were prepared by resolution of dl-8-methoxy-2-benzylaminotetralin

with tartaric acid, followed by acylation with propionyl chloride, reduction with LAH,
debenzylation with Pd and H2, acylation with propionyl chloride, reduction with LAH,
and demethylation with HBr (Arvidsson et al., 1981).

PAT

m / z: 247.1936 (100.0% ), 248.1970 (17.3% ), 249.2003 (1.4% )
HBr salt m.p. 221 .5-222 °C (Arvidsson et al., 1981)

(+)-Isomer HBr salt m.p. 1 78.5-179.5 °C [aJ ;1j1 +67.5° (Arvidsson et al., 1981) (MeOH)
(-)-Isomer HBr salt m.p. 1 78.5-179.5 °C [aJ ;1j1 -66.5° (Arvidsson et al., 1981) (MeOH)

N- Name CAS # Ref
-- HHAT [118298-09-2] (1)
Me MHAT [78950-80-8] (1)
Me2 MMAT [87394-81-8] (1)
Et EHAT [87394-70-5] (1)
Et2 EEAT [87394-83-0] (1)
Pr PHAT [81185-33-3] (1)
Pr, Et PEAT [81185-37-7] (1)
Pr2 PAT (this entry)
iPr iPHAT [81185-35-5] (1)
Bu BHAT [ 81185-34-4] (1)
Bu2 BBAT [ 81185-39-9] (1)
(1) PAT and related compounds evaluated as central serotonin receptor agonists (Arvidsson et al., 1984).
Biochemistry
In reserpinized rats, 8-0H-PAT is a serotonin receptor agonist with no dopamine recep
tor action, whereas the 5-0H, 6-0H, and 7-0H analogues are dopamine receptor agonists
with no serotonin receptor activity (Feenstra et al., 1980; Arvidsson et al., 1981, 1984; note
that different authors may have adopted different ring numbering schemes). Tritiated PAT
distribution was studied in the rat brain (Marcinkiewicz et al., 1984) .
The serotonin mechanism for the induction of the cardiovascular activation o f respiration
was studied by the separate actions of the three major agonists: PAT for 5-HT 1 N TFMPP for
5-HT 1 w and DOI for 5-HT2 (King and Holtman, 1990) . The effects of three different sero
tonin receptor agonists (PAT for 5-HT 1 N mCPP for 5-HT 1 w and DOI for 5-HT2) were com
pared in preweanling rat pups, with observations on differences in behavioral responses
with animal age (Frambes et al., 1990); the 5-HT 1 A agonist PAT was compared with the
5-HT2 antagonist ritanserin in rats implanted for chronic sleep recordings (Monti et al.,
2
1990) . The 5-HT2 binding site of PAT was located with [ 1 5 1]-labeled 2C-I (Johnson et al.,
1990b). PAT and DOI (as 5-HT2A ; 2c receptor agonists) effects on monosynaptic transmis
sion in spinalized rats were evaluated (Hasegawa and Ono, 1 996). Isoteolin, a putative
serotonin antagonist, inhibited mCPP but not DOI, and PAT induced increases in serum
prolactin levels (Zhelyazkova-Savova and Negrev, 2000) .
Pharmacology
Injection of PAT into male rats (0.25 mg / kg i.p.) markedly facilitated sexual behavior, as
did lisuride at 0.4 mg / kg. As pretreatment with haloperidol (a dopamine receptor-block-

PAT / PCA
ing agent) at 0.16 mg / kg i.p. had no effect on this action, the effect was not due to a do
paminergic mechanism (Ahlenius and Larsson, 1984) . PAT attenuated antinociception in
duced by morphine in the mouse (Berge et al., 1 985) . Rats trained to distinguish DOI from
saline did not display a generalized response when challenged with PAT (Glennon, 1 986a),
and DOI-induced head-twitching was inhibited by PAT (Arnt and Hyttel, 1 989) . The 5-HT2
receptor antagonist ketanserin did not attenuate acute behavioral effects of PAT in rats
(Wing et al., 1990) .
Human psychedelic activity of PAT has not been reported.
Legal Status
PAT is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
# 106. PCA
1-(4-Chlorophenyl)propan-2-amine
4-Chloroamphetamine
4-Chloro-a-methylphenethylamine
4-CA
NSC 287208
Ro 4-6614 / 001
Registry Numbers
CAS # CAS #
HCl salt [3706-38-5] R-(-)-Isomer HCl salt [ 16064-31 -6]
Bisulfate [34176-59-5] S-( +)-Isomer HCl salt [ 16064-30-5]
x-Citrate [34203-22-0] S-Isomer, R-N-acetyl leucine salt [24116-85-6]
Cyc!ohexane sulfate [34176-61-9] S-Isomer, R-N-formyl leucine salt [24116-86-7]
x-Fumarate [34622-16-7] S-Isomer, R-x-R-tartrate [28357-54-2]
x-Maleate [34622-1 7-8] S-Isomer R-bitartrate [33423-88-0]
D-Mannopyranose sulfate [59963-26-7] R-Isomer mandelate [141725-82-8]
Phosphate ester [34176-60-8] S-Isomer mandelate [141725-81 -7]
Pi crate [22490-82-0] R-(-)-Isomer freebase [405-47-0]
Sulfate [24116-87-8] S-( +)-Isomer freebase [ 405-46-9]
x-Sulfate [51395-16-5] f3-[ 1 4 C]-Labeled HCl salt [61040-91-3]
Freebase [64-12-0] f3-[ 14 C]-Labeled freebase [61040-64-0]

From chlorobenzene (with allyl chloride, FeCI31 HCl) to j3,p-dichlorophenyl propane; (with
NH3 ) to PCA (Patrick et al., 1946a) .
Synthesis by Leuckart reaction (Ingersoll et al., 1936; Cavallini et al., 1956).

m / z: 169.0658 (100.0% ), 171.0692 (32.0%), 170.0692 (9.7% ), 1 72.0662 (3. 1 % )
Elemental Analysis: C, 63.72; H, 7. 13; Cl, 20.90; N , 8.26
HCl salt m.p. 164-165 °C (Patrick et al., 1946a)

Freebase b.p. 93-94 °C / 5 mm (Patrick et al., 1946a)
LC resolution with four chiral reagents (Miller et al., 1984) .

PCA

4- a- Other Name CAS # Ref
F Me -- PFA [459-02-9] (1-9) --
F Me N-Me PFMA [861007-48-9] (7)

Cl Me -- PCA --- �
(this entry)
Cl Me N-Me PCMA [1199-85-5] (2,3,1 0,11)
Cl Me N-Et N-Et-PCA [2275-67-4] (3)
Cl Me N-iPr N-iPr-PCA [65114-99-0] (3)
Cl Me2 -- 4-Cl-a,a-MePEA [151-06-4] (12-15)
Cl Et -- CAB [2275-64-1 ] (16) --
Cl Me �-F 2 �,�-F-PCA [38473-95-9] (17)

Br Me -- PBA [13235-83-1 ] (2,9,10)
NH2 Me -- PAA [57736-33-1] (11,18-21 )
NH2 Me N-Me PAMA [4302-87-8] (11)
NHMe Me -- MePAA [88753-19-9] (21-23)
NMe2 Me -- DMePAA [57294-60-7] (19,21,23)
N02 Me -- PNA [13026-03-4] (10,18,19)
N02 Me N-Me N-Me-PNA [4302-88-9] (18)

(2) Synthesis (Patrick et al., 1946a).
(3) PCA, and several structurally related compounds, lowers rat brain serotonin levels but not nor
epinephrine (Fuller et al., 1965).
(4) Correlation of chemical structure with phenethanolamine N-methyltransferase reactivity
(5) Behavioral effects of PMeA, PCA, and PFA in animals used to predict psychedelic effects in
humans (Beaton et al., 1968) .
(6) Relationship between serotonergic activity and reinforcing effects studied (Wee et al., 2005).
(7) Active in humans at 80-240 mg i.m.; duration 3-7 hours (Igor, 2006).
(8) A reproducible, simple, and small-scale method for detecting uptake and release of monoamines
(dopamine, serotonin, and norepinephrine) by rat brain synaptosomes was developed (Nagai et
al., 2007) .
(9) PCA, PBA, and PFA effects on brain serotonin metabolism compared in the rat (Fuller et al.,
1975a).
( 10) Binding at 5-HT 1 c and 5-HT2 receptors measured (Glennon et al., 1992).
(11) Synthesis (Cavallini et al., 1956).
(12) Effective at releasing cardiac norepinephrine in the rat (Daly et al., 1966).
(13) TLC analysis (Bussey and Backer, 1974).
(14) Synonyms: Chlorphentermine, Clorfentermina, Desopimon, Effox, Lucofen SA, Teramine.
(15) Analysis by gas chromatography (Canfield et al., 1977).
(16) Behavioral, biochemical and neurotoxicological actions of the a-ethyl homologue of p-chloro
amphetamine (Johnson et al., 1990a).
(17) Effect of �,�-F-PCA on the disposition and pharmacological effects of 4-chloroamphetamine in
rats (Fuller et al., 1973).
(18) Synthesis (Patrick et al., 1946b).
(19) Proposed as an anorectic agent (Holland et al., 1963).
(20) Synthesis (Hoover and Hass, 1947).
(21 ) A MAO inhibitor in serotonergic neurons (Ask et al., 1985).

PCA
(22) A potent, reversible MAO inhibitor (Ask and Ross, 1980).

(23) In vitro and in vivo MAO inhibitor studies performed on the racemate and the optical isomers
(Reyes-Parada et al., 1994).
Isomers With Ring Modifications *

4- 2- I a- Other Name CAS # Ref
-- -CC- -- PCAT [ 60480-00-4] (1)
F -C- -- PFAI [2340-06-9] (2)
Cl -- I Me
r----- ---
-- PCA (this entry)
Cl -C- - - PCAI [73536-86-4] (2,3)
Cl -C- NMe2 N,N-Me-PCAI [73536-81-9] (3)
Br -C- -- PBAI [73536-88-6] (3)
N02 -C- -- PNAI [73536-87-5] (3)
*With the fusion of the a-methyl group, directly or with the inclusion of an additional carbon atom,
to the 2-position of the aromatic ring
(1) Several psychedelic amphetamines were compared with their 2-aminoindan or 2-aminotetralin
analogues as serotonin uptake inhibitors, and in rats trained to discriminate between MDMA and
MBDB (Johnson et al., 199la).
(2) Patented as an analgesic for human use (Huebner, 1965).
(3) Patented as an inhibitor of phenylethanolamine N-methyltransferase, to limit production of epi
nephrine (Bondinell and Pendleton, 1980) .
With Other Than 2-Carbon Chains

Chain 4- a- Other Name CAS # Ref
1 Cl Me -- PCBA [3886-69-9] (1,2)
3 Cl Me -- homo-PCA [53896-12-1] (1)
(1) One-carbon and three-carbon homologues of PCA (PCA and homo-PCA) compared to PCA ef
fects on brain serotonin metabolism in the rat (Fuller et al., 1974).
(2) Synthesis (Ingersoll et al., 1936).
Biochemistry
PCA is effective in releasing cardiac norepinephrine (Daly et al., 1966). Optical (3-isomers of
PCA were compared to those of methamphetamine in several rodent studies. The ( + )-iso
mer had twice the potency of the (-)-isomer in reducing food intake (Nielsen et al., 1967) .
There is a substantial amount of animal data illustrating PCA neurotoxicity. Unlike am
phetamine, p-chloroamphetamine causes a marked decrease in cerebral serotonin in rats.
This effect on serotonin metabolism persists after the psychomotor stimulation has subsid
ed and exerts a continuing effect on the metabolism of intraventricularly administered nor
epinephrine (Strada et al., 1970) . In vivo investigations of the mechanism of action showed
selective depletion of cerebral serotonin (Sanders-Bush and Sulser, 1970, 1973) . PCA does
not appear to evoke a serotonin mediated learning deficit with phenyketonuria in rat
studies (Schaefer et al., 1 974). 3-CA and PCA led to a long-lasting serotonin reduction in
iprindole-treated rats (Fuller and Baker, 1974) . One-carbon and three-carbon homologues
of PCA (PCA and homo-PCA) were compared to PCA on brain serotonin metabolism and
serotonin depletion (Fuller and Perry, 1974; Fuller et al., 1974; Fuller et al., 1975b) . PCA,
PBA and PFA effects on the metabolism of brain serotonin in rats were compared (Fuller et

PCA
al., 1975a). Serotonin was depleted in mesencephalic nuclei of rat brain following a single
injection of PCA (Bertilsson et al., 1975) . Methadone did not prevent the depletion of brain
5-hydroxyindoles by PCA (Fuller and Perry, 1976) . Neurotoxic action of PCA in the rat
was revealed by Nissl and silver stains (Harvey and McMaster, 1976). PCA caused acute
and chronic effects on habituation and sensitization of the acoustic startle response in rats
(Davis and Sheard, 1976), and upon shock-elicited aggression (Sheard and Davis, 1 976) .
Antagonism of the long-term effects of PCA were produced with a selective inhibitor of
serotonin uptake (Ogren et al., 1976) . The actions of fenfluramine and PCA on serotonergic
mechanisms were compared in rat brain nuclei (Neckers et al., 1976b) . Long-term effects
of continuous exposure to PCA were identified in catecholamine synthesis and serotonin
levels, and central serotonergic mechanisms in mice (Steranka and Sanders-Bush, 1977,
1 978) . PCA was shown to influence serotonin content of the rat pineal gland (Fuller and
Perry, 1977) . Chronic oral administration of PCA caused depletion of brain serotonin in
rats and dogs (Fuller et al., 1979) . MOMA and PCA both cause brain serotonin levels to
decrease in two temporal phases; an acute reversible phase and a later irreversible phase
(Schmidt, 1987a) . PCA is metabolized to OMA in the rat brain (Sherman and Gal, 1 976; Sil
verman and Ho, 1979), but the neurotoxicity of PCA may be the result of the conversion of
serotonin to 5,6-dihydroxytryptamine (Ames et al., 1977; Commins et al., 1987) . PCA was
shown to cause serotonergic neurotoxicity (Fuller, 1992) . The effects of MOMA and several
MAO inhibitors were evaluated for influence on PCA-induced neurotoxicity (Sprague et
al., 1996) . PCA induced long-lasting neurotoxicity in mice, resulting in extended sensitiza
tion to stimulants such as MOMA and cocaine (Itzhak et al., 2004) .
The potency of PCA as an inhibitor of phenylethanolamine N-methyltransferase was de

termined (Fuller et al., 1971 ) . Long-term effects of PCA on tryptophan hydroxylase activ
ity and on the levels of serotonin and 5-hydroxyindole acetic acid in brain were studied
(Sanders-Bush et al., 1972; Fuller and Snoddy, 1974). Effect of PCA on cerebral tryptophan-
5-hydroxylase, in vivo was described (Gal et al., 1975) . In rats, PCA was metabolized with
the "NIH" shift to yield 3-chloro-4-hydroxyamphetamine (Parli and Schmidt, 1975). Re
duction of tryptophan hydroxylase activity and serotonin concentration in certain rat brain
nuclei after PCA was described (Neckers et al., 1976a) . The stereoisomeric metabolism was
determined by GC / MS analysis of the (S)-a-methoxy-a-(trifluoromethyl)phenylacetyl
amides (Gal, 1978) . PCA inhibited tryptophan hydroxylase activity and reduced the levels
of serotonin and 5-hydroxyindoleacetic acid in several regions of the rat brain (Peat et al.,
1985; Gibb et al., 1 987) .
PCA influenced female sexual reflexes and brain monoamine levels (Zemlan et al., 1977),
and p-chlorophenylalanine (PCPA) or PCA facilitated avoidance acquisition in rats (Vor
hees, 1979) . Serum prolactin levels are acutely elevated after administration of PCA in rats
(Fuller et al., 1980).
Release and inhibition of labeled serotonin was studied in rats and mice (Clemens et al.,
1978; Hwang and Van Woert, 1980) . PCA promoted the release of serotonin and dopa
mine (McKenna et al., 1991), and inhibition of serotonin reuptake (Huang et al., 1 992) .
Substituted amphetamines MOMA, methamphetamine, PCA, and fenfluramine t o induce
synaptosomal serotonin release were compared using a novel microassay system (Berger
et al., 1992) . Several compounds were synthesized and assayed for their ability to inhib
it MAOA and MAOB. Most were potent against MAOA; none were appreciably active
against MAOB (Gallardo-Godoy et al., 2005).

PCA / PEA
Rabbit hyperthermia studies to correlate phenethylamine structure with psychedelic activ

ity included PCA (Aldous et al., 1 974) . PCA-induced hyperthermia was later shown to be
pharmacologically distinct from fenfluramine-induced hyperthermia (Quock and Weick,
1979).
Pharmacology
Behavioral effects of PMeA, PCA, and PFA in animals were used to predict psychedelic
effects in humans (Beaton et al., 1968) . However, PCA produced aggression and increased
locomotor activity in male mice (Gianutsos and Lal, 1975), and significant decreases in the
intake of ethanol, saccharin, food, and water (Stein et al., 1978a,b). PCA increased urination
and defecation, salivation, locomotor activities, and body weight losses in the rat (Stein et
al., 1981), and affected locomotor activity and serotonin levels in neonatal and adult rats
(Lucot et al., 1981 ) .
Effects o f PCA o n locomotor activity and brain 5-hydroxyindoles were observed (Messing
et al., 1 976), and behavioral evidence was given for the rapid release of CNS serotonin by
PCA and fenfluramine (Trulson and Jacobs, 1976) .
We have been unable t o locate reports o n psychedelic, stimulant, o r anorectic activity o f

PCA i n humans.
Legal Status
PCA is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#107. PEA
2-Phenylethanamine
Phenethylamine
Ethanamine
NSC 1 0811
(PEA can also mean p-ethoxyamphetamine)
Registry Numbers
CAS # CAS # CAS #
HCl salt [60-19-5] x-Sulfate [71750-39-5] a-[ 11 C] Freebase [79482-02-3]
HBr salt [53916-94-2] Acid salt [32218-88-5] a-[ 1 3C] Freebase [67519-19-1]
HI salt [151059-43-7] Freebase [64-04-0] a-[ 1 4C] HCl salt [114307-16-3]
Acetate [24722-38-1 ] �-[d2] HCl salt [95864-27-0] a-[ 1 4C] Freebase [ 85336-78-3]
Bisulfate [209064-25-5] �-[d2 ] Freebase [101153-74-6] �-[14C] HCl salt [ 42006-59-7]
Carbonate [855383-01-6] a,a-[d2 ] Freebase [77970-78-6] �-[ 1 4C] Freebase [77956-20-8]
Nitrate [120375-47-5] a,�-[ dJ Freebase [81541-03-9] [1 3N] Freebase [102415-94-1]
Phosphate [127755-12-8] a,�-[d4 ] Freebase [87620-08-4] [ 1 5N] HCl salt [155755-37-6]
Picrate [25566-62-5] Ring [d ]-labeled [912627-99-7] [ 15N] Freebase [41498-55-9]
5
Sulfate [5471-08-9]
Natural Sources
PEA has been found in the cacti Islaya minor, Pereskia autumnalis, P. pititache, P. tampicana,
and Pereskiopsis chapistle (Doetsch et al., 1980), and Turbinicarpus species (Starha et al., 1 999).
PEA is present in the stems (and to a lesser extent, the roots) of Alhagi pseudalhagi (Ghosal
and Srivastava, 1973b), in Desmodium gangeticum (Ghosal and Bhattacharaya, 1 972), and D.
triflorum (Ghosal et al., 1973) .

PEA
PEA was isolated from Haloxylon salicornicum (El-Shazly et al., 2005). PEA was reported to
be present in Acacia berlandieri (Clement et al., 1997) and A. rigidula (Clement et al., 1998) .
Phenethylamine was found in peanut oil and chocolate (Hurst et al., 1982) .

From benzene (with ethyleneimine, AlC13 ) to PEA (Braz, 1952) .
From benzyl cyanide (with Ni, H2; Sasa, 1954), or (with Fe black and Co black cathodes;
Krishnan and Muthukumaran, 1983) to PEA.
Syntheses of several phenethylamines described, with comparison of reduction methods

(Liu and Cui, 2002).

m I z: 121 .0891 (100.0% ), 122.0925 (8.7% )
Elemental Analysis: C, 79.29; H, 9.15; N, 11 .56
HCl salt m.p. 218.5-220 °C (Braz, 1952)

HCl salt 216-21 7 °C (Sasa, 1954)
Freebase b.p. 84 °C I 12 mm (Braz, 1952)
Freebase b.p. 95-102 °C / 26 mm (Sasa, 1954)
(Kappe and Armstrong, 1965); a quantitative colorimetric screening method was described
for urine analysis (Rutter, 1972), and TLC methods were described (Bussey and Backer,
1974) . Synthesis, TLC and Gas chromatographic properties, UV spectra, and other physical
properties were reported (Ono et al., 1976) . Analysis of phenethylamine, tyramine, and oc
topamine from human plasma by GC / MS of the trifluoroacetate derivatives was described
(Baker et al., 1980). The conformation of the aryl methoxy groups of several psychedelics
was established by [ 13 C]-NMR spectral analysis (Knittel and Makriyannis, 1981), and [ 13 C]
NMR spectra for methoxylated phenethylamines and amphetamines were shown to be
distinctive and suitable for identification (Bailey and Legault, 1983). Analysis by HPLC
employing fluorescamine derivatization for detection was described (Shimamine, 1 984) .
An exacting crystallographic analysis was made of PEA (Horn et al., 1 990). FTIR spec
tral analysis was used for PEA identification (Praisler et al., 2000) . Fragmentation patterns
techniques (Kolliker and Oehme, 2004) . Identification of phenethylamines with IR data
analyzed with neural networks and neural networks coupled with principal component
analysis was reported (Gosav et al., 2005). Assay of PEA in rat brain and human CSF by
chemical ionization GC / MS was reported (Lauber and Waldmeier, 1984), and quantitative
determination of PEA in human blood plasma was achieved by GC / MS analysis of the
heptafluorobutyrate amides (Habrdova et al., 2005).

a- �- N- Name CAS # Ref
-- --
-- PEA (this entry)
-- --
Me2 N,N-MePEA -
[1126-71-2] (1-8)

PEA
a- f3- N- Name CAS # Ref

-- -- Et N-EtPEA [22002-68-2] (9)
-- -- Pr N-PrPEA [27906-91-8] (9)
-- -- iPr N-iPrPEA [52007-97-3] (9)
-- -- -CCCCC- pip-PEA [1135-33-7] (3,10)
-- HO -- f3-HO-PEA [7568-93-6] (3)
-- HO Me2 f3-HO-N,N-Me-PEA [1 797-76-8] (3)
-- Me Me f3,N-MePEA [ 5969-39-1 ] (11-13)
-- Me Et f3-Me-N-Et-PEA [91339-14-9] (14)
Me -- HO AMPH-OH [114562-60-6] (15)
Me -- Me2 DIME TH [33286-27-0] (5,6, 16, 1 7)
Et -- -- AEPEA [30543-88-5] (7,8)
-C- -- cPr-PEA [3721-28-6] (18,19)
(2) Effect on alkaline phosphatase activity and pyruvate utilization in rat brain homogenates and
supernatants (Clark et al., 1956).
(3) Effective in releasing cardiac norepinephrine in the mouse (Daly et al., 1966).
(4) Spasmolytic activity on isolated rabbit small intestine (Stolyarchuk et al., 1975).
(5) Reported present in Acacia berlandieri (Clement et al., 1997).
(7) Analysis of human urine by LC-MS-MS (Nordgren et al., 2005).
(8) Evaluated as an MAO inhibitor (Vallejos et al., 2005).
(9) Correlation between structure and locomotor activity of mice (van der Schoot et al., 1962).
(10) The nitrogen is of a piperidine ring.
(11) Vonedrine (f3,N-dimethylphenethylamine) has therapeutic adrenergic activity (see Merck Index,
1996; #7462).
(15) Discriminative stimulus properties against DOM observed in rats (Glennon et al., 1988d).
(16) Baboons trained to self-inject cocaine were switched to MDA, MDOH, DIMETH, and 2C-B;
changes in behavior were noted (Sannerud et al., 1996).
(17) An NMR procedure for identification of drugs (Hays, 2005).
(18) Quantitative colorimetric urine screening method for urine analysis (Rutter, 1972).
(19) R-Isomer sulfate salt.
With Other Than 2-Carbon Chains

Chain a,f3- N- Other Name CAS # Ref
1 -- -- -- benzylamine [100-46-9] (1)
1 a-Me -- -- a-Me-benzylamine [61 8-36-0] (2,3)
1 -- -- 4-MeO 4-M-benzylamine [2393-23-9] (1)
3 -- -- -- homo-PEA [2038-57-5] (4,5)
3 f3-Me Me -- homo-f3,N-MePEA [1041 78-02-1] (6)
(1) Effects on rat brain enzymes (Clark et al., 1956).
(2) Quantitative colorimetric urine screening (Rutter, 1972).

PEA
(3) Synonyms: APEA and NSC 8391.

(4) homo-PEA was assayed for serotonin receptor site activity (Glennon et al., 1980a).
(5) Correlation between structure and locomotor activity of mice (van der Schoot et al., 1962) .
(6) homo-f3,N-MePEA acts o n oxidative and hydrolytic enzymes i n the brain (Clark e t al., 1956).
Biochemistry
[ 1 4 C]-labeled PEA was used to explore the biosynthesis of mescaline in Lophophora williamsii
(Lundstrom and Agurell, 1968b).
PEA action on isolated frog heart was studied (Ellis, 1 949) . Effects on the sensitivity of
acetylcholine-reactive receptors in peripheral vascular systems were studied in the cat
(Matthies, 1957) . Effects of PEA were evaluated on alkaline phosphatase activity and pyru
vate utilization in rat brain homogenates and supernatants (Clark et al., 1956), and on the
dog peroneal tibialis anticus nerve muscle (Schopp and Walsh, 1964) . Release of cardiac
norepinephrine was measured in the mouse heart (Daly et al., 1966) . Spasmolytic activity
was observed on isolated rabbit small intestine (Stolyarchuk et al., 1975) . Effect of PEA on
intraocular pressure was studied in the rabbit (Miyake et al., 1 979) . Direct effects of PEA
upon isolated rat aortic strip were noted (Hansen et al., 1980) .
The effects of ring methoxy groups on oxidative deamination of phenethylamines were

evaluated (Clark et al., 1965) . PEA was investigated as a monoamine oxidase inhibitor in
the rat liver (Takagi and Gomi, 1966) . Imipramine inhibited deamination of PEA by mono
amine oxidase (Roth and Gillis, 1974) .
PEA is a constituent of tissue extracts, and was suggested as a regulatory compound of

cardiac health (Jackson and Temple, 1970); effects of PEA on spontaneous motor activity in
mice were also observed (Jackson, 1972) . Distribution of PEA in discrete regions of the rat
brain and its effect on brain noradrenaline, dopamine, and serotonin levels were described
(Jackson and Smythe, 1973) . Pharmacokinetics in the rat brain, liver and plasma were stud
ied (Cohen et al., 1974) .
PEA, PBA, and PFA were compared as to their effects on the metabolism of serotonin in
rat brain (Fuller et al., 1975a) . Mechanisms were characterized for hyperactivity induction
from the nucleus accumbens by phenethylamine derivatives (Costall et al., 1 976) . Sero
tonin receptor site affinity was determined (Glennon et al., 1980a) .
The human metabolism of PEA was observed after oral administration of deuterium-la
beled PEA. The major metabolite was phenylacetic acid, but 3-HPEA and 4-HPEA were
detected in significant amounts along with their respective hydroxylated phenylacetic ac
ids (Davis and Boulton, 1980) .
Phenethylamine metabolism to tyramine by postmortem human brain preparations was

confirmed (Wolf et al., 1987) .
Pharmacology
A correlation between structure and the locomotor activity of mice was made (van der
Schoot et al., 1962) . Action on the iris of the cat was studied (Marley, 1962), as was action on
the CNS of the chicken (Dewhurst and Marley, 1965). Oxidative deamination and effects
on cat behavior were observed (Clark et al., 1964) . Cardiovascular actions of PEA in dogs
were suggested, likely due to release of endogenous norepinephrine from the adrenergic

PEA / PeMPEA
nerve endings (Liang and Sprecher, 1979). Tolerance development to a disruptive effect of
PEA on a learned behavior in rats was noted (Stoff et al., 1979) .
A relationship between psychedelic activity and electronic configuration was established

(Snyder and Merril, 1965), and the relationship between partition coefficients, steric bulk,
and in vitro activity was used to predict psychedelic potency in humans (Nichols et al.,
1977) . In a large number of methoxylated amphetamines, rabbit hyperthermia paralleled
human potency as a psychedelic (Anderson et al., 1978b).
Phenethylamine administration to rhesus monkeys produced behavioral effects reminis

cent of amphetamines, but did not produce tolerance. Implications in the physiology of
schizophrenia were addressed (Tinklenberg et al., 1978) . Urinary PEA excretion was sig
nificantly higher in paranoid chronic schizophrenics than in normal controls (Potkin et al.,
1979), and was elevated in humans after profound stress (Paulos and Tessel, 1982) .
An orally active psychedelic dose level in humans was not reached at 1 600 mg; any effect
duration is unknown (Shulgin and Shulgin, 1991).
Legal Status
PEA is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#108. PeMPEA
2-(2,3,4,5,6-Pentamethoxypheny l)ethanamine
Pentamethoxyphenethylamine
2,3,4,5,6-Pentamethoxyphenethylamine
Registry Numbers
CAS #
HCl salt [3167-09-7]
Freebase [13022-04-3]

From pentamethoxybenzene (with chloromethyl ether and glacial acetic acid) to penta
methoxybenzyl chloride; (with potassium cyanide) to pentamethoxybenzylnitrile; (with
LAH) to PeMPEA (Benington et al., 1955a) .

m / z: 271 . 1420 (100.0% ), 272.1453 (14. 1 % ), 273.1462 (1 .0%)

2- 3- 4- 5- 6- a- Name CAS # Ref
Cl Meo Meo Meo Cl -- 2,6-CM [ 65995-44-0] (1)
Br Meo Meo MeO Br -- 2,6-BM [40393-73-5] (2)
Me Me Me Me Me -- PeMePEA [3167-13-3] (3,4)
Me Me Me Me Me Me PeMeA [32156-21-1] (5)

PeMPEA / PHA
2- 3- 4- 5- 6- a- Name CAS # Ref

Meo Me Me Meo Me -- 3,4,6-Me-2,5-DMPEA [ 861007-05-8] (6,7)
Meo Meo Meo Meo Meo -- PeMPEA (this entry)
Meo Meo Meo MeO MeO Me PeMA [23693-29-0] (8)
Meo -OCO- Meo Meo Me TMMDA [22969-85-3] (9)
(1) 2-CM was an artifact in the isolation of mescaline from Trichocereus peruvianus; 2,6-CM is syn
thetic (Pardanani et al., 1977).
(2) Studies were made of injection into the rat optic nerve and the cat sciatic nerve (Paulson and
McClure, 1973).
(3) Pharmacological studies in the cat (Clark et al., 1964).
(5) Correlation between native fluorescence and psychedelic potency in humans (Antun et al., 1971 ) .
(6) Effects o n alkaline phosphatase activity and pyruvate utilization i n rat brain homogenates (Clark
et al., 1956).
(7) For the pentamethyl analogue, see # 123.
(8) Human potency affected by changes in substitution patterns (Shulgin et al., 1969).
(9) Synthesis (Dallacker, 1969).
Biochemistry
Effect on alkaline phosphatase activity and pyruvate utilization were studied with rat
brain homogenates and supernatants (Clark et al., 1956). Effects of ring methoxy groups
on oxidative deamination were evaluated (Clark et al., 1965). Physiological disposition and
pharmacokinetics were evaluated in rat brain liver and plasma (Cohen et al., 1974) .
Pharmacology
Enzymatic oxidative deamination and effects on cat behavior were studied (Clark et al.,
1 964) . A series of mono-, di-, tri,- tetra- and penta-methoxylated phenethylamines was test
ed on rats trained with various avoidance programs; only PeMPEA, TeMPEA, and mes
caline showed activity; potency increased with increased degree of substitution (Smythies
et al., 1967a) . Several phenethylamines and tryptamines were compared in discrimination
stimulus studies with rats (Kier and Glennon, 1978b). Using molecular connectivity analy
sis of ten psychedelic phenethylamines, the importance of the 2,5-positions of the methoxy
groups, and the 4-substituent was demonstrated (Glennon et al., 1979a).
Human activity of PeMEA us unknown.
Legal Status
PeMPEA is not a scheduled compound under federal drug law, or under District of Colum
#109. PHA
4-(2-Aminopropyl)phenol
4-HA
4-Hydroxyamphetamine
p-Hydroxyamphetamine
a-Methyltyramine
Norveritol
Paredrine
Paredrinex

PHA
Pedrolon
Pulsoton
NSC 61065
NSC 1 70995
Registry Numbers
CAS # CAS #
HCl salt [876-26-6] R-Isomer HBr salt [41509-97-1]
HBr salt [306-21-8] S-Isomer HBr salt [41509-98-2]
HI salt [61 70-28-1] R-lsomer sulfate [13990-47-1]
Acid salt [33462-22-5] R-lsomer-R,R-tartrate [151 8-88-3]
Mandelate [94753-97-6] R-Isomer-S-mandelate [1518-91-8]
Sulfate [23771-48-4] S-Isomer-R,R-tartrate [151 8-87-2]
Freebase [103-86-6] S-Isomer-R-mandelate [1518-90-7]
R-Isomer HCl salt [ 67323-60-8] a,f3-[ d2] HCl salt [64357-23-9]
S-Isomer HCl salt [71295-78-8] a, f3-[d2 ] HBr salt [38875-32-0]
R-Isomer freebase [1518-89-4] f3-[ 3H] [ 58278-83-4]
S-Isomer freebase [1693-66-9] f3-[1 4C] HCl salt [ 60756-93-6]
Natural Sources
Reported to be present in Acacia berlandieri (Clement et al., 1997), A. rigidula (Clement et al.,
1998), and Haloxylon salicornicum (El-Shazly et al., 2005) .

From PMA (with red P, HI) to PHA (Mannich and Jacobsohn, 1910).
From 4-methoxyamphetamine (with cone. HCl, heating, pressure) to PHA (Alles, 1 932) .
From PMA (with HCI) (Woodruff and Conger, 1938) .

m / z: 151.0997 (100.0% ), 152. 1 031 (9.7% )
HCl salt m.p. 1 71-1 72 °C (Alles, 1932)

HCl salt m.p. 1 70 °C (Woodruff and Conger 1938)
HCl salt m.p. 1 71-172 °C (Shulgin and Shulgin, 1991) (aq. ethanol)
HI salt m.p. 155 °C (Mannich and Jacobsohn, 1910)
Freebase m.p. 125-126 °C (Mannich and Jacobsohn, 1910) (benzene)
HPLC separation techniques for the identification of drugs addressed this compound
(Cashman et al., 1973) . A method for the rapid forensic identification of phenethylamines
is described using TLC in six different solvent systems and five color reactions (Neuninger,
1987) . Cross-reactivity of several substituted amphetamines was evaluated with the Roche
Abuscreen® radioimmunoassay for amphetamine (Cody, 1990a) . HPLC-UV analysis of hu
man urine could detect amphetamine (and its metabolite PHA), MDMA (and its metabo
lite, MDA), 2C-B, and MTA (Soares et al., 2004) .

N- f3- Name
- ·-- � ------"--
CAS # Ref
- -----� ----- - --�----- - --
-- -- PHA (this entry)

-
- HO f3-HO-PHA [552-85-2] (1,2)

PHA
N- f3- Name CAS # Ref

Me -- Pholedrine [370-14-9] (3-9)
Me HO f3-HO-HMA [365-26-4] (10-13)
(1) Pressor-activity rating was predicted by molecular structure pattern recognition (Zotov and
Altymyshev, 1980).
(2) Kinetics of mydriatic action of f3-HO-DHA on mouse iris (Freundt, 1973).
(3) Synonyms: Pholedrin, Isodrin, Knoll H75, Pressitan, Pulsotyl, Veritol, Paredrine, 4-hydroxy-
methamphetamine.
(4) A major metabolite of PMMA in the rat (Staack et al., 2003a).
(5) Effects on renal blood flow in dogs (Aviado et al., 1958).
(6) Action on the iris of the cat (Marley, 1962)
(7) Clinical uses include antihypotensive action and circulatory stimulation (see Merck Index, 1996;
#7485).
(8) Effects on acetylcholine-reactive receptors in peripheral vascular systems (Matthies, 1957).
(9) Interaction with the liver enzyme CYP2D6 (Wu et al., 1997).
(10) Synonyms for the R,S-isomer: Oxilofrine, p-hydroxyephedrine, Methylsympatol, Suprifen.
(11) Analysis of the R,S-isomer phosphate salt crystal properties (Datta et al., 1994).
(12) Studies, in humans, on oxygen consumption, blood pressure, pulse rate, and cardiac minimum
volume (Liljestrand and Linde, 1933; Fasching, 1937).
(13) With s.c. injection, cardiac output and pulmonary ventilation increased in dogs and humans
(Oremus, 1938).
Biochemistry
Action on isolated frog heart was studied (Ellis, 1949) . Inhibition of tyramine transformation
by amine oxidase was observed (Fellows and Bernheim, 1950) . Agonist and antagonist
activity with dopamine (3-oxidase was revealed (Creveling et al., 1962) . Effectiveness at
releasing cardiac norepinephrine was measured in the mouse (Daly et al., 1966) . Potency
as an inhibitor of phenethanolamine N-methyltransferase was determined (Fuller et al.,
1971), and chemical structure was correlated with phenethanolamine N-methyltransferase
reactivity (Hansch and Glave, 1972) . Incubation of 4-alkoxyamphetamines with yeast
or fungal microorganisms yielded primarily PHA with traces of the N-acetyl derivative
(Foster et al., 1 990) . PMA and 4-EA were compared with amphetamine in rats employing
a subcutaneous infusion for up to 14 days (Martin-Iverson and Lodge, 199 1 ) . Interaction
with the liver cytochrome P450 enzyme CYP2D6 was evaluated (Wu et al., 1997) . Effects
on intrauterine development, pregnancy outcome, postnatal growth, and survival were
compared in Swiss-Webster mice (Buttar et al., 1996) . The role of the metabolite PHA in the
toxicity of PMA was evaluated (Kaminskas et al., 2002).
Pharmacology
Effects of PHA on pulmonary circulation (Aviado et al., 1957) and renal blood flow (Aviado
et al., 1958) were measured in the dog. PHA effects on catecholamine excretion were studied
in humans (Vonstudnitz, 1965). A correlation was made between the energy of the highest
occupied molecular orbital of the drug and psychedelic potency in humans (Kang and
Green, 1970) . Behavioral and neurochemical effects of psychedelic drugs were evaluated
in neonate chicks (Wallach et al., 1972a) . PHA was evaluated in rats trained to discriminate
d-amphetamine from saline (Huang and Ho, 1974a); pressor-activity rating was predicted
by pattern recognition of molecular structures (Zotov and Altymyshev, 1980).
[ 14 C]-labeled PHA, administered to rats, guinea pigs, and human subjects was excreted
in the urine within 24 hours; humans excreted it as the sulfate ester (Sever et al., 1 976) .

PHA / PMA
Rat brain microsomes contain a cytochrome P450-dependent monooxygenase, which

synthesized catecholamphetamine from PHA; the formation of this metabolite may be
involved in the development of tolerance in chronic amphetamine use (Hoffman et al.,
1979) . PHA is a metabolite of EA (Matsushima et al., 1998) .
Human activity of PHA is unknown.
Legal Status
PHA is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#110. PMA
1-(4-Methoxypheny l)propan-2-amine
Paramethoxyamphetamine
Paramethoxy-a-methy lphenethylamine
p-Methoxy-a-methy1 phenethylamine
1-p-Methoxyphenyl-2-aminopropane
1 -p-Methoxyphenyl-2-propylamine
2-(4-Methoxyphenyl)-1-methylethylamine
2-Amino-1-(4-methoxyphenyl)propane
4-Methoxy-a-methylbenzeneethanamine
4-Methoxy-a-methylphenethylamine
4-MA
Chicken Power
Chicken Yellow
Death
White Mitsubishi
NSC 32757
Registry Numbers
CAS # DEA# CAS #
HCl salt [3706-26-1 ] 7412 R-(-)-Isomer tartrate [ 67346-52-5]
dl-HC1 salt [52740-56-4] 7414 S-( +)-Isomer tartrate [ 67346-53-6]
Sulfate salt [6461 0-41-9] 7413 R-(-)-Isomer freebase [58993-79-6]
Acid salt [87059-53-8] S-( +)-Isomer freebase [ 58993-78-5]
di-Freebase [ 23239-32-9] 7283 R-a,f3-[d2] Isomer HCl salt [38875-30-8]
Freebase [64-13-1] 7411 f3-[ 14C] HCI salt [ 60756-92-5]
R-(-)-Isomer HCl salt [50505-80-1 ]
S - (+)-Isomer HCl salt [50505-81-2]
Natural Sources
Reported to be present in Acacia rigidula (Clement et al., 1998).

From 4-methoxyphenylacetone (with hydroxylamine) to 4-methoxyphenylacetone oxime;
(with Na, Hg, acetic acid) to PMA (Mannich and Jacobsohn, 1910).
From anisaldehyde (with nitroethane, acetic acid, and ammonium acetate) to

1 -(4-methoxyphenyl)-2-nitropropene; (with electrolysis, Hg, Pd) to PMA (Alles, 1932) .

PMA
From 4-methoxybenzaldehyde (with methylethyl ketone, hypohalite) to 4-methoxy-a

methylcinnamic acid; (with H2) to 4-methoxy-a-methyldihydro-cinnamic acid; (with
SOC12, NH3 ) to 4-methoxy-a-methyldihydrocinnamamide; (with Br2, KOH) to PMA
(Woodruff and Conger, 1938) .
From anethole (with NaN02) to anethol-[3-pseudonitrite; (with NH3, EtOH) to [3-nitroane

thole; (with Fe, NH20H) to 4-methoxyphenylacetone oxime; (with Na, Hg) to PMA (Sav
itskii and Makhnenko, 1940; Dessi, 1952) .
From anethole (with Pb(OAc) 4 ) to 1-(p-methoxyphenyl)-1,2-diacetoxypropane; (with

H2S04 ) to 4-methoxyphenylacetone; (with formamide, then 20% NaOH in ethanol) to PMA
(Doeuvre and Chervet, 1947) .

1 -(4-methoxyphenyl)-2-nitropropene; (with LAH) to PMA (Moed et al., 1955; Shulgin and
Shulgin, 1991).
From anisole (with methacrylonitrile, A1Cl3 ), to 4-(3-cyanopropyl)anisole; (with saponifi

cation) to the corresponding amide; (with NaBrO) to PMA (Grebenyuk, 1972) .
From 4-methoxyphenyl acetone (with R-(+)- (or 5-(-)-) a-methylbenzylamine, Raney Ni,
H2) to R,R-( +)- (or 5, 5-(-)-) N-(a-phenethyl)-4-methoxyphenylisopropylamine (with Pd / C,
H2) to R-(-) (or 5-(+)-) PMA (Nichols et al.,1973) .

1-(4-methoxyphenyl)-2-nitropropene; (with Pd / C, H2) to PMA (Ohshita and Ando, 1992) .
From anisaldehyde (with 2-(dimethoxyphosphinyl)propanoic acid ethyl ester) to the cou

pled ester, to the amide; (with Br2, NaOH) to PMA (Mereyala and Koduru, 2001).
Synthesis methods compared for yield (Liu and Cui, 2002).
From anethole (with performic acid) to 4-methoxyphenylacetone; (with formic acid, NH3 )
to PMA (Waumans et al., 2003a) .

m / z: 165.1154 (100.0% ), 166. 1187 (10.8% )
HCl salt m.p. 210 °C (Mannich and Jacobsohn, 1910) (EtOH)

HCl salt m.p. 205-206 °c (Woodruff and Conger, 1938)
HCl salt m.p. 210-211 °C (Savitskii and Makhnenko, 1940)
HCl salt m.p. 208-209 °C (Doeuvre and Chervet, 1947)
R-(-)-Isomer HCl salt m.p. 251-253 °C [aJ;gi -22.5° (Nichols et al., 1973)
5-(+)-Isomer HCl salt m.p. 250.5-251 .5 °C [aJ;gi +22.4° (Nichols et al., 1973)
Freebase b.p. 158 °C / 15 mm (Mannich and Jacobsohn, 1910)
Freebase b.p. 142-144 °C / 25 mm (Savitskii and Makhnenko, 1940)
Freebase b.p. 129-132 °C / 8 mm (Moed et al., 1955)

PMA
Identification of 2-, 3-, and 4-methoxyamphetamines and corresponding methylamphet

amines was achieved through comparison of UV, NMR, IR, and mass spectra; TLC and GC
systems for distinguishing these isomers were also specified (Bailey et al., 1 974b). Synthe
sis, TLC and GC chromatographic properties, UV spectra, and other physical properties
were also reported (Ono et al., 1976) . TLC and color tests were defined for the identification
of substituted amphetamines (O'Brien et al., 1982) .
1971 ) . NMR spectral shifts with europium reagents were reported (Smith et al., 1976) . The
conformation of the aryl methoxy groups of several psychedelics was established by [ 13 C]
NMR spectral analysis (Knittel and Makriyannis, 1981); [ 13C]-NMR spectra for methoxy
amphetamines were also shown to be distinctive and suitable for identification (Bailey et
al., 1981; Bailey and Legault, 19
HPLC analysis employing fluorescamine derivatization for fluorescence detection was re
ported (Shimamine, 1984) . Synthesis, chromatographic characterization, and mass spec
tral analysis were performed (Noggle et al., 1989c) . Procedures employing HPLC and
photodiode-array detection were developed to analyze plant and urine samples for PMA
and other phenylalkylamines (Helmlin and Brenneisen, 1992) . Analysis and identification
by capillary electrophoresis was reported (Trenerry et al., 1 995) . PMA analytical methods
were developed for urine and plasma samples as the pentafluorobenzamide derivatives,
by GC with electon capture detection (Midha et al., 1979a), and with derivatization with
heptafluorobutyryl-L-proline for chiral analysis by GC (Srinivas et al., 1 989), for GC analy
sis as the heptafluorobutyl derivative (Lillsunde and Korte, 1991), in biological fluids by
chemical ionization GC / MS (Mariani et al., 1999), and for GC / MS analysis of serum by
extraction, and derivatization with trifluoroacetic anhydride (Hidvegi et al., 2006). PMA
was identified by a rapid planar chromatographic screening method (Fater et al., 1998).
Analytical details were presented for distinguishing between 2-MA, 3-MA, and PMA,
and their synthetic precursors (Dal Cason, 2001 ) . Identification of PMA by LC / MS was
reported (Mortier et al., 2002), and plasma screening with GC / MS was described (Peters et
al., 2003). The MS fragmentation patterns of some fifty-five phenethylamines were deter
mined by a variety of mass spectrometry techniques (Kolliker and Oehme, 2004) .
The presence of a substituted pyrimidine in a street-sample of PMA suggested the use of

the Leuckart reaction in its synthesis (Kirkbride et al., 2001 ) . A neolignan-type compound
has also been observed in street samples, and has been used as a forensic marker (cf:
Waumans et al., 2004a, 2004b ). In street samples, both p-methoxyphenol (Waumans et al.,
2003b) and 1-( 4-methoxyphenol)-1-aminopropane (Waumans et al., 2004a) were reported;
this report also identified the three-carbon chain analogue of PMA (with the amino group
on the benzylic carbon) as an impurity.
4-Methoxyphenylacetone was converted to the R-isomer of PMA by a bacterial culture

(Nabe et al., 1988), and microorganisms fed L-alanine were effective in converting 4-me
thoxyphenylacetone to the 5-(+)-isomer of PMA (Nakamichi et. al., 1990). Optically active
PMA was synthesized from the corresponding ketone by bacteria (Sato et al., 1990; Iwasaki
et al., 2006) .

PMA

4- a- f3- N- Name CAS # Ref
HO Me -- Me2 PHMMA [69792-61-6] (1,2)
HO Me -- Et PHEA [ 69389-96-4] (3)
HO Me -- Bu N-Bu-PHA [ 855400-90-7] (2)
HO Et -- -- a-Et-4-HPEA [100131-85-9] (2)
Meo Me -- -- PMA (this entry)
MeO Me2 -- -- a,a-Me-PMPEA [ 56490-94-9] (4)
--
MeO Me Me2 N,N-Me-PMA [26070-48-4] (5-11 )
MeO Me -- Et N-Et-PMA [14367-46-5] (12-16)
Meo Me -- Pr N-Pr-PMA [93309-51-4] (8, 1 7)
Meo Me -- iPr N-iPr-PMA [124206-65-1 ] (8,16)
Meo Et -- -- a-Et-MPEA [78108-18-6] (18,19)
EtO Me -- -- 4-EA [129476-58-0] (20-30)
MeO Me HO -- f3-HO-PMA [50802-67-0] (31 )
Meo Me HO Pr f3-HO-N-Pr-PMA [108873-47-8] (32-33)
-
Meo Me - HO N-HO-PMA [1454-68-8] (34)
Meo Me C=O -- PMA-f3k [42416-75-1] (35)
EtO Me -- Me 4-EtO-METH [827611-18-7] (36,37)
EtO Et -- -- 4-EtO-a-EtPEA [827611-21-2] (36,37)
Pro Me -- -- 4-PA [129476-60-4] (26,38)
PhO Me -- -- PPhA [32560-67-1] (39,40)
BzO Me -- -- 4-BzA [7176-39-8] (25,26,38)
(1) Action on isolated frog heart (Ellis, 1949).

(2) Effects on the oxidation of tyramine by amine oxidase (Fellows and Bernheim, 1950).
(3) A metabolite of EA (Matsushima et al., 1998).
(4) Effect on release of serotonin from rat synaptosomes (Nichols et al., 1982).
(5) Evaluated as a bronchodilator in comparison to 2-MMA (Graham and Kuizenga, 1948).
(6) Among several psychedelic drugs verified in the Japanese street drug scene (Katagi et al., 2002).
(7) Synthesis and reaction with [18F] acetyl hypofluorite (Mathis et al., 1986a).
(8) Synthesis described; chromatographic characterization and mass spectral analysis (Noggle et.
al., 1989c).
(10) NMR spectral shifts with europium agents (Smith et al., 1976).
(11) Behavioral effects in rats (Smythies et al., 1970).
(12) Made illegal in Maine in 200 1 .
(13) Synthesis (Woodruff e t al., 1940; Fusco and Caggianelli, 1948; Casale e t al., 2006).
(14) PMEA evaluated as a bronchodilator, with comparison made to Orthoxine (2-MMA) (Graham
and Kuizenga, 1948).
(15) Synonyms: PMEA, N-ethyl-4-methoxyamphetamine.
(16) Synthesis (Fusco and Caggianelli, 1948).
(17) Correlation between structure and the locomotor activity of mice (van der Schoot et al., 1962).
(18) Microorganisms fed L-alanine were effective in converting 4-(methoxyphenyl)-2-butanone to
the S-( +)-isomer of a-Et-MPEA (Nakamichi et al., 1990).

PMA
(19) Fragmentation patterns of some fifty-five phenethylamines determined by a variety of mass

spectrometry techniques (Ki:illiker and Oehme, 2004).
(20) The code 4-EA is used to avoid confusion with PEA, a common abbreviation for phenethylamine.
(21 ) MAOI properties evaluated (Scorza et al., 1997).
(22) Compounds synthesized and assayed for ability to inhibit MAOA and MAOB. Most were potent
against MAOA; none were appreciably active against MAOB (Gallardo-Godoy et al., 2005).
(23) PMA and 4-EA compared with amphetamine in rats employing a subcutaneous infusion for up
to 14 days (Martin-Iverson and Lodge, 1991 ).
(24) Changes in rat brain chemistry were studied following long-term exposure to PMA (Martin
Iverson and Lodge, 1991).
(25) Binding at 5-HT 1 c and 5-HT2 receptors (Glennon et al., 1992).
(26) The effects on intrauterine development, pregnancy outcome, postnatal growth, and survival
were compared in Swiss-Webster mice (Buttar et al., 1996).
(27) 4-EA appeared in street sales in Canada in 1986 (By et al., 1991 ).
(28) Synthesis and spectral characterization (By et al., 1991 ).
(29) Brain changes were observed following the s.c. administration of amphetamine, PMA, and 4-EA
to rats (Martin-Iverson and Lodge, 1991 ).
(30) Studies to ascertain whether PMA and 4-EA maintain self-administration behavior, and if they
(and amphetamine) maintain drug discrimination properties (Corrigall et al., 1992b).
(32) The chemical structure drawn in Chemical Abstracts was for the para-methoxy isomer, but the
name stated was the ortho-isomer. The latter is unreported in the scientific literature.
(34) Metabolite of PMA (Beckett and Midha, 1974).
(36) Analysis by non-polar GC and MS comparison to MDMA (Aalberg et al., 2004) .
(37) Analysis by LC and ESI-MS-MS, with comparison to MDMA (Pihlainen et al., 2005).
(38) Incubation with yeast or fungal microorganisms yielded primarily PHA with trace evidence of
N-acetylation (Foster et al., 1990).
(39) Potency as an inhibitor of phenethanolamine N-methyltransferase determined (Fuller et al.,
1971 ).
(40) Correlation of chemical structure and phenethanolamine N-methyltransferase reactivity (Han
sch and Glave, 1972).
Homologue with a 3-Carbon Chain

a- Name CAS # Ref
Me homo-PMA [51062-15-8] (1)
Biochemistry
Metabolism of PMA in guinea pig, rabbit and rat liver preparations yielded 4-methoxy
phenylacetone, 4-methoxyphenylisopropanol, p-methoxyphenyl-propanone oxime, and
N-HO-PMA (Beckett and Midha, 1974) . In dogs, PMA was excreted 26% unchanged, 13%
as PHA (largely unconjugated), and also as 4-hydroxybenzoic acid; in rhesus monkeys, 3%
of the PMA dose was excreted unchanged and 44% as PHA, largely conjugated (Hubbard
et al., 1977) . Stereospecific metabolism was determined by GC / MS of the (S)-a-methoxy
a-(trifluoromethyl)phenylacetylamides (Gal, 1978) . The dog and monkey metabolize
PMA to form MHA, 3-hydroxyphenylacetone, 4-hydroxyphenylacetone, and possibly
its (:3-hydroxy analogue (Hubbard et al., 1981). Biotransformation was studied with 2-, 3-,
and 4-methoxyamphetamine by Cunninghamella echinulata (Foster et al., 1991); the rate of
demethylation to p-hydroxyamphetamine was intermediate between the rates for the or-

PMA
tho- and meta-isomers. In human liver microsomes, the cytochrome P450 enzyme CYP206
0-demethylated PMA to the hydroxy metabolite; the reaction was negligible in CYP206-
deficient liver microsomes (Wu et al., 1997) . In the rat, PMA was a minor metabolite of
PMMA (Staack et al., 2003a) .
Correlation was made between the chemical structure and phenethanolamine N-methyl
transferase reactivity (Hansch and Glave, 1972) . PMA was a potent inhibitor of brain
MAOA in both in vitro and in vivo studies (Green and El Hait, 1980) . Several compounds
were synthesized and assayed for their ability to inhibit MAOA and MAOB; most were
potent against MAOA, and none were appreciably active against MAOB (Gallardo-Godoy
et al., 2005).
Stereoisomers of five psychedelic amphetamines contracted isolated strips of sheep um

bilical arteries, the R-(-)- being more active than the S-( +)-isomers; there was a general cor
relation between the smooth muscle contracting ability and the psychedelic potency of the
compounds (Dyer et al., 1973) . Serotonin turnover in rat brain and spinal cord was reduced
by PMA and DOM at doses of 5 mg / kg (although mescaline at ten times this dose did not
produce any change); the authors suggested this was not a result of MAO inhibition, but
probably a direct consequence of serotonin receptor stimulation (Anden et al., 1974) . The
action of several psychedelic drugs on superfused vascular strips of the dorsal metatarsal
vein of a dog was reported (Cheng et al., 1974b) . Pharmacological evidence for the central
serotonergic effects of PMA was presented (Menon et al., 1976); the d- and I-isomers of
PMA were equally potent in the release of serotonin in the rat brain, but the d-isomer was
more potent than the I-isomer in blocking serotonin uptake (Tseng et al., 1976) . Action on
the uptake and release of serotonin by human blood platelets was reported (Tseng and
Loh, 1977) . Effects on the suprahyoidal muscle of rats and mice were reported (Menon et
al., 1976), and both PMA and 2,5-DMA, administered to rats, increased the activation of
myoclonic twitch activity of suprahyoidal muscle, which had been reported previously
to involve central serotonergic and dopaminergic mechanisms (Tseng, 1978) . All of the
mono-, di-, and tri-methoxylated amphetamines were evaluated for the uptake and release
of serotonin in human blood platelets (Tseng and Loh, 1977), and, using a rat fundus mod
el, serotonin receptor site affinity was determined (Glennon et al., 1980a) . PMA was effec
tive in increasing the release or blocking the uptake of serotonin by brain tissue slices (Loh
and Tseng, 1978) . Using calculated energy interactions between several amphetamines and
a model compound (3-methylindole), a receptor model for psychedelics was developed
(DiPaolo et al., 1978) . The calculated electrostatic potential of PMA was related to that of
serotonin (G6mez-Jeria et al., 1984) . PMA 5-HT 1 and 5-HT2 receptor-binding properties
were reported (Shannon et al., 1984) .
The action o n isolated frog heart was studied (Ellis, 1949). The effects o n cardiac function
were observed in the cat and dog (Ellis, 1965). PMA effects on intrauterine development,
pregnancy outcome, postnatal growth, and survival were compared with other 4-substi
tuted amphetamines in Swiss-Webster mice (Buttar et al., 1996). PMA inhibited uptake of
metaraminol (an a 1 -adrenergic receptor agonist and antihypotensive), and efflux of nor
adrenaline by rabbit atria (Paton, 1975). Effects of R-PMA and S-PMA on release of sero
tonin from rat synaptosomes were evaluated (Nichols et al., 1982) . PMA and 4-EA were
compared with amphetamine in rats employing a subcutaneous infusion for up to 14 days;
the study focused on brain distribution and effects on dopamine levels (Martin-Iverson
and Lodge, 1991). Neurotoxicity of PMA and PMMA was compared to that of MOMA in

PMA
subcutaneous injection into rats; PMMA caused prolonged, dose-related depletion of sero
tonin, and the density of serotonin uptake sites (Steele et al., 1992) . Cardiovascular effects
of MDMA and PMA were compared at different doses in rats (Irvine et al., 2001).
Pharmacology
PMA was evaluated as a bronchodilator in comparison to 2-MMA, in an effort to find bron
chodilators as effective as ephedrine, but with little or no pressor activity (Graham and
Kuizenga, 1948). Correlations were made between structure and the locomotor activity of
mice (van der Schoot et al., 1962) . EEG responses in the rabbit brain were monitored fol
lowing i.v. administration of PMA (Fujimori and Himwich, 1969). PMA was a highly dis
ruptive drug in rats, with behavioral effects at 3 mg / kg that were comparable to mescaline
at 25 mg / kg (Smythies et al., 1970) . Behavioral and neurochemical effects of psychedelics
were evaluated in neonate chicks (Wallach et al., 1972a) . PMA was the most effective of the
three mono-methoxy amphetamines in disrupting rat behavior (Tseng et al., 1976) . Acute
toxicology and gross behavioral effects were described in rodents, dogs, and monkeys (Da
vis et al., 1978) . PMA inhibition of food intake in the dog was almost as intense as with
d-amphetamine (Vaupel et al., 1979) .
Amphetamine, and t o a greater extent several psychedelics (PMA, MDA, DOM, DOB,
and 4C-M) protected rats from electroshock seizure (Davis et al., 1982) . Comparison of the
spontaneous behavior of rats was made with PMA, MDMA, MDA, and MOE (Hegadoren
et al., 1995). With rats trained with various avoidance programs, PMA was the most potent
of the three methoxyamphetamines tested (Smythies et al., 1967b). PMA was evaluated in
rats trained to discriminate d-amphetamine from saline (Huang and Ho, 1974a) . Effects
were observed in rats trained to respond to food presentation trials; in general psychedel
ics decreased response rate, and this was negatively correlated with known psychedelic
potency (Harris et al., 1978) .
tive phenylisopropylamines including R- and S-isomers of PMA; these substituted for the
training compound, suggesting their mechanisms of action might be serotonergic (Glen
non et al., 198lb). A comparison of serotonin receptor affinity and behavioral responses
was reported (Glennon et al., 1982a). Rats trained to distinguish PMA from saline were
tested with LSD, and vice versa; intermediate responses were obtained when the drugs
were interchanged, suggesting that only part of the PMA response was based on serotoner
gic receptor activation (Winter, 1984) . Using discrimination methodology with rats trained
with d-amphetamine, PMA produced only partial generalization (12-60% amphetamine
appropriate responses), although this was measurably higher than responses observed for
several di- and tri-substituted amphetamines (Glennon et al., 1985) .
About a dozen psychedelics were compared to stimulants, in rats trained in a conditioned

avoidance study (Davis and Hatoum, 1987). In a study focused on potential bioactivity of
MDMA metabolites, PMA was assayed in rats trained to discriminate between MDMA
and saline, and produced about 50% MOMA-appropriate responses (Glennon and Higgs,
1992) . PMA and 4-EA were tested in rats trained to distinguish either amphetamine or co
caine from saline, and found that the animals' responses to the test compounds were more
closely comparable to the cocaine responses, with limited generalization in amphetamine
trained animals (Corrigall et al., 1992b). Ring-substituted amphetamines such as PMA and
DOM did not substitute for amphetamine in trained rhesus monkeys, in parallel with the

PMA
responses observed in rats (Woolverton and English, 1997) . The optical isomers of PMA
produced PMMA-like, but not amphetamine-like responses in trained rats (Dukat et al.,
2002).
The absence of urinary PMA in humans who were heavily dosed with amphetamine (5-50
mg orally per hour, for an average of 51 hours) provided evidence that it was improbable that
PMA could be responsible for the induced psychosis associated with chronic amphetamine
abuse (Angrist et al., 1970) . In a related study, metabolic studies in human subjects given
PMA showed excretion of detectable amounts of unchanged PMA (as much as 6.75% of
the administered dose); again, no detectable PMA was detected following amphetamine
ingestion (Schweitzer et al., 1971 ) .
A number o f studies have attempted correlation between molecular parameters, organ

correlations were made between psychedelic potency and changes in substitution patterns
(Shulgin et al., 1969), the degree of native fluorescence (Antun et al., 1971), the stability of
molecular complexes (as determined by NMR; Sung and Parker, 1972), and lipophilicity
(as determined by octanol-water partition coefficients; Barfknecht et al., 1975), and be
tween partition coefficients, steric bulk, and in vitro activity (Nichols et al., 1977) . For the
compounds PMA, 2,4-DMA, 2,5-DMA, TMA, TMA-2, and TMA-3 (but not for OMA and
TMA-6), the lower energy of the n-n* transition and the increased probability of occurrence
was positively correlated with human potency (Bailey and Verner, 1972) . For a large num
ber of methoxylated amphetamines, the rabbit hyperthermia response paralleled human
potency as psychedelics (Anderson et al., 1978b); a series of amphetamines were studied
for correlation between 5-HT2 receptor affinity, charge complex stability, rabbit hyperther
mia, and human activity (Domelsmith et al., 1981).
Several toxic overdose cases were reported with this drug. Three deaths were attributed
to PMA in Australia (James and Dinan, 1998), and four in Belgium (Jacobs et al., 2002).
Hypoglycemia (blood glucose level, < 1 .5 mmol / L) and hyperkalemia (K+ concentration
> 7.5 mmol / L) were conditions specifically associated with PMA poisoning (Ling et al.,
2001 ) . An evaluation was made of the role of the metabolite PHA in the toxicity of PMA
(Kaminskas et al., 2002).
Tablets containing PMA and PMMA were sold as being MOMA (Dal Cason, 2001). PMA
was among several psychedelic drugs verified in the Japanese street drug scene (Katagi et
al., 2002).
Orally active in humans at 60 mg (Shulgin et al., 1969), and at 50-80 mg, with a "relatively
short" duration of action (Shulgin and Shulgin, 1991).
Legal Status
PMA is a Schedule I hallucinogen under federal drug law, and under District of Columbia
and all state laws except for Delaware, Kentucky, Massachusetts, New Jersey, New Mexico,
and Pennsylvania.
PMA has two positional isomers (2-MA and 3-MA), which are also Schedule I hallucinogens
under federal drug law, but are only explicitly named in the state laws of South Dakota.
These compounds have their own, separate entries in this book.

PMeA
#111. PMeA
1-(p-Tolyl)propan-2-amine
4-Methylamphetamine
p-Tolylaminopropane
1 -(p-Tolyl)-2-aminopropane
Aptrol
4-MeA
p-TAP
PAL 313
NSC 27114
Registry Numbers
CAS # CAS # CAS #
HCI salt [41632-56-8] Freebase [64-11-9] R-Isomer freebase [788775-45-1 ]
Bisulfate [878794-34-4] R-Isomer HCI salt [81601-12-9] 5-Isomer freebase [81601-14-1]
Sulfate [50650-74-3] 5-Isomer HCl salt [81601-11-8] a, j3-[d2 ] Isomer [147702-23-6]

From p-tolylaldehyde (with nitroethane, acetic acid, and ammonium acetate) to 1-(p-tolyl)-
2-nitropropene; (with LAH) to PMeA (Moed et al., 1955).
From p-tolylaldehyde (with nitroethane, acetic acid, and ammonium acetate) to l-(p-tolyl)-
2-nitropropene; (with Zn, AcOH) to the oxime; (with EtONa) to PMeA (Kreisky and
Kreisky, 1959).

m / z: 149.1204 (100.0%), 150.1238 (10.8%)
HCI salt m.p. 155-157 °C (Gajda et al., 1997)
Freebase b.p. 1 03-105 °C / 10 mm (Moed et al., 1955)
The NMR spectrum was obtained and intramolecular interactions analyzed (Bailey et
al., 1971 ) . The [ 1 3 C]-NMR spectra of ring mono- and di-methylated amphetamines were
obtained and compared (Bailey and Legault, 1981). Positive identification of 2-,3-, and
4-methoxyamphetamines and methylamphetamines was achieved by NMR and mass
spectrometry, but not by UV spectrometry; application of TLC and GC was discussed (Bai
ley et al., 1974b) .

Me -- -- -- 2-MeA [5580-32-5] (1-9)
-- Me -- -- 3-MeA [588-06-7] (1,4-12)
-- -- Me -- PMeA (this entry)
-- -- Me Me PMeMA [113358-79-5] (13,14)
-
-- -- Pr - 4-PrA [139102-18-4] (15)
-- -- iPr -- 4-iPrA [32560-62-6] (6,9,16,17)
(1) 2-MeA, 3-MeA, and PMeA have amphetamine-like stimulant activity in the rat; the ortho-isomer
is the most effective (Higgs and Glennon, 1990).

PMeA

(3) 2-MeA is a clinical anorexic with the trade name Ortetamine.
(4) Correlation between structure and the locomotor activity of mice (van der Schoot et al., 1962).
(5) General pharmacology in several laboratory animals and humans (Marsh and Herring, 1950).
(7) [ 1 3C]-NMR spectra of ring mono- and di-methylated amphetamines were obtained and
compared. (Bailey and Legault, 1981 ).
(8) Correlation of chemical structure and phenethanolamine N-methyltransferase reactivity (Hansch
and Glave, 1972).
(9) Identification of 2-,3-, and 4-methoxyamphetamines and methylamphetamines (Bailey et al., 1974b).
(10) Correlation made between the degree of native fluorescence and psychedelic potency in humans
(Antun et al., 1971).
(11) NMR spectrum obtained and intramolecular interactions analyzed (Bailey et al., 1971).
(12) Also called PAL 303.
(13) Active in humans at 80 mg i.m.; duration short, with some visual distortions, hyperthermia and
aphasia (Igor, 2006).
(14) Synthesis described in three patents (Hoffmann-La Roche, 1942a, 1942b, 1945).
(15) Binding at 5-HT 1 c and 5-HT2 receptors studied (Glennon et al., 1992).
(16) Substituted phenylpropylamines are anorexigenic agents (Holland et al., 1963).
(17) MAO inhibitor in serotonin neurons (Ask et al., 1985).
Biochemistry
Action on the isolated frog heart was studied (Ellis, 1 949) . Potency as an inhibitor of phe
nethanolamine N-methyltransferase was determined (Fuller et al., 1 971 ), and chemical
structure was correlated with phenethanolamine N-methyltransferase reactivity (Hansch
and Glave, 1972) .
2-MeA, 3-MeA, and PMeA all possess amphetamine-like stimulant activity i n the rat; the
ortho-isomer was the most effective (Higgs and Glennon, 1990). Binding at 5-HT 1 c and
5-HT2 receptors was studied (Glennon et al., 1992) . The relationship between serotonergic
activity and reinforcing effects was studied (Wee et al., 2005).
Pharmacology
General pharmacology of PMeA was studied in several laboratory animals and in humans
(Marsh and Herring, 1950), who observed it was slightly less active than amphetamine
in dogs, and orally active in humans at 75 mg, producing anorexia but little stimulation.
PMeA was compared with amphetamine, methamphetamine, and hexahydrometham
phetamine as stimulants in animal studies (Haas and Forth, 1956), and evaluated in rats
using stimulus discrimination testing against d-amphetamine (Huang and Ho, 1974a).
The behavioral effects of PMeA, PCA, and PFA in animals were used to predict psychedelic
effects in humans (Beaton et al., 1968), and a correlation was made between the degree of
native fluorescence and psychedelic potency of the methoxy derivatives in humans (Antun
et al., 1971 ). Serotonin receptor site affinity was determined (Glennon et al., 1980a), and
5-HT 1 and 5-HT2 binding properties were evaluated (Shannon et al., 1984) .
PMeA is a recognized anorexic with the trade name Aptrol, from Smith Kline and French
Laboratories. Orally at 75 mg there is clear adrenergic stimulation, and at 150 mg there are
signs of mild toxicity such as salivation, coughing, and vomiting (Shulgin and Shulgin,
1991). Oral psychedelic activity was reported in humans at 160 mg, or from 80-120 mg i.m.;
plateau at two hours, and baseline at four hours (Igor, 2006) .

PMeA / PMMA
Legal Status
PMeA is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.
#112. PMMA
1-( 4-Methoxyphenyl)-N-methylpropan-2-amine
METHYL-MA
4-Methoxy-N-methylamphetamine
p-Methoxymethamphetamine
4-MMA
Doone
Registry Numbers
CAS # CAS #
HCl salt [3398-68-3] R-Isomer freebase [251321-76-3]
Freebase [22331-70-0] 5-Isomer freebase [113429-54-2]

From anethole (with NaN02) to anethol-f3-pseudonitrite; (with NH3, EtOH) to f3-nitroane
thole; (with Fe, NHpH) to 4-methoxyphenylacetone oxime; (with Na, Hg) to PMA; (with
benzaldehyde) to the benzinylimine; (with methyl iodide) to PMMA (Savitskii and Makh
nenko, 1940; Dessi, 1952) .
Synthesis of several secondary and tertiary f3-phenylpropylamines and f3-phenylisopro

pylamines were described (Woodruff et al., 1940) .

m / z: 1 79.1310 (100.0% ), 1 80. 1344 (11.9%)
HCl salt m.p. 166.5-167.5 °C (Woodruff et al., 1940)

Freebase b.p. 127-128 °C / 8 mm (Woodruff et al., 1940)
An NMR spectral shift with europium agents was reported (Smith et al., 1976) . Synthesis,
infra-red spectra, NMR and GC / MS data were presented (Clark, 1984); synthesis, and LC /
MS analysis were reported (Noggle et al., 1989d). Cross-reactivity of several substituted
amphetamines was evaluated with the Roche Abuscreen® (Cody, 1990a), and the Diagnostic
Products Corporation (Cody, 1990b) amphetamine radioimmunoassays. PMMA was identi
fied by a rapid planar chromatographic screening method (Fater et al., 1998) . Characteristic
markers of PMMA synthesis obtained by the Leuckart reaction were described (Blachut et
al., 2002; Kochana et al., 2003). A plasma screening and quantitative GC / MS analysis has
been reported (Peters et al., 2003), and analysis of serum by extraction, derivatization with
trifluoroacetic anhydride, and GC / MS was reported (Hidvegi et al., 2006).

4- N- f:I- Name CAS # Ref
MeO Me -- PMMA (this entry)
Meo Me Me f:\-Me-PMMA [827611-30-3] (1,2)
Meo Me -·
C=O PMMA-f:\k [530-54-1 ] (1,3-6) ·-

PMMA
(1) Action on cardiac output and coronary circulation of the dog (Mercier et al., 1959).
(2) Analysis by non-polar GC, and MS comparison to MDMA (Aalberg et al., 2004) .
(3) GC / MS compared with that of the isomeric compound MDMA (Awad et al., 2006).
(4) Synonyms for PMMA-Bk are: 1-(4-methoxyphenyl)-2-(methylamino)-1-propanone, 4' -methoxy
a-(methylamino)-propiophenone, B-keto-4-methoxy-N-methylamphetamine, methedrone, me
thophedrinum, and methoxyphedrine.
(5) Synthesis (Lespagnol and Hallot, 1954).
(6) Active in humans at 120-160 mg i.m., producing a euphoric state similar to that of MDMA (Igor,
2006).
Biochemistry
The neurotoxicity of PMA and PMMA was compared to that of MOMA in subcutaneous
injections into rats (Steele et al., 1992) .
The major metabolite of PMMA in the rat is the 0-demethylated product, Pholedrine (an
antihypotensive agent); also detected by GC / MS were PMA, Oxilofrine and its enantio
mers, �-HO-HMA, HMMA, MHMA, and MHA (Staack et al., 2003a) . Human cytochrome
P450 CYP206 was identified as a major enzyme involved in the 0-demethylation of PMMA
(Staack et al., 2004c) .
Seven effects of structural factors of rat hair were studied for their effect on the incorpora
tion rate (Nakahara and Kikura, 1996).
Pharmacology
PMMA was evaluated as a bronchodilator in comparison to 2-MMA (Graham and Kuizen
ga, 1948) . Behavioral studies were made in rats trained on amphetamine, DOM, or saline,
and in mice trained on amphetamine, methamphetamine, or PMA. PMMA did not appear
to have amphetamine-like properties (Glennon et al., 1988a) . It was also assayed in rats
trained to discriminate between MOMA and saline; PMMA was the only drug in this study
that completely generalized for the MOMA reponse (Glennon and Higgs, 1992). In dis
crimination stimulus experiments where rats were trained to discriminate racemic PMMA
from saline, properties of PMMA optical isomers and conformationally restricted materials
(aminotetralins and tetrahydroisoquinolines) were evaluated (Young et al., 1 999). Optical
isomers of PMMA, DOM, MBDB, MOMA, and OMA were also compared as stimulants
in rats (Rangisetty et al., 2001 ) . PMMA-discriminating rats were again used to distinguish
related compounds (such as PMA and MTA) from amphetamine (Dukat et al., 2002) .
Tablets containing PMA and PMMA were misrepresented as MOMA (Dal Cason, 2001;
Blachut et al., 2002), and PMMA was among several psychedelics verified in the Japanese
street drug scene (Katagi et al., 2002).
PMMA has oral psychedelic activity in humans at greater than 1 00 mg; the duration is
"short" (Shulgin and Shulgin, 1991)
Legal Status
PMMA is not a scheduled compound under federal drug law, or under District of Columbia
or any state laws.

TeMA
#113. TeMA
N-Methyl-1-(2,3,4,5-tetramethoxyphenyl)propan-2-amine
2,3,4,5-Tetramethoxyamphetamine
TA
Registry Numbers
CAS #
Freebase [23693-26-7]
5-Isomer [67225-65-4]
R-Isomer [ 67225-66-5]
Synthesis
From 2,3,4-trimethoxybenzalehyde (with peracetic acid, HOAc) to 2,3,4-trimethoxyphe
nol; (with KOH, allylbromide) to 2,3,4-trimethoxyphenol-1-allyl ether; (with extensive
heating) to 6-allyl-2,3,4-trimethoxyphenol; (with KOH, methyl iodide) to 2,3,4,5-tetrame
thoxyallyl benzene; (with KOH, methyl iodide) to 2,3,4,5-tetramethoxypropenyl benzene;
(with tetranitromethane) to 2-nitro-(2,3,4,5-tetramethoxyphenyl)propene; (with LAH) to
TeMA (Shulgin and Shulgin, 1991).

m / z: 269.1627 (100.0%), 270.1661 (15.1 % ), 271 .1694 ( 1 . 1 % )
HCl salt m.p. 135.5-136.5 °C (Shulgin and Shulgin, 1991 )

2- 3- 4- 5- Name CAS # Ref
Meo Meo Meo Meo TeMA (this entry)
Meo Me Me Meo G [207740-37-2] (1-3)
Meo Me Et Meo G-12 -- (4)
MeO Et Me MeO G-21 -- (4)
Meo Et Et Meo G-22 -- (4)
MeO -C- Meo G-1 -- (4)
MeO -CC- MeO G-2 -- (4)
Meo -CCC- MeO G-3 [207740-36-1] (1,5)
Meo -CCCC- MeO G-4 -- (1,4)
Meo -C=C-C=C- Meo G-N [ 477904-62-4] (1,6)
MeO -CCCC(l,4C)- MeO G-5 [133787-68-5] (1,7-9)
MeO -CCCC(l,4CC)- Meo G-6 -- (4)
(3) "G" is the abbreviation of the trivial name GANESHA.
(6) One of several compounds patented for treatment of glaucoma (Hellberg and Namil, 2002).

TeMA I TeMPEA
(9) In (Clare, 1998), there is an error in the structure of G-5, calling it 3,4-dihydro-2,7-dimethoxy-a
methyl-1,4-methanonaphthalene-1 (2H)-ethanamine, (CAS # 214414-89-8).
Biochemistry
A correlation was made between the degree of native fluorescence and psychedelic
potency of the methoxy derivatives in humans (Antun et al., 1971 ) . Using calculated energy
interactions between several amphetamines and a model compound (3-methylindole), a
receptor model for psychedelics was developed (DiPaolo et al., 1978) .
TeMA was among selected phenylisopropylamines was evaluated for anti-Parkinsonian

action (Caron et al., 2007) .
Pharmacology
TeMA was evaluated in a study of psychedelic potency in humans, as affected by changes
in substitution patterns (Shulgin et al., 1969) . Correlation was made between the energy
of the highest occupied molecular orbital of the drug, and psychedelic potency in humans
(Kang and Green, 1970) .
Threshold oral activity i n humans a t 5 0 mg; duration unknown (Shulgin and Shulgin,
199 1 ) .
Legal Status
TeMA is not a scheduled compound under federal drug law, or under District of Columbia
V::
or any state laws.
#114. TeMPEA
2-(2,3,4,5-Tetramethoxyphenyl)ethanamine H3CO NH2
2,3,4,5-Tetramethoxyphenethylamine � I
H3CO �
Registry Numbers OCH3
CAS # CAS # OCH3
Synthesis
From gallacetophenone (with methyl iodide) to 3,4-dimethoxy-2-hydroxyacetophenone;
(with Hp2) to 1,2-dihydroxy-3,4-dimethoxybenzene; (with (CH3 )2S04 ) to 1,2,3,4-tetrame
thoxybenzene; (with N-methylformanilide, POC13 ) to 2,3,4,5-tetramethoxybenzaldehyde;
(with nitromethane) to 1-(2,3,4,5-tetramethoxy)-2-nitroethene; (with LAH) to TeMPEA (Be
nington et al., 1955a) .

m / z: 241 . 1314 (100.0% ), 242.1348 (13.0% )

2- 3- 4- 5- 6- a- Name CAS # Ref
Cl Meo Meo Meo -- -- 2-CM [ 65995-43-9] (1)
- -
Br Meo Meo MeO - - 2-BM [37015-19-3] (2)

TeMPEA
2- 3- 4- 5- 6- a- Name CAS # Ref

---- -
Meo Me Me MeO -- -- 2C-G [207740-1 8-9] (3-5)

MeO Me Et MeO -- -- 2C-G-12 -- (6)
-
MeO Et Me Meo -- - 2C-G-21 -- (6)
-
MeO Et Et MeO -- - 2C-G-22 -- (6)
Meo MeO MeO MeO -- -- TeMPEA (this entry)
MeO -C- MeO -- -- 2C-G-1 -- (6)
MeO -CC- MeO -- -- 2C-G-2 -- (6)
Meo -CCC- MeO -- -- 2C-G-3 [ 207740-19-0 l (3,7,8)
Meo -CCCC- MeO -- -- 2C-G-4 -- (6)
MeO -C=C-C=C- MeO -- -- 2C-G-N [207740-21 -4] (3,9)
MeO -CCCC(l,4C)- Meo -- -- 2C-G-5 [207740-20-3] (3,10,11)
- -
Meo -CCCC(l,4CC)- MeO - - 2C-G-6 -- (6)
(1) 2-CM is an artifact in the isolation of mescaline from Trichocereus peruvianus with a chlorinated
solvent (Pardanani et al., 1977).
(2) Synthesis (Pecherer et al., 1972).
(5) Patent application with no pharmacological information (Ohkawa et al., 2001).
(8) All references to this compound in Chemical Abstracts are QSAR studies.
(9) Orally active in humans at 20-40 mg; duration of 20-30 hours (Shulgin and Shulgin, 1991).
(10) In abstracting the Clare (1998) paper, there is an error in the structure of 2C-G-5, calling it 3,4-
dihydro-2,7-dimethoxy-l,4-methanonaphthalene-(2H)-ethanamine (CAS # 214414-84-3).
Biochemistry
Effects on alkaline phosphatase activity and pyruvate utilization were studied in rat brain
homogenates and supernatants (Clark et al., 1956). Effects of ring methoxy substitutions on
oxidative deamination were evaluated (Clark et al., 1965).
Pharmacology
Enzymatic oxidative deamination and effects on cat behavior were evaluated (Clark et al.,
1964). A series of mono-, di-, tri-, tetra- and penta-methoxylated phenethylamines were
tested on rats trained with various avoidance programs, and only PeMPEA, TeMPEA,
and mescaline showed activity. Potency increased with increased degree of substitution
(Smythies et al., 1967a).
Legal Status
TeMPEA is not a scheduled compound under federal drug law, or under District of Colum

TeMPEA-3
#115. TeMPEA-3
2-(2,3,5,6-Tetramethoxyphenyl)ethanamine
2,3,5,6-Tetramethoxyphenethylamine
Registry Numbers
CAS # CAS #

From hydroquinone (with MeOH, ZnC12) to 2,5-dimethoxy-1,4-benzoquinone; (with
Na2Sp4 ) to 2,5-dimethoxy-1,4-dihydroxybenzene; (with (CH3 )2S04 ) to 1,2,4,5,-tetrame
thoxybenzene; (with chloromethyl methyl ether) to 2,3,5,6- tetramethoxybenzylchloride;
(with KCN) to 2,3,5,6-tetramethoxybenzylcyanide (with LAH) to TeMPEA-3 (Benington
et al., 1955a).

m / z: 241 .1314 (100.0%), 242. 1348 (13.0%)

2- 3- 4- 5- 6- a- Name CAS # Ref
Br MeO -- Meo Br H 2,3,5,6-BMMB [200264-69-3] (1)
Br Meo -- Meo Br Me 2,3,5,6-BMMBA [60887-76-5] (2,3)
MeO Meo Meo -- Meo H TeMPEA-2 [3166-92-5] (4-9)
Meo Meo Meo Meo -- Me TeMA-2 [23693-27-8] (10-12)
-
MeO MeO - Meo Meo -- TeMPEA-3 (this entry)
MeO MeO -- Meo Meo Me TeMA-3 [23693-28-9] (11)
(1) The bromination products of all six dimethoxyphenethylamines were isolated and characterized
by GC / MS (DeRuiter et al., 1998a).
(2) A product of the bromination of dimethoxyamphetamines for LC / MS analysis (DeRuiter, et al.,
1998a).
(3) A product of bromination of 3,5-DMA (Bailey et al., 1976).
(4) Synonym: 2,3,4,6-tetramethoxyphenethylamine.
(5) Synthesis (Benington et al., 1955a).
et al., 1956).
(7) Effects of ring methoxy groups on oxidative deamination (Clark et al., 1965).
(8) Effectiveness of releasing cardiac norepinephrine in the mouse (Daly et al., 1966).
(9) Studies on enzymatic oxidative deamination and effects on cat behavior (Clark et al., 1964) .
(10) Correlation made between the degree of native fluorescence and psychedelic potency of the
methoxy derivatives in humans (Antun et al., 1971).
(12) Synonym: 2,3,4,6-tetramethoxyamphetamine.
Biochemistry
and supernatants were determined (Clark et al., 1956). TeMPEA-3 was metabolized by oxi-

TeMPEA-3 I mTFMPP
dative deamination in rabbit liver (Clark et al., 1965) . The effectiveness of releasing cardiac
norepinephrine was measured in the mouse heart (Daly et al., 1966).
Pharmacology
Enzymatic oxidative deamination of TeMPEA-3, and its effects on cat behavior was stud
ied (Clark et al., 1964) . In a series of mono-, di-, tri-, tetra- and penta-methoxylated phen
ethylamines tested on rats trained with various avoidance programs, only PPEA, TPEA,
and mescaline showed activity. Potency increased with increased degree of substitution
(Smythies et al., 1967a).
Human psychedelic activity of TeMPEA is unknown.
Legal Status
TeMPEA-3 is not a scheduled compound under federal drug law, or under District of Co
("NH
(Y N _J
#116. mTFMPP
1 -(3-(Trifluoromethyl)phenyl)piperazine
3-(Trifluoromethyl)phenylpiperazine
TFMPP
y
TFTP
Molly*
NSC 128882
*This is more often a slang term for MDMA.
Registry Numbers
CAS # CAS # DEA#
HCl salt [16015-69-3] L-Glutamate [ 135014-39-0 l
di-HCl salt [76835-14-8] Oxalate [378758-87-3]
x-HCl salt [78056-41-4] Freebase [15532-75-9] 7494
HBr salt [2394-89-0] 2,3,5,6-[ d4 ] Oxalate [859843-14-4]
xHBr salt [15532-74-8] [ 1 8F]-labeled [ 132785-03-6]
Aspartate [135014-40-3]

From m-trifluoromethylaniline (with diethanolamine, HBr, heat) to mTFMPP (Ash et al.,
1964) .
Additional syntheses were reported (Bysouth and Clarke, 1970a, 1970b; Jain et al., 1967).
C 11 H 1 3F 3N2 Exact Mass: 230.1031
m / z: 230.1031 (100.0%), 231 . 1 064 (11 .9%)
Elemental Analysis: C, 57.39; H, 5.69; F, 24.76; N, 12.17
HBr salt m.p. 250-253 °C (Ash et al., 1964)

HCl m.p. 232 °C (Jain et al., 1967)
mTFMPP identification and analysis by HPLC-UV was reported (de Boer et al., 2001).
A plasma screening and quantitative GC / MS analysis was reported (Peters et al., 2003) .
Employing HPLC-PDA, LC I MS, TLC and NMR, a library of 35 illegal drugs was assembled
and used to identify street samples (Nakashima et al., 2005).

m TFMPP

Ar Name CAS # Ref
2-CF 3 oTFMPP [30645-73-9] (1)
3-CF3 mTFMPP (this entry)
4-CF 3 pTFMPP [30459-1 7-7] (2)
(1) Syntheses described (Bysouth and Clarke, 1970a, 1972).
(2) Synthesis (Bysouth and Clarke, 1972) .
Biochemistry
mTFMPP was shown to be an agonist at central serotonin receptors, but a potent antago
nist of peripheral serotonin receptors, inducing contractions of the rat jugular vein, show
ing that this compound affects these receptors in various tissues differently (Cohen and
Fuller, 1983). mTFMPP may produce its stimulus effects via a 5-HT 1 8 related mechanism
(McKenney and Glennon, 1986). mTFMPP stimulus properties were used as a model of
5-HT 1 8 receptor activation (Schechter, 1988). The serotonin mechanism for initiation of the
cardiovascular activation of respiration was studied by separate activation by three major
agonists: PAT for 5-HTIN mTFMPP for 5-HT 1 w and DOI for 5-HT2 (King and Holtman,
2
1990). The 5-HT2 binding site of mTFMPP was located with [ 1 5 I]-labeled 2C-I (Johnson et
al., 1990b). Serotonergic properties of arylpiperazines, including mTFMPP, were reviewed
(Murphy et al., 1991).
In rats, mTFMPP is metabolized by hydroxylation of the aromatic ring and degradation of

the piperazine ring (Staack et al., 2003b). The hydroxylation is largely achieved with the
cytochrome P450 component CYP2D6 (Staack et al., 2004b ) .
Short-term effects o f fluoxetine and mTFMPP o n electroencephalographic sleep i n the rat

were evaluated (Pastel and Fernstrom, 1987) . Hypothermia was induced in mice by mCPP
and mTFMPP (Maj et al., 1988).
Pharmacology
Discriminative stimulus properties of mTFMPP against DOM and other compounds sug
gested its effects may be mediated by 5-HT 1 receptors (Glennon et al., 1984a) . Serotonin
agonist effects included induced head-twitching in rodents (Simansky and Schechter,
1988). mTFMPP and mCPP suppressed spontaneous locomotor activity, and inhibition of
these effects with other materials suggested involvement of 5-HTic, and possibly 5-HT 1 8
receptors (Lucki et al., 1989). mTFMPP effects were observed on animal behavior, and were
attributed to mediation by 5-HT I C receptors in the rat (Kennett and Curzon, 1 988), and by
5-HT 1 8 receptors in mice (Frances, 1988). Gender-related differences in effects of mTFMPP
and mCPP on the copulative behavior of rats were observed (Mendelson and Gorzalka,
1 990). mTFMPP-induced anorexia in the rat was probed with several antagonists of se
rotonin receptor subtypes; they concluded the anorexigenic response was mediated by
5-HT2, and possibly 5-HTic (Klodzinska and Chojnacka-Wojcik, 1990). At doses of 1-20
mg / kg hyperthermia was evoked in rats at a high ambient temperature (28 °C) (Klodz
inska and Chojnacka-Wojcik, 1992). Behavioral effects of the 5-HT2 agonist 1 -NP on the
squirrel monkey, alone or in combination with DOB, mCPP or mTFMPP, were reported
(McKearney, 1989).
mTFMPP was among several psychedelic drugs verified in the Japanese street drug scene
(Katagi et al., 2002).

mTFMPP / TMA
Benzylpiperazine (BZP), a Schedule I stimulant, is reported to potentiate the effects of

mTFMPP and elicit psychedelic effects that neither will produce alone (Wilkins et al., 2008;
Sheridan et al., 2007) . Mixtures of mTFMPP and BZP have sometimes been marketed as
legal MDMA substitutes, particularly in Southeast Asia and the Pacific (Wilkins et al., 2008) .
Orally active in humans at 25-1 00 mg; duration 5-8 hours (Erowid, 2007) .
Legal Status
mTFMPP is not a scheduled compound under federal drug law, or under District of
Columbia or any state laws, except for Hawaii, where mTFMPP is a state Schedule I drug.
This compound was proposed for emergency definition as a Schedule I compound in the
United States (FR, 2003). The proposal was dropped in March, 2004. As of December 3 rct,
2005, mTFMPP became illegal in Denmark. As of March 1, 2006, it became scheduled as a
"dangerous substance" in Sweden (Erowid, 2007). Note that BZP is a Schedule I stimulant
in the United States (FR, 2004) and is illegal in numerous other countries.
#117. TMA
1-(3,4,5-Trimethoxyphenyl)propan-2-amine
3,4,5-Trimethoxyamphetamine
1 -(3,4,5-Trimethoxyphenyl)-2-aminopropane
3,4,5-Trimethoxyphenylisopropylamine
a-Methyl-3,4,5-trimethoxyphenethylamine
1 -(3,4,5-Trimethoxybenzyl)ethylamine
2-Amino-1 -(3,4,5-trimethoxyphenyl)propane
dl-a-Methylmescaline
NSC 167759
Registry Numbers
CAS # DEA#
HCl salt [ 5688-80-2] CAS #
dl-HC1 salt [ 13071-39-1 ] R-Isomer HCl salt [ 50505-86-7]
Pi crate [ 856823-05-7] S-Isomer HCl salt [19065-14-6]
Sulfate [ 64610-48-6] di-Isomer freebase [22199-1 7-3]
Acid salt [ 87059-65-2] 7390 R-Isomer freebase [ 64778-77-4]
Freebase [1082-88-8] S-Isomer freebase [708198-43-0]

From 3,4,5-trimethoxybenzaldehyde (with methyl propionate, hydrolysis) to 2-methyl-3-
phenyl)propanoic acid; (with SOC12, NH) to 2-methyl-3-(3,4,5-trimethoxyphenyl)propi

(3,4,5-trimethoxyphenyl)propenoic acid; (with Na, Hg) to 2-methyl-3-(3,4,5-trimethoxy
onamide; (with NaOMe, Br2) to TMA-N-carbamate methyl ester; (with HCI) to TMA (Hey,
1947) . This was the first synthesis of a psychoactive mescaline analogue.
From 3,4,5-trimethoxybenzaldehyde (with nitroethane, acetic acid, and ammonium ac

etate) to 1 -(3,4,5-trimethoxyphenyl)-2-nitropropene; (with electrolytic reduction) to TMA
(Hey, 1 947) .
From 3,4,5-trimethoxybenzaldehyde (with nitroethane, acetic acid, and ammonium ac

etate) to 1 -(3,4,5-trimethoxyphenyl)-2-nitropropene; (with LAH) to TMA (Shulgin et al.,
1961; Shulgin, 1963; Ho et al., 1970a).

TMA
From 3,4,5-trimethoxybenzaldehyde (with nitroethane, acetic acid, and ammonium ace

tate) to 1 -(3,4,5-trimethoxyphenyl)-2-nitropropene; (with Pd / C, H2) to TMA (Ohshita and
Ando, 1992) .
From 3,4,5,trimethoxyphenyl acetone (with R-(+)- or -5-(-)-) a-methylbenzylamine, Raney

Ni, H2) to R,R-(+)- (or 5,5-(-)-N-(a-phenethyl)-3,4,5-trimethoxyphenylisopropylamine
(with Pd / C, H2) to R-(-)- (or 5-(+)-) TMA (Nichols et al., 1973).
TMA was resolved into its optical isomers (Aldous et al., 1974) .
LAH reduction o f 1 -(3,4,5-trimethoxyphenyl)-2-nitropropene was found t o give 81% TMA

together with 19% of the incompletely reduced 1-(3,4,5-trimethoxyphenyl)propan-2-hy
droxylamine. In addition, NaBH4-catalysed reduction of this nitroalkene derivative with
borane yielded only 5% of the desired TMA. The product was predominantly the hydrox
ylamine (Guy et al., 2008).

m / z: 225. 1365 (100.0%), 226.1398 (13.0%)
HCl salt m.p. 219-220 °C (Hey, 1947) (MeOH)

HCl salt m.p. 220-221 °C (Benington et al., 1958a) (EtOH / EtOAc)
HCl salt m.p. 208-209 °C (Shulgin, 1963)
HCI salt m.p. 209 °C (Shulgin, 1966)
HCl salt m.p. 216-21 7 °C (Ho et al., 1970a)
[ aJ;g1 -17.7°
Pier ate m.p. 171-173 °C (Shulgin, 1963)
R-(-)-Isomer HCI salt m.p. 206-208 °C (Nichols et al.,. 1973) (IPA / Etp)
S-( +)-Isomer HCl salt m.p. 206-208 °C [ a J;g1 + 1 7.3° (Nichols et al., 1973) (IPA / Etp)
S-( +)-Isomer HCl salt m.p. 200 °C (Aldous et al., 1974)
R-(-)-Isomer HCl salt m.p. 205-206 °C (Aldous et al., 1974)
Synthesis, TLC and Gas chromatographic properties, UV spectra, and other physical prop
erties were reported (Ono et al., 1976). TLC and color tests were defined for the iden
tification of substituted amphetamines (O'Brien et al., 1982) . [ 13 C]-NMR spectra for me
thoxylated phenethylamines and amphetamines were shown to be distinctive and suitable
for identification (Bailey and Legault, 1981, 1983), and conformation of the aryl methoxy
groups of several psychedelics was established by [ 13 C]-NMR spectroscopy (Knittel and
Makriyannis, 1981). Analysis by HPLC employing fluorescamine derivatization for fluo
rescence detection was reported (Shimamine, 1984), and cross-reactivity of several substi
tuted amphetamines with the Roche Abuscreen radioimmunoassay for amphetamines was
evaluated (Cody, 1990a) .
GC identification as the substituted amphetamine heptafluorobutyl derivatives was report

ed (Lillsunde and Korte, 1991). Procedures employing HPLC and photodiode-array detec
tion were developed to analyze plant and urine samples for phenylalkylamines (Helmlin
and Brenneisen, 1992) . Screening of substituted amphetamine derivatives by fluorescence
polarization immunoassay was demonstrated (Cody and Schwarzhoff, 1993) . TMA was
identified by rapid planar chromatographic screening methods (Pater et al., 1998). Employ
ing HPLC-PDA, LC / MS, TLC, and NMR, a library of 35 illegal drugs was assembled and
used to identify street samples (Nakashima et al., 2005) . Fragmentation patterns of some

TMA
fifty-five phenethylamines were determined by a variety of mass spectrometry techniques

(Kolliker and Oehme, 2004).
Five street drugs (TMA, TMA-2, 2C-B, 2C-T-2, and 2C-T-7) were identified and distin
guished by HPLC (Takahashi et al., 2003), and TMA was found to be present in street
drugs in Japan, with confirmational analysis by GC / MS and LC-ESI-MS (Kikura-Hanajiri
et al., 2005).
2- 3- 4- 5- 6- Other Name Entry
-- MeO Meo MeO -- -- TMA (this entry)
Meo -- MeO MeO -- -- TMA-2 see #118
MeO MeO Meo -- -- -- TMA-3 see #119
-
MeO MeO -- Meo - -- TMA-4 see # 120
-
Meo MeO -- - MeO -- TMA-5 see #121
MeO -- Meo -- MeO -- TMA-6 see #122
*Note that all entries in this table are Schedule I compounds (see Legal Status, this entry), and have
separate entries. The six positional isomers of TMA were compared as to synthesis chemistry and
physical properties (Shulgin, 1966).

5- 4- 3- 2- a- Other Name CAS # Ref
-
Me HO Me -- Me - 3,5-Me-PHA [24973-31 -7] (1,2)
HO HO HO -- Me -- THA [91240-37-8] (3)
Meo MeO OH -- Me -- a-Me-3-DESMETHYL [146285-47-4] (4-6)
1 221 22
Meo Meo -- Me NMe2 3,5- 1 IDNNA-4 [ 1 09421-50-3 J (7,8)
Meo HO Meo -- Me -- a-Me-DESMETHYL [146285-46-3] (6,9)
MeO MeO MeO -- Me -- TMA (this entry)
Meo Meo MeO -- Me (3-HO (3-HO-TMA [77158-46-4] (10,11)
-
MeO Meo Meo - Me N-HO N-HO-TMA [149607-37-4] (6)
MeO MeO MeO -- CH2Cl -- a-CMe-M [49557-34-8] (12,13)
MeO Meo Meo -- CHpH -- a-HMe-M [49557-38-2] (12)
MeO Meo Meo -- Me2 -- a-MM-M [4340-07-2] (14)
Meo Meo Meo -- Me, Ve -- a-MV-M [ 4340-08-3] (14)
MeO MeO MeO -- Pr -- APM [ 67293-58-7] (15)
Meo MeO MeO -- Bu -- ABM [15886-81-4] (15)
Meo Meo Meo -- Am -- AAM [ 67293-57-6] (15)
MeO MeO MeO -- He -- AHM [67293-52-1 ] (15)
-
MeO MeO MeO -- Se - ASM [ 67293-51-0] (15)
Meo Meo Meo -- Oc -- AOM -- (16)
-
MeO MeO MeO -- No -
-- ---- �-
ANM [ 67293-56-5] (17)
MeO Meo Meo -- -CC=CC-N- a,N-Butenyl-M [ 62028-50-6] (18)

TMA
---
5-
------
4- 3- 2- a- Other Name
------- --- -- --- - -
CAS #
-- - --·----
Ref
MeO MeO Meo -CC- -- TMAT [33446-12-7] (19)
MeO MeO Meo -- Me N-Me N-Me-TMA [93675-34-4] (20)
Meo EtO MeO -- -- -- 3C-E [146849-92-5] (21-23)
Meo FCCO MeO -- -- -- 3C-FEM [501 700-06-7] (24)
MeO F2CCO Meo -- -- -- 3C-F2EM [501 700-07-8] (24)
MeO F3 CCO Meo -- -- -- 3C-F 3EM [501 700-08-9] (24)
MeO PrO Meo -- -- -- 3C-P [501 700-11-4] (24)
MeO iPrO Meo -- -- -- 3C-IP [501700-12-5] (24)
MeO AllylO MeO -- -- -- 3C-AL [214414-87-6] (24)
MeO iBuO MeO -- -- -- 3C-IB [501 700-1 0-3] (24)
MeO BzO Meo -- -- -- 3C-BZ [147947-26-0] (21,25,26)
(2) Pharmacology evaluated for toxicity, effects on barbiturate sleeping time, and ability to disrupt
mouse behavior (Ho et al., 1970a).
(3) Neurotoxicity mechanisms of MDMA metabolites (Capela et al., 2007).
(4) Reported present in Acacia berlandieri (Clement et al., 1997).
(5) Reported present in Acacia rigidula (Clement et al., 1998).
(6) TMA is metabolized by demethylation (to 3,5-dimethoxy-4-hydroxyamphetamine and 3,4-di
methoxy-5-hydroxyamphetamine) and N-oxidation (to N-hydroxy-3,4,5-trimethoxyamphet
amine). Synthesis and analytic procedures reported (Ohmori et al., 1992).
(7) The suffix -4 identifies the location of the radiolabel, opposite the side-chain. The positional
22
isomer 3,5- 1 IDNNA-2 has the radiolabel adjacent to the side chain (see # 120).
(8) Patented as a tool for measuring cerebral blood flow in mammals (Sargent et al., 1987) .
(9) Synthesis (Benington et al., 1954a).
(10) Compounds tested at the microgram levels as plant growth inhibitors (Mandava et al., 1981).
(12) Synthesis (Cooper, 1973).
(13) Dose (i.p.) of over 40 mg / kg produced a twitch syndrome in mice similar to that produced by
mescaline (Cooper, 1973).
(14) Of a number of mescaline homologues and analogues, only a-MM-M and a-M,V-M showed
properties that were similar to mescaline (Foussard-Blanpin et al., 1963) .
(15) Synthesis via the nitrostyrene (Shulgin, 1963).
(17) Synthesis via the carboxamide (Stockel and Hall, 1963).
(18) Synthesis and disruption of swimming of mice (Desantis and Nieforth, 1976).
(19) Synthesis and pharmacological screening (Violland et al., 1971).
(20) Synthesis, infra-red spectra, NMR, and GC / MS data presented (Clark, 1984).
(23) Interaction with imidazolium chloride were studied (Makriyannis et al., 1993) .
(24) Synthesis (Trachsel, 2002) .
(25) The eight references to this compound in the literature are all QSAR reports.
Biochemistry
Action on oxidative and hydrolytic enzymes in the rat brain was studied (Clark et al.,
1956). Blockage of progestational proliferation by TMA as an antimitotic agent in the rab
bit endometrium was reported (Miyake and Nagata, 1961). Effects on the dog peroneal

TMA
tibialis anticus nerve muscle (Schopp and Walsh, 1964), and on brain electrical activity in
the cat (Fairchild et al., 1967) were reported. A relationship between psychedelic activity
and electronic configuration was proposed (Snyder and Merril, 1 965). Interaction of
mescalinoids (and other potentially psychedelic drugs) with monoamine oxidase was re
ported (Hellot et al., 1970b), and a correlation was made between the energy of the highest
occupied molecular orbital of the drug and potency in humans (Kang and Green, 1 970) .
Correlations were also made between the potency of psychedelic methoxyamphetamines
and their inhibition of [ 3 H] -normetanephrine uptake in rat cerebral cortex (Hendley and
Snyder, 1971 ). For the compounds PMA, 2,4-DMA, 2,5-DMA, TMA, TMA-2, and TMA-3
(but not for DMA and TMA-6), the lower energy of the n-n * transition and the increased
probability of it occurring was positively correlated with human potency (Bailey and
Verner, 1972) . Correlation was made between the octanol-water partition coefficient
and psychedelic potency (Barfknecht et al., 1975), and, similarly, between octanol-water
partition coefficients, steric bulk, and in vitro activity (Nichols et al., 1977). Calculated energy
interactions between several amphetamines and a model compound (3-methylindole)
allowed for the development of a receptor model for psychedelics (DiPaolo et al., 1978).
In a series of psychoactive compounds, those with greater potency had lower ionization
potential as measured by photoelectron spectroscopy (Domelsmith and Houk, 1978).
All mono-, di-, and tri-methoxylated amphetamines were evaluated for the uptake and
release of serotonin by human blood platelets (Tseng et al., 1977) . Serotonin receptor site
affinity by TMA was determined (Glennon et al., 1980a) . Inhibition of serotonin binding
to rat brain membranes was reported (De Jong et al., 1982) . Research evidence for the in
volvement of serotonin in the mechanism of the action of psychedelic drugs was present
ed (Glennon et al., 1984b). Affinity with human brain 5-HT2 receptors was studied with
[ 3H]-ketanserin-labeled receptors from human cortical samples (Sadzot et al., 1989). The
5-HT2 receptor was shown to be the preferred site of psychedelic action as its radiolabel
ing marker (tritiated DOB) was preferentially targeted. The three controls (appropriately
radiolabeled 5-HT 1 N 5-HT 1 w and 5-HT 1 c were not as strongly stimulated (Titeler et al.,
1988). TMA binding at 5-HTic and 5-HT2 receptor was compared (Glennon et al., 1992) .
Interaction with imidazolium chloride was used to simulate complex formation relevant
to the postulated binding sites of serotonin receptors (Makriyannis et al., 1 993) . Interaction
with the liver enzyme CYP2D6 was reported (Wu et al., 1997) . Binding at 5-HT2A receptors
compared to binding affinity of several [3-carbolines (Glennon et al., 2000).
Pharmacology
Synthesis was described, with pharmacological evaluation in cats (Benington et al., 1958a) .
Correlations were made between mouse behavioral responses and human psychoactivity
(Corne and Pickering, 1967) . TMA was among the group of psychedelics that affected rat
swimming responses in rats (Uyeno, 1968), rat disrupted maze performance (Uyeno and
Mitoma, 1969), and nest-building behavior of mice (Schneider and Chenoweth, 1970). Dis
ruption of barbiturate-induced sleeping responses was used to evaluate action of several
related amphetamines in the mouse (Ho et al., 1970a) . Mescaline, DMPEA, MDPEA, TMA,
MDA, DMA, BDB, and MDMA were compared pharmacologically in five animal species
(Hardman et al., 1973) . Studies were made of injection into the rat optic nerve and the cat
sciatic nerve (Paulson and McClure, 1973) . Behavioral and endocrine effects of 3,4,5-tri
methoxyamphetamine were observed in male mice (Weltman et al., 1976). TMA inhibited
food intake in the dog (Vaupel et al., 1979) .
<
TMA
TMA and its optical isomers produced hyperthermia in the rabbit (Aldous et al., 1974); lat
er it was shown that for a large number of methoxylated amphetamines, the rabbit hyper
thermia response paralleled human psychedelic potency (Anderson et al., 1 978b). A series
of amphetamines were studied for correlation between serotonin receptor affinity, charge
complex stability, rabbit hyperthermia, and human activity (Domelsmith et al., 1 981).
A series of mono-, di-, tri- tetra- and penta-methoxylated phenethylamines were tested on
rats trained with various avoidance programs. Only PPEA, TPEA, and mescaline showed
activity. Potency increased with increased degree of substitution (Smythies et al., 1967a);
in rats trained with various avoidance programs, four positional isomers were studied.
They decreased in potency with TMA-2 > TMA > TMA-6 > TMA-3 (Smythies et al., 1967b).
Several amphetamines (TMA, TMA-2, TMA-3, TMA-4, TMA-6) were compared with LSD
in visual discrimination performance studies in the monkey. Amphetamine and mesca
line were standards; 2-Br-LSD and TMA-3 were inactive controls (Uyeno et al., 1969). Rats
phenylisopropylamines (Glennon et al., 1981b). Rats trained to distinguish between DOM
and saline in a discrimination task with a series of methoxylated amphetamines, showed
2,4-DMA, 2,3,4-, 2,3,5-, 2,4,6-, and 3,4,5-TMA to be active isomers, but 2,3-, 2,6-, and 3,5-
DMA to be relatively inactive (Glennon and Young, 1982) . Discrimination methodology
with rats trained on racemic amphetamine generalized to TMA, but with less sensitiv
ity than the training compound (Glennon et al., 1985). Discriminative properties of TMA,
MEM, and ALEPH were determined with rats trained to discriminate amphetamine from
saline (Corrigan et al., 1992a), and in a shock-avoidance paradigm, discrimination was
evaluated in rhesus monkeys (Woolverton and English, 1997).
The first human trial with TMA was by Hey, on or after 1947, who described its action
as euphoric (cited as a private communication in Peretz et al., 1955, who studied the oral
activity of TMA in humans at the 100-1 50 mg range with visual stroboscopic stimulation,
usually with prior Dramamine® administration to limit nausea) . TMA was used to study
the effects of changes in substitution patterns on human potency (Shulgin et al., 1 969). With
a series of psychedelic amphetamines, positive correlation was found between the stability
of molecular complexes (as determined by NMR), and the threshold active dose in humans
(Sung and Parker, 1972) . An optimum lipophilicity for maximum psychedelic activity in
humans could be determined from the octanol-water partition coefficient (Barfknecht et
al., 1975); relationship between partition coefficients, steric bulk, and in vitro activity was
also used to predict potency in humans (Nichols et al., 1977) . TMA was evaluated in exten
sive QSAR studies (Clare, 1998; Beuerle et al., 1997) .
TMA was confirmed to have psychedelic effects by several people. It was reported to be
orally active in humans at 225-280 mg with some side-effects (Shulgin et al., 1961), at ap
proximately 200 mg (Lemaire et al., 1985), and at 100-250 mg; duration 6-8 hours (Shulgin
and Shulgin, 1991).
Legal Status
TMA is a Schedule I hallucinogen under federal drug law (FR, 1970), and under District of
Columbia and all state laws.

TMA-2
#118. TMA-2
1 -(2,4,5-Trimethoxyphenyl)propan-2-amine
2,4,5-TMA
2,4,5-Trimethoxy-a-methylphenethy lamine
1 -(2,4,5-Trimethoxyphenyl)-2-aminopropane
2,4,5-Trimethoxylphenylisopropylamine
Registry Numbers
CAS # CAS #
HCl salt [15995-72-9] R-(-)-Isomer HCl salt [53626-22-5]
x-Oxalate [ 65955-48-8] 5-( +)-Isomer HCl salt [ 19065-13-5]
Freebase [1083-09-6] 5-Isomer freebase [67173-94-8]

Early synthesis, via the pseudonitrosite of asarone (Bruckner, 1933) .
From 3,4-dimethoxyphenol (with allylbromide) to 3,4-dimethoxyphenyl allyl ether; (with

heat) to 2-allyl-4,5-dimethoxyphenol; (with methyliodide) to 2,4,5-trimethoxyallylbenzene;
(with KOH) to 2,4,5-trimethoxypropenylbenzene (asarone); (with tetranitromethane) to
1 -(2,4,5-trimethoxyphenyl)-2-nitropropene; (with LAH) to TMA-2 (Shulgin, 1964a) .

tate) to 1-(2,4,5-trimethoxyphenyl)-2-nitropropene; (with LAH) to TMA-2 (Ho et al., 1 970a).

tate) to 1-(2,4,5-trimethoxyphenyl)-2-nitropropene; (with sodium bis(2-methoxyethoxy)
aluminum dihydride) to TMA-2 (Guy et al., 2008).

m / z: 225. 1365 (100.0% ), 226. 1398 (13.0% )
HCl salt m.p. 1 87 °C (Bruckner, 1933) (EtOAc / EtOH)

HCl salt m.p. 181 °C (Shulgin, 1966; Shulgin, 1968)
HCl salt m.p. 1 88-190.5 °C (Ho et al., 1970a)
HCl salt m.p. 1 88.5-189.5 °C (Shulgin and Shulgin, 1991)
HCl salt m.p. 190-192 °C (Squella et al., 1992) (IPA)
(-)-Isomer HCl salt m.p. 159 °C (Aldous et al., 1974)
(+)-Isomer HCl salt m.p. 163 °C (Aldous et al., 1974)
Preparation and configuration of optically active TMA-2 was reported (Pratesi et al., 1964) .
The chemistry and properties of the six positional isomers of TMA were compared (Shul
gin, 1966) . The NMR spectrum was obtained and intramolecular interactions analyzed
(Bailey et al., 1971 ) . TMA-2 was resolved (post-synthesis) into its optical isomers (Aldous et
al., 1974). TMA-2 was analyzed in urine and plasma samples as the pentafluorobenzamide
derivative, by GC with electron capture detection (Midha et al., 1 979a) . The [ 13 C]
NMR spectra for methoxylated phenethylamines and amphetamines were shown to be
distinctive and suitable for identification (Bailey and Legault, 1981, 1983). Analysis by

TMA-2
HPLC employing fluorescamine derivatization for detection was reported (Shimamine,

1984) . TLC and color tests were defined for the identification of substituted amphetamines
(O'Brien et al., 1982) . The conformation of the aryl methoxy groups of several psychedelics
was established by [ 1 3C]-NMR spectral analysis (Knittel and Makriyannis, 1981), and the
4-position substituent location was confirmed by NMR (Dawson and Avdovich, 1 987) .
TMA-2, DOB, DOM, and DON were electrochemically compared with the 4-unsubstituted
2,5-DMA (Squella et al., 1992) .
A method for the rapid forensic identification of phenethylamines was described using
TLC in six different solvent systems, with visualization using five color reactions (Neun
inger, 1987) . Five street drugs (TMA, TMA-2, 2C-B, 2C-T-2, and 2C-T-7) were identified
and distinguished by HPLC (Takahashi et al., 2003). Fragmentation patterns of fifty-five
phenethylamines were determined by a variety of mass spectrometry techniques (Kol
liker and Oehme, 2004) . Detection in urine by MS analysis reported (Nordgren and Beck,
2004). Employing HPLC-PDA, LC / MS, TLC, and NMR, a library of 35 illegal drugs was
assembled and used to identify street samples (Nakashima et al., 2005). TMA-2 was found
to be present in street drugs in Japan, with confirmational analysis by GC / MS and LC-ESI
MS (Kikura-Hanajiri et al., 2005). Analysis of human urine by LC-MS-MS methods was
reported (Nordgren et al., 2005).
Homologues
HO HO HO Me -- THA-2 [41241-36-5] (1-3)
HO HO HO Me Me THMA-2 [136706-32-6] (1,4,5)
Meo HO MeO Me -- DOOH [125903-57-3] (6-9)
MeO HO Meo Et -- 4C-HO [72667-83-5] (10,11)
Meo Meo Meo Me -- TMA-2 (this entry)
MeO MeO Meo Me Me N-Me-TMA-2 [93675-32-2] (12-13)
MeO Meo MeO Me Me2 N,N-Me-TMA-2 -- (14)
Meo Meo MeO Et -- 4C-Me0 [ 84055-86-7] (15-17)
MeO Meo EtO Me -- MME [1 7231-78-6] (18-25)
Meo EtO MeO Et -
- 4C-Et0 [72667-84-6] (10,11)
MeO EtO EtO Me -- MEE [1 7231-82-2] (18,19,22)
MeO PrO Meo Me -- MPM [123643-24-3] (8,26)
Meo PrO MeO Et -- 4C-Pr0 [72667-85-7] (10,11)
MeO 2-HO-PrO Meo Me -- M(20P)M [146724-77-8] (8)
MeO 3-HO-PrO MeO Me -- M(30P)M [146724-76-7] (8)
MeO iPrO MeO Me -- MIPM -- (14,27)
Meo iPrO MeO Et -- 4C-iPrO [72667-86-8] (10,11)
Meo BuO Meo Me -- MBM -- (14,28)
Meo AmO Meo Me -- MAM -- (14,29)
Meo HOCH2 MeO Et -- 4C-HM [ 69294-24-2] (30,31)
Meo CH3 CH(OH) MeO Et -- 4C-HE [ 69294-25-3] (31 )

TMA-2

EtO Meo Meo Me -- EMM [17231-77-5] (18-22,32, 33)
EtO MeO EtO Me -- EME [1 7231-79-7] (18,22)
EtO EtO MeO Me -- EEM [17231-81-1] (18,22)
EtO EtO EtO Me -- EEE [ 1 7231-83-3] (18,22)
(1) A metabolite of MDMA studied for effects on tryptophan hydroxylase (Elayan et al., 1993).
(3) THA-2, THMA, and DHA are metabolites of MDMA (Elayan et al., 1993).
(4) Also known as THM in the scientific literature.
(5) Effects of two hydroxy metabolites of MDMA (DHMA and THMA-2) on serotonin and dopamine
in the CNS (Johnson et al., 1992).
(6) Affinity for 5-HT2 receptors was measured and compared to structurally related compounds
(7) DOOH is a minor metabolite of DOM in the rabbit and the guinea pig (Nagamatsu et al., 1978).
(8) Metabolism studied with the filamentous fungus Cunninghamella echinulata; TMA-2 and MEM
were poorly metabolized. MPM was acetylated and 0-dealkylated. ALEPH was oxidized to the
sulfoxide (Foster et al., 1992).
(9) A large study of psychedelics showed that the lipophilicity of the 4-position substituent was of
primary importance in determining 5-HT2 receptor affinity (Glennon and Seggel, 1989).
(11) Studied in cats (Stanridge et al., 1980).
(13) Among several N-methylated psychedelics compared to methcathinone in stimulant-trained
rats (Glennon et al., 1987b).
(15) Synthesis described, patented as a hypotensive agent (Stone, 1963).
(16) Inhibition of serotonin binding to rat brain membranes (De Jong et al., 1982).
(17) Fragmentation patterns of fifty-five phenethylamines determined by a variety of mass spec
trometry techniques (Kolliker and Oehme, 2004).
(19) Serotonin agonist and psychedelic potency of MEM, EMM, and MME do not correlate with rat
stomach fundus assay predictions (Nichols et al., 1984).
(20) Studies were made comparing mouse behavior and the activity of the brain enzymes MAO and
DOPA decarboxylase (De Ropp and Kastl, 1970).
(21 ) Rats trained to discriminate 5-MeO-DMT from saline were tested with several psychoactive
(23) Behavioral properties in trained rats correlated with structure (Glennon and Young, 1982).
(24) Orally active in humans at 40 mg; duration probably 6-1 0 hours (Shulgin and Shulgin, 1991).
(25) Anti-Parkinsonian action of phenylisopropylamines (Caron et al., 2007).
(26) Threshold to minimal oral activity in humans at greater than 30 mg; duration probably short
(27) Orally active in humans at 30 mg (Shulgin and Shulgin, 1991).
(29) Not orally active in humans at 1 6 mg (Shulgin and Shulgin, 1991).
(30) A possible active metabolite of 4C-D (Partyka et al., 1978).
(31 ) Patented for increasing mental alertness in geriatric patients (Partyka et al., 1978).
(32) A drug called EMM appeared for sale in 1 80 mg doses in Amsterdam. Analysis proved it to be
methylone (Murple, 2005).

TMA-2
Analogues
p Meo Meo Me -- 2-P-4,5-DMA [155831-43-9] (1)
NH2 HO HO Me -- 4,5-H0-2-AA [ 1 68699-63-6] (3)
NH2 Meo MeO Me -- 2-NH2-4,5-DMA [ 92058-62-3] (1,2)
HO NH2 HO Me -- 2,5-HO-PAA [ 1 68699-64-7] (3)
HO HO NH2 Me -- 2,4-H0-5-AA [ 1 06868-44-4] (3)
Meo BzO Meo Me -- MBZM [207740-08-7] (4)
MeO MeO NH2 Me -- 5-NH2-2,4-DMA [168699-72-7] (3)
MeO Meo p Me -- 5-P-2,4-DMA [155831-44-0] (1,5)
Meo Meo p Me Me2 2,4-PDNNA [ 105466-93-1 ] (6)
Meo Meo !Sp Me Me2 1 8P-2,4-DNNA [ 105466-93-1 ] (5,7)
MeO Meo I Me -- 5-I-2,4-DMA [159432-47-0] (8)
MeO MeO I Me Me2 2,4-IDNNA [105371-59-3] (9)
1 22J 22
Meo Meo Me Me2 2,4- 1 IDNNA [ 1 02145-23-3] (9,10)
MeO MeO 1 25J Me Me2 2,4- 1 25IDNNA [105363-41-5] (9)
Meo Meo Meo Me -- TMA-2 (this entry)
(2) Patented as a hypotensive drug (Stone, 1963).
(4) This drug has been researched in an extensive QSAR study (Beuerle et al., 1997).
(5) Reaction with [ 1sp] acetyl hypofluorite gave 5-P-2,4-DMA (Mathis et al., 1986a) .
(6) [ 1 SP]-labeled N,N-dimethylamphetamine analogues for brain imaging studies (Mathis et al., 1986a).
(7) The heavier N-substituents (ethyl, propy!, isopropyl, hexyl, and N,N-diethyl homologues) were
explored as radiolabeling precursors, but are not in the published scientific literature (Shulgin
and Shulgin, 1991).
(8) Synthesis from 2,4-DMA with 12, Ag2S04 (Sy, 1993).
(9) The [ 1 221 ]- and [ 1 25 1 ]-substituted analogues of dimethoxy substituted N,N-dimethyl amphetamines
(Mathis et al., 1986b ).
22
(10) Conversion of 2,4-DNNA to labeled 5-1 -2,4-DNNA (2,4- 1 IDNNA), and its use in the PET scan
ning of a dog brain (Mathis et al., 1985).
Biochemistry
Effects on EEG response in the rabbit brain following i.v. administration of TMA-2 were
reported (Fujimori and Himwich, 1969) . Studies were made comparing mouse behavior
and the activity of the brain enzymes MAO and DOPA decarboxylase (De Ropp and Kastl,
1 970) . TMA-2 was metabolically demethylated by liver microsomal enzymes (Mitoma,
1970) . A correlation was made between the energy of the highest occupied molecular or
bital of the drug and potency in humans (Kang and Green, 1970) . TMA-2 was evaluated
with other "mescalinoids" for interaction with monoamine oxidase (Hellot et al., 1970b) .
Correlation between psychedelic potency of methoxyamphetamines and their inhibition
of [ 3H] -normetanephrine uptake in rat cerebral cortex was reported (Hendley and Snyder,
1971 ) . For the compounds PMA, 2,4-DMA, 2,5-DMA, TMA, TMA-2, and TMA-3 (but not
for OMA and TMA-6), the lower energy of the n-n * transition and the increased probability
of it occurring was positively correlated with human potency (Bailey and Verner, 1 972) . A
positive correlation was found with a series of psychedelic amphetamines, between the

TMA-2
stability of molecular complexes (as determined by NMR) and the threshold active dose
in humans (Sung and Parker, 1972) . Mutagenic activity of TMA-2 was not detected in Sal
monella typhimurium assays (White et al., 1977) . In a series of psychoactive compounds,
those with greater potency had lower ionization potential as measured by photoelectron
spectroscopy (Domelsmith and Houk, 1978) . Cerebral and peripheral demethylation of
TMA-2 was measured from each of the separately labeled [ 1 4C] CH 30-groups in the rat
(Sargent et al., 1989). Four psychedelic amphetamines were incubated with the filamen
tous fungus Cunninghamella echinulata: TMA-2 and MEM were poorly metabolized, MPM
was acetylated and 0-dealkylated, and ALEPH was oxidized to the sulfoxide (Foster et al.,
1992) . The structure and identification of metabolites of TMA-2 were determined in the rat
(Ewald et al., 2006b).
TMA-2 showed activity on the uptake and release of serotonin by human blood plate
lets (Tseng and Loh, 1977) . Using calculated energy interactions between several amphet
amines and a model compound (3-methylindole), a receptor model for psychedelics was
developed (DiPaolo et al., 1978) . Serotonin receptor site affinity was determined (Glennon
et al., 1978, 1980a, 1982a) . Inhibition of serotonin binding to rat brain membranes was dem
onstrated (De Jong et al., 1982) . Evidence for the involvement of serotonin in the mecha
nism of the action of psychedelic drugs was presented (Glennon et al., 1984b). Binding
properties of the 5-HT 1 and 5-HT2 receptors were characterized (Shannon et al., 1984) . The
5-HT2 receptor was shown to be the preferred site of psychedelic action, as its radiolabel
ing marker (tritiated DOB) was preferentially targeted; three controls (appropriately ra
diolabeled 5-HTl A 5-HT 1 w and 5-HTic receptors) were not as strongly stimulated (Titeler
'
et al., 1988) . A large study of psychedelics showed that the lipophilicity of the 4-position
and Seggel, 1989) . Affinity properties of 5-HT2 receptors were measured and compared
with structurally related compounds (Seggel et al., 1990); binding properties of 5-HT 1 c and
5-HT2 receptors were also studied (Glennon et al., 1992), as were cloned human 5-HT2A
'
5-HT2w and 5-HT2c receptors (Nelson et al., 1999). Interaction with imidazolium chloride
was used to simulate complex formation relevant to the postulated binding sites of sero
tonin receptors (Makriyannis et al., 1993) . A reproducible, simple, and small-scale method
was developed for detecting the re-uptake and release of monoamines dopamine, sero
tonin and norepinephrine, using rat brain synaptosomes (Nagai et al., 2007) . Selectivity of
psychedelic phenylisopropylamines was evaluated with cloned human 5-HT2A and 5-HT2c
receptors, and included assay of TMA-2 (Moya et al., 2007) .
Pharmacology
Psychedelic compounds influenced swimming responses in rats (Uyeno, 1968) . Several
psychedelics had variable effectiveness in disrupting maze performance by rats (Uyeno
and Mitoma, 1969) . TMA-2 pharmacology was evaluated for toxicity, effects on barbiturate
sleeping time, and ability to disrupt mouse behavior (Ho et al., 1970a). Studies were made
of injection into the rat's optic nerve and the cat's sciatic nerve (Paulson and McClure,
1973) . TMA-2 and its optical isomers produced different degrees of rabbit hyperthermia
(Aldous et al., 1974) . DMPEA and TMA-2 labeled with [ 1 4C] at the methoxyl groups were
used to correlate behavior with [ 14 C]-C02 respiration, as evidence of metabolism (Sargent
et al., 1976) . Relationships between serotonin level and sexual behavior in the rat were
studied (Everitt and Fuxe, 1977). Effects were observed in rats trained to respond to food
presentation schedules (Harris et al., 1978) . In a large number of methoxylated amphet
amines, rabbit hyperthermia paralleled human potency as psychedelics (Anderson et
al., 1978b). Gross behavioral and physiological effects of psychedelics were monitored in

TMA-2
conscious, restrained monkeys (Wilson et al., 1981 ) . A comparison of the serotonin recep
tor affinity and the behavioral properties of TMA-2 was reported (Glennon et al., 1 982a).
Synaptosomal neurotransmitter uptake was inhibited by psychedelics (Whipple et al.,
1983). Several psychedelic drugs elicited myoclonic jumping behavior in the guinea pig
(Carvey et al., 1989) .
A series of mono-, di- and tri-substituted amphetamines were tested on rats trained with
various avoidance programs; potency increased with the loss of methoxy groups. Of the
tri-substituted, TMA-2 > TMA > TMA-6 > TMA-3. With the di-substituted derivatives,
2,3-DMA, 2,5-DMA, 3,4-DMA and 3,5-DMA, only the 3,4-DMA showed activity; of the
three mono-substituted amphetamines, PMA was the most potent (Smythies et al., 1967b).
in visual discrimination performance studies in the monkey; amphetamine and mesca
line were standards; 2-Br-LSD and TMA-3 were inactive controls (Uyeno et al., 1969) . Rats
phenylisopropylamines (Glennon et al., 1981b). Drug discrimination with rats trained on
racemic amphetamine generalized with TMA-2, but with less sensitivity than the training
compound (Glennon et al., 1985) . About a dozen psychedelics were compared to stimu
lants in rats trained in a conditioned avoidance study (Davis and Hatoum, 1987) . TMA-2
was N-methylated to form N-Me-TMA-2 (Glennon et al., 1 987b), which did not generalize
with the training response, in rats trained to discriminate amphetamine from saline; the
study focused on the role of N-methylation in cathinone and methcathinone activity. Dis
crimination studies were also conducted with amphetamine-trained animals (Corrigall et
al., 1992a) .
TMA-2 was patented as a hypotensive drug (Stone, 1963). Synthesis and human pharma
cology of the ethyl homologues of TMA-2 was reported (Shulgin, 1968), and it was pro
posed that human potency was affected by changes in substitution patterns (Shulgin et al.,
1969). A correlation was made between the degree of native fluorescence and psychedelic
potency of the methoxy derivatives, in humans (Antun et al., 1971 ) . An optimum lipophi
licity was proposed, as determined by octanol-water partition coefficient, for maximum
psychedelic activity in humans (Barfknecht et al., 1975); relationships between partition
coefficients, steric bulk, and in vitro activity were also used to predict potency in humans
(Nichols et al., 1977) . A profile of the history and activity of TMA-2 was presented (Shulgin,
1976) . A series of amphetamines were studied for correlation between serotonin receptor
affinity, charge complex stability, rabbit hyperthermia, and human activity (Domelsmith
et al., 1981). A comparison of steric properties with animal and human potency of several
phenethylamines, tryptamines and lysergide derivatives was made (Nichols, 1986a) . This
drug has been evaluated in extensive QSAR studies (Clare, 1998; Beuerle et al., 1997) . The
electron withdrawing or donating nature of the 4-position substituent was also correlated
with the human psychedelic potency (Neuvonen et al., 2006).
TMA-2 is orally active as a psychedelic in humans at 20-40 mg; duration 8-12 hours
Legal Status
TMA-2 is a positional isomer of TMA, and therefore a Schedule I hallucinogen under

TMA-3
#119. TMA-3
2,3,4-Trimethoxy-a-methylphenethylamine
Registry Numbers
CAS # CAS #
HCl salt [6010-77-1] Freebase [1082-23-1 ]
dl-HCI salt [15995-73-0] di-Freebase [22199-12-8]
x-Oxalate [52850-84-7] (+)-Isomer HCl salt [19065-15-7]
Acid salt [87059-60-7] R-Isomer freebase [ 64838-26-2]

From 2,3,4-trimethoxybenzaldehyde (with nitroethane, acetic acid, and ammonium acetate)
to 1-(2,3,4-trimethoxyphenyl)-2-nitropropene; (with LAH) to TMA-3 (Shulgin 1964a, 1966).

m / z: 225.1365 (100.0% ), 226.1398 (13.0% )
HCl salt m.p. 149 °C (Shulgin, 1964a, 1966) (IPA)

HCl salt m.p. 148-149 °C (Shulgin and Shulgin, 1991) (IPA)
gin, 1966). The NMR spectrum was obtained and intramolecular interactions analyzed
(Bailey et al., 1971). In a series of psychoactive compounds, those with greater potency
had lower ionization potential as measured by photoelectron spectroscopy (Domelsmith
and Houk, 1978) . Urine and plasma samples were analyzed as the pentafluorobenzamide
derivatives, by GC with electron capture detection (Midha et al., 1979a). The conformation
of the aryl methoxy groups of several psychedelics was established by [ 13 C]-NMR spectral
analysis (Knittel and Makriyannis, 1981). [ 13C]-NMR spectra for methoxylated phenethyl
amines and amphetamines were shown to be distinctive and suitable for identification
(Bailey and Legault, 1981, 1983) . Analysis by HPLC employing fluorescamine derivatiza
tion for fluorescence detection was reported (Shimamine, 1984) . Fragmentation patterns

Meo MeO MeO Me -- TMA-3 (this entry)
Meo Meo MeO Me Me N-Me-TMA-3 [93675-31-1] (1)
Meo Meo Meo Et -- 4C-TMPEA-3 [722550-59-6] (2)
(1) Synthesis, infra-red spectra, NMR, and GC / MS data were presented (Clark, 1984) .
(2) The fragmentation patterns of some fifty-five phenethylamines were determined
by a variety of mass spectrometry techniques (Kolliker and Oehme, 2004)

TMA-3
Biochemistry
A relationship between psychedelic activity and electronic configuration was established
(Snyder and Merril, 1965). A correlation was made between the potency of 2,3-DMA, 2,5-
DMA, TMA-3, and TMA-6, and the EEG arousal location in rabbit brain (Fujimori et al.,
1971). TMA-3 was shown to be metabolically demethylated by liver microsomal enzymes
(Mitoma, 1970) . A correlation was made between the energy of the highest occupied mo
lecular orbital of the drug and potency in humans (Kang and Green, 1970) . Correlation
was made between psychedelic potency of methoxyamphetamines and their inhibition of
[ 3H]-normetanephrine uptake in rat cerebral cortex (Hendley and Snyder, 1971 ) . For the
compounds PMA, 2,4-DMA, 2,5-DMA, TMA, TMA-2, and TMA-3 (but not for OMA and
TMA-6), the lower energy of the Jt-J't* transition and the increased probability of it occur
ring was positively correlated with human psychedelic potency (Bailey and Verner, 1972),
and a positive correlation was found with a series of psychedelic amphetamines, between
the stability of molecular complexes (as determined by NMR) and the threshold active
dose in humans (Sung and Parker, 1972).
TMA-3 affected the uptake and release of serotonin by human blood platelets (Tseng and
Loh, 1977) . Using a rat fundus model, serotonin receptor site affinity was determined
(Glennon et al., 1980a), and TMA-3 inhibited serotonin binding to rat brain membranes
(De Jong et al., 1982). Interaction with imidazolium chloride was used to simulate complex
formation relevant to the postulated binding sites of serotonin receptors (Makriyannis et
al., 1993). Binding at 5-HT2A receptors was compared with binding affinity of several f3-
carbolines (Glennon et al., 2000).
Pharmacology
The relative effectiveness of several psychedelics in disrupting maze performance by rats
was evaluated (Uyeno and Mitoma, 1969) . TMA-3 effects were observed in rats trained
to respond to food presentation schedules (Harris et al., 1978), and for a large number of
methoxylated amphetamines, the rabbit hyperthermia response paralleled human psyche
delic potency (Anderson, 1978b). A series of amphetamines were studied for correlation
between 5-HT2 affinity, charge complex stability, rabbit hyperthermia, and human activity
(Domelsmith et al., 1981).
With rats trained with various avoidance programs, four positional TMA isomers were
studied; they decreased in potency with TMA-2 > TMA > TMA-6 >> TMA-3 (Smythies
et al., 1967b). Several amphetamines (TMA, TMA-2, TMA-3, TMA-4, TMA-6) were com
pared with LSD in visual discrimination performance studies in the monkey. Amphet
amine and mescaline were standards; 2-Br-LSD and TMA-3 were inactive controls (Uyeno
et al., 1969). A series of methoxylated amphetamines were evaluated using a two-lever
drug discrimination study, with rats trained to distinguish between DOM and saline. 2,4-
DMA, 2,3,4-, 2,3,5-, 2,4,6-, and 3,4,5-TMA were active isomers, but 2,3-, 2,6-, and 3,5-DMA
were relatively inactive (Glennon and Young, 1982) . Discrimination methodology with rats
trained on racemic amphetamine generalized to TMA-3, but with less sensitivity than the
training compound (Glennon et al., 1985) .
Human potency, as affected by changes in substitution patterns, was evaluated (Shulgin

et al., 1969). A correlation was made between the degree of native fluorescence and psy
chedelic potency of the methoxy derivatives in humans (Antun et al., 1971). A correlation
between the octanol-water partition coefficient, steric bulk, and in vitro activity was used
to predict potency in humans (Barfknecht et al., 1975; Nichols et al., 1977) .

TMA-3 / TMA-4
Not orally active in humans at 1 00 mg (Shulgin and Shulgin, 1991).
Legal Status
TMA-3 is a positional isomer of TMA, and therefore a Schedule I hallucinogen under fed
eral drug law, and in states where isomers are included in the controlled drug definition.
# 120. TMA-4
2,3,5-Trimethoxyphenylisopropy lamine
Registry Numbers
. CAS# CAS #
dl-HCl salt [72739-09-4] Freebase [23693 14-3 ]
-
dl-x-Maleate [79002-10-1] di-Freebase [22199-1 3-9]

x-Oxalate [52948-32-0] R-lsomer freebase [ 67313-95-5]

From 2,4-dimethoxybenzaldehyde (with peracetic acid) to 2,4-dimethoxyphenyl formate;
(with base) to 2,4-dimethoxyphenol; (with KOH, allyl bromide,) to allyl-2,4-dimethoxy
phenyl ether; (with heating to 215 °C) to 2-allyl-4,6-dimethoxyphenol; (with KOH, methyl
iodide) to 2,3,5-trimethoxyallylbenzene; (with KOH, ethanol at 1 00 °C) to 2,3,5-trimethoxy
propenylbenzene; (with tetranitromethane) to 1-(2,3,5-trimethoxyphenyl-2-nitropropene;
(with LAH) to TMA-4 (Shulgin, 1966).
From 2-hydroxy-5-methoxybenzaldehyde (with concentrated nitric acid) to 2-hydroxy-

5-methoxy-3-nitrobenzaldehyde; (with potassium carbonate, dimethylformamide and
dimethyl sulfate) to 2,5-dimethoxy-3-nitrobenzaldehyde; (with powdered iron, iron (II)
sulfate heptahydrate in an aqueous calcium carbonate suspension) to 3-amino-2,5-di
methoxy-benzaldehyde; (with aqueous hydrochloric acid and aqueous sodium nitrite)
to 3-hydroxy-2,5-dimethoxybenzaldehyde; (with methyl iodide and sodium carbonate
in acetone) to 2,3,5-trimethoxybenzaldehyde; (with ammonium acetate, nitroethane) to
1 -(2,3,5-trimethoxyphenyl-2-nitropropene; (with LAH) to TMA-4 (Zaitsu et al., 2008)

m / z: 225.1365 (100.0%), 226.1398 (13.0%)
HCl salt m.p. 119 °C (Shulgin, 1966) (IPA)

The chemistry and properties of the six positional isomers of TMA were compared
(Shulgin, 1966). Urine and plasma samples were analyzed as the pentafluorobenzamide
derivatives, by GC with electron capture detection (Midha et al., 1 979a). [ 13C]-NMR spectra
for methoxylated phenethylamines and amphetamines were shown to be distinctive and
suitable for identification. (Bailey and Legault, 1981 and 1983).

TMA-4

I Meo Meo Me -- 2-I-3,5-DMA [159432-50-5] (1)
I MeO MeO Me Me2 3,5-IDNNA-2 [105363-47-1 ] (2)
1 221 22
Meo Meo Me Me2 3,5- 1 IDNNA-2 [ 1 05363-45-9] (2-4)
1 25 ! 2
Meo MeO Me Me2 3,5- 1 5IDNNA-2 [ 1 05363-43-7] (2)
Meo Meo MeO -- -- TMPEA-4
·- �- -------- r----�----
[3166-77-6] (5-8)
MeO Meo MeO Me -- TMA-4 (this entry)
-OCO- Meo Me -- MMDA-4 [23693-21-2] (9-10)
(1) Synthesis from 3,5-DMA with 12, Ag2S04 (Sy, 1993).
2
(2) Synthesis of [ 1 221 ] and [ 1 51 ] substituted analogues of dimethoxy substituted N,N-dimethylam
phetamines (Mathis et al., 1986b).
(3) The suffix -2 identifies the location of the radiolabel, adjacent to the side-chain. The positional
22
isomer, 3,5- 1 IDNNA-4, has the radiolabel opposite the side chain, and is entered in #117.
(4) Patented as a tool for measuring cerebral blood flow in mammals (Sargent et al., 1987).
(5) Studies on enzymatic oxidative deamination and effects on cat behavior (Clark et al., 1964).
(6) The effects of ring methoxy groups on oxidative deamination (Clark et al., 1965).
(8) TMPEA-4 is a positional isomer of mescaline, therefore a Schedule I hallucinogen under federal
drug law.
(10) MMDA-4 is a positional isomer of MMDA, therefore a Schedule I hallucinogen under federal
drug law.
Biochemistry
TMA-4 affected the uptake and release of serotonin by human blood platelets (Tseng and
Loh, 1977) . Using calculated energy interactions between several amphetamines and a mod
el compound (3-methylindole), a receptor model for psychedelics was developed (DiPaolo
et al., 1978). Using a rat fundus model, serotonin receptor affinity was determined (Glennon
et al., 1980a).
Pharmacology
Correlation was made between psychedelic potency of methoxyamphetamines, and their
inhibition of [ 3H]-normetanephrine uptake in rat cerebral cortex (Hendley and Snyder,
1971). Relative effectiveness of several psychedelics in disrupting maze performance by
rats was studied (Uyeno and Mitoma, 1969). Correlation was made between the energy
of the highest occupied molecular orbital of the drug and potency in humans (Kang and
Green, 1970) .
Effects were observed in rats trained to respond to food presentation schedules (Harris
et al., 1978) . Rats trained to distinguish between DOM and saline in a drug discrimina
tion task, showed 2,4-DMA, 2,3,4-, 2,3,5-, 2,4,6-, and 3,4,5-TMA to be active isomers, but
2,3-, 2,6-, and 3,5-DMA to be relatively inactive (Glennon and Young, 1982) . Discrimina
tion methodology with rats trained on racemic amphetamine generalized with TMA-4, but
with less sensitivity than the training drug (Glennon et al., 1985). Several amphetamines
(TMA, TMA-2, TMA-3, TMA-4, TMA-6) were compared with LSD in visual discrimination
performance studies in the squirrel monkey. Amphetamine and mescaline were standards;
2-Br-LSD and TMA-3 were inactive controls (Uyeno et al., 1969).
300 The Shu/gin Index - Psychedelic Phenethylamines and Related Compounds

TMA-4 / TMA-5
Evaluated in extensive SAR (Shulgin et al., 1969) and QSAR studies (Beuerle et al., 1997;
Clare, 1998).
TMA-4 had threshold to minimal oral activity in humans at 80 mg; duration perhaps six
hours (Shulgin and Shulgin, 1991).
Legal Status
#121. TMA-5
Registry Numbers
CAS # CAS #
dl-x-Oxalate [52948-33-1] di-Freebase [22199-14-0]

From 1,2,4-trimethoxybenzene (with n-butyl lithium, propionaldehyde) to ethyl-2,3,6-tri
methoxyphenylcarbinol; (with PBr3 ) to 1-bromo-1 -(2,3,6-trimethoxyphenyl)propane; (with
KOH, ethanol, then H2S04) to 2,3,6-trimethoxypropenylbenzene; (with tetranitromethane)
to 1 -(2,3,6-trimethoxyphenyl)-2-nitropropene; (with LAH) to TMA-5 (Shulgin, 1966).
From 1,2,4-trimethoxybenzene (with n-butyl lithium) to 2,3,6-trimethoxybenzoic acid;

(with LAH) to 2,3,6-trimethoxybenzyl alcohol; (with manganese dioxide in benzene) to
2,3,6-trimethoxybenzaldehyde; (with ammonium acetate, nitroethane) to 1 -(2,3,6-trime
thoxyphenyl-2-nitropropene; (with LAH) to TMA-5 (Zaitsu et al., 2008) .

m / z: 225.1365 (100.0% ), 226.1398 (13.0%)
HCl salt m.p. 125 °C (Shulgin, 1966) (IPA)

The chemistry and properties of the six positional isomers of TMA were compared (Shulgin,
1966). The [ 1 3 C]-NMR spectra for methoxylated phenethylamines and amphetamines are
distinctive and suitable for identification (Bailey and Legault, 1981, 1983) .

Meo I Meo Me -
-
3-1-2,6-DMA [159432-48-1 ] (1)
MeO I MeO Me Me2 2,6-IDNNA [ 105363-46-0l (2,3)
Meo 1221 Meo Me Me2 2,6- 122IDNNA [ 105363-44-8] (3,4)
MeO 12s1 Meo Me Me2 2,6- 125IDNNA [ 105363-42-6] (3)

TMA-5 / TMA-6

MeO Meo MeO -- -- TMPEA-5 [3166-84-5] (5-9)
Meo Meo MeO Me -- TMA-5 (this entry)
(1) Synthesis from 2,6-DMA with 121 Ag2S0 (Sy, 1993).

4
(2) Iodination product of 2,6-DNNA (Mathis et al., 1986b).
(3) Synthesis of [1 221] and [1 251] substituted analogues of dimethoxy substituted N,N-dimethylam-
phetamines (Mathis et al., 1986b).
(4) Patented as a tool for monitoring cerebral blood flow in mammals (Sargent et al., 1987).
(5) Studies on the enzymatic oxidative deamination and effects on cat behavior (Clark et al., 1964).
(6) Effects of ring methoxy groups on deamination by soluble amine oxidase, isolated from rabbit
liver (Clark et al., 1965).
(7) Studies compared mouse behavior and the activity of the brain enzymes MAO and DOPA decar
boxylase (De Ropp and Kastl, 1970).
(8) [13C]-NMR spectra for methoxylated phenethylamines and amphetamines are distinctive and
suitable for identification (Bailey and Legault, 1983).
(9) TMPEA-5 is a positional isomer of mescaline, and therefore a Schedule I hallucinogen under
federal drug law.
Biochemistry
A correlation was made between the energy of the highest occupied molecular orbital of
the drug and potency in humans (Kang and Green, 1 970) . TMA-5 affected uptake and
release of serotonin by human blood platelets (Tseng and Loh, 1 977) . Using calculated
energy interactions between several amphetamines and a model compound (3-methylin
dole), a receptor model for psychedelics was developed (DiPaolo et al., 1 978) .
Pharmacology
Correlation was made between psychedelic potency of methoxyamphetamines and their
inhibition of [ 3 H]-normetanephrine uptake in rat cerebral cortex (Hendley and Snyder,
1 971 ) . A positive correlation was found with a series of psychedelic amphetamines, be
tween the stability of molecular complexes (as determined by NMR) and the threshold
active dose in humans (Sung and Parker, 1 972) . Behavioral effects were observed in rats
trained to respond to food presentation schedules (Harris et al., 1 978).
This drug has been evaluated in extensive computational (Beuerle et al., 1 997; Clare, 1 998)
and clinical SAR studies (Shulgin et al., 1 969).
TMA-5 had threshold oral activity in humans at 30 mg; duration perhaps 8-1 0 hours
Legal Status
#122. TMA-6
a-Methy1-2,4,6-trimethoxyphenethylamine
NSC 367445

TMA-6
Registry Numbers
CAS # CAS # CAS #
dl-HCI
HCl salt [23815-74-9] Acid salt [ 87059-64-1 ] R-Isomer freebase [ 67225-64-3]
salt [72739-10-7] Freebase [ 15402-79-6]
Sulfate [64610-49-7] di-Freebase [22199-16-2]
Synthesis
From 1,3,5-trihydroxybenzene (with methanol and sulfuric acid; removing methanol and
adding KOH) to 1,3,5-trimethoxybenzene; (with ZnC12, HCN, then HCl) to 2,4,6-trime
thoxybenzaldehyde; (with nitroethane, acetic acid, and ammonium acetate) to 1 -(2,4,6-tri
methoxyphenyl-2-nitropropene; (with LAH) to TMA-6 (Benington et al., 1954b).

m/ z : 225.1365 (100.0% ), 226.1398 (13.0%)
Elemental Analysis: C,
63.98; H, 8.50; N, 6.22; 0, 21.31
°C
°C
HCI salt m.p. 214-215 (Benington et al., 1954b) (MeOH / EtOAc)
°C
HCI salt m.p. 214 (Shulgin, 1966) (IPA)
Pierate m.p. 212-213 (Benington et al., 1954b) (EtOH)
gin, 1966) . The NMR spectrum was obtained and intramolecular interactions analyzed
(Bailey et al., 1971 ) . Synthesis, TLC and GC chromatographic properties, UV spectra,
and other physical properties were reported (Ono et al., 1 976) . In a series of psychoactive
compounds, those with greater potency had lower ionization potential as measured by
photoelectron spectroscopy (Domelsmith and Houk, 1 978). The conformation of the aryl
methoxy groups of several psychedelics was established by [ 13 C]-NMR spectral analysis
(Knittel and Makriyannis, 1 981), and [ 13 C]-NMR spectra for methoxyamphetamines were
shown to be distinctive and suitable for identification (Bailey and Legault, 1 981, 1 983) . TLC
and color tests were defined for the identification of substituted amphetamines (O'Brien
et al., 1 982) . Analysis by HPLC employing fluorescamine derivatization for fluorescence
detection was reported (Shimamine, 1984), and employing HPLC-PDA, LC / MS, TLC, and
NMR, a library of 35 illegal drugs was assembled and used to identify street samples (Na
kashima et al., 2005). The fragmentation patterns of some fifty-five phenethylamines were
determined by a variety of mass spectrometry techniques (Kolliker and Oehme 2004) .

Me MeO Me -- -- 2,6-Me-MPEA [52670-12-9] (1,2 )
Meo Meo Me -- -- 6-Me-2,4-DMPEA [ 109036-65-9] (1,2)
Me EtO Me -- -- 2,6-Me-4-EPEA [1 09469-29-6] (1,2)
Me EtO EtO -- -- 6-Me-2,4-DEPEA [101863-62-1 ] (1,2)
MeO Me Me -- -- 4,6-Me-2-MPEA [ 109036-63-7] (1,2)
Meo Me MeO -- -- 4-Me-2,6-DMPEA [109035-91-8] (1,2)
EtO Me Me -- -- 4,6-Me-2-EPEA [ 109471-03-6] (1,2)
EtO MeO Me -- -- 6-Me-2,4-EMPEA [101 787-06-8] (2)

TMA-6

---
Meo HO MeO -- -- DES-TMPEA-6 [91252-61-8] (4,5)

Meo Meo Meo -- -- TMPEA-6 [31 66-90-3] (6-15)
MeO MeO Meo Me -- TMA-6 (this entry)
MeO MeO Meo Me Me N-Me-TMA-6 [93675-33-3] (16)
Meo Meo Meo Et -- 4C-TMPEA-6 [722550-60-9] (14)
EtO Me MeO Me --
-·- -- - · .
4-Me-2,6-MEA
--·--·---
- --
[22702-16-5] (17)
EtO EtO EtO -- -- 2,4,6-TRIS [108013-35-0] (5,6,15)
BuO Bu BuO Me -- 'ljl-BBB [22702-22-3] (17)
(4) Studies were made of both agonist and antagonist activity with dopamine-[3-oxidase (Creveling
et al., 1962).
(7) Enzymatic oxidative deamination and effects on cat behavior (Clark et al., 1964).
(8) Orally active in humans at 1 05 mg (Ratzeburg, 2005).
(9) Effects of ring methoxy groups on oxidative deamination (Clark et al., 1965).
(10) Effects on rat brain enzymes observed (Clark et al., 1956).
(11) TMPEA-6 is a positional isomer of mescaline, and a Schedule I hallucinogen under federal drug
law.
(12) Comparison of mouse behavior and the activity of MAO and DOPA decarboxylase in the brain
(De Ropp and Kastl, 1970).
(13) [ 1 3C]-NMR spectra for methoxylated phenethylamines and amphetamines are distinctive and
suitable for identification (Bailey and Legault, 1983).
(14) Fragmentation patterns of fifty-five phenethylamines determined by a variety of mass spec-
trometry techniques (Kolliker and Oehme, 2004).
(15) Synthesis, TLC and GC, and the UV spectrum reported (Ono et al., 1976) .
(17) Synthesis described, and patented as CNS stimulants (Shulgin, 1970).
Biochemistry
Effect on alkaline phosphatase activity and pyruvate utilization in rat brain homogenates
and supernatants was reported (Clark et al., 1956) . A correlation was made between the
potency of 2,3-DMA, 2,5-DMA, TMA-3, and TMA-6, and the EEG arousal location in rabbit
brain (Fujimori et al., 1971 ) . Interactions with the liver cytochrome P450 enzyme CYP2D6
were studied (Wu et al., 1997).A positive correlation was found with a series of psychedelic
amphetamines, between the stability of molecular complexes (as determined by NMR) and
the threshold active dose in humans (Sung and Parker, 1972) . For the compounds PMA,
2,4-DMA, 2,5-DMA, TMA, TMA-2, and TMA-3 (but not for DMA and TMA-6), the lower
energy of the n:-n: * transition and the increased probability of it occurring was positively
correlated with human potency (Bailey and Verner, 1972) . TMA-6 affected the uptake and
release of serotonin by human blood platelets (Tseng and Loh, 1977) . Using calculated
energy interactions between several amphetamines and a model compound (3-methyl
indole), a receptor model for psychedelics was developed (DiPaolo et al., 1978) . Using a
rat fundus model, serotonin receptor site affinity was determined (Glennon et al., 1980a) .

TMA-6 / TMePEA
TMA-6 inhibited serotonin binding to rat brain membranes (De Jong et al., 1982) . Binding
at 5-HT2 A receptors was compared with binding affinity of several f3-carbolines (Glennon
et al., 2000) . A reproducible, simple, and small-scale method for detecting the re-uptake
and release of monoamines (dopamine, serotonin, and norepinephrine) by rat brain syn
aptosomes was developed (Nagai et al., 2007) .
Pharmacology
The relative effectiveness of several psychedelics in disrupting maze performance by rats
was determined (Uyeno and Mitoma, 1969) . Correlation was made between psychedelic
potency of methoxyamphetamines and their inhibition of [ 3H]-normetanephrine uptake in
rat cerebral cortex (Hendley and Snyder, 1971 ) . Effects observed in rats trained to respond
to food presentation schedules (Harris et al., 1978) .
In a large number of methoxylated amphetamine, the rabbit hyperthermia paralleled hu

man psychedelic potency (Anderson et al., 1978b); a series of amphetamines were studied
for correlation between 5-HT2 affinity, charge complex stability, rabbit hyperthermia, and
With rats trained with various avoidance programs, four positional isomers were studied.
They decreased in potency with TMA-2 > TMA > TMA-6 >> TMA-3 (Smythies et al., 1967b).
in visual discrimination performance studies in the monkey, with amphetamine and mes
caline as standards; 2-Br-LSD and TMA-3 were inactive controls (Uyeno et al., 1969) . Rats
phenylisopropylamines (Glennon et al., 1981b). Rats trained to distinguish between DOM
and saline in a drug discrimination task with a series of methoxylated amphetamines,
showed 2,4-DMA, 2,3,4-, 2,3,5-, 2,4,6-, and 3,4,5-TMA to be active isomers, but 2,3-, 2,6-,
and 3,5-DMA to be relatively inactive (Glennon and Young, 1982) . Discrimination method
ology with rats trained on racemic amphetamine generalized with TMA-6, but with less
sensitivity than the training drug (Glennon et al., 1985) . About a dozen psychedelics were
compared to stimulants, evaluated in rats trained in a conditioned avoidance study (Davis
and Hatoum, 1987) .
Changes in substitution patterns influenced human potency (Shulgin et al., 1969). A cor
relation was made between the degree of native fluorescence and psychedelic potency of
the methoxy derivatives in humans (Antun et al., 1971 ), and between the octanol-water
partition coefficient and psychedelic potency (Barfknecht et al., 1975) .
TMA-6 is an orally active psychedelic in humans at 25-50 mg; duration 12-16 hours (Shul
gin and Shulgin, 1991).
Legal Status
-
------ -----------------�-----
#123. TMePEA
2-(3,4,5-Trimethylphenyl)ethanamine
3,4,5-TMePEA
3,4,5-Trimethylphenethylamine
3,4,5-tris-Desoxymescaline

TMePEA
Registry Numbers
CAS #
HCI salt [3166-71-0]
Freebase [76935-66-5]

From mesitylene (with acetic anhydride, AIC13} to 2,4,6-trimethylacetophenone; (with
AIC13) to 3,4,5-trimethylacetophenone; (with morpholine, sulfur) to 3,4,5-trimethylaceto
thiomorpholide; (with acetic acid, sulfuric acid) to 3,4,5-trimethylphenylacetic acid; (with
PC151 then ammonia) to 3,4,5-trimethylphenylacetamide; (with LAH) to TMePEA (Bening
ton et al., 1957b).

m / z: 163.1361 (100.0% ), 164. 1395 (11 .9% )
HCl salt m.p. 249-250 °C (Benington et al., 1957b) (MeOH / EtOAc)

2- 3- 4- 5- 6- a- Other Name CAS # Ref
-- Me Me Me -- -- -- TMePEA (this entry)
-- Me Me Me -- Me -- TMeA [32156-17-5] (1)
Me -- Me Me -- -- -- TMePEA-2 [3167-03-1] (2)
Me -- Me Me -- Me -- TMeA-2 [ 91 0404-30-7] (3)
Me Me Me -- -- -- -- TMePEA-3 [76935-62-1 ] (4,5)
Me Me Me -- -- Me -- TMeA-3 -- (3)
Me Me -- Me -
- -- -- TMePEA-4 [76935-63-2] (5)
Me Me -- Me -- Me -- TMeA-4 -- (3)
Me Me -- -- Me -- -- TMePEA-5 [76935-64-3] (5)
Me Me -- -- Me Me -- TMeA-5 -- (3)
Me -- Me -- Me -- -- TMePEA-6 [3167-10-0] (2,6)
Me Me Me Me -- -- -- TeMePEA [3166-72-1 ] (2,7)
Me Me Me Me -- Me -- TeMeA [32156-18-6] (1)
Me Me Me -- Me -- -- TeMePEA-2 [3167-11-1] (2,7)
Me Me Me -- Me Me -- TeMeA-2 [32156-19-7] (1)
Me Me -- Me Me -- -- TeMePEA-3 [3167-12-2] (2,7)
Me Me -- Me Me Me -- TeMeA-3 [32156-20-0] (1)
Me Me Me Me Me -- -- PeMePEA [3167-13-3] (2,7)
Me Me Me Me Me Me -- PeMeA [32156-13-3] (1)
Et -- Et -- Et -- -- TEtPEA-6 [108123-62-2] (8)
Me -- Me -- Me Me -- TMeA-6 [24973-32-8] (9,10)

TMePEA / TMPEA-2
(1) A correlation was made between the degree of native fluorescence and psychedelic potency in
humans (Antun et al., 1971).
(2) Studies on the enzymatic oxidative deamination and effects on cat behavior (Clark et al., 1964).
(4) A synonym for TMePEA-3 is NSC 93714.
(5) Molecular connectivity analysis (Kier, 1980) .
(9) Pharmacology evaluated for toxicity, effects on barbiturate sleeping time, and ability to disrupt
mouse behavior (Ho et al., 1970a).
(10) Synthesis (Milstein, 1968; Ho et al., 1970a).
Pharmacology
Studies on oxidative deamination, and effects on cat behavior were reported by Clark et
al., 1964).
Human psychedelic activity of TMePEA is unknown.
Legal Status
TMePEA is not a scheduled compound under federal drug law, or under District of Co
# 124. TMPEA-2
2,4,5-Trimethoxy-j3-phenethylamine
2C-O
2C-TMA-2
Registry Numbers
CAS # CAS # CAS #
HCl salt [3166-78-7] a,f:3-[d2] HCl salt [ 82698-45-1 ] a,a-[ d2] Freebase [82698-37-1 ]
Sulfate [64610-37-3] a,f3-[ d2] Freebase [ 82698-39-3] f3,f3-[d2] Freebase [86917-28-4]
Acid salt [87059-76-5] 3,6-[d2] Freebase [86917-32-0] a,a,f3-[d ] Freebase [82698-38-2]
3
Freebase [15394-83-9] f3-[d] Freebase [ 82698-36-0l f3,f3-[3H] 2 Freebase [70097-42-6]

From 2,4,5-trimethoxybenzaldehyde (with nitromethane) to 1-(2,4,5-trimethoxy}-2-nitro
ethene; (with LAH) to TMPEA-2 (Cheng and Castagnoli, 1984; Shulgin and Shulgin, 1991).
A number of salts and derivatives were described for identification purposes (Jansen,
1931) . Synthesis, TLC and GC chromatographic properties, UV spectra, and other physi
cal properties were reported (Ono et al., 1976). [1 3C]-NMR spectra for methoxylated
phenethylamines and amphetamines were shown to be distinctive and suitable for iden
tification (Bailey and Legault, 1983). HPLC analysis employing fluorescamine derivatiza
tion for fluorescence detection was reported (Shimamine, 1984). Fragmentation patterns
techniques (Kolliker and Oehme, 2004). Techniques were explored for the analysis of street
drugs without the use of primary reference standards, utilizing liquid chromatography

TMPEA-2
with time-of-flight mass spectrometry for compound identification, and LC with chemi
luminescence nitrogen detection for quantitation (Laks et al., 2004).

m / z: 211 .1208 (100.0% ), 212.1242 (11 .9% )
HCl salt m.p. 1 87-188 °C (Cheng and Castagnoli, 1984) (EtOH)

NH2 HO HO 4,5-H0-2-APEA [38411 -80-2] (1)
HO NH2 HO 2,5-H0-4-APEA [41241-40-1 ] (1)
HO HO NH2 2,4-H0-5-APEA [41241-41-2] (1)
HO HO HO 2,4,5-HO-PEA [28094-15-7] (2,3)
HO MeO HO 2,5-HO-MPEA [13062-74-3] (4)
MeO NH2 Meo 2C-NH [168699-66-9] (1)
MeO Meo NH2 5-NH2-2,4-DMPEA [ 168699-69-2] (1)
MeO MeO Meo TMPEA-2 (this entry)
MeO EtO MeO 2C-0-2 -- (5,6)
Meo PrO MeO 2C-0-7 -- (5,7)
MeO iPrO MeO 2C-0-4 -- (5,8)
MeO BuO MeO 2C-0-19 -- (5,9)
MeO MeSe MeO 2C-SE -- (5, 1 0)
(1 ) Neurotoxicity was determined through both in vivo and in vitro studies (Ma et al., 1995).
(2) Other names: 6-hydroxydopamine, oxidopamine, topamine.
(3) There are thousands of references to this in the chemical literature as a dopamine-like biochemical,
but no human trials as a potential psychedelic.
(4) Effectiveness of releasing cardiac norepinephrine was measured in the mouse (Daly et al., 1966).
(6) The oxygen analogue of the sulfur compound 2C-T-2.
(8) The oxygen analogue of the sulfur compound 2C-T-4, which is orally active in humans at 8 to 20
mg; 2C-0-4 is inactive at 60 mg (Shulgin and Shulgin, 1991 ).
(IO) Threshold oral activity in humans at 1 00 mg; duration 6-8 hours (Shulgin and Shulgin, 1991 ).
Biochemistry
Effects of ring methoxy groups on oxidative deamination were studied (Clark et al., 1965) .
Effectiveness at releasing cardiac norepinephrine was measured in the mouse (Daly et al.,
1966). Studies comparing mouse behavior and the activity of the brain enzymes MAO and
DOPA decarboxylase were conducted (De Ropp and Kastl, 1970) . Physiological responses
were observed in the rat brain, liver, and plasma (Cohen et al., 1974) . Cerebral and periph
eral demethylation of TMPEA-2 was measured from each of the separately labeled [ 14 C]
CH30 groups in the rat (Sargent et al., 1989) . Adrenergic and 5 HT2 serotonergic effects on
-
the rat thoracic aorta were compared (Saez et al., 1994) .

TMPEA-2 I Trichocereine
Pharmacology
Studies on oxidative deamination and effects on cat behavior were reported (Clark et al.,
1964) . Human potency was affected by changes in substitution patterns (Shulgin et al., 1969);
the compound was further evaluated in an extensive QSAR study (Beuerle et al., 1997) . Sev
eral phenethylamines and tryptamines were compared in discrimination stimulus studies
with rats trained with 5-MeO-DMT (Kier and Glennon, 1978b). Using molecular connectiv
ity analysis of ten psychedelic phenethylamines, the importance of the 2,5-positions of the
methoxy groups, and the 4-substituent was demonstrated (Glennon et al., 1979a) .
TMPEA-2 pretreatment potentiated the effects of mescaline in humans (Dittrich, 1971);
however, there was no oral activity of TMPEA-2, alone, in humans at 300 mg (Shulgin and
Shulgin, 1991).
Legal Status
TMPEA-2 is a positional isomer of mescaline, and therefore a Schedule I hallucinogen
under federal drug law, and in states where isomers are included in the controlled drug
definition.
#125. Trichocereine
N,N-Dimethyl-2-(3,4,5-trimethoxyphenyl)ethanamine
N,N-Dimethyl-3,4,5-trimethoxyphenethylamine
N,N-Dimethylmescaline
3,4,5-Trimethoxy-N,N-dimethylbenzeneethanamine
MM-M
Registry Numbers
CAS #
HCI salt [54547-01-2]
Freebase [529-91-9]
Natural Sources
This compound was first reported from Trichocereus terchscheckii (Luduena, 1935), and later
confirmed in this cactus (Reti and Castrill6n, 1951). It was also found in cactus of the Gym
nocalycium spp. (Starha et al., 1997), and Turbinicarpus spp. (Starha et al., 1999) .
Trichocereine was also reported present in Acacia berlandieri (Clement et al., 1997), and A.
rigidula (Clement et al., 1998) .
Synthesis
From mescaline (with HCl and NaN02, then dimethylamine) to trichocereine (Reti and
Castrill6n, 1951).

acetophenone; (with dimethylamine) to N,N-dimethyl-3,4,5-trimethoxyphenylacetamide;
(with LAH) to trichocereine (Banholzer et al., 1952) .
From 3,4,5-trimethoxyphenylacetic acid (with SOC12) to the acid chloride; (with dimethyl
amine) to the corresponding dimethyl acetamide; (with LAH) to trichocereine (Benington
et al., 1957a) .

Trichocereine I Tyramine

m / z: 239.1521 (100.0% ), 240.1555 (14.1%)
HCl salt m.p. 205 °C (Reti and Castrill6n, 1951) (EtOH)

HCl salt m.p. 207-208 °C (Benington et al., 1957a) (EtOH / EtOEt)
Chloroaurate m.p. 136-139 °C (Reti and Castrill6n, 1951) (Hp, dee.)
Chloroplatinate m.p. 1 84-185 °C (Reti and Castrill6n, 1951) (Hp)
Picrate m.p. 1 71-172 °C (Reti and Castrill6n, 1951) (acetone)
Picrolonate m.p. 166 °C (Reti and Castrill6n, 1951) (EtOH / acetone)
Biochemistry
Trichocereine had effects on alkaline phosphatase activity and pyruvate utilization in rat
brain homogenates and supernatants (Clark et al., 1956).
Pharmacology
The lethal dose in rats was 240 mg /kg, but unlike mescaline, trichocereine did not produce
mental disturbances in humans (Luduefia, 1935). The conditioned avoidance response of
the rat was studied for both trichocereine and DMPEA and related to that of mescaline
(Smythies and Sykes, 1966). In rats trained to distinguish mescaline from saline, following
intraventricular administration, neither the N-methyl nor the N,N-dimethyl homologues
(M-M and trichocereine, respectively) evoked activity (Browne et al., 1974).
Trichocereine did not produce psychological effects in human trials up to 550 mg (Lu
duefia, 1935).
Legal Status
Trichocereine is not a scheduled compound under federal drug law, or under District of
# 126. Tyramine
4-(2-Aminoethyl)phenol
4-Hydroxyphenethylamine
p-Tyramine
Systogene
Tocosine
Tyrosamine
Uteramine
HPEA
4-HPEA
4-HO-PEA
NSC 249188
Registry Numbers
CAS # CAS #
HBr salt [ 17605-58-2] Amine anion [219919-55-8]
Hemihydrate [62722-95-6] Phenoxyl radical [308271-86-5]
Monohydrate [924281 -00-5] Freebase [51-67-2]
4-Phenolate HCl salt [78569-00-3] d- (loc. unspecified) [69275-17-8]

Tyramine
CAS # CAS #
a-[d], R-Isomer freebase [124454-73-5] a,a,j3-2,3,5,6-[d7] Isomer [114076-86-7]
a-[d], S-Isomer freebase [ 124454-75-7] 2-[3H] Isomer [60745-26-8]
13-[d] Isomer freebase [108748-74-9] a-[ 3H] HCl R-Isomer [74447-59-9]
a,a-[ dz] Freebase [81541-01-7] a-[ 3H] HCl S-Isomer [74447-55-5]
a,j)-[dz] Freebase [81541 -02-8] a-[11C] Isomer [ 151560-60-0 l
j),j)-[ dz] HCl salt [95864-32-7] a-[1 3C] Isomer [151459-88-0]
j),j)-[dz] Isomer freebase [92400-90-3] a-[1 4C] Isomer [ 13822-12-3]
a,a,j3-[d ] R-Isomer [52009-74-2] a-[1 4C]-j3-[3H], R-Isomer [39236-10-7]
3
a,a,j)-[ d ] S-Isomer [52009-73-1] a-[14C] Isomer HCl salt [80787-62-8]
3
2,3,5,6-[d4] Isomer [944386-63-4] [15N] Isomer [ 98985-53-6]
a,a, j3,j3-[d ] Isomer [ 105233-20-3]
4
Natural Sources
Tyramine is ubiquitous in the living world, as it is a metabolite of the amino acid tyrosine.
It is found in many plants, including dozens of psychoactive cacti (Trout, 1997). It has
been reported Trichocereus peruvianus (Agurell, 1969a), T. pachanoi, and T. werderman n ianus
(Agurell 1969b), Pilosocereus maxonii {Pummangura et al., 1977), Coryphan tha (Neobesseya)
caline, tyramine, and HMePEA were all isolated from the cactus Opuntia ficus-indica (El
missouriensis (Pummangura et al., 1981), and in Gymnocalycium spp. (Starha, 1996). Mes
Moghazy et al., 1984).
Precursors and metabolites of phenethylamine, m- and p-tyramine and tryptamine were

found in human lumbar and cistemal cerebrospinal fluid (Young et al., 1982), and there is
evidence for the presence of m-tyramine, p-tyramine, tryptamine, and phenethylamine in
the rat brain and several areas of the human brain (Philips et al., 1978).
Synthesis
From anisaldehyde (with malonic acid) to 4-methoxycinnamic acid; (with Na, Hg) to
4-methoxyhydrocinnamic acid; (with sulfonyl chloride, NH3) to the amide; (with NaO
Cl, NaOH) to 4-methoxyphenethylamine; {with HBr) to tyramine (Gryszkiewicz-Trochi
mowski, 1937).
From 4-hydroxyphenylglyoxal {with benzylamine and Raney Ni, H2) to 2-{benzylamino)-1-

(4-hydroxyphenyl)ethanone; (with N-methylamine) to tyramine (Fodor and Kovacs, 1951).

Molecular Weight: 1 37. 1 8
m / z: 1 37.0841 (100.0% ), 138.0874 (8.7%)
Freebase m.p. 158-160 °C (Gryszkiewicz-Trochimowski, 1937) (HzO)
A procedure was described for extraction, separation, and analysis by GC with electron
capture detection of phenethylamine, tyramine, and octopamine from human plasma
(Baker et al., 1980).
Biochemistry
[14C]-labeled tyramine was used to explore the biosynthesis of mescaline in Lophophora
williamsii {Lundstrom and Agurell, 1968b).
Human metabolism of PEA was observed by the oral administration of deuterium labeled
PEA; the major metabolite was phenyl acetic acid, but 3-HPEA and 4-HPEA were detected

Tyra mine
in significant amounts, along with their respective hydroxylated phenylacetic acids (Davis
and Boulton, 1980) . Phenethylamine was shown to be metabolised to 4-HPEA by postmor
tem human brain preparations (Wolf et al., 1987) . The metabolism of ingested deuterium
labeled tyramine was studied in normal human subjects (Boulton et al., 1987) . Kinetic study
of tyramine metabolism in humans utilized stable isotope-labeled tracers (Shimamura et
al., 1993b). Dramatic increases of tyramine in postmortem cerebrospinal fluid after death
have the potential of becoming a new tool in forensic science for better defining the time
of death (Balbi et al., 2005).
In a study of Fisher 's syndrome (a pharmacological study of the pupils), instillation of 5%

tyramine produced pupillary dilation (Okajima et al., 1977) . Influence of nomifensine and
desipramine on tyramine pressor responses was studied in healthy human male volun
teers (McEwen, 1977) . Methods of administering tyramine to raise systolic blood pressure
in humans were evaluated (Pace et al., 1 988) .
Decreased urinary output of conjugated tyramine has been associated with lifetime vul
nerability to depressive illness (Carter et al., 1980; Sandler et al., 1980). p-Tyramine, nor
mally found in the mammalian hypothalamus, inhibited prolactin release in vivo (Becu
Villalobos et al., 1985) . Tyramine sulfate excretion was shown to be a better predictor of
antidepressant response than monoamine oxidase activity in humans (Stewart et al., 1988),
and a tyramine conjugation test distinguished unipolar from bipolar depressed patients
and controls (Hale et al., 1991).
Tyramine was investigated as a monoamine oxidase inhibitor in the rat liver (Takagi and
Gomi, 1966) . Atrial fibrillation is precipitated by tyramine containing foods (Jacob and
Carron, 1987), and in healthy human volunteers tyramine pretreatment caused a tempo
rary, dose-dependent increase in systolic and diastolic blood pressure (Colombo et al.,
1 988). Effects of MAO inhibitors on blood pressure and the pharmacokinetics of tyramine
was studied in healthy humans (Bieck, 1990); tyramine effects on the human uterine artery
were studied, in vitro (Garcia de Boto et al., 1991 ) . Tyramine-mediated activation of sym
pathetic nerves inhibited insulin secretion in humans (Gilliam, Palmer, Taborsky, 2007) .
Pharmacology
Comparative action of tyramine and 4-MPEA on conditioned behavior was studied in
the rat (Xhenseval, 1965) . The mechanisms for hyperactivity induction from the nucleus
accumbens by phenethylamine derivatives were characterized (Costall et al., 1976) . Spe
cific enhancement of neuronal responses to catecholamine by tyramine was demonstrated
(Jones, 1981 ) . The effect of nutritional stress at various ages on the levels of the p- and m
isomers of tyramine in the caudate nucleus of the rat was studied (Bhave et al., 1988) .
Tyramine is not known to have psychedelic properties in humans.
Legal Status
Tyramine is not a scheduled compound under federal drug law, or under District of Co

313
"It is our attitude toward free thought and free
expression that will determine our fa te. There must be
no limit on the range of temperate discussion, no limits
on thought. No subject must be taboo. No censor mus t
preside at o u r assemblies. "
William 0. Douglas
TABLES
Table of Abbreviations
Table 1. Abbreviations for parent structures and substituents.

Abbrev. Structure Abbrev. Structure
PEA phenethylamine 2HOPrO 2-hydroxypropoxy
A amphetamine 3HOPrO 3-hydroxypropoxy
pp phenylpiperazine BuO butoxy
F fluoro iBuO isobutoxy
Cl chloro Amo amyloxy
Br bromo HeO hexyloxy
I iodo SeO septyloxy
NH2 amino OcO octyloxy
NHMe methylamino NoO nonyloxy
NMe2 N-dimethylamino PhO phenoxy
NHOH hydroxylamino BzO benzyloxy
N02 nitro PhEtO phenethyloxy
Me (or M) methyl Ve veratryl
CHl fluoromethyl -CCO- dihydrofuryl
CH,QH hydroxymethyl -COC- dihydroisofury I
CHO formyl -OC=C- fury!
CN cyano fur furfuryl
CCN cyanomethyl mor morpholyl
Et ethyl pyrr pyrrolidinyl
Pr (n-) propyl -OCMeO- methyldioxole
cPr cyclopropyl -OCMep- dimethyldioxole
cPM methylcyclopropyl -OC 3- tetrahydropyranyl
iPr isopropyl -CMe2CO- dimethyldihydrofuryl
Al ally! -OCO- methylendioxy
PR propargyl -OCFp- difluorodioxole
Bu butyl -OCp- ethylenedioxy
sBu sec-butyl Ac acetyl
tBu tert-butyl AcO acetoxy
Am (or Pe) amyl (pentyl) MeS methylthio
He hexyl EtS ethylthio
Se septyl FCCS fluoroethy!thio
Oc octyl F2CCS difluoroethylthio
No nonyl F3CCS trifluoroethylthio
Bz benzyl PrS propylthio
Ph CCC phenylpropyl iPrS isopropylthio
COOH carboxyl cPrS cyclopropylthio
CCOH hydroxyethyl AIS allylthio
C02Pr propionyl FC3S fluoropropylthio
C02Bu butyryl Bus butylthio
CO Me acetyl iBuS isobutylthio
COEt propionyl sBuS sec-butylthio
CONHPr propyl amide tBuS tert-butylthio
-C- methylene MeAIS methallylthio
-C2- ethylene cPrMS cyclopropylmethylthio
-C3- propylene or cyclopropyl coccs methoxyethy!thio
-C4- butylene or cyclobutyl FC4S fluorobutylthio
-C=CC=C- cyclobutadienyl AmS amylthio
-Cs- cyclopentyl Hes hexylthio
-CCNMeCC- methyl piperidyl SeS septylthio
HO hydroxy OcS octylthio
co keto NoS nonylthio
MeO (or M) methoxy PhS phenylthio
EtO ethoxy BzS benzylthio
PrO propoxy PhEtS phenethylthio
iPrO isopropoxy MeSe methylseleno
cPrO cyclopropoxy d deuterio
AIO allyloxy
Tables 317
Unsubstitu ted
Table 2. Unsubstituted phenethylamines and amphetamines.

6- 5- 4- 3- 2- a- 13- N- Entry Name
-- -- -- -- -- -- - -
-- #107 PEA: 2-Phenylethanamine
-- -- -- -- -- -- -- Me #89 N-MePEA
-- -- -- -- -- -- -- Me2 see #107 N,N-MePEA
-- -
- -- -- -- -- -- Et see #107 N-EtPEA
-- -- -- -- -- -- -- Pr see #107 N-PrPEA
-- -- -- -- -- -- -- iPr see #107 N-iPrPEA
-- -- -- -- -- -- -- -Cs- see #107 pip-PEA
-- -- -- -- -- -- Me Me see #107 13,N-MePEA
-- -- -- -- -- -- Me Et see #107 13-Me-N-Et-PEA
-- -- -- -- -- -- HO -- see #107 13-HO-PEA
-- -- -- -- -- -- HO Me2 see #107 13-HO-N,N-Me-PEA
-- -- -- -
- -- -- C=O -- see #40 AA
-- -- -- -- -- -- C=O Me see #40 MAA
-- -- -- -- -- -- C=O Me2 see #40 DMAA
-- -- -- -- -- Me -- -- -- Amphetamine, Aa
-- -- -- -- -- Me -- Me -- Methamphetamine, MAa
-- -- -- -- -- Me -- Me2 see #107 DIMETH
-- -- -- -- -- Me - -
Et -- EAa
-- -- -- -- -- Me -- Et2 -- EEAa
-- -- -- -- -- Me -- Pr -- PAa
-- -- -- -- - -
Me -- Bu -- BA a
-- -- -- -- -- Me -- HO see #107 AMPH-OH
-- -- -- -- -- Me HO -- -- nor-Ephedrineb
-- -- -- -- -- Me HO -- -- norPseudoephdrineb
-- -- -- -- -- Me HO Me -- Ephedrineb
-- -- - -- -- Me HO Me -- Pseudoephedrineb
-- -- -- -- -- Me HO Me2 -- Methylephedrine
-- -- -- -- -- Me -OCC- -- Phenmetrazine
-- -- -- -- -- Me C=O -- -- Cathinonea
-- -- -- -- -- Me C=O -C4- see #40 PPP
-- -- -- -- -- Me C=O -Cs- see #40 PIAP
-- -- -- -- -- Me C=O -CCNMeCC- see #40 PZAP
-- -- -- -- -- Me C=O Me #92 Methcathinone
-- - -
-- -- -- Me C=O Me2 #40 DMAP
-- -- -- -- -- Me C=O Et see #40 EAP
-- -- -- -- -- Me C=O Et2 see #40 DEAP

Unsubstituted I Monosubstitu ted
6- 5- 4- 3- 2- a- 13- N- Entry Name
-- -- -- -- -- Me C=O Pr see #40 PAP

-- -- -- -- -- Me C=O iPr see #40 i-PAP
-- -- -- -- -- Me C=O Bu see #40 BAP
-- -
- -- -- -- Me C=O tBu see #40 t-BAP
-- -- -- -- -- -C- -
- see #107 cPr-PEA
-- -- -- -- -- Me2 -- Me -- Mephenterminec
-- -- -- - -
-- Me2 -- -- -- Phentermine•
-- -- -- -- -- Me2 Me -- -- Pentorex•
-- -- -- -- -- Et -- -- see #107 AEPEA
3Clinically defined as a stimulant, and is not covered in this book.

bThe isomers of ephedrine have a variety of clinical applications and are not covered in this book.
cClinically defined as an antihypotensive, and is not covered in this book.
Table 3. Monosubstituted phenethylamines and amphetamines.

6- 5- 4- 3- 2- a- 13- N- Entry Name
-- - -
-- -- F Me -- -- see #74 2-FA
-- -- -- -- Cl -- -- -- see #100 2-Cl-PEA
-- -- -- -- Cl Me -- -- see #74 2-CA
-- -- -- -- Cl Me -- Me see #74 2-CMA
-- -- -- -- Cl Me2 -- -- see #74 2-Cl-a,a-MePEA
-- -- -- -- Br -- -- -- see #100 2-BPEA
-- -- -- -- Br Me -- -- see #74 2-BA
-- -- -- -- NH2 -- HO -- see #100 13-H0-2-APEA
-- -- -- -- NH2 -- C=O -- see #100 2-APEA-13k
-- -- -- -- Me -- -- -- see #100 2-MePEA
-- -- -- -- Me Me -- -- see #111 2-MeA
-- -- -- -- CF3 Me -- -- see #63 2-TFMA
-- -- -- -- HO -- -- -- see #71 2-HPEA
-- -- -- -- HO -- -- Me see #71 N-Me-2-HPEA
-- -- -- -- HO -- -- Me2 see #71 N,N-Me-2-HPEA
-- -- -- -- HO -- HO -- see #71 13-H0-2-HPEA
-- -- -- -- HO Me -- -- see #74 2-HA
-- -- -- -- HO Me -- Me see #74 2-HMA
-- -- -- -- MeO -- -- -- #100 2-MPEA
-- -- -- -- MeO -- -- Me see #100 N-Me-2-MPEA
-- -- -- -- Meo -- -- Me2 see #100 N,N-Me-2-MPEA
-- -- -- -- Meo -- Me -- see #100 13-Me-2-MPEA
-- -- -- -- MeO -- Me Me see #100 13,N-Me-2-MPEA
Tables 319
Monosubstituted
- -··r -
a-
-------
6- 5- 4- 3- 2- f3- N-
- �----·--
Entry Name
-- -- -- -- MeO Me -- -- #74 2-MA
--
-f---
-- -- -- MeO Me Me Me see #74 [3-Me-2-MMA
-- -- -- -- MeO Me -- Me - - 2-MMN
-- -- -- - - -- - --
MeO Me C=O Me see #74 2-MMA-f3k
-- -- -- -- MeO Me -- Me2 see #74 N,N-Me-2-MA
------
-- -- -- -- MeO Me -- Et see #74 N-Et-2-MA
-- -- -- -- Meo Me -- Et2 see #74 N,N-Et-2-MA
--
-- -- -- -- MeO Me -- iPr see #74 N-iPr-2-MA
- - -- -- -- MeO Me -- Bu see #74 N-Bu-2-MA
-- -- - - - - Meo Me -- iBu see #74 N-iBu-2-MA
-- -- -- - - MeO Me -- He see #74 N-He-2-MA
-- - - -- -- MeO Me -- Me-fur see #74 N-fur-2-MA
-- -- -- -- MeO Me -- mor see #74 N-mor-2-MA
-- -- -- -- MeO Me -- pip see #74 N-pip-2-MA
-- -- -- -- MeO Et -- -- see #74 4C-2-MPEA
-- -- -- -- EtO -- -- Me see #100 N-Me-2-EPEA
-- -- -- -- EtO -- -- Me2 see #100 N,N-Me-2-EPEA
-- -- -- -- EtO Me -- -- see #74 2-EA
-- -- -- -- MeS -- -- -- see #103 2-MTPEA
-- -- -- -- MeS Me -- -- see #103 2-MTA
-- -- -- F -- Me -- -- see #75 3-FA
-- -- -- F -- Me -- Et see #75 N-Et-3-FA
-- -- -- Cl -- -- -- -- see #101 3-Cl-PEA
-- -- -- Cl -- Me -- -- see #75 3-CA
-- -- -- Cl -- Me -- Et see #75 N-Et-3-CA
--
-----
-- -- -- Cl Me
·- -�-
C=O tBu see #92 Bupropion
-- -- -- Br -- Me -- Et see #75 N-Et-3-BA
-- - - -- Br -- Me C=O Me see #93 3-BMAP
-- -- -- I -- Me -- Et see #75 N-Et-3-IA
-- -- -- N02 -- Me - - Et see #75 N-Et-3-N02A
-- -- -- CF3 -- -- -- -- see #63 3-TFMPEA
- - -- -- CF3 -- Me -- -- see #63 3-TFMA
- - - - -- CF3 -- -- -- Me see #63 3-TFMMPEA
-- -- -- CF3 -- -- -- Et see #63 N-Et-3-TFMPEA
-- -- -- CF3 -- Me -- Et -- Fenfluramineb
-- - - -- CF3 -- Me C=O Me2 see #92 3-TFMDMAP
-- -- -- Me -- -- - - -- see #101 3-MePEA

Monosubstituted
6- 5- 4- 3- 2- a- P- N- Entry Name
·-----·-----
-- -- -- Me -- Me -- -- see #111 3-MeA

-- -- -- HO -- -- -- -- see #71 3-HPEA
-- -- -- HO -- -- -- Me see #71 3-HMPEA
-- -- -- HO -- -- -- Me2 see #71 N,N-Me-3-HPEA
-- -- -- HO -- -- -- Me3 see #71 Leptodactyline
-- -- -- HO -- -- HO -- see #71 P-H0-3-HPEA
-- -- -- HO -- -- HO Me see #71 p-HO-N-Me-3-HPEA
-
-- -- -- HO -- Me -- -- see #75 3-HA
-- -- -- HO -- Me -- Et see #75 N-Et-3-HA
-- -- -- HO -- Me HO -- see #75 P-H0-3-HA
-- -- -- MeO -- -- -- - - #101 3-MPEA
-- - - -- Meo -- -- -- Me see # 1 01 N-Me-3-MPEA
-- -- -- MeO -- -- -- Me2 see #101 N,N-Me-3-MPEA
-- -- -- MeO -- -- -- Et see #101 N-Et-3-MPEA
-- -- -- MeO -- -- -- Et2 see #101 N,N-Et-3-MPEA
-- - - -- MeO -- -- Me -- see #101 p-Me-3-MPEA
-- -- -- MeO -- -- Me Me2 see #101 p,N,N-Me-3-MPEA
-- -- -- MeO -- -- Meo -- see #101 B03M
-- - - -- MeO -- -- MeO Me see # 1 01 B03MM
>---
-- -- -- MeO -- -- Meo Me2 see # 1 01 B03MDM
-- -- -- MeO -- -- EtO -- see #101 B03ME
-- -- -- MeO -- -- Meo iPr see #101 B03MIP
-- -- -- MeO -- -- Meo Bu see # 1 01 B03MB
-- -- -- Meo -- Me Meo -- see # 1 01 B03MA
-- -- -- Meo -- Me EtO -- see #101 B03MEA
-- -- -- MeO -- Me -- - - #75 3-MA
-- -- -- MeO -- Me -- Me see #75 3-MMA
-- -- -- MeO -- Me Me Me see #75 P-Me-3-MMA
-- -- -- Meo -- Me C=O Me see #75 3-MMA-pk
--�
-- -- -- Meo -- Me -- Me2 see #75 N,N-Me-3-MA
-- -- - - MeO -- Me -- Et see #75 N-Et-3-MA
-- -- -- MeO -- Me -- Et2 see #75 N,N-Et-3-MA
-- -- -- Meo -- Me -- Bu see #75 N-Bu-3-MA
-- -- -- Meo -- Et -- -- see #101 4C-3-MPEA
-- -- -- EtO -- -- -- Me see #101 N-Me-3-EPEA
-- -- -- EtO -- Me -- Me see #75 N-Me-3-EA
-- -- -- EtO -- -- -- Me2 see #101 N,N-Me-3-EPEA
Tables 32 1
Monosubs tituted
6- 5- 4- 3- 2- a- f3- N- Entry Name

-- -- -- EtO - -
-- Meo -- see #101 B03E
-- -- -- EtO -- -- EtO -- see #101 B03EE
-- -
- - -
EtO -- Me -
- - -
see #75 3-EA
-- -- -- Pro -- -- MeO -- see #101 B03P
-- -- -- AlO -- -- Meo -- see #101 B03A
-- -- -- MeS -- Me -- -- see #103 3-MTA
-- -- F -
- -- -- -- -- see #102 4-FPEA
-- -- F -- -- Me -- --
see #106 PFA
-
- -- F -- -- Me -- Me see # 106 PFMA
-- - -
F -- -- Me C=O -- see #92 4-F-MCAT
-- -- Cl -- -- -- -
- - -
see #102 4-Cl-PEA
-- -- Cl -- --
-- -- iPr see # 102 N-iPr-4-Cl-PEA
-- -- Cl -- -- Me -- see #102 f3-Me-4-Cl-PEA
-- -- Cl -- -- Me F2 -- see #106 f3,f3-F-PCA
-
- - -
Cl -- -- Me -- -- #106 PCA
-- -- Cl -- - -
Me -- Me see # 106 PCMA
-- -- Cl -- -- Me -- Et see #106 N-Et-PCA
-- -- Cl -- -- Me -- iPr see #106 N-iPr-PCA
-- -- Cl -- -- Me2 -- -
- see #106 4-Cl-a,a-MePEA
-- -- Cl -- -- Et -- -- see #106 CAB
-- -- Cl -- -- -C- -- see #41 CCPA
-- -- Br -
- -- -- -- -- see #102 4-Br-PEA
-- -- Br -- -- Me -- -- see #106 PBA
-
- -- Br -- -- Me C=O Me see #92 4-BMAP
-
- -- Br -- -C- -- -- see #41 BCPA
-- -- I -- -- -- -- -- see #102 4-I-PEA
-- -- NH2 -- -- -- -
- -- see #102 PAPEA
-- -- NH2 -- - - Me -- -- see #106 PAA
-- -- NH2 -- -- Me -- Me see # 106 PAMA
-- -- MeNH -- -- Me -- -- see # 106 MePAA
-- - -
NMe2 -- -- -- -- -- see #102 4-N,N-MePEA
-- -- NMe2 -- -- Me -- -- see #106 DMePAA
-- -- N02 -- -- Me -- - -
see #106 PNA
-- -- N02 -- -- Me -- Me see #106 N-Me-PNA
-- -- CF3 -- -- Me - - -
- see #63 TFMA
-- -- Me -- -- - - -- - -
see #102 4-MePEA
-- -- Me -- -- Me -- -- # 111 PMeA

Monosubs tituted
6- 5- 4- 3- 2- a- �- N- Entry Name
-- -- Me -- -- Me -- Me see #111 PMeMA
-- -- Me -- -- Me C=O Me see #92 4-Me-MCAT
- - -
- Me -- -- Me C=O Pyrr see #92 MPPP
-- -- Me -- -- Pr C=O Pyrr see #92 MPHP
-- -- Et -- -- -- -- -- see #102 4-EtPEA
- -
-- Pr -- -
- -- -- -- see #102 4-PrPEA
--
-- Pr -- -- Me -- -- see #111 4-PrA
-- -- iPr -- -- -- -- -- see #102 4-iPPEA
-- -- iPr -- -- Me -- - -
see #111 4-iPrA
-- -- Bu -- -- -- -- -- see #102 4-BuPEA
-- -- tBu -- -- -- -- -- see #102 4-tBuPEA
-- -- He -- -- -- -- -- see #102 4-HePEA
-- -- HO -- -- -- -- -- #126 Tyramine
-- -- HO -- -- -- -- Me #70 HMePEA
-- -- HO - - --
- -
- -
Me2 #71 Hordenine
-- -- HO -- -- -- -- Me3+ see #71 Candicine
-- -- HO -- -- -- Me -- see #71 �-Me-HPEA
-- -- HO -- - - -
- HO -- see #71 �-HO-HPEA
-- -- HO -- - -
- -
HO Me see #71 �-HO-N-Me-HPEA
-- -- HO -- - - --
HO Me2 see #71 �-HO-Hordenine
-- -- HO -- -- -- MeO Me see #71 �-MeO-HMePEA
-- -- HO -- -- Me -- -- #109 PHA
-- -
- HO -- -- Me -- Me see #109 Pholedrine
-- -- HO -- -- Me -- Bu see #110 N-Bu-PHA
-- -- HO -- -- Me HO -- see #109 �-HO-PHA
- -
-- HO -- - -
Me HO Me see #109 �-HO-HMA
-- -- HO -- - -
Me -- Me2 see #110 PHMMA
-- -- HO -- -- Me -- Et see #110 PHEA
-- -
- HO -- -- Et -- -- see #110 a-Et-4-HPEA
-- -
- AcO - -
-- - -
-- Me see #71 AcO-MePEA
-- -- AcO -- -- -- -- Me2 see #71 Hordenine acetate
-- -- MeO -- -
- -- -- -- #102 4-MPEA
-- -- Meo - -
-- -- -- Me see #102 N-Me-4-MPEA
-- --
MeO -
- -
- - -
-- Me2 see #102 N,N-Me-4-MPEA
-- -- Meo -- -- -- HO -- see #102 �-H0-4-MPEA
-- -- MeO -- -- -- Me -- see #102 �-Me-4-MPEA
-- -- MeO -- - -
-- Me Me see #102 �,N-Me-4-MPEA
Tables 323
Monosubstituted
6- 5- 4- 3- 2- a- f3- N- Entry Name

-- -- Meo -- -- -- Me Me2 see #102 f3,N,N-Me-4-MPEA
-
-- -- MeO -- -- - Me Et see # 1 02 f3-Me-N-Et-4-MPEA
-
-- -- MeO -- - -- Meo -- see #102 f3,4-DMPEA
-- -- MeO -
- -- Me -- �·
-- -- #110 PMA
-- -- Meo -- -- Me -- HO see #110 N-HO-PMA
-- --
� -�--··- ------·
MeO -- -- Me HO -- see #110 f3-HO-PMA
-- -- MeO -- -- Me -- Me #112 PMMA
-- -- MeO -- -- Me -- Me2 see #110 N,N-Me-PMA
-
- -- Meo -- -- Me Me Me see #112 f3-Me-PMMA
-- - -
MeO -- -- Me -- Et see #110 N-Et-PMA
-- -- MeO -- -- Me -- Pr see #110 N-Pr-PMA
-- -- MeO -- -- Me C=O -- see #110 PMA-f3k
-- -- Meo -- -- Me C=O Me see #112 PMMA-f3k
-- -- MeO -- -- Me HO Pr see #110 f3-HO-N-Pr-PMA
-
- -- MeO -- -- Me -- iPr see #110 N-iPr-PMA
-- -- MeO -- -- Me C=O Pyrr see #92 MeOPPP
-
-
- -- MeO -- - Me2 -- -- see #110 a,a-Me-PMPEA
-- -- Meo -- -- Et -- -- see #110 a-Et-MPEA
-
- -- EtO -- -- -- -- -- see #102 4-EPEA
-- -- EtO -- -- -- -- Me see #102 N-Me-4-EPEA
-- -- EtO -- -- -- -- Me2 see #102 N,N-Me-4-EPEA
-- -- EtO -- -- Me -- -- see #110 4-EA
-
-- -- EtO -- - Me -- Me see #110 4-EtO-METH
-
-- -- EtO -- - Et -- -- see #110 4-EtO-a-EtPEA
-- -- PrO -- -- -- -- -- see #102 4-PPEA
-- -- PrO -- -- Me -- -- see #110 4-PA
-
-
- -- BuO -- -- - -- -- see # 1 02 4-BPEA
-
-- -- Amo -- -- -- - -- see #102 4-APEA
-
-- -- HeO -- - -- -- -- see # 1 02 4-HePEA
-- -- Seo -- -- -- -- -- see # 1 02 4-SPEA
-- -- OcO -- -- -- -- -- see #102 4-0PEA
-- -- NoO -- -- -- -- -- see #102 4-NPEA
-- -- iPrS -- -- Me -- -- see # 1 03 IPTA
-- -- PhO -- -- Me -- -- see #110 PPhA
-- -- BzO -- -- Me -- -- see #110 4-BzA
-- -- MeS -- -- Me -- -- # 1 03 MTA
-- -- MeS -- -- Me -- Me see # 1 03 MTMA

Monos ubstituted I Disubstituted
6- 5- 4- 3- 2- a- B- N- Entry Name
-- -- MeS -- -- Me -- Me2 see # 1 03 MTDMA
- -
-- -- Mes - - Me -- Et see #103 MTEA
-- -- MeS -- -- Me -- Et2 see #103 MTDEA
-- -- Mes -- -- Me -- Pr see #103 MTPA
�lly�
-- -- Mes -- -- Me -- Pr2 see #103 MTDPA
-- -- MeS -- -- Me -- see #103 MTALA
- --- �--- �- ---- - ---
� _
-- -- Mes -- -- Me -- Allyl2 see #103 MTDALA
-- -- MeS -- -- Me HO -- see #103 MTC
-- -- Mes -- -- Et -- -- see # 1 03 a-EMTPEA
-- -- EtS -- -- Me -- -- see # 1 03 ETA
aclinically defined as a bronchodilator and is not covered in this book.
b C!inically defined as an anorexic and is not covered in this book.
Table 4. Disubstituted p henethylamines and amp hetamines.

6- 5- 4- 3- 2- a- B- N- Entry Name
-- -- -- Me Me -- -- -- see #43 2,3-DMePEA
-- -- -- Me Me Me -- -- see #42 2,3-DMeA
-- -- -- Me HO -- -- -- see #34 2,3-HMePEA
-- -- -- Me HO -- -- Me see #34 2,3-HMeMPEA
-- -- -- Me HO -- -- Me2 see #34 2,3-HMeMMPEA
-- -- -- Me HO Me - -
-- see #34 2,3-HMeA
-- -- -- Me HO Me -- Me see #34 2,3-HMeMA
-- -- -- Me HO Me -- Me2 see #34 2,3-HMeMMA
-- -- -- Me Meo Me -- - -
see #34 2,3-MMeA
-- -- -- Me MeO Me -- Me see #34 2,3-MMeMA
-- -- -- Me MeO Me -- Me2 see #34 2,3-MMeMMA
-
- -- -- HO -CC- -- Pr2 see #34 5-HO-PPAT
-
-- -- - HO HO -- -- -- see #34 2,3-DHPEA
N,N-Me-2,3-
-- -- -- HO HO -- -- Me2 see #34
DHPEA
-- -- -- Meo Cl -- MeO -- see #46 B03M2C
-- -- -- Meo HO -- - -
-- see #34 2,3-HMPEA
-- -- - -
MeO MeO -- -- -- #46 2,3-DMPEA
-- -- -- MeO Meo -- -- Me see #46 N-Me-DMPEA-2
-- -- -- MeO Meo -- -- Me2 see #46 N,N-Me-DMPEA-2
-
-- - -- Meo MeO Me -- -- #34 2,3-DMA
-- -- -- Meo Meo Me -- Me see #34 N-Me-2,3-DMA
Tables 325
Dis ubstitu ted
6- 5- 4- 3- 2- a- �- N- Entry Name
-- -- -- Meo MeO Et -- -- see #34 4C-2,3-DMPEA

-- -- -- Meo EtO -- -- -- see #46 2,3-EMPEA
-- -- -- Meo EtO -- - -
Me see #46 N-Me-2,3-EMPEA
N,N-Me-2,3-
-- -- -- Meo EtO -- -- Me2 see #46
EMPEA
-- -- -- -OCO- -
- -- -- see #77 2,3-MDPEA
-- -- -- -OCO- -- -- Me see #77 2,3-MDMPEA
N,N-Me-2,3-
-- -- -- -OCO- -- -- Me2 see #77
MDPEA
-- -- -- -OCO- -- -
- Et see #77 N-Et-2,3-MDPEA
-- - -
-- -OCO- -- MeO -- #15 BOH
-- -- -
- -OCO- Me -- -- see #77 2,3-MDA
-- -- -- -OCO- Me -- Me see #77 2,3-MDMA
-- -- -- -OCO- Me -- Me2 see #77 2,3-MDDMA
-- -- -- -OCO- Me -- Et see #77 2,3-MDE
a,a-Me-2,3-
-- -- -- -OCO- Me2 -- -- see #77
MDPEA
-- - -
-- -OCO- Et -- -- see #77 2,3-BDB
-- -- -- -OCO- Et -- Me see #77 2,3-MBDB
-- -- -- -OCO- Et -- Me2 see #77 2,3-MMBDB
-- -- - -
-OCO- Et -- Et see #77 2,3-EBDB
-- -- N02 -- -C- -- -- see #106 PNAI
-- -- NMe2 -- Me Me -
- -- see #42 Amiflamine
-- -- F -- F Me -- -- see #35 2,4-DFA
-- -- F -- -C- - -
-- see #106 PFAI
-- -- Cl -- Cl Me -- -- see #35 2,4-DCA
-- -- Cl -- -C- -- -- see #106 PCAI
-- -- Cl -- -C- -- Me2 see #106 N,N-Me-PCAI
-- -- Cl -- -CC- -- -- see #106 PCAT
-- -- Cl -- Meo Me -- -- see #35 4-Cl-2-MA
-- -- Br -- MeO -- -- - -
see #47 4-Br-2-MPEA
-
- -- Br -- Meo Me -- -- see #35 4-Br-2-MA
-- -- Br -- -C- -- -- see # 1 06 PBAI
-- -- I -- Meo Me -- -- see #35 4-1-2-MA
-- -- CF3 -- MeO Me -- -- see #63 2-MTFMA
-- -- Me -
- Me -- -- -- see #43 2,4-DMePEA
-- -- Me -- Me Me -- -- see #42 2,4-DMeA
-- -- Me -- MeO -- - -
-- see #47 2,4-MMPEA

Disubs tituted
6- 5- 4- 3- 2- a- �- N- Entry Name
-- -- Me -- MeO Me -- -- see #35 2,4-MMA

-- -- Me -- MeO Me -- Me see #35 4,N-Me-2-MA
-- -- HO -- N02 -- -- -- see #47 2-N02-HPEA
-- -- HO -- -CC- -- Pr2 see #35 6-HO-PPAT
-- -- HO -- HO -- -- -- see #47 2,4-DHPEA
-- -- HO - - Meo -- -- -- see #47 2,4-MHPEA
-- -- HO -- MeO -- Me -- see #47 �,2-MHPEA-3
-- -- Meo -- HO Me -- -- see #35 2,4-HMA
-- -- Meo -- MeO -- -- -- #47 2,4-DMPEA
-- -- Meo -- MeO -- -- Me see #47 N-Me-DMPEA-3
-- -- MeO -- MeO Me -- -- #35 2,4-DMA
-- -- MeO -- MeO Me C=O -- see #35 2,4-DMA-�k
-- -- Meo -- MeO Me -- Me see #35 2,4-DMMA
-- -- MeO -- Meo Me -- Me2 see #35 2,4-DNNA
-- -- Meo -- MeO Et -- -- see #35 4C-2,4-DMPEA
-- -- Meo -
- EtO -- -- -- see #35 2,4-EMPEA
-- -- Mes -- -C- -- -- see #103 MTAI
-
- -- EtO -- EtO -- -- -- see #47 2,4-DEPEA
-- -- F F -- Me -- -- see #38 DFA
-- -- Cl Cl -- -- -- -- see #49 DC PEA
-- -- Cl Cl -- Me -- -
- see #38 DCA
-- -- Cl Cl -- Me -- Me see #38 N-Me-DCA
-- -- Cl MeO -- Me -
- -- see #38 4-Cl-3-MA
-- -- Br Meo -- Me -- -- see #38 4-Br-3MA
-- -- CF3 Meo -- Me -- -- see #63 3-MTFMA
-- -- -CCC- -- Me -- -- see #42 IAP
-- -- -CCC- -- Me -
- Me see #42 IMA
-- -- -CCCC- -- Me -- -- see #42 TAP
-- -- -CCO- -- Me -- -- see #77 BF6AP
-- -- -COC- -- Me -
- -- see #77 IBF5AP
-- -- -COC- -- Me -- Me see #77 IBF5MAP
-- -- Me Me -- -- -- -- #43 DMePEA
-- -- Me Me -- -- HO -- see #43 �-H0-3,4-MePEA
�-H0-3,4,N-
-- -- Me Me -- -- HO Me see #43
MePEA
-- -- Me Me -- Me -- -- #42 DMeA
-- -- Me Me -- Me -- Me see #42 N-Me-DMeA
Tables 327
Disubstituted
6- 5- 4- 3- 2- a- B- N- Entry Name
-- -- Me HO -- Me -- -- see #96 3,4-HMeA
- - -
- Me HO -
- Et -- -- see #96 HM-a-EPEA
-- -- Me MeO -- Me -- -- #96 3,4-MMA
-- -- Me MeO -- Me -- Me see #96 N-Me-3,4-MMA
-- -- HO Br -- Me -- -- see #38 3-Br-PHA
-- -- HO Cl -- -- -- -- see #49 3-Cl-4-HPEA

-
- -- HO Cl -- Me - - -
- see #38 3-Cl-PHA
-- -- HO N02 -- -- -- -- see #49 3-N02-HPEA
-- -- HO HO -- -- -- -- -- Dopaminea
-- -- HO HO -- -- -- Me see #49 N-Me-DHPEA

N-Me,N-iPr-
-- -- HO HO -- -- -- Me,iPr see #49
DHPEA
-- -
- HO HO -- -- -- Me2 see #49 N,N-Me-DHPEA
-
- -- HO HO -- -- -
- Me3+ see #49 Coryneine
-- -- HO HO -- -- -- Et see #49 N-Et-DHPEA
-- -- HO HO -- -- -- Bu see #49 N-Bu-DHPEA
-- -- HO HO -- -
- -- iBu see #49 N-iBu-DHPEA
-- -- HO HO -- -- Me -- see #49 B-Me-DHPEA
-- -- HO HO -- -- HO -- -- N orepinephrineb
-
- -- HO HO -
- -- HO Me -- Epinephrineb
B,3,4-HO-N,N-
-- -- HO HO -- -- HO Me2 see #49
MePEA
B,3, 4-HO-N-Et-
-- -- HO HO -- -- HO Et see #49
PEA
B-HO-N-iPr-
-- -- HO HO -- -- HO iPr see #49
DHPEA
-- -- HO HO -- -- C=O -- see #49 DHPEA-Bk
-- -- HO HO -- -- C=O Me see #49 N-Me-DHPEA-Bk

-
- -- HO HO -- -- C=O iPr see #49 N-iPr-DHPEA-Bk
-- -- HO HO -- Me -- -- #33 DHA
-- -- HO HO -- Me -- HO see #33 DHAOH

-- -
- HO HO -- Me -- Me see #33 DHMA
-- -
- HO HO -- Me -- Me,HO see #33 DHMAOH
-
- -
- HO HO -- Me -- Me2 see #33 N,N-Me-DHA
�·
-- -- HO HO - -
Me HO - -
see #33 B-HO-DHA
-- -- HO HO -- Me HO Me see #33 B-HO-DHMA
-- -- HO HO -- Me C=O iPr see #33 N-iPr-DHA-Bk
-- -- HO HO -- Me -- Et see #33 DHEA

----

Disubs tituted
6- 5- 4- 3- 2- a- f3- N- Entry Name

-- -- HO HO -- Et -- -- see #33 DH-a-Et-PEA
-- -- HO HO -- Et HO -- see #33 f3,3,4-HO-a-Et-PEA
-- -- HO MeO -- -- -- -- #69 GEA
-- -- HO MeO -- -- -- Me see #49 N-Me-GEA
-
-- -- HO Meo - -- -- Me2 see #49 MM-GEA
-- -- HO MeO -- -- Me -- see #49 f3-Me-GEA
-- -- HO MeO -- -- HO -- -- Normetanephrine<
-- -- HO Meo -- -- HO Me -- Metanephrine<
-- -- HO Meo -- -- HO iPr see #49 f3-HO-N-iPr-GEA
-
- -- HO MeO -- -- C=O -- see #49 GEA-f3k
-- -- HO MeO -- -- C=O Me see #49 N-Me-GEA-f3k
-- -- HO MeO -- Me -- -- #94 MHA
-- -- HO MeO -- Me -- HO see #33 MHAOH
-- -- HO MeO -- Me -- Me see #94 MHMA
-- -- HO MeO -- Me -- Me,HO see #33 MHMAOH
-- -- HO MeO -- Me -- Et see #94 MHEA
-- -- HO Meo -- Me C=O -- see #92 HMMC
-- -- HO Meo -- Et -- -- see #33 HM-a-Et-PEA
-
- -- HO MeO -- Et -- Me see #49 N-Me-a-Et-GEA
-- -- AcO AcO -- -- -- Me see #49 N-Me-DHPEA-AA
N,N-Me-DHPEA-
-- -- AcO AcO -- -- -- Me2 see #49
AA
-- -- AcO AcO -- Me -- Me2 see #33 N,N-Me-DHA
-- -- Meo Cl -- -- -- Me see #49 N-Me-3-Cl-MPEA
-- -- MeO Br -- Me -- -- see #38 3-Br-PMA
-- -- MeO I -- Me -- -- see #38 3-1 -PMA
-- -- Meo Me -- Me -- Me see #38 3-Me-PMMA
-- -- MeO Me -- Me2 -- -- see #38 a,a,3-Me-MPEA
-- -- Meo Me -- Et -- -- see #38 3-Me-a-Et-MPEA
-- -- Meo HO -- -- -- -- see #49 HMPEA
-- -- MeO HO -- -- -- Me see #49 N-Me-HMPEA
-- -- MeO HO -- -- -- Me3+ see #49 Salicifoline
-- -- MeO HO -- -- HO -- see #49 HME
-- -- MeO HO -- -- HO Me see #49 N-Me-HME
-- -- MeO HO -- -- HO Me2 see #49 N,N-Me-HME
-- -- MeO HO -- -- C=O -- see #49 HMPEA-f3k
-- -- MeO HO -- -- C=O Me see #49 N-Me-HMPEA-f3k
Tables 329
Disubstituted
6- 5- 4- 3- 2- a- f)- N- Entry Name

-
-- - MeO HO -- Me C=O -- see #92 MHMC
-- -- MeO HO -- Me - -
-- see #33 HMA
-- -- MeO HO - -
Me -- Me see #33 HMMA
-- -- MeO HO -- Me -- Et see #33 HMEA
-- -- MeO MeO -- -- -- -- #49 DMPEA
-
- -- MeO MeO -- -- Me -- see #49 f)-Me-DMPEA
-- -- Meo Meo -- -- HO -- see #49 DME
-- -
-- -- Meo Meo - HO Me see #49 N-Me-DME
-- -- Meo Meo -- -- HO Me,CHO see #49 N-Me,CHO-DME
-
-- -- Meo Meo - -- HO Me2 see #49 N,N-Me-DME
-- -- Meo Meo -- -- Meo -- see #49 f),3,4-TMPEA
-
N-Me-f),3,4-
-- - Meo Meo -- -- Meo Me see #49
TMPEA
--
N,N-Me-f),3,4-
-- MeO MeO -- -- Meo Me2 see #49
TM PEA
-- -- Meo Meo -- -- - -
Me see #49 N-Me-DMPEA
-- -
- Meo Meo -- -- -- Me2 see #49 N,N-Me-DMPEA
-
-- -- MeO MeO - -- -- Et see #49 N-Et-DMPEA
-- -- MeO MeO -- Me -- - -
#38 DMA
-- -- MeO MeO -- -C- -- see #41 3,4-DMCPA
-- -- Meo MeO -- Me --
HO see #38 DM
-- -- MeO MeO -- Me -- Me see #38 DMMA
-- -
- MeO MeO -- Me Me2 -- see #38 N,N-Me-DMA
-
-- -- Meo MeO - Me -- Et see #38 DMEA
-
-- -- MeO MeO -- Me - Pr see #38 DMPA
-- -- MeO MeO -- Me -- Bz see #38 DMBZ
--
-- -- MeO MeO Me -- Me,HO see #38 DMMAOH
-- -- MeO MeO -- Me HO -- see #38 f)-HO-DMA
-- -- Meo Meo -- Et -- -- see #38 4C-DMPEA
-
-- -- Meo EtO - -- -- -- see #49 EMPEA
-- -- MeO EtO -- -- -- Me see #49 N-Me-EMPEA
N,N-Me-3,4-
-- -- MeO EtO -- -- -- Me2 see #49
EMPEA
-- -- MeO EtO -- Me -- -- see #38 EMA
-- -- EtO Meo -- -- -- -- #90 ME PEA
--
N,N-Me-4,3-
-- -- EtO Meo -- -- Me2 see #49
EMPEA
-- -- EtO MeO -- -- HO -- see #49 f)-HO-EMPEA

Disubstituted
6- 5- 4- 3- 2- a- f3- N- Entry Name

-- -- EtO MeO -- Me -- -- see- #38 MEA
-- -- EtO EtO -- -- -- -- see #49 DEPEA
-- -- EtO EtO -- -- -- Me see #49 N-Me-DEPEA
-- -- EtO EtO -- -- -- Me2 see #49 N,N-Me-DEPEA
-
-- -- EtO EtO -- - HO -- see #49 DEE
-
-- -- EtO EtO -- Me -- - see #38 DEA
-- -- AIO MeO -- -- -- -- see #90 MAPEA
-- -- MeS Me -- Me -- -- see #103 MMTA
-- -- -OCC- -- Me -- -- see #77 BF5AP
-- -- -OCO- -- -- -- -- #85 MD PEA
-- -- -OCO- -- -- -- Me see #85 N-Me-MDPEA
-- -- -OCO- -- -- -- Me2 see #85 N,N-Me-MDPEA
N-Me-N-Et-
-- -- -OCO- -- -- -- Me,Et see #85
MD PEA
-- -- -OCO- -- -- -- Et see #85 N-Et-MDPEA
-- -- -OCO- -- -- -- Pr see #85 N-Pr-MDPEA
-- -- -OCO- -- -- -- iPr see #85 N-iPr-MDPEA
-
-- -- -OCO- -- -- Me - see #85 f3-Me-MDPEA
-- -- -OCO- -- -- Me Me see #85 f3,N-Me-MDPEA
-- -- -OCO- -- -- Meo -- #15 BOH
-
-- -- -OCO- -- Me - -- #77 MDA
-- -- -OCO- -- Me -- Me #82 MDMA
-- -- -OCO- -- Me -- Meo see #77 MDMEO
-- -- -OCO- -- Me -- Me,OH see #84 FLEA
-- -- -OCO- -- Me -- Me2 #80 MDDMA
-- -- -OCO- -- Me -- Me, Et see #77 MDMEA
-- -- -OCO- -- Me -- Me,Pr see #77
· --··--
MD MPA
-- -- -OCO- -- Me -- Me,iPr see #77 MDMIPA
-
-- - -OCO- -- Me -- Et #81 MDE
-----
- -
-- -- -OCO- -- Me -- Et2 see #77 MDDEA

- -
- -- -OCO- -- Me - NCC- see #77 MDCM
-- -- -OCO- -- Me -- HOCC- see #77 MDHOET
-- -- -OCO- -- Me -- MeOCC- see #77 MDMEOET --
- -
-- - -OCO- -- Me - Pr #86 MDPR
-- -- -OCO- -- Me -- iPr see #77 MDIP
-
-- -- -OCO- -- Me - Ally! see #77 MDAL
-- -- -OCO- -- Me -- PR see #77 MDPL ·-
Tables 331
Disubstituted
6- 5- 4- I 3- 2- a- f:\- N- Entry Name

-- -- -OCO- -- Me -- Bu see #77 MDBU
-- -- -OCO- -- Me -- iBu see #77 MDIB
-- -- -OCO- -- Me -- sBu see #77 MDSB
-- -- -OCO- -- Me -- tBu see #77 MDTB
-- -- -OCO- -- Me -- Pe see #77 MDAM
-- -- -OCO- -- Me -- He see #77 MDHE
-- -- -OCO- -- Me -- Bz see #77 MDBZ
-- -- -OCO- -- Me -- Oc see #77 MDOC
-- -- -OCO- -- Me -- HO #84 MDOH
-
-- -- -OCO- -- Me - cPrM see #77 MDC PM
-- -- -OCO- -- Me -- MeO see #77 MD MEO
-
-- -- -OCO- -- Me - tBuNH see #77 MDBA
-- -
- -OCO- -- Me HO -- see #77 f:\-HO-MDA
-- -- -OCO- -- Me C=O -- see #93 ONE
-
-- -- -OCO- - Me C=O Me #93 METHYLONE
-- -- -OCO- -- Me C=O Me2 see #93 DMONE
-- -- -OCO- -- Me C=O Et see #93 EtONE
-
-- -- -OCO- - Me C=O Et2 see #93 DEONE
-- -- -OCO- -- Me C=O Pr see #93 PrONE
-- -- -OCO- -- Me C=O iPr see #93 iPrONE
-- -- -OCO- -- Me C=O cPr see #93 cPrONE
-- -- -OCO- -- Me C=O Allyl see #93 ALONE
-- -- -OCO- -- Me C=O PR see #93 PRONE
-- -- -OCO- -- Me C=O Bu see #93 BuONE
-- -- -OCO- -- Me C=O iBu see #93 iBuONE
-- -- -OCO- -- Me C=O sBu see #93 sBuONE
-- -- -OCO- -- Me C=O tBu see #93 tBuONE
-- -- -OCO- -- Me C=O Pyrr see #93 MD PPP
-- -- -OCO- -- -C- see #41 MDCPA
-- -- -OCO- -- Me2 -- -- see #77 MDPH
-- -- -OCO- -- Me2 -- Me see #77 MDMP
-- -- -OCO- -- Me,Et -- -- see #77 a-Et-MDA
-
-- - -OCO- -- Et -- -- #9 BDB
-- -- -OCO- -- Et -- Me #76 MBDB
-- -- -OCO- -- Et C=O Me see #93 MDMBP
- -
-- -OCO- -- Et -- Me2 see #77 MMBDB
-- -- -OCO- -- Et C=O Me2 see #93 MDDMBP

Disubstituted
6- 5- 4- I 3- 2- a- 13- N- Entry Name

-- -- -OCO- -- Et -- Et see #77 EBDB
-- -- -OCO- -- Et C=O Et see #93 MDEBP
-- -- -OCO- -- Et C=O Et2 see #93 MDDEBP
-- -- -OCO- -- Et -- Pr see #77 PBDB
-- -- -OCO- -- Et C=O Pr see #93 MDPBP
- -
-- -OCO- -- Et -- iPr see #77 IPBDB
-- -- -OCO- -- Et C=O iPr see #93 MDIPBP
-- -
- -OCO- -- Et -- HO see #77 HOBDB
-- -- -OCO- -- Pr -- -- see #77 K
-
- -- -OCO- -- Pr -- Me see #77 METHYL-K
-- -- -OCO- -- Pr C=O Me see #93 MDMVP
-- -- -OCO- -- Pr C=O Me2 see #93 MDDMVP
-- -- -OCO- -- Pr -- Et see #77 ETHYL-K
-- -- -OCO- -- Pr C=O Et see #93 MDEVP
-- -- -OCO- -- Pr C=O Et2 see #93 MDDEVP
-- -- -OCO- -- Pr C=O Pr see #93 MDPVP
-- -- -OCO- -- Pr C=O iPr see #93 MDIPVP
-- -- -OCO- -- Pr C=O Bu see #93 MDBVP
-- -- -OCO- -- Pr C=O sBu see #93 MDSBVP
-- -- -OCO- -- iPr -- -- see #85 a-iPr-MDPEA
-- -- -OCO- -- Bu -- -- see #77 L
-- -- -OCO- -- Bu -- Me see #77 METHYL-L
-- -- -OCO- -- Bu C=O Me2 see #93 MDDMHP
-- -- -OCO- -- Bu C=O Et2 see #93 MDDEHP
-- -
- -OCF20- -- -- -- -- see #85 F2-MDPEA
-- -- -OCF20- Me -- -- see #77 F2-MDA
-- -- -OCF20- -- Me -- Me see #82 F2-MDMA
-- -- -OCFp- -- Me -- Et see #81 F2-MDE
-- -- -OCFp- -- Et - -
-- see #9 F2-BDB
-- -- -OCF20- - -
Et -- Me see #76 F2-MBDB
-- -- -OC(CH)O- -- Me -- -- see #77 7-Me -MDA
-- -
- -OC(CH)p- -- Me -- -- see #77 IDA
-- -- -OCCO- -- -- -- -- #65 EDPEA
-- -- -OCCO- -- -- -- Me2 #65 ED-N-DMPEA
-- -- -OCCO- -- Me -- -CCCC- #82 ED-pyr-PEA
-- -- -OCCO- -- Me -- -CCOCC- #65 ED-mor-PEA
-- -- -OCCO- -- Me -- -- #65 EDA
Tables 333
Disubstituted
6- 5- 4- 3- 2- a- 13- N- Entry Name

-- -- -OCCO- -- Me -- Me see #65 EDMA
-- -- -OCCO- -- Me -- Me2 see #65 ED-ND MA
-- -- -OCCO- -- Me -- Et see #65 EDEA
-- -- -OCCO- -- Me -- -CCCC- see #82 ED-pyr-A
-- -- -OCCO- -- Me -- -CCOCC- see #65 ED-mor-A
-- F -- -- F Me -- -- see #36 2,5-DFA
-- I - -
-- Meo Me -- -- see #36 5-I-2-MA
-- Me -- -- Me -- -- -- see #43 2,5-DMePEA
-- Me -- -- Me Me -- -- see #42 2,5-DMeA
-- Me -- -- Me Me -- Me see #42 N-Me-2,5-DMeA
-- Me -- -- Me Me -- Me2 see #42 N,N-Me-2,5-DMeA
-- Me -- -- HO -- HO -- see #22 j),2-H0-5-MePEA
j),2-H0-5,N-
-- Me -- -- HO - -
HO Me see #22
MePEA
-- Me -- -- HO -- C=O -- see #22 2-H0-5-MePEA-j)k
2-H0-5,N-MePEA-
-- Me -- -- HO -- C=O Me see #22
j)k
-- Me -- -- HO Me HO -- see #36 j),2-H0-5-MeA
-- Me -- -- HO Me HO Me see #36 j),2-H0-5,N-DMeA
j)-H0-2-M-5-
-- Me -- -- Meo -- HO -- see #22
Me PEA
j)-HO-N-Me-2-M-
-- Me -
- -- Meo -- HO Me see #22
5-MePEA
- -
Me -- -- MeO Me HO -- see #36 j)-H0-2-M-5-MeA
j)-H0-2-M-N-Me-
-- Me -- -- MeO Me HO Me see #36
+--- ---
-- - r------- --
--------
MeA
- -
Me -- -- MeO - -
C=O -- see #22 2-M-5-MePEA-j)k
-- HO
---- ------
--
--·-- ----
--
--·---- -�---
-CC-
--
--
- -----·- - -
Pr2 see #36 7-HO-PPAT
- .......-------- ----..-
j),5-HO-N-Me-2-
-- HO -
- - -
Meo -- HO Me see #22
- --..---- ·------
MPEA
5-HO-N-Me-2-
-- HO -- --
MeO -- C=O Me see #22
-- - ---
MPEA-j)k
-- HO -- -- MeO Me -- Me see #36 2,5-MH-MMA
-- -- ·- - ·--·-· ---
-- MeO - -
-- Br Me -- -- see #36 2-Br-5-MA
-- MeO - -
-- I Me -- -
- see #36
----·-
- ----
2-I-5-MA
-- Meo -- -- HO -- -- --
see #22
--·· - --------
2,5-HMPEA
--
N,N-Me-2,5-
-- Meo -- -- HO -- -- Me2 see #22
HMPEA
-- MeO -- -- HO -- HO --
see #22 j),2-H0-5-MPEA

Disubstituted
6- 5- 4- 3- 2- a- 13- N- Entry Name

j),2-HO-N-Me-5-
-- Meo -- -- HO -- HO Me see #22
MPEA
-- Meo -- -- HO -- C=O -- see #22 2-H0-5-MPEA-j)k
-- MeO -- -- HO Me -- -- see #36 2,5-HMA
-- MeO -- -- HO Me -- Me2 see #36 N,N-Me-2,5-HMA
-- MeO -- -- HO Me HO -- see #36 j),2-H0-5-MA
j),2-HO-N-Me-5-
-- MeO -- -- HO Me HO Me see #36
MA
-
- MeO -- -- MeO - -
-- -- #22 2C-H
-- MeO -- - -
MeO -- -- Me see #22 N-Me-2,5-DMPEA
N,N-Me-2,5-
-- MeO -- -- Meo -- -- Me2 see #22
DMPEA
-- Meo -- -- MeO -- Me -- see #22 j)-Me-2,5-DMPEA
j),N-Me-2,5-
-- Meo -- - -
MeO -- Me Me see #22
DMPEA
j),N,N-Me-2,5-
-- MeO -- -- MeO -- Me Me2 see #22
DMPEA
-- MeO -- -- MeO -- HO -- see #22 j)-H0-2,5-DMPEA
-- MeO -- -- Meo -- C=O -- see #22 2,5-DMPEA-j)k
j)-HO-N-Me-2,5-
-- Meo -- -- MeO -- HO Me see #22
DMPEA
j)-HO-N,N-Me-2,5-
-- MeO -- -- Meo -- HO Me2 see #22
DMPEA
-- MeO -- -- Meo -- Meo -- see #14 BODM
j)-H O,M e-2, 5-
-- Meo -- -- MeO -- HO,Me -- see #22
DMPEA
j3-HO-j3,N-Me-2,5-
-- MeO -
- -- Meo -- HO,Me Me see #22
DMPEA
j3-HO-j3,N,N-Me-
-- MeO -- -- Meo -- HO,Me Me2 see #22
2,5-DMPEA
N,N-Me-2,5-
-- MeO -- -- MeO -- C=O Me2 see #22
DMPEA-j)k
-- MeO -- -- Meo Me -- -- #36 2,5-DMA
-- Meo -- -- Meo Me -- Ac see #36 2,5-DMA-Ac
-- Meo -- -- MeO Me -- Me see #36 2,5-DMMA
- -
MeO -- -- Meo Me -- Me2 see #36 2,5-DNNA
-- MeO -
- -- MeO Me HO -- see #36 j)-H0-2,5-DMA
j)-HO-N-Me-2,5-
-- MeO -- -- MeO Me HO Me see #36
DMA
j)-HO-N, N-Me-2,5-
-- MeO -- -- MeO Me HO Me2 see #36
DMA
Tables 335
Disubstituted
6- 5- 4- 3- 2- a- f3- N- Entry Name

-- Meo -- -- MeO Me HO iPr -- f3-H0-2,5-lJMIPJ\<l
-- Meo -- -- MeO Me C=O -- see #36 2,5-lJMJ\-f3k
-- MeO -- -- Meo Me C=O Me see #36 2,5-lJMMJ\-f3k
-- MeO -- -- MeO Et -- -- see #7 4C-H
-- EtO -- -- HO -- HO -- see #22 f3,2-H0-5-EPEJ\
[3,2-HO-N-Me-5-
-- EtO -- -- HO -- HO Me see #22
EPEJ\
-- EtO -- -- HO -- C=O -- see #22 2-H0-5-EPEJ\-f3k
2-HO-N-Me-5-
-
- EtO -- -- HO -- C=O Me see #22
EPEJ\-f3k
-- EtO -- -- HO Me HO -- see #36 [3,2-H0-5-EJ\
-- EtO -- -- HO Me HO Me see #36 [3,2-HO-N-Me-5-EJ\
2-HO-N-Me-5-EJ\-
-- EtO -- -- HO Me C=O Me see #36
f3k
-- EtO -- -- EtO -- HO -- see #22 f3-H0-2,5-lJ EPEJ\

f3-HO-N-Me-2,5-
-- EtO -- -- EtO -- HO Me see #22
lJEPEJ\
N-Me-2,5-lJEPEJ\-
-- EtO -- -- EtO - -
C=O Me see #22
f3k
-- EtO -
- -- EtO Me HO -- see #36 [3-H0-2,5-lJEJ\
f3-HO-N-Me-2,5-
-- EtO -- -- EtO Me HO Me see #36
lJEJ\
-- EtO -- -- EtO Me C=O -- see #36 2,5-lJEJ\-f3k
-- Me -- Me -- -- -- -- see #43 3,5-lJMePEJ\
-- Me -- Me -- Me -- -- see #42 3,5-lJMeJ\
-- HO -- HO -
- -- -- -- see #50 3,5-HPEJ\
-- MeO -- HO -- -- -- -- see #50 3,5-HMPEJ\
-- MeO -- MeO -- -- -- -- #50 3,5-lJMPEJ\
-- MeO -- MeO -- -- - -
Me see #50 N-Me-3,5-lJMPEJ\
N,N-Me-3,5-
-- MeO -- Meo -- -- -- Me2 see #50
lJMPEJ\
-- Meo -- Meo -- -- HO -- see #50 [3-H0-3,5-lJMPEJ\
[3-HO-N-Me-3,5-
-- Meo -- Meo -- -- HO Me see #50
lJMPEJ\
[3-HO-N,N-Me-3,5-
-- Meo -- Meo -- -- HO Me2 see #50
lJMPEJ\
-- MeO -- MeO -- Me -- -- #39 3,5-lJMJ\
-- Meo -- MeO -- Me -- Me see #39 N-Me-3,5-lJMJ\
-- MeO -- MeO -- Me -- Me2 see #39 3,5-lJNNJ\

Disubstituted I Trisubstituted
-·
6- 5- 4- 3- 2- a- f3- N- Entry Name

�-
-- Meo -- MeO -- Et -- -- see #39 4C-3,5-DMPEA

Cl -- -- -- Cl Me -- -- see #37 2,6-DCA
Me -- -- -- Me -- -- -- see #43 2,6-DMePEA
HO -
- -
- -- -CC- -- -- see # 105 HHAT
HO -- -
- -- -CC- -- Me see # 105 MHAT
HO -- -- -- -CC- -- Me2 see # 1 05 MMAT
HO -
- -- -- -CC- -- Et see # 105 EHAT
HO -- -- -- -CC- -- Et2 see # 1 05 EEAT
HO -- -
- -- -CC- -- Pr see # 1 05 PHAT
HO -- --
-��·
-- -CC- -- Pr, Et see # 1 05 PEAT
HO -- - -
-- -CC- -- Pr2 # 105 PAT
HO -- -
- -- -CC- - iPr see # 105 iPHAT
HO -
- -- -- -CC- -- Bu see # 105 BHAT
HO -- -- -- -CC- -- Bu2 see # 105 BBAT
HO -- -- -- HO -- - -
-- see #48 2,6-HPEA
MeO -- -- - -
Br Me -- -- see #37 6-Br-2-MA
Meo -- -- -
- HO -- -- -- see #48 2,6-HMPEA
Meo -- -- -- MeO -- -- -- #48 2,6-DMPEA
MeO -- -- -- Meo -- -- Me see #48 N-Me-2,6-DMPEA
N,N-Me-2,6-
MeO -- - -
-- Meo -- -- Me2 see #48
DMPEA
MeO -
- -- -- MeO -- HO -
- see #48 f3-H0-2,6-DMPEA
f3-HO-N-Me-2,6-
MeO -
- -- -- Meo -- HO Me see #48
DMPEA
MeO -- -- -- Meo Me - -
-- #37 2,6-DMA
Meo -- -- -- MeO Me -- Me see #37 N-Me-2,6-DMA
Meo -- -- -- MeO Me - -
Me2 see #37 2,6-DNNA
aDopamine. Pharmacologically defined as a hormone and is not covered in this book.

hEpinephrine and norepinephrine (adrenaline and noradrenaline), are pharmacologically defined as
hormones and are not covered in this book.
cMetanephrine and normetanephrine are metabolites of epinephrine and norepinephrine, respec
tively, and are not covered in this book.
df3-H0-2,5-DMIPA is an adrenergic blocking agent, and is not covered in this book.
Table 5. Trisubstituted p henethylamines and amp hetamines.

6- 5- 4- 3- 2- a- f3- N- Entry Name
-- -- Br MeO Meo -- -- -- see # 1 8 2,3,4-MMB
-- -- Br MeO Meo Me -- -- see #52 4,2,3-DOB
-- -- Me Me Me -- -- -- see # 123 TMePEA-3
Tables 337
Trisubstituted
6- 5- 4- 3- 2- a- f3- N- Entry Name

-- -- Me Me Me Me -- -- see # 123 TMeA-3
4-Me-2,3-
-- -- Me MeO MeO Me -- -- see #60
DOM
-- -- Et MeO MeO Me -- -- see #56 4,2,3-DOET
-- -- MeO Br Meo -- -- -- see # 1 8 2,3,4-MBM
-- -- MeO Br MeO Me -- -- see #52 3,2,4-DOB
3-Me-2,4-
-- -- Meo Me MeO Me -- -- see #60
DOM
-- -- MeO Et MeO Me -- -- see #56 3,2,4-DOET
-- -- MeO PrS MeO -- -- -- see #27 2,4,3-2C-T-7
2-Cl-3,4-
-- -- MeO MeO Cl -- -- -- see # 1 9
DMPEA
-- -- MeO MeO Br -- -- -- see # 1 8 2,3,4-BMM
-- -- Meo MeO Br Me -- -- see #52 2,3,4-DOB
2-Me-3,4-
-- -- Meo MeO Me Me -- -- see #60
DOM
-- -- MeO Meo Et Me -- -- see #56 2,3,4-DOET
-- -- MeO MeO MeO -- -- -- #72 IM
-- -- MeO MeO MeO Me -- -- #119 TMA-3
-- -- MeO MeO MeO Me -- Me see #119 N-Me-TMA-3
-- -- MeO MeO Meo Et -- -- see #119 4C-TMPEA-3
-- -- MeO -OCO- -- -- see #99 2C-3b
-- -- MeO -OCO- Me -- see #97 MMDA-3b
-- -- MeO MeO MeS -- -- -- see #72 2-TIM
-- -- MeO MeO PrS -- -- -- see #27 3,4,2-2C-T-7
-- -- Meo MeS MeO -- - -
-- see #72 3-TIM
--- r--·
-- -- EtO EtO EtO -- -- -- see # 72 I-TRIS

-- -- -OCO- Me Me -- -- see #77 2-Me-MDA
-- -- -OCO- -C- -- -- see #77 4,5-MDAI
-- - -
-OCO- -C- -- Me see #77 4,5-MDMAI
-- -- -OCO- -CC- -- -- see #77 5,6-MDAT
-- -- -OCO- HO Me -- Me see #82 2-MDMOH
-- -- -OCO- MeO -- -- -- see #99 2C-3a
-- -- -OCO- MeO -- -- Me see #99 N-Me-2C-3a
-- -- -OCO- MeO Me -- -- #99 MMDA-3a
-- -- -OCO- MeO Et -- -- see #99 4C-3a
2T-MMDA-
-- -- -OCO- MeS Me -- -- see #99
3a

Trisubstituted
6- 5- 4- 3- 2- a- 13 - N- Entry Name
-- -- MeS MeO Meo -- -- -- see # 72 4-TIM
-- -- PrS Meo MeO -- -- -- see #27 2,3,4-2C-T-7
-- Br -- MeO MeO -- -- --
see # 1 8 2,3,5-MMB
-- Br -- Meo Meo Me -- -- see #52 5,2,3-DOB
-- Me -- Me Me -- -- -- see #123 TMePEA-4
-- Me -- Me Me Me -- -- see #123 TMeA-4
5-Me-2,3-
-- Me -- MeO Meo Me -- -- see #60
DOM
-- Et -- MeO MeO Me -- -- see #56 5,2,3-DOET
-- MeO -- Br MeO -- -- -- see # 1 8 2,3,5-MBM
-- Meo -- Br MeO Me -- -- see #52 3-DOB
-- MeO -- N02 Meo Me -- -- see #61 3-DON
-- Meo -- Me MeO Me -- -- see #60 3-DOM
-- MeO -- Et MeO Me -- -- see #56 3,2,5-DOET
-- MeO -- PrS MeO -- -- -- see #27 2,5,3-2C-T-7
-- MeO -- MeO Br -- -- -- see # 1 8 2,3,5-BMM
-- Meo -- MeO Br Me -- - -
see #52 2,3,5-DOB
-- MeO -- Meo I Me -- -- see # 120 2-I-3,5-DMA
-- MeO -- MeO I Me -- Me2 see #120 3,5-IDNNA-2
2-Me-3,5-
-- Meo -- MeO Me Me -- -- see #60
DOM
-- MeO -- MeO Et Me -- -- see #56 2,3,5-DOET
-- Meo -- MeO Meo -- -- -- see #120 TMPEA-4
-
- Meo -- MeO Meo Me -- -- #120 TMA-4
- -
MeO -- MeO PrS -- -- -- see #27 3,5,2-2C-T-7
-- MeO -- -OCO- -- -- -- see #98 2C-2
-- MeO -- -OCO- Me -- -- see #97 MMDA-4
-- PrS -- MeO Meo -- -- -- see #27 2,3,5-2C-T-7
-- F MeO -- MeO Me -- -- see # 1 1 8 5-F-2,4-DMA
-- F MeO -- MeO Me -- Me2 see #118 2,4-FDNNA
-- Br MeO -- Meo -- -- -- see # 1 8 2,4,5-MMB
-- Br MeO -- MeO Me -- -- see #52 m-DOB
-- I MeO -- MeO Me -- -- see #118 5-1-2,4-DMA
-- I MeO -- MeO Me -- Me2 see #118 2,4-IDNNA
2,4-H0-5-
-- NH2 HO -- HO -- -- -- see # 124
APEA
-- NH2 HO -- HO Me -- -- see #118 2,4-H0-5-AA
Tables 339
Trisubstituted
6- 5- 4- 3- 2- a- 13 - N- Entry Name
5-NH2 -2,4-
-- NH 2 MeO -- MeO -- -- -- see #124
DMPEA
5-NH2-2,4-
-- NH2 MeO - -
MeO Me -- -- see #118
DMA
-- Me Me -- Me -- -- -- see #123 TMePEA-2
-- Me Me -- Me Me -- -- see #123 TMeA-2
-- Me MeO -- MeO Me -- -- see #60 m-DOM
-- Et MeO -- Meo Me -
- -- see #56 5,2,4-DOET
2,5-H0-4-
-- HO NH2 -- HO -- -- -- see # 124
APEA
-- HO NH2 -- HO Me -- -- see # 1 1 8 2,5-HO-PAA
2,5-DES-Me-
-- HO Me -- HO Me -- -- see #60
DOM
5-DES-Me-
-- HO Me -- Meo Me -- -- see #60
DOM
4,5-H0-2-
-- HO HO -- NH2 -- -- -- see #124
APEA
-- HO HO -- NH2 Me -- -- see #118 4,5-H0-2-AA
2,4,5-HO-
-- HO HO -- HO -- -- -- see # 124
PEA
-- HO HO -- HO Me -- -- see # 11 8 THA-2
- -
HO HO -- HO Me -- Me see #118 THMA-2
2,5-HO-
-- HO MeO -- HO -- -- -- see # 124
MPEA
-- MeO F -- MeO -- -- -- see #20 2C-F
-- MeO F -- Meo Me -- -- #57 DOF
-- MeO Cl -- MeO -- -- -- #19 2C-C
-- MeO Cl - -
MeO Me -- -- #54 DOC
-- MeO Cl -- MeO Me -- Ac see #54 DOC-Ac
-- MeO Cl -- MeO Et -- -- see #54 4C-Cl
-- Meo Br -- Meo -- -- -- #18 2C-B
-- MeO Br -
- MeO -- - -
Me see # 1 8 2C-B-M
- -
Meo Br -- MeO -- -- Me2 see # 1 8 2C-B-MM
-- Meo Br -- MeO -- -- Et see # 1 8 2C-B-E
-- MeO Br -- Meo -
- - -
-C5- see # 1 8 pip-2C-B
-- MeO Br -- MeO Me -- -- #52 DOB
-- MeO Br -- MeO Me -- Ac see #52 DOB-Ac
-- MeO Br -- Meo Me -- Me see #52 N-Me-DOB
-- MeO Br -- Meo Me -- Me2 see #52 N,N-Me-DOB

Trisubstituted
6- 5- 4- 3- 2- a- f3- N- Entry Name

- -
Meo Br -- MeO Me -- Pr see #52 N-Pr-DOB
-- Meo Br -- MeO -- Meo -- #13 BOB
-- MeO Br -- Meo -- EtO --
see #14 BOBE
-- Meo Br -- Meo Me HO -- see # 1 3 f3-HO-DOB
-- MeO Br -- Meo Me Meo -- see # 1 3 f3-Me0-DOB
- -
MeO Br -- MeO Me C=O -- see #52 DOB-f3k
-- MeO Br -- MeO Et -- -- see #52 4C-DOB
-- Meo I -- Meo -- -- -- #23 2C-I
-- Meo I -- MeO -- -- 2-MeOBz see #58 INBMeO
-- MeO I -- MeO -- -- 2,3-MeOBz see #58 INBMDO
-- MeO I -- Meo -- MeO -- see #14 BOI
-- MeO I -- Meo Me -- -- #58 DOI
-- Meo I -- MeO Me -- Ac see #58 DOI-Ac
-- MeO I -- Meo Me -- Me see #58 2,5-IDNA
-- MeO I -- Meo Me -- NH 2 see #58 2,5-INAA
-- MeO I -- Meo Me -- HO see #58 2,5-INHA
-- Meo I -- MeO Me -- NCCH2 see #58 2,5-INCNMA
2,5-INMeO-
-- MeO I -- Meo Me -- MeOEt see #58
EtA
-- Meo I -- Meo Me -- Me2NC3 see #58 2,5-IDMAPA
-- Meo I -- MeO Me -- iPr see #58 2,5-INiPrA
-- Meo I -- MeO Me -- C3 H5 C see #58 2,5-INCPMA
-- MeO I -- Meo Me -- He see #58 2,5-INHeA
-- MeO I -- Meo Me -- Do see #58 2,5-INDoA
-- MeO I -- MeO Me -- Me2 see #58 2,5-IDNNA
2,5-IDMN-
-- Meo I -- MeO Me -- Me,iPr see #58
iPrNMeA
-- MeO I -- Meo Me -- Et2 see #58 2,5-INNEA
2,5-INHeN-
- -
MeO I -- Meo Me -- He,Me see #58
MeA
- -
Meo I -- MeO Et -- -- see #58 4C-I
-- MeO NH2 -- MeO -- -- -- see #124 2C-NH
-- Meo NH2 -- MeO Me -- -- see #61 DONH
-- MeO NH2 -- Meo Me -- Ac see #61 DONH-Ac
-- MeO NH2 -- Meo Et -- -- see #61 4C-NH
-- Meo NMe2 -- Meo Me -- -- see #61 DONMM
-- MeO NHAc -- Meo Me -- -- see #61 DOAA
Tables 341
Trisubstituted
6- 5- 4- 3- 2- a- f3- N- Entry Name

-- Meo N02 -- Meo -- -- -- see #20 2C-N
-- MeO N02 -- Meo -- Meo -- see # 1 4 BON
-- MeO N02 -- MeO Me -- -- #61 DON
-- Meo N02 -- Meo Me -- Ac see #61 DON-Ac
-- Meo N02 -- Meo Et -- -- see #61 4C-NO
- -
MeO Me -- -C- -- see #96 MMAI
-- MeO Me -- -CC- -- -- see #96 7,6-MMAT
2-DES-Me-
-- Meo Me -- HO Me -- -- see #60
DOM
-- Meo Me -- Meo -- -- -- #20 2C-D
-- Meo Me -- Meo -- -- HO see #20 N-H0-2C-D
-- MeO Me -- Meo -- Me -- see #20 f3-Me-2C-D
-- Meo Me -- Meo -- Me2 -- see #20 f3, f3-Me-2C-D
-- Meo Me -- Meo Me Me -- see #60 f3-Me-DOM
-- MeO Me -- MeO Me Me2 -- see #60 f3, f3-Me-DOM
-- Meo Me -- Meo Me -- -- #60 DOM
-- MeO Me -- MeO -- -- Me see #20 N-Me-2C-D
-- Meo Me -- Meo Me -- HO see #60 N-HO-DOM
-- Meo Me -- Meo Me -- Me #11 BEATRICE
N,N-Me-
-- Meo Me -- Meo Me -- Me2 see #11
DOM
-- MeO Me -- Meo Me -- Et see #11 N-Et-DOM
-- Meo Me -- MeO Me2 -- -- see #60 a-Me-DOM
-- Meo Me -- MeO < C2 -- -- see #60 a-CP-2C-D
N,N-Me-
-- MeO Me -- MeO -- -- Me2 see # 1 9
2C-D
a, f3,f3-Me-
-- MeO Me -- MeO Me2 Me -- see #60
DOM
-- Meo Me -- Meo Me2 Me2 -- see #60 a, f3-Me-DOM
-- MeO Me -- MeO Et -- -- #7 ARIADNE
-- Meo Me -- MeO -C- -- #41 DMCPA
-- Meo Me -- Meo -CMe- -- see #41 DMMCPA
-- Meo Me -- Meo -- Meo -- #14 BOD
-- MeO Me -- EtO -- -- -- see #20 2C-D-2-Et0
-- Meo Me -- EtO Me -- -- see #60 FLORENCE
-- MeO Me -- Mes -- -- -- see #56 2C-2-TOM
-- Meo Me -- MeS Me -- -- see #3 2-TOM
-- MeO CH2F -- Meo Me -- -- see #60 DOFM

Trisubstituted
6- 5- 4- 3- 2- a- f3- N- Entry Name

-- Meo CF3 - -
Meo -- -- -- #28 2C-TFM
-- Meo CF3 -- Meo Me -- -- #63 DOTFM
-- MeO COH -- MeO -- -- -- see #20 2C-HM
-- MeO COH -
- Meo Me -
- - -
see #60 DOHM
-- Meo COH - -
Meo Et -- -- see #118 4C-HM
-- Meo COHC -- MeO Et -- -- see #118 4C-HE
-- MeO CN -- MeO -- -- -- see #55 2C-CN
-- Meo CN -- MeO Me -- -- #55 DOCN
-- Meo C02H -
- MeO -- -- -- see #55 2C-CA
-- MeO C02H -- MeO Me - -
-- see #55 DOCA
-
- MeO Et -- Meo - -
-- -- #21 2C-E
-- Meo Et -- Meo Meo -- -- see #14 BOE
-- MeO Et -- Meo Me -- -- #56 DOET
-- Meo Et -- Meo Et -- -- see #7 4C-E
-- MeO Et -- MeS -- -- -- see #56 2C-2-TOET
-- Meo Et -- MeS Me -- -- see #56 2-TOET
-- Meo Seo -- MeO Me -- -- see #60 DOHP
-- Meo No -- MeO Me -- -- see #60 DONO
-- Meo C=C -- MeO -- -- -- see #20 2C-VI
-- MeO C=C - -
Meo Me -- -- see #60 DOVI
-- Meo C=C -
- MeO -- -- -- see #20 2C-YN
-- MeO C=C -- Meo Me -- -- see #60 DOYN
-- MeO FCC -- Meo - -
-- -- see #20 2C-EF
-- MeO FCC -- Meo Me -- - -
see #60 DOEF
-- Meo HOCC -- MeO Me -- -- see #60 DOEH
-- Meo COMe - -
Meo Me -- -- see #55 DOAC
-- MeO CONHPr -- MeO Me -- -- see #55 DOCONHP
-- MeO COEt -- Meo Me -- -- see #55 DOCOE
-- Meo C02 Pr -- MeO Me -- - -
see #55 DOCEP
-- MeO C02Bu -- Meo Me -- -- see #55 DOCEB
-- MeO Pr -- Meo -- -- -- see #20 2C-P
-
- MeO Pr -- MeO Me -- -- #62 DOPR
-- Meo Pr -- Meo Et -- -- see #7 4C
-- Meo iPr -- Meo Me -- -- #59 DOIP
-- Meo iPr -- MeO Et -- -- see #7 4C-iP
- -
Meo Bu -- Meo Me -- -- #53 DOBU
Tables 343
Trisubstituted
6- 5- 4- 3- 2- a- 13 - N- Entry Name
-- MeO Bu -- Meo Et -- -- see #7 4C-BU
-- Meo iBu -- MeO -- -- -- see #20 2C-IB
-- Meo iBu -- Meo Me -- -- see #60 DOIB
-- MeO sBu - -
Meo Me -- -- see #60 DOSB
-- MeO tBu -- Meo Me -- -- see #60 DOTB
-- Meo Pe -- MeO Me -- -- #51 DOAM
-- Meo He -- MeO Me -- -- see #60 DOHE
-- MeO Oc -- Meo Me -- -- see #60 DOOC
-- MeO Bz -- MeO Me -- -- see #60 DOBZ
-- Meo Ph CCC -- MeO Me -- see #60 DOPh3
-- Meo HO -- MeO Me -- -- see #118 DOOH
-- MeO HO -- Meo Et - -
-- see #118 4C-HO
-- MeO MeO -- F Me -- -- see #118 2-F-4,5-DMA
2-Cl-4,5-
-- Meo Meo -- Cl -- -- -- see #19
DMPEA
-- Meo MeO -- Br -- --
--- 1------
-- see # 1 8 2,4,5-BMM
-- Meo Meo -- Br Me - -
-- see #52 a-DOB
2-NH 2-4,5-
-- Meo Meo -- NH 2 Me -- -- see #118
OMA
-- MeO Meo -- N02 Me -- -- see #61 a-DON
-- MeO Meo -- Me Me -- -- see #60 a-DOM
-- MeO Meo -- Et Me -- -- see #56 2,4,5-DOET
-- Meo MeO -- MeO -- -- -- # 1 24 TMPEA-2
-- Meo Meo -- Meo -- MeO -- see #14 BOT
-- MeO MeO -- Meo Me -- -- #118 TMA-2
-- MeO MeO -- MeO Me -- Me see #118 N-Me-TMA-2
N,N-Me-
-- Meo Meo -- MeO Me -- Me2 see #118
TMA-2
-- Meo Meo -- Meo -C- -- see #41 TM CPA
-- Meo Meo -- MeO Et -- -- see # 1 1 8 4C-Me0
-- Meo Meo -- EtO Me -- -- see # 1 1 8 EMM
-- MeO MeO -- Mes Me -- -- see #3 a-DOT
-- Meo MeO -- PrS -- -- -- see #27 4,5,2-2C-T-7
-- Meo EtO -- MeO -- - -
-- see # 124 2C-0-2
-- Meo EtO -- Meo Me -- -- #87 MEM
- -
MeO EtO -- Meo Et -- -- see #118 4C-Et0
-- Meo EtO -- EtO Me -- -- see #118 EEM
-- Meo PrO -- Meo -- -- -- see # 124 2C-0-7

Trisubstituted
6- 5- 4- 3- 2- a- 13 - N- Entry Name
-- MeO PrO -- Meo Me -- -- see #118 MPM
-- Meo Pro -- MeO Et -- -- see #118 4C-Pr0
-- Meo 2HOPrO -- MeO Me -- -- see #118 M(20P)M
- -
MeO 3HOPrO -- Meo Me -- -- see #118 M(30P)M
-- MeO iPrO -- Meo -- -- -- see #124 2C-0-4
- -
Meo iPrO -- MeO --
Me -- -- see #118 MIPM
-- Meo iPrO -- MeO Et -- -- see #118 4C-iPrO
-- Meo BuO -- Meo -- -- -- see # 124 2C-0-19
-- MeO BuO -- MeO Me -- -- see # 1 1 8 MBM
-- Meo AmO -- MeO Me -- -- see #118 MAM
-- Meo BzO -- MeO Me -- - -
see #118 MBZM
-- MeO MeS -- MeO -- -- -- #25 2C-T
-- MeO MeS -- Meo Me -- -- #3 ALEPH
N-Me-
-- Meo MeS -- MeO Me -- Me see #3
ALEPH
-- MeO MeS -- Meo Et -- -- see #3 4C-T
-- Meo MeS -- MeO Et -- Me see #3 N-Me-4C-T
-- MeO EtS -- Meo -- -- -- #26 2C-T-2
-- MeO EtS -- Meo -- -- HO see #25 HOT-2
-- Meo EtS -- MeO Me -- -- #4 ALEPH-2
N-Me-
-- MeO EtS -- Meo Me -- Me see #3
ALEPH-2
- �-
-- Meo EtS -- MeO Et -- -- see #3 4C-T-2

-- Meo EtS -- MeO Et -- Me see #3 N-Me-4C-T-2
-- MeO FCCS -- Meo -- -- -- see #25 2C-T-21
-- Meo F 2CCS -- Meo -- -- -- see #25 2C-T-21 .5
-- Meo F3 CCS -- MeO -- -- -- see #25 2C-T-22
-- MeO PrS -- Meo -- -- -- #27 2C-T-7
-- Meo PrS -- MeO -- -- HO see #25 HOT-7
-- MeO PrS -- Meo -- Meo -- see #14 BOPS
-- MeO PrS -- Meo Me -- -- #6 ALEPH-7
N-Me-
-- MeO PrS -- MeO Me -- Me see #3
ALEPH-7
-- Meo PrS -- MeO Et -- -- see #3 4C-T-7
-- Meo PrS -- MeO Et - -
Me see #3 N-Me-4C-T-7
-- MeO iPrS -- Meo -- -- -- see #25 2C-T-4
-- Meo iPrS -- MeO Me -- -- #5 ALEPH-4
-- MeO cPrS -- MeO -- -- -- see #25 2C-T-15
Tables 345
Trisubstituted
6- 5- 4- 3- 2- a- �- N- Entry Name
-- MeO AlS -- Me o -- -- -- see #25 2C-T-16
-- MeO FCC CS -- MeO -- -- -
- see #25 2C-T-28
-- Meo Bus -- MeO -- -- -- see #25 2C-T-19
-
- Meo BuS -- MeO Me -- -- see #3 ALEPH-19
-- MeO iBuS -- MeO -- -- -- see #25 2C-T-25
-- MeO sBuS -- Meo -- -- -- see #25 2C-T-17
-- Meo sBuS -- Meo -- -- HO see #25 HOT-17
-- MeO tBuS -- Meo -- -- -- #25 2C-T-9
-- MeO MeAlS -- Meo -- -- -- see #25 2C-T-3
-- MeO cPrMS -- Meo -- -- -- see #25 2C-T-8
-- Meo coccs -- Meo -- -- -- see #25 2C-T-13
-- MeO FCCCCS -- Meo - -
-- -- see #25 2C-T-30
ALEPH-S-
-- Meo AmS -- Meo Me -- -- see #3
amyl
-- Meo PhS -- MeO Me -- -- see #3 ALEPH-6
ALEPH-S-
-- Meo PhEtS -- Meo Me -- -- see #3
PhEt
-- MeO MeS0 2 -- Meo Me -- -- see #3

ALEPH
sulfone
- -
MeO Me Se -- Meo -- -- -- see # 124 2C-SE
-- EtO Me -- MeO - -
-- -- see #20 2C-D-5-Et0
-- EtO Me -- MeO Me -- -- see #60 IRIS
- -
EtO Br -- MeO -- - -
-- see #18 2C-B-5-Et0
-- Me o Br -- EtO -- -- -- see # 1 8 2C-B-2-Et0
2C-B-2,5-
-- EtO Br -- EtO -- -- -- see # 1 8
DIEtO
2C-D-2,5-
-- EtO Me -- EtO -- -- -- see #20
DIEtO
DOM-2,5-
-- EtO Me -- EtO Me -- -- see #60
DIEtO
-- BuO He -- BuO Me - -
-- see #60 BHB
-- EtO MeO -- MeO Me -- -- see #118 MME
-- EtO Me o -- EtO Me -- -- see #118 EME
-- EtO EtO -- Me o Me -- -- see #118 MEE
-- EtO EtO -- EtO Me -- -- see #118 EEE
-- -COC- Br Me -- -- -- see #77 6-B-IBF5AP
-
- -COC- Cl Me -- -- -- see #77 6-C-IBF5AP
6-N02-
-
- -COC- N02 Me -- -- -- see #77
IBF5AP

Trisubstituted
6- 5- 4- 3- 2- a- f3- N- Entry Name

-- -OCC- Meo Me -- -- -- #66 F
-- -OCMeC- Meo Me -- -- -- see #66 F-2
-- -OCMe2 C- Meo Me -- -- -- see #66 F-22
-- -OCMeCMe- MeO Me -- -- -- see #66 F-23
-- -OCMeCMe2- Meo Me -- -- -- see #66 F-233
-- -OCO- -- F Me -- -- see #98 2-F-4,5-MDA
-- -OCO- -- Cl Me -- -- see #98 2-Cl-4,5-MDA
2-Cl-4,5-
-- -OCO- -- Cl Me -- Me see #98
MDMA
2-Br-4,5-
-- -OCO- -- Br Me -- -- see #98
MDA
2-1-4,5-
-- -OCO- -- I -- -- Me2 see #98
MD PEA
-- -OCO- -- I Me -- -- see #98 2-1-4,5-MDA
2-1-4,5-
-- -OCO- -- I Me -- Me see #98
MDMA
2-1-4,5-
-- -OCO- -- I Me -- Me2 see #98
MDDMA
2-N02 -4,5-
-- -OCO- -- N02 Me -- -- see #98
MDA
-- -OCO- -- Me Me -- -- see #77 6-Me-MDA
-- -OCO- -- Me Me -- Me see #77 MADAM-6
-- -OCO- -- HO Me -- -- see #82 6-MDOH
--
-OCO- -- HO Me -- Me see #82 6-MDMOH
-
- -OCO- -- Meo -- -- -- see #98 2C-2
-- -OCO- -- MeO Me -- -- #98 MMDA-2
-- -OCO- -- Meo Me Me -- see #98 f3-Me-2C-2
N-Me-
-- -OCO- -- Meo Me -- Me see #98
MMDA-2
-- -OCO- -- MeO Et -- -
- see #98 4C-2
-- -OCO- -- -C- -- -- see #77 5,6-MDAI
-
- -OCO- -- -C- -- Me see #77 5,6-MDMAI
-- -OCO- -- -CC- -- -- see #77 6,7-MDAT
-- -OCO- -- -CC- Me -- see #77 6,7-MDMAT
-- -OCS- -- -- Meo Me -- see #98 4T-MMDA-2
-- Mes Me -- Meo Me -- -- see #3 5-TOM
-- Mes Me -- Mes Me -- -- see #3 BIS-TOM
-- MeS Me -- MeO -- -- -- see #56 2C-5-TOM
-- MeS Et -- Meo -- -- -- see #56 2C-5-TOET
Tables 347
Trisubstituted
6- 5- 4- 3- 2- a- 13 - N- Entry Name
-- MeS Et -- Meo Me -- -- see #56 5-TOET
-- MeS Et -- Mes Me -- -- see #56 BIS-TOET
-- MeS MeO -- MeO Me -- -- see #3 m-DOT
-- PrS Meo -- MeO -- -- -- see #27 2,4,5-2C-T-7
-- MeSO Me -- Meo Me -- -- see #60 5-TOMSO
3,5-Cl-4-
-- Cl Meo Cl -- -- -- -- see # 1 9
MPEA
-- Cl MeO Cl -- Me -- -- see # 1 9 3,5-Cl-4-MA
3,5-Cl-4-
-- Cl EtO Cl -- -- -- -- see # 1 9
-
EPEA
-
3,5-Cl-4-
-- Cl PrO Cl -- -- -- -- see # 1 9
PPEA
3,5-Cl-4-
-- Cl AlO Cl -- -- -- -- see # 1 9
ALPEA
3,5-Cl-4-
-- Cl BuO Cl -- -- -- -- see # 1 9
BPEA
3-Cl-4,5-
-- Cl Meo Meo -- -- -- -- see # 1 9
DMPEA
-- Cl Meo Meo -- Me -- -- see #91 3-Cl-4,5-DMA
3-Cl-4,5-
-- Cl -OCO- -- -- -- -- see #73
MD PEA
5-Br-
-- Br HO MeO -- -- -- -- see #29
DESMETHYL
3,5-Br-
-- Br HO Br -- -- -- -- see #29
DESMETHYL
3,5-Br-4-
-- Br Meo Br -- -- -- -- see #91
MPEA
-- Br -OCCO- Me -- -- -- see #97 BEDA
-- Me -OCO- -- Me -- -- see #77 5-Me-MDA
-- Me Me Me -- -- -- -- #123 TMePEA
13-H0-3,4,5,N-
-- Me Me Me -- -- HO Me see #123
Me-PEA
-- Me Me Me -- Me -- -- see #123 TMeA
-- Me HO Me -- Me -- -- see # 1 1 7 3,5-Me-PHA
3,5-Me-4-
-- Me MeO Me -- -- -- -- see #91
MPEA
- r--·---
-- Me Meo Me -- Me -- -- see #91 3,5-Me-PMA

5-Me-3,4-
-- Me Meo MeO -- Me -- -- see #60
DOM
3,4,5-
-- HO HO HO -- -- -- -- see #29
DESMETHYL

Trisubstituted
·-·-
6- 5- 4- 3-
--
2- a- f3- N- Entry Name
N-Me-3,4,5-
-- HO HO HO -- -- -- Me see #29
DESMETHYL
-- HO HO HO -- Me -- -- see #117 THA

[3-M -3,4 -
-- HO HO MeO -- -- Meo -- see #29
DESMETHYL
3,5-
-- HO MeO HO -- -- -- -- see #30
- +----�---- f-------·- r--·�-- r--·-
DESMETHYL
3-
-- HO MeO Meo -- -- -- -- #30
DESMETHYL
N-Me-3-
-- HO MeO Meo -- -- -- Me see #30
DES METHYL
N,N-Me-3-
-- HO Meo Meo -- -- -- Me2 see #30
DESMETHYL
f3,5-HO-
-- HO MeO MeO -- -- HO -- see #30
DMPEA
a-Me-3-
-- HO MeO MeO -- Me -- -
- see # 1 1 7
DESMETHYL
-----
-- MeO Br Meo -- -- -- -- see # 1 8 3,4,5-MBM

-
- MeO Br Meo -- Me -- -- see #52 4,3,5-DOB
-- MeO I Meo -- Me -- Me2 see # 1 1 7 3,5-IDNNA-4
-- Meo Me MeO -- -- -- -
- #31 DESOXY
4-Me-3,5-
-- Meo Me Meo -- Me -- -- see #60
DOM
-- Meo Et Meo - -
Me -- -
- see #56 4,3,5-DOET
3,4-
-- Meo HO HO -- -- -- -- see #29
DESMETHYL
- ------ ---- - ------
�
-- MeO HO Meo -- -- -- -- #29 DESMETHYL
DESMETHYL-
-
- Meo HO Meo -- -- -- Me see #29
M
DESMETHYL-
-- MeO HO Meo - -
-- -- Me2 see #29
MM
DESMETHYL-
-- MeO HO MeO -- -- -- iPr see #29
---·-----
iPr
[3-HO-
-- Meo HO Meo -- -- HO -- see #29
DESMETHYL
a-Me-
-- Meo HO Meo -- Me -- -- see # 1 1 7
DES METHYL
-- Meo Meo Br -- -- -- -- see # 1 8 3,4,5-BMM

-- MeO MeO Br -- Me --
- --·------ -- ----- _,_____,,___
-- see #52 3,4,5-DOB
-- Meo MeO Et -- Me -- -- see #56 3,4,5-DOET
-- Meo Meo Meo
-- ----
-- -- -- -- #91 Mescaline, M
-- Meo Meo
-- -
Meo -- Me -- -- -- --
#117 TMA
Tables 349
Trisubstituted
6- 5- 4- 3- 2- a- f3- N- Entry Name

-- Meo Meo Meo -- Me -- HO see # 1 1 7 N-HO-TMA
-- Meo MeO Meo -- Me -- Me see # 1 1 7 N-Me-TMA
-- MeO MeO MeO -- Me HO -- see # 1 1 7 f3-HO-TMA
-- Meo Meo MeO -- CHpH -- see # 1 1 7 a-HMe-M
-- Meo Meo MeO -- CH2Cl -- -- see # 1 1 7 a-CMe-M
-- MeO Meo Meo -- -C- -- see #41 MCPA
a,N-
-- MeO MeO Meo -- -- -- a-CC=CC-N see # 1 1 7
Butenyl-M
N,N-
- -
MeO Meo Meo -- -- -- -CC=CC- see #91
Butenyl-M
-- MeO MeO MeO -- Me2 -- -- see # 1 1 7 a-MM-M
-- MeO MeO MeO -- Me, Ve -- -- see # 1 1 7 a-MV-M
-- Meo Meo Meo -- Et -- -- #1 AEM
-- MeO MeO Meo -- Pr -- -- see # 1 1 7 APM
-- Meo Meo Meo -- Bu -- -- see #117 ABM
-- Meo Meo Meo -- Pe -- -- see #117 AAM
-- Meo Meo Meo -- He -- -- see # 1 1 7 AHM
-- Meo Meo MeO -- Se -- -- see #117 ASM
-- Meo MeO MeO -
- Oc -- -- see #117 AOM
-- MeO MeO MeO -- No -- -- see #117 ANM
-- MeO MeO MeO -- -- d2 -- see #91 f3-D
-- MeO MeO Meo -- -- HO -- see #91 f3-HOM
-- Meo Meo MeO -- -- HO Me see #91 f3-HO-M-M
-- Meo Meo Meo -- -- Meo -- #16 BOM
-- MeO Meo MeO -- -- C=O -- see #91 M-f3k
-
- Meo Meo Meo -- -- -- Me #97 M-M
-- MeO Meo Meo -- -- -- Me2 # 125 Trichocereine
-- Meo MeO MeO -- -- -- Me3 + see #91 I-Mel
-- MeO Meo Meo -- -
- -
- Ally! see #91 N-AL-M
-- Meo Meo MeO -- -- -- -CCCI see #91 N-CCCl-M
-- Meo Meo MeO -- -- -- -CCC- see #91 N-cPr-M
-- Meo MeO Meo -- -- -- -CCC see #91 N-Pr-M
-- Meo MeO Meo -- -- -- -C(-CCC-) see #91 N-CPM-M
-- Meo Meo Mes -- -- -- -- see #91 3-TM
-- MeO Meo EtS -- -- -- -- see #91 3-TME
-- PrS Meo Meo - -
-- -- -- see #27 3,4,5-2C-T-7
-- Meo Cdp Meo -- -- -- - -
see #91 4-D
-- Meo EtO Meo -- -
- -- -- #64 Escaline

Trisubstituted
6- 5- 4- 3- 2- a- 13 - N- Entry Name
-- MeO EtO MeO -- Me -- -- see # 1 1 7 3C-E
-- MeO EtO EtO -- -- -- -- #8 ASB
-- Meo EtO MeS -- -- -- -- see #91 3-TE
-- MeO EtO EtS -- -- -- -- see #91 3-TASB
-- MeO FCCO MeO -- -- -- -- see #29 FEM
-- Meo FCCO MeO -- Me -- -- see # 1 1 7 3C-FEM
-- MeO F2 CCO MeO -- -- -- -- see #29 F2 EM
-- MeO F2CCO MeO -- Me -- -- see # 1 1 7 3C-F2 EM
-- Meo F3CCO MeO -- -- -- -- see #29 F3 EM
-- MeO F 3CCO MeO -- Me -- -- see # 1 1 7 3C-F3 EM
-- MeO PrO MeO -- -- -- - - # 1 04 Proscaline
-- MeO PrO MeO -- Me -- -- see # 1 1 7 3C-P
-- MeO iPrO MeO -- -- -- -- see #91 IP
-- Meo iPrO MeO -- Me -- -- see # 1 1 7 3C-IP
-- MeO AlO MeO -- -- -- -- #2 AL
-- MeO AlO MeO -- Me -- -- see # 1 1 7 3C-AL
-- Meo PRO MeO -- -- -- -- see #91 Propynyl
-- MeO cPrCO Meo -- -- -- -- see #91 CPM
-- MeO BuO MeO -- -- -- -- see #91 B
-- MeO iBuO MeO -- -- -- -- see #91 IB
-- Meo iBuO Meo -- Me -- -- see # 1 1 7 3C-IB
-- MeO MAIO MeO -- -- -- -- see #91 MAL
-- MeO BzO MeO -- -- -- -- see #91 BZ
-- Meo BzO MeO -- Me -- -- see # 1 1 7 3C-BZ
-- MeO PhEtO MeO -- -- -- -- see #91 PE
-- MeO MeS MeO -- - - - - -- see #91 TM
-- MeO Mes EtO -- -- -- -- see #91 4-TME
-- MeO EtS MeO -- -- -- -- see #91 TE
-- MeO EtS EtO -- -- -- -- see #91 4-TASB
-- MeO PrS MeO -- -- -- -- see #27 TP
-- Meo Bus MeO -- -- -- -- see #91 TB
-- EtO MeO MeO -- -- -- -- see #91 ME
-- EtO MeO EtO -- -- -- -- see #91 SB
-- EtO MeO MeS -- -- -- -- see #91 5-TME
-- EtO Meo EtS -- -- -- -- see #91 3-TSB
-- EtO EtO MeO -- -- - - -- #8 ASB
-- EtO EtO EtO -- -- -- -- see #91 TRIS
Tables 35 1
Trisubstituted
6- 5- 4- 3- 2- a- 13 - N- Entry Name
-- -
-- EtO EtO MeS -- -- -- -- see #91 5-TASB

- -
EtO EtO EtS - -
-- -- -- see #91 3-T-TRIS
----- -----
-- EtO MeS EtO -- - -

-- - -
see #91 4-TSB
-- EtO EtS EtO -- -- -- -- see #91 4-T-TRIS
-- PrO MeO Meo -- -- -
- -- see #91 MP
3-Cl-4,5-
-- -OCO- Cl -- -- -- -- see #73
MD PEA
-- -OCO- HO -- Me -- Me see #82 5-MDMOH
-- -OCO- MeO -- -- -- -- # 73 Lophophine
N-Me-
-- -OCO- MeO -- -- - -
Me see # 73
Lophophine
-- -OCO- MeO -- Me -- -- #97 MMDA
-- -OCO- Meo -- Me -- Me see #97 MMDMA
---
a-Et-
-- -OCO- MeO -- Et -- -- see #73
Lophophine
-- -OCCO- MeO Me -- -- -- see #97 MEDA
-- -OCCCO- MeO -- Me -- -- see #97 MPDA
Br -- -- Meo Meo -- -- -- see # 1 8 2,3,6-MMB
Br -- -- MeO MeO Me -- -- see #52 6,2,3-DOB
Me -- -- Me Me -- -- -- see # 123 TMePEA-5
Me -- -- Me Me Me -- -- see # 123 TMeA-5
6-Me-2,3-
Me -- -- Meo MeO Me -- -- see #60
DOM
Et -- -- MeO MeO Me -- -- see #56 6,2,3-DOET
Meo -- -- Br Meo -- -- -- see # 1 8 2,3,6,MBM
�----
---- ----- ------- --------
-
MeO -- --
Br MeO Me -- -- see #52 3,2,6-DOB
N,N-Me-
Meo -- -- Br MeO Me -
- Me2 see #52
3,2,6-DOB
MeO -- - -
I MeO Me -- -
- see #121 3-I-2,6-DMA
�-- -· -- �·
MeO -- -- I MeO Me -- Me2 see # 121 2,6-IDNNA

3-Me-2,6-
MeO -- -- Me Meo Me -- -
- see #60
DOM
MeO -- -- Et Meo Me -
- -- see #56 3,2,6-DOET
MeO -- -- PrS MeO -- -- -
- see #27 2,6,3-2C-T-7
---- r------·-- �·--- ------ -------
Meo -- -- MeO Br -
- -- -- see # 1 8 2,3,6-BMM
Meo -- -- Meo Br Me -- -- see #52 2,3,6-DOB
2-Me-3,6-
Meo -- -- Meo Me Me -- -- see #60
DOM
-- �
--
MeO -- -- MeO Et Me -
- -- see #56 2,3,6-DOET
----- ·---- -- -- -- ---- ---- --- �---- �--� �-----,--- -------------·

Trisubstituted
6- 5- 4- 3- 2- a- f:I- N- Entry Name

MeO -- -- Meo MeO -- -- -- see #121 TMPEA-5
MeO -- -- MeO Meo Me -- -- #121 TMA-5
Meo -- -- Meo PrS -- -- -- see #27 3,6,2-2C-T-7
MeO -- -- -OCO- Me -- -- see #97 MMDA-5
MeO -- -- -OCC- Me -- -- see # 1 7 SF
PrS -- -- MeO MeO -- -- -- see #27 2,3,6-2C-T-7
Me -- Me -- Me -- -- -- see # 1 23 TMePEA-6
Me -- Me -- Me Me -- -- see # 123 TMeA-6
2,6-Me-
Me -- MeO -- Me -- -- -- see #122
MPEA
6-Me-2,4-
Me -- MeO -- Meo -
- -- -- see # 1 22
DMPEA
4,6-Me-2-
Me -- Me -- Meo -- -- -- see # 122
MPEA
2,6-Me-4-
Me -- EtO -- Me -- -- -- see # 122
EPEA
Et -- Et -- Et -- -
- -- see # 123 TEtPEA-6
MeO -- Br -- Meo -- -- -- see # 1 8 2,4,6-MBM
MeO -- Br -- MeO Me -- -- see #52 4,2,6-DOB
Meo -- CF 3 -- Meo Me -- -- see #63 DOTFM-6

4-Me-2,6-
MeO -- Me -- MeO -- -- -- see # 122
DMPEA
MeO -- Me -- Meo Me -- -- see #60 'ljl-DOM
MeO -- Et -- MeO Me -- -- see #56 4,2,6-DOET
DES-
MeO -- HO -- Meo -- -- -- see #122
TMPEA-6
MeO -- MeO -- Br -- -- --
see # 1 8 2,4,6-BMM
MeO -
- Meo -- Br Me -- -- see #52 2,4,6-DOB
6-Me-2,4-
MeO -- MeO -- Me Me -- -- see #60
DOM
MeO -- MeO - -
Et Me -- -- see #56 2,4,6-DOET
MeO -- Meo -- MeO -- -- -- see # 1 22 TMPEA-6
MeO -- MeO -- Meo Me -- -- # 1 22 TMA-6
MeO -- MeO -- MeO Me -- Me see #122 N-Me-TMA-6

Meo -- MeO -- Meo Et -- -- see # 122 4C-TMPEA-6
Meo -- MeO -- PrS -- -- -- see #27 4,6,2-2C-T-7
Meo -- MeS -- MeO -- -- -- see #25 'ljl-2C-T
MeO -- MeS -- MeO Me -- -- see #3 'ljl-ALEPH
MeO -- EtS -- MeO Me -- -- see #3 'ljJ-ALEPH-2
--·--- ---
Tables 353
Trisubstituted I Tetrasubstituted
6- 5- 4- 3- 2- a- �- N- Entry Name
MeO -- PrS -- MeO -- -- -- see #27 1jJ-2C-T-7
Meo - -
iPrS -- Meo -- -- -- see #25 1jJ-2C-T-4
4,6-Me-2-
EtO -- Me -- Me -- -- -- see #122
EPEA
4-Me-2,6-
EtO -- Me - -
Meo Me -- -- see #122
MEA
6-Me-2,4-
EtO -- Meo -- Me -- -- -- see # 1 22
EM PEA
6-Me-2,4-
EtO -- EtO - -
Me - -
-- -- see # 1 22
DEPEA
EtO -- EtO -- EtO -- -- -- see #122 2,4,6-TRIS
BuO -- Bu -- BuO Me -- -- see #122 1jJ-BBB
Table 6. Tetrasubstituted phenethylamines and amp hetamines.

6- 5- 4- 3- 2- a- �- N- Entry Name
-- Me Me Me Me -- -- -- see #114 TeMePEA
-- Me Me Me Me Me -- -- see #114 TeMeA
-
- Meo Me Me Meo -- -- -- see #114 2C-G
-- Meo Me Me MeO Me -- -- see #113 G
-- MeO Me Et MeO -- -- -- see #114 2C-G-21
-- MeO Me Et MeO Me -- -- see #113 G-21
-- MeO Et Me Meo -- -- -- see #114 2C-G-12
-- MeO Et Me Meo Me -- -- see #113 G-12
-- MeO Et Et MeO -- -- -- see #114 2C-G-22
-- Meo Et Et Meo Me -- -- see #113 G-22
-- MeO -C- MeO -- -- -- see #114 2C-G-1
- -
Meo -C- Meo Me -- -- see #113 G-1
-- Meo -CC- Meo -- -- -- see # 114 2C-G-2
-- Meo -CC- MeO Me -- -- see # 11 3 G-2
-- MeO -CCC- MeO -
- -
- -- see #114 2C-G-3
-- MeO -CCC- MeO Me -- -- see #113 G-3
-- MeO -CCCC- Meo -- -- -- see #114 2C-G-4
-- Meo -CCCC- Meo Me -- -- see #113 G-4
-- MeO -C=CC=C- MeO -- -- -- see #114 2C-G-N
-- Meo -C=CC=C- MeO Me -- -- see #113 G-N
-- Meo -CCCC(l,4-C)- Meo -- -- -- see #114 2C-G-5
-- MeO -CCCC(l,4-C)- MeO Me -- -- see #113 G-5
-- Meo -CCCC(l,4CC)- MeO -- -- -- see #114 2C-G-6
-- MeO -CCCC(l,4CC)- Meo Me -- -- see #113 G-6

Tetrasubstituted
6- 5- 4- 3- 2- a- 13 - N- Entry Name
-- MeO Meo MeO Cl -- -- -- see #114 2-CM
-- MeO MeO Meo Br -- - -
-- see #114 2-BM
-- MeO Meo MeO MeO -- - -
-- #114 TeMPEA
-- MeO MeO MeO MeO Me -- -- #113 TeMA
-
- Meo MeO Meo -CC- -- -- see # 1 1 7 TMAT
-- MeO MeO -OCC- -- -- -- see # 1 7 Me0-2C-ISF
-- MeO MeO -OCO- -- -- -- see #44 2C-DMMOA-3
-- Meo Meo -OCO- -- -- Me see #44 N-Me-2C-DMMOA-3
-- MeO Meo -OCO- Me -- -- see #44 DMMDA-3
-- MeO -OCO- MeO -- -- -- see #44 2C-DMMDA
-- MeO -OCO- MeO -- -- Me see #44 N-Me-2C-DMMDA
-- MeO -OCO- Meo Me -- -- #44 DMMDA
-- Meo -OCO- Meo Me -- Me see #44 Methyl-DMMDA
-- -OCO- Meo MeO -- -- -- see #44 2C-DMMDA-2
-- -OCO- Meo MeO -- -- Me see #44 N-Me-2C-DMMDA-2
-- -OCO- MeO Meo Me -- -- see #44 DMMDA-2
Me -- Me Me Me -- -- -- see #114 TeMePEA-2
Me -- Me Me Me Me -- -- see #114 TeMeA-2
Meo -- Me Meo -C- -- -- see #60 DOMAI
Meo -- Me Meo -C- -- Me2 see #60 N,N-Me-DOMAI
Meo -- Me Meo -C=C- -- -- see #60 DOMAD
MeO -- Me MeO -CC- -- -- see #60 DOMAT
MeO -- MeO MeO MeO -- -- -- see #115 TeMPEA-2
Meo -- MeO Meo --
Meo Me -- -- see #115 TeMA-2
MeO -- Br -OCC- Me -- -- #17 B-SF
MeO -
- I -OCC- Me -- -- see # 1 7 I-SF -�-
MeO -- Meo -OCO- -- -- -- see #44 2C-DMMDA-5

MeO -- Meo -OCO- Me -- -- see #44 DMMOA-5
----�
MeO --
-OCO- MeO -- -- -- see #44 2C-DMMDA-4
�-
Meo -- -OCO-
--· -------·-·--- ___,,
Meo
---------
Me --
--·---------
-- see #44 DMMDA-4
-- -----
- -------
f--
Br MeO -- MeO Br -- -- -- see #115 2,3,5,6-BMMB

Br MeO -- MeO Br Me - -
-- see #115 2,3,5,6-BMMBA
�- ---------- - ------
Me Me -- Me Me -- -- - -
see #114 TeMePEA-3
---- - -- �
Me Me - -
Me Me Me -- -- see #114
---------------- -
TeMeA-3
�- - -- - f.--- ------
--- -- --- -------- f--------- 1-------- -- -- -
MeO MeO -- MeO MeO -

- -- -
- #115 TeMPEA-3
Meo MeO -- --
MeO MeO Me -- -- see #115 TeMA-3
----�--- ---- ------ ---- -
Meo MeO -- -OCO- -- -- -- see #44 2C-DMMDA-6
Tables 355
Tetrasubstituted I Pentasubstituted
-·
6- 5- 4-
� �-·"- ···-�::_ _J _� a- 13 - N- Entry Name
Meo MeO -
- -OCO- Me -- -- see #44 DMMDA-6
-OCC- -- -OCC- -- -- -- see #68 2C-FLY
-OCC- -- -OCC- Me -- -- #68 FLY
-OC=C- -- ·-
-OC=C- -- -- -- see #32 2C-DFLY
-OC=C- -- -OC=C- Me -- -- #32 DFLY
-OCCC- -- -OCCC- -- -- -- see #68 2C-PLY
-OCCC- -- -OCCC- Me -- -
- see #68 PLY
Table 7. Pentasubstituted phenethylamines and am p hetamines. -
6- 5- 4- 3- 2- a- 13 - N- Entry Name
Cl Meo MeO MeO Cl -- -- -- see # 1 08 2,6-CM
Br MeO MeO MeO Br -
- -- -- see # 1 08 2,6-BM
Me Me Me Me Me -- -- -- see # 1 08 PeMePEA
Me Me Me Me Me Me -- -- see # 1 08 PeMeA
Me MeO Me Me MeO -- -- -- see # 1 08 3,4,6-Me-2,5-DMPEA
MeO MeO Meo Meo Meo --
-- -- # 1 08 PeMPEA
MeO MeO Meo Meo Meo Me -- -- see # 1 08 PeMA
MeO MeO -OCO- MeO Me -- -- see # 1 08 TMMDA
-CCO- Meo -OCC- -- -- -- see #68 Me0-2C-2,6-IFLY
-OCC- Me -CCO- Me --
-- see #68 Me-3,5-IFLY
-OCC- Br -OCC- -- -- -- see #68 2C-B-FLY
-OCC- Br -OCC- Me -- -- #10 B-FLY
-OCC- I -OCC- -- -- -- see #68 2C-I-FLY
-OCC- I -OCC- Me -- -- see #68 I-FLY
-OCC- CF3 -OCC- Me -- -- see #68 TFM-FLY
-OCC- Me -OCC- Me -- see #68 DOM-FLY
-OC=C- Br -OC=C- -- - - -
- see #32 2C-B-DFLY
-OC=C- Br -OC=C- Me -- -- #10 B-DFLY
-OC=C- I -OC=C- -- -- -- see #32 2C-I-DFLY
-OC=C- I -OC=C- Me -- -- see #32 I-DFLY
-OC=C- Me -OC=C- Me -- -- see #32 DOM-DFLY
-OC=C- CF 3 -OC=C- Me -- -- see #32 TFM-DFLY
-OCCC- Br -OCCC- -- -- -- see #68 2C-B-PLY
-OCCC- Br -OCCC- Me -
- -- see #68 B-PLY

Related compounds
Table 8. Phenethylamine-like molecules with a chain from the aromatic ring to the nitro
gen atom other than two carbons long: No carbons between the benzene and nitrogen.
I
-�---- -·----
Ring N- N- Entry Name

-- -CCNCC- see #24 pp
2-CF3 -CCNCC- see #116 oTFMPP

3-CF3 -CCNCC- #116 mTFMPP
4-CF3 -CCNCC- see #116 pTFMPP
2-Cl -CCNCC- see #24 oCPP
3-Cl -CCNCC- #24 mCPP
3-Cl, 4-HO -CCNCC- see #24 HO-mCPP
4-Cl -CCNCC- see #24 pCPP
4-F -CCNCC- see #24 4-FPP
4-HO -CCNCC- see #88 HOPP
2-MeO -CCNCC- see #88 2-MeOPP
3-MeO -CCNCC- see #88 3-MeOPP
4-MeO -CCNCC- #88 MeOPP
1-Naphthyl -CCNCC- see #24 1-NP
2-Quinolyl -CCNCC- see #24 Quipazine
2-Pyrimidyl -CCNCC- see #24 2-PmP
Table 9. Phenethylamine-like molecules with a one-carbon chain between the benzene

ring and nitrogen.
Ring a- N- N- Entry Name
-- -- -- -- see # 1 07 benzy lamine
-- Me -- -- see # 1 07 a-Me-benzylamine
-- -- -CCNCC- -- Bzra
-- -- -CCNMeCC- -- MBZPb
4-Cl -- -CCNCC- -- Cl-BPa
4-Cl Me -- -- see #105 PCBA
4-MeO -- -
- -- see # 1 07 4-M-benzylamine
4-N02 -- -CCNCC- -- N02 -BP•
3,4-di-OH -- -- -- see #49 DHBA
3,4-0CO- -- -CCNCC- #79 MDBP
3,4-0CO- -- Me -- see #45 N-MMDBA
3,4-0CO- -- Me Me see #45 N,N-DMMDBA
3,4-0CO- Me -- -- see #45 a-Me-MD BA
3,4-0CO- Me2 -- -- see #45 a,a-DMMDBA
3,4-0CO- Me2 Me -- see #45 a,a,N-TMMDBA
Tables 357
Related compounds

3,4-0CO- Me2 Me2 -- see #45 a,a,N,N-TMMDBA
3,4-0CO- Me Me -- #45 a,N-DMMDBA
3,4-0CO- Me Me2 -- see #45 a,N,N-TMMDBA
3,4-0CO- Me Et -- see #45 a-Me-N-Et-MDBA
3,4-0CO- Me Pr -- see #45 a-Me-N-Pr-MDBA
3,4-0CO- Me iPr -- see #45 a-Me-N-iPr-MDBA
4-Br-2,5-MeO -- -CCNCC- see # 79 2C-B-BZP
aclassified as an antidepressant and / or stimulant (Staack et al., 2002) and is not covered in this book.
bThis is classified as a stimulant (Baltzly et al., 1944) and is not covered in this book.
Table 10. Phenethylamine-like molecules with three-carbon chains between the benzene
ring and nitrogen.
Ring a,j3- N- Entry Name
-- -- -- see #107 homo-PEA
-- j3-Me Me see #107 homo-j3,N-MePEA
4-Cl Me -- see #105 homo-PCA
3-MeO -- Et see # 1 01 homo-N-Et-3-MPEA
3-MeO -- Et2 see #101 homo-N,N-Me-3-MPEA
4-MeO a-Me -- see #110 homo-PMA
3,4-HO -- -- see #38 homo-Dopamine
3,4-MeO a-Me -- see #38 homo-DMA
3-0C0-4 -- -- see #78 homo-MD PEA
3-0C0-4 a-Me -- #78 homo-MD A
3-0C0-4 a-Me Me #83 homo-MD MA
3-0C0-4 a-Me Me2 see #78 homo-MDDMA
3-0C0-4 a-Me
------ -------
Et see #78
--- --- -·
homo-MDE (HMDE)
3-0C0-4 a-Me Pr see #78 homo-MD PR
---- ---
3-0C0-4 a-Me
---------�
iPr
----------
see #78
---- ---- --··-· -- - ·----- - --- - -- -----
homo-MDIP
3-0C0-4 a-Me HO see #78 homo-MDOH (HMDOH)
2,5-MeO - -
Me see #22 homo-N-Me-2,5-DMPEA
2,5-MeO -- Me2 see #22 homo-N,N-Me-2,5-DMPEA
--
3,4,5-MeO -- -- see #91 homo-Mescaline

---·---
-- ·--··---- --
2,4,5-MeO a-Me -- see #91 homo-TMA-2

2,5-Me0-4-Me a-Me -- see #60 homo-DOM
---�-------- ·--·-- -- ------ --�------ ·--

- .-- --·------ ·-- ------------ - --

----- ----------- ---- --------
'< 5 8 The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

Tables 359
uTo demand that a person pee in a cup whenever
you wish him to, without a documented reason to
suspect that he has been using an illegal drug, is
intolerable in our republic. You are saying to him,
u1 wonder if you are not behaving in a way that I
approve of. Convince me that you indeed are.
Outrageous.
Intolerable. "
- Alexander Shulgin
(Pihkal: A Chemical Love Story)
CHEMICAL ABSTR ACTS
REGISTRY NUMBERS INDEX
CAS Index (Alphabetical)
Table 10a. Chemical Ab stracts Service (CAS) Registry Numb ers;

Alphab etical Index.
Name CAS # Entry# Name CAS # Entry#

AAM [67293-57-6] see #117 a-Me-3-NEA [97561 -43-8] see #67
a-A-ThEA [1 8620-27-4] see #67 AMPH-OH [ 114562-60-6] see # 1 07
ABM [1 5886-81-4] see #117 a-Me-3-ThEA [861 88-25-2] see #67
AcO-MePEA [ 99985-96-3] see #71
-------·-
a-Me-TH-FEA [ 100868-39-1 ] see #67
AEM [1 7097-73-3] #1 ANM [ 67293-56-5] see # 1 1 7
AEM [40393-68-8] #1 4-APEA [57224-68-7] see # 1 02
AEPEA [ 30543-88-5] see # 1 07 2-APEA-j)k [13078-85-8] see # 1 00
a-Et-ThEA [5934-00-9] see #67 APM [ 67293-58-7] see # 1 1 7
AHM [67293-52-1] see #117 R-(-)-ARIADNE [52663-86-2] #7
AL [39201-75-7] #2 ARIADNE [52842-58-7] #7
AL [39201-76-8] #2 R-(-)-ARIADNE [52842-59-8] #7
AL [39477-28-6] #2 R-(-)-ARIADNE [52842-60-1] #7
AL [39697-36-4] #2 S-( +)-ARIADNE [52881 -88-6] #7
AL [ 5411 0-94-0 l #2 S-( +)-ARIADNE [52881-89-7] #7
ALEPH [61638-07-1] #3 ARIADNE [52918-31-7] #7
ALEPH [61638-08-2] #3 ARIADNE [ 54690-19-6] #7
R-ALEPH [ 64813-14-5] #3 S-( +)-ARIADNE [54713-06-3] #7
ALEPH-2 [1 78485-02-4] #4 ASB [6391 8-08-1] #8
ALEPH-2 [1 85562-00-9] #4 ASB [90132-30-2] #8
R-ALEPH-2 [255732-51-5] #4 ASM [67293-51-0] see # 1 1 7
ALEPH-4 [123643-26-5] #5 B [64778-75-2] see #91
R-ALEPH-4 [255732-52-6] #4 2-BA [ 861006-36-2] see #74
ALEPH-4 [849919-77-3] #5 BAP [52597-16-7] see #40
ALEPH-7 [207740-1 6-7] #6 t-BAP [ 34509-36-9] see #40
ALEPH-7 [84991 9-74-0] #6 BBAT [811 85-39-9] see # 1 05
ALEPH-19 [84991 9-75-1] see #3 'ljl-BBB [22702-22-3]
-----·--·-- ·---
- -- - ---�-------- ---- -----·---------- -·--
see #122
f---
-
ALEPH-S-amyl [84991 9-76-2] see #3
--------
BCPA
-
[26568-24-1 ] see #41
f-----
ALEPH-S-PhEt [84991 9-78-4] see #3 BDB [42542-07-4] #9

----
ALEPH sulfone [146724-75-6] see #3 --- -

R-BDB
-- -------·-·· -- - -
[103882-47-9] #9
---
N-AL-M [ 62028-46-0 l see #91 S-BDB

------- -· ----
[ 103882-48-0 l #9
ALONE [ 1 86028-85-3] see #93 R-(-)-BDB [1 03882-51-5] #9
�
--
------ !------·------- ------- ---- ------- - -------
a-Me-FEA [57580-64-0] see #67 S-(+)-BDB [1 03882-52-6]

---- ----
#9
a-Me-3-FEA [ 860003-93-6] see #67 BDB ------·---
[107447-03-0] #9
Ami fl amine [55875-51-9]
----- --- --- -- ------.- --------
see #42
- - - - -- -
2,3-BDB [337464-36-5] see #77
�-------------- -·---- -- .-- --
a-Me-NEA [ 90000-40-1 ] see #67

--------
dl-B-DFLY [21 9986-78-4] #10
- -
CAS Registry Numbers Index 363


dl-B-DFLY [219986-94-4] #10 B03MA [24578-46-9] see #101
R-(-)-B-DFLY [332012-24-5] #10 ------
B03MB [24550-1 7-2] see #101
S-( + )-B-DFLY [332012-25-6] #10 B03MDM [24550-1 8-3] see #101
R-(-)-B-DFLY [502759-67-3] #10 B03ME [23582-49-2] see #101
BEATRICE [25505-68-4] #11 B03MEA [24550-20-7] see #101
BEATRICE [92206-37-6] #11 -�--
B03MIP
-------.-- ----�-
-·---- -
[24550-16-1] see #101
R-BEATRICE [92282-59-2] #11 B03MM [23582-55-0] see # 1 01
[11C]-BEATRICE [201162-24-5] #11 B03P [24550-24-1] see # 1 01
----·---·-- --
BEDA [860003-91-4] see #97 BOB [98537-39-4] #13

Benzylamine [1 00-46-9] see # 1 07 BOB
-
[98537-42-9] #13
BF5AP [1 52624-03-8] see #77 BOBE [168783-22-0] see #14
BF6AP [ 152623-93-3] see #77 BOD [98537-38-3] #14
B-FLY [1 78557-19-2] #12 BOD [98537-41-8] #14
B-FLY [219986-75-1 ] #12 BODM [168783-21-9] see #14
R-(-)-B-FLY [332012-1 8-7] #12 BOE [ 168783-38-8] see #14
S-( + )-B-FLY [332012-19-8] #12 BOH [65615-1 7-0] #15
R-B-FLY [740790-11 -8] #12 BOH [73304-06-0] #15
S-B-FLY [766498-58-2] #12 BOH [98537-37-2] #15
BHAT [811 85-34-4] see #105 BOI [ 168783-26-4] see #14
BHB [22702-21-2] see #60 BOM [98537-36-1] #16
6-B-IBF5AP [201407-53-6] see #77 BOM [98537-40-7] #16
BIS-TOM [756225-27-2] see #3 BON [ 1 68783-27-5] see #14
2-BM [37015-1 9-3] see #114 BOPS [ 1 68783-23-1] see #14
2,6-BM [40393-73-5] see # 1 08 BOT [ 1 68783-25-3] see #14
3-BMAP [ 486459-02-3] see #92 2-BPEA [69587-09-3] see # 1 00
4-BMAP [ 486459-03-4] see #92 4-BPEA [ 65423-11-2] see # 1 02
2,3,4-BMM [72912-40-4] see # 1 8 3-Br-PHA [32560-72-8] see #38
2,3,5-BMM [200264-67-1] see # 1 8 B-PLY [ 502659-23-6] see #68
2,4,5-BMM [63375-81-5] see # 1 8 5-Br-a-Me-FEA [ 860003-96-9] see #67
3,4,5-BMM [92015-1 8-4] see # 1 8 4-Br-a-Me-ThEA [860003-94-7] see #67
2,3,5,6-BMMB [200264-69-3] see #115 5-Br-a-Me-ThEA [860003-95-8] see #67
2,3,5,6-BMMBA [ 60887-76-5] see #115 5-Br-DESMETHYL [90485-24-8] see #29
B03A [24550-23-0] see # 1 01 3,5-Br-DESMETHYL [ 13062-88-9] see #29
B03E [23582-50-5] see #101 2-Br-5-MA [321 56-24-4] see #36
B03EE [ 23642-63-9] see #101 4-Br-3-MA [321 56-23-3] see #38
B03M [24566-01-6] see # 1 01 4-Br-2-MA [99632-51-6] see #35
B03M2C [24550-13-8] see #46 6-Br-2-MA [ 1 391 02-29-7] see #37

--
1------- -- ----·--
2-Br-4,5-MDA [151920-03-5] see #98 2C-C [88441-14-9] #19
-- - ------ -- -- ----
3,5-Br-4-MPEA [991 80-14-0] see #91 2C-C [88441-15-0] #19
-----�
4-Br-2-MPEA [1391 02-26-4] see #47 2C-CA [88441-11-6] see #55
---·- --- ----- --

see # 1 02 4C-E
c-----
4-Br-PEA [7391 8-56-6] [72667-79-9] see #7
3-Br-PMA [32156-22-2] see #38 4C-2CH [722550-58-5] see #7
B-SF [1 30933-09-4] #17 N-CCCl-M [15257-73-5] see #91
B-SF [1 78557-1 0-3] #17 4C-iP [72667-80-2] see #7
N-Bu-DHPEA [ 1 3076-06-7] see #49 4C-Cl [ 69294-22-0 l see #54
N-Bu-2-MA [92330-91-1] see #74 2C-CN [88441 -07-0] see #55
N-Bu-3-MA [71250-1 9-6] see #75 CCPA [26568-25-2] see #41
4-BuPEA [3166-76-5] see #102 4C-P [72667-81 -3] see #7
N-Bu-PHA [ 855400-90-7] see #110 N-PrPEA [27906-91-8] see # 1 07
Bupropion f 34911-55-2] see #92 2C-D [24333-19-5] #20
a,N-Butenyl-M [ 62028-50-6] see #117 2C-D [25505-65-1] #20
N,N-Butenyl-M [ 62028-47-1 ] see #91 2C-DFLY [260809-97-0] see #32
BZ [2176-16-1] see #91 2C-DMMDA [ 33542-94-8] see #44
4-BzA [71 76-39-8] see #110 2C-DMMDA-2 [ 33542-95-9] see #44
2C-2 [ 13062-96-9] see #98 2C-DMMDA-3 [33542-96-0] see #44
2C-3a [2220-19-1] see #99 4C-DMPEA [551 74-55-5] see #38
4C-3a [23693-39-2] see #99 4C-2,3-DMPEA [722550-56-3] see #34
2C-3b [104958-31-8] see #99 4C-2,4-DMPEA [722550-57-4] see #35
2-CA [21193-23-7] see #74 4C-3,5-DMPEA [129556-97-4] see #39
3-CA [32560-59-1] see #75 4C-DOB [69294-23-1] see #52
CAB [2275-64-1] see # 1 06 4C-Et0 [72667-84-6] see #118
3C-Al [214414-87-6] see #117 2C-E [71539-34-9] #21
Candicine [198821 -67-9] see #71 2C-E [923013-67-6] #21
2C-B [56281-37-9] #18 3C-E [146849-92-5] see # 1 1 7
2C-B [66142-81 -2] #18 2C-F [207740-1 5-6] see #20
2C-B-DFLY [260809-98-1] see #32 3C-F 2EM [501 700-07-8] see # 1 1 7
2C-B-E [1 55639-24-0] see # 1 8 3C-F3EM [501 700-08-9] see # 1 1 7
2C-B-2-Et0 [207740-1 7-8] see #18 3C-FEM [501 700-06-7] see # 1 1 7
2C-B-FLY [733720-95-1] see #68 2C-FLY [1 78557-20-5] see #68
2C-B-M [155638-82-7] see # 1 8 2C-G [207740-1 8-9] see #114
2C-B-MM [155639-23-9] see # 1 8 2C-G-3 [ 207740-19-0 l see #114
2C-B-PLY [502659-24-7] see #68 2C-G-5 [ 207740-20-3] see #114
4C-Bu [72667-82-4] see #7 2C-G-N [207740-21-4] see #114
3C-BZ [147947-26-0] see #117 2C-H [3166-74-3] #22


2C-H [3600-86-0] #22 4,5-Cl-a-Me-ThEA [67482-62-6] see #67
2C-H [ 64610-33-9] #22 3,5-Cl-4-MPEA [27164-1 8-7] see # 1 9
2C-H [87059-70-9] #22 2-Cl-PEA [ 13078-80-3] see # 1 00
2C-H [ 108774-13-6] #22 4-Cl-PEA [156-41-2] see # 1 02
4C-HE [69294-25-3] see #118 2-CM [ 65995-43-9] see #114
4C-HM [ 69294-24-2] see #118 2,6-CM [ 6599 5-44-0 l see # 1 08
4C-HO [72667-83-5] see #118 2-CMA [4302-93-6] see #74
2C-I [ 64584-32-3] #23 a-CMe-M [49557-34-8] see # 1 1 7
2C-I [69587-11-7] #23 4C-Me0 [ 84055-86-7] see #118
2
[1 5 I]-2C-I [12621 0-33-1] #23 4C-2-MPEA [223923-44-2] see #74
4C-I [ 64584-33-4] see #58 4C-3-MPEA [35149-78-1 ] see #101
3C-IB [501 700-10-3] see #117 2C-N [261 789-00-8] see #20
6-C-IBF5AP [ 201407-55-8] see #77 2C-NH [ 168699-66-9] see #124
2,5-11CIDNA [844888-61-5] see #58 4C-NH [72667-88-0] see #61
2,5-11CIDNN A [ 844888-62-6] see #58 4C-NO [72667-87-9] see #61
3C-IP [501 700-12-5] see #117 Coryneine [7224-66-0] see #49
4C-iPr0 [72667-86-8] see #118 2C-P [207740-22-5] see #20
3,5-Cl-4-ALPEA [27164-25-6] see # 1 9 3C-P [501 700-11-4] see # 1 1 7
3,5-Cl-4-BPEA [27164-23-4] see # 1 9 3-Cl-PHA [31338-31 -5] see #38
3-Cl-4,5-DMA [27164-30-3] see #91 2C-PLY [502924-26-7] see #68
2-Cl-3,4-DMPEA [67287-36-9] see #19 CPM [207740-23-6] see #91
2-Cl-4,5-DMPEA [27164-31-4] see # 1 9 N-CPM-M [ 62028-44-8] see #91
3-Cl-4,5-DMPEA [27164-28-9] see # 1 9 4C-Pr0 [72667-85-7] see # 1 1 8
3-Cl-4-HPEA [32560-59-1] see #49 cPrONE [ 1 86028-87-5] see #93
4-Cl-2-MA [53581-61 -6] see #35 cPr-PEA [3721 -28-6] see # 1 07
4-Cl-3-MA -
[27572-11-8] see #38 2C-T [ 61 638-09-3] #25
3,5-Cl-4-MA [27164-26-7] see #19 2C-T [61 638-1 0-6] #25
2-Cl-4,5-MDA [271 64-29-0] see #98 2C-T-2 -
[207740-24-7]
- -- r-----------
#26
2-Cl-4,5-MDMA [319920-71-3] see #98 2C-T-2 [681160-71-4] #26
3-Cl-4,5-MDPEA [29401-05-6] see #73 2C-T-3 [648957-40-8] see #25
2-Cl-a,a-MePEA [1 0389-72-7] see #74 2C-T-4 [207740-25-8] see #25
4-Cl-a,a-MePEA
�------ -----
[151-06-4] see # 1 06 1j!-2C-T-4 [952006-71-2] see #25
3-Cl-a-Me-ThEA [67482-59-1 ] see #67 2C-T-7 [207740-26-9] #27
4-Cl-a-Me-ThEA [ 67482-60-4] see #67 2C-T-7 [850140-15-7] #27
5-Cl-a-Me-ThEA [67482-58-0] see #67 2C-T-8 [207740-27-0] see #25
3,4-Cl-a-Me-ThEA [67482-61-5] see #67
---·- ------ -
2C-T-9
- --·--- -------- -
[207740-28-1] see #25
3,5-Cl-a-Me-ThEA [67482-63-7] see #67 2C-T-13 [207740-30-5] see #25


2C-T-15 [952006-95-0] see #25 DESMETHYL [94783-21-8] #29
2C-T-16 [648957-42-0] see #25 DES METHYL [ 1 08774-54-5] #29
2C-T-17 [207740-32-7] see #25 a-[ 14 C]-
[802035-74-1 ] #29
DESMETHYL
2C-T-19 [648957-44-2] see #25
a, j3-[ 3Hk
2C-T-21 [ 207740-33-8] see #25 [802035-75-2] #29
DES METHYL
2C-T-21 .5 [648957-46-4] see #25
3-DESMETHYL [13062-71 -0] #30
2C-T-22 [648957-48-6] see #25
3-DESMETHYL [16046-07-4] #30
2C-T-25 [648957-50-0] see #25
3,4-DESMETHYL [5090-25-5] see #29
2C-T-28 [648957-54-4] see #25
3,5-DESMETHYL [5090-32-4] see #30
2C-T-30 [648957-56-6] see #25
3,4,5-DESMETHYL [5720-26-3] see #29
4C-T [ 69501-21-9] see #3
DESOXY [4395-23-7] #31
4C-T-2 [84991 9-79-5] see #3
DESOXY [ 63037-49-0] #31
4C-T-7 [84901 0-80-8] see #3
DES-TMPEA-6 [91252-61-8] see # 1 22
2C-TFM [159277-08-4] #28
DFA [31338-32-6] see #38
2C-TFM [159277-13-1] #28
2,4-DFA [2021 -64-9] see #35
4C-TMPEA-3 [722550-59-6] see #119
2,5-DFA [32560-78-4] see #36
4C-TMPEA-6 . [722550-60-9] see #122
dl-DFLY [260809-94-7] #32
2C-YN [ 633290-73-0] see #20
R-(-)-DFLY [332012-22-3] #32
DCA [4806-87-5] see #38
S-(+)-DFLY [332012-23-4] #32
2,4-DCA [32560-77-3] see #35
R-(-)-DFLY [730933-68-3] #32
2,6-DCA [32560-79-5] see #37
S-(+)-DFLY [787538-82-3] #32
DCPEA [21581-45-3] see #49
DHA [555-64-6] #33
DEA [ 94640-33-2] see #38
DHA [828-06-8] #33
2,5-DEA-j)k [856814-48-7] see #36
R-DHA [1 892-59-7] #33
DEAP [90-84-6] see #40
R-DHA [2743-78-4] #33
DEE [861078-07-1] see #49
DHA [3459-15-2] #33
DEONE [19191 6-44-6] see #93
S-DHA [4998-74-7] #33
DEPEA [61381 -04-2] see #49
S-DHA [14513-20-3] #33
2,4-DEPEA [101 787-05-7] see #47
a,j3, j3-[ 3HkDHA [19523-1 6-1] #33
2-DES-Me-DOM [52336-49-9] see #60
DHA [ 51 080-00-3] #33
5-DES-Me-DOM [7881 00-96-9] see #60
a, j3-[d2]-DHA [76381 -67-4] #33
2,5-DES-Me-DOM [52336-29-5] see #60
R-DHA [1 72967-65-6] #33
DESMETHYL [2176-14-9] #29
DHAOH [ 13662-98-1 ] see #33
DESMETHYL [2413-00-5] #29
DHBA [11 24-40-9] see #49
a-[ 14C]-
[27954-82-1] #29 DHEA [181425-74-1 ] see #33
DESMETHYL
DHMA [15398-87-5] see #33
a, j3-[ 3HJ 2-
[27954-91-2] #29
DESMETHYL DHMAOH [674368-64-0] see #33

Name CAS # Entry# �-

Name CAS # Entry#
2,3-DHPEA [1 972-58-3] see #34 DMA [120-26-3] #38
2,4-DHPEA [2039-62-5] see #47 R-(-)-DMA [2656-14-6] #38
DHPEA-f3k [499-61 -6] see #49 S-(+)-DMA [2811-24-7] #38
[3-Me-DHPEA [ 66432-25-5] see #49 DMA [ 13078-75-6] #38
DH-a-Et-PEA [2014-52-0] see #33 S-(+)-DMA [ 1 7279-41-3] #38
DIMETH [33286-27-0] see #1 07 DMA [58379-90-1 ] #38
2,3-DMA [ 1 5402-81 -0] #34 DMA [ 64610-45-3] #38
d/-2,3-DMA [25068-96-6] #34 R-(-)-DMA [ 64778-78-5] #38
R-2,3-DMA [ 50505-82-3] #34 DMA [87059-59-4] #38
S-2,3-DMA [ 50505-83-4] #34 DMA [91 340-28-2] #38
2,3-DMA [ 64610-42-0 l #34 R-DMA [161121-04-6] #38
2,3-DMA [87059-55-0] #34 R-DMA [199527-10-1 ] #38
S-2,3-DMA [741616-71 -7] #34 S-DMA [199527-11-2] #38
R-2,3-DMA [744974-27-4] #34 3,5-DMA [1 5402-82-1 ] #39
2,4-DMA [23690-13-3] #35 3,5-DMA [24973-29-3] #39
2,4-DMA [331 89-36-5] #35 3,5-DMA [ 64610-46-4] #39
2,4-DMA [ 6461 0-43-1] #35 3,5-DMA [87920-96-5] #39
R-2,4-DMA [67313-94-4] #35 S-( + )-3,5-DMA [104371-22-4] #39
2,4-DMA [ 87059-56-1 ] #35 S-( + )-3,5-DMA [1 04371 -23-5] #39
2,4-DMA-f)k [72739-16-3] see #35 R-(-)-3,5-DMA [153379-46-5] #39
2,5-DMA [2801-68-5] #36 R-(-)-3,5-DMA [ 1 77971 -34-5] #39
2,5-DMA [24973-25-9] #36 homo-DMA [27487-78-1 ] see #38
R-2,5-DMA [50505-84-5] #36 DMAOH [ 58380-00-0 l see #38
S-2,5-DMA [ 50505-85-6] #36 DMAP [101 05-90-5] #40
2,5-DMA [52948-31-9] #36 DMAP [ 1 5351-09-4] #40
S-( + )-2,5-DMA [ 58993-80-9] #36 S-DMAP [35026-77-8] #40
R-(-)-2,5-DMA [58993-81-0] #36 S-DMAP [ 35026-78-9] #40
2,5-DMA [ 64610-44-2] #36 S-DMAP [ 35026-79-0 l #40
2,5-DMA [ 69321-45-5] #36 R-DMAP [ 35026-80-3] #40
2,5-DMA [71 832-30-9] #36 R-DMAP [65528-82-7] #40
2,5-DMA [87059-57-2] #36 [d ]-DMAP [87258-67-1] #40
5
2,5-DMA [1821 89-03-3] #36 DMAP [102321 -77-7] #40
2,5-DMA-Ac [42311-1 6-0] see #36 DMAP [ 1 08479-33-0 l #40
2,5-DMA-f)k [854685-37-3] see #36 DMAP [115121-90-9] #40
2,6-DMA [3904-11-8] #37 S-(-)-DMAP [12131 6-76-5] #40
2,6-DMA [23690-14-4] #37 N-(C[ d ]) 2-DMAP [ 160977-87-7] #40
3
2,6-DMA [ 87059-58-3] #37 S-(-)-DMAP [ 444289-41-2] #40

------
r-�-·
DMAP [857982-44-6] #40 3,5-DMePEA [6632-31-1] see #43
DMBZ [2980-07-6] see #38 2,5-DMPEA-f3k [ 860538-19-8] see #22
R,S-trans-(-)-DMCPA [53581-71-8] #41 DMMA [33236-61-2] see #38
R,S-trans-(-)-DMCPA [ 67890-16-8]
---··�-·--·
#41 2,4-DMMA [93675-27-5] see #35
R,S-trans-( + )-DMCPA [67890-1 7-9] #41 2,5-DMMA [54687-43-3] see #36
DMCPA [ 69854-49-5] #41 2,5-DMMA-f3k [854685-49-7] see #36
R,S-trans-(-)-DMCPA [ 69980-34-3] #41 DMMAOH [ 583 79-99-0 l see #38
R, S-trans-(-)-DMCPA [ 69980-35-4] #41 DMMCPA [81129-32-0] see #41
S,R-trans-( + )-DMCPA [ 69980-36-5] #41 DMMCPA [811 77-10-8] see #41
S,R-trans-( + )-DMCPA [ 69980-3 7-6] #41 DMMDA [151 83-13-8] #44
R,R-cis-DMCPA [101468-37-5] #41 DMMDA [151 83-24-1 ] #44
--
R,S-trans-(-)-DMCPA [714903-64-7] #41 R-DMMDA [67313-98-8] #44
3,4-DMCPA [61114-45-2] see #41 DMMDA-2 [151 83-25-2] see #44
DME [6924-1 5-8] see #49 a,N-DMMDBA [121 734-65-4] #45
DMeA [102-31-8] #42 (-)-a,N-DMMDBA [ 1 09881-35-8] #45
-�-
DMeA [5973-70-6] #42 ( + )-a,N-DMMDBA [ 109922-33-0 l #45
DMeA [ 6009-73-0 l #42 a,a-DMMDBA [ 556053-68-0 l see #45
DMeA [7437-51-6] #42 N,N-DMMDBA [58995-64-5] see #45
DMeA [14543-76-1 ] #42 DMONE [19191 6-43-5] see #93
DMeA [61079-92-3] #42 DMPA [33236-63-4] see #38
(+)-DMeA [ 124866-26-8] #42 DMPEA [1 20-20-7] #49
(-)-DMeA [124866-27-9] #42 DMPEA [635-85-8] #49
DMeA [ 861 007 -60-5] #42 DMPEA [5006-63-3] #49
DMEA [ 33236-63-3] see #38 DMPEA [ 14456-33-8] #49
2,3-DMeA [34332-74-2] see #42 DMPEA [14457-28-4] #49
2,4-DMeA [32560-60-9] see #42 f3-[ d2]-DMPEA [271 60-05-0] #49
2,5-DMeA [ 19064-48-3] see #42 f3-[d]-DMPEA [27167-81-3] #49
2,6-DMeA [63223-62-1] see #42 a-[d2 ]-DMPEA [37699-47-1] #49
3,5-DMeA [321 56-1 6-4] see #42 DMPEA [37852-37-2] #49
DMePAA [57294-60-7] see # 1 06 DMPEA [42047-49-4] #49
DMePEA [ 5470-35-9] #43 DMPEA [ 543 73-56-7] #49
DMePEA [1 7283-14-6] #43 DMPEA [ 54373-57-8] #49
DMePEA [ 1 7283-1 5-7] #43 f3-[1 4 C]-DMPEA [55323-11 -0] #49
2,3-DMePEA [67685-71-6] see #43 DMPEA [ 63286-43-1 ] #49
2,4-DMePEA [76935-60-9] see #43 DMPEA [ 64610-34-0] #49
2,5-DMePEA [ 6632-32-2] see #43 f3-[ 3HkDMPEA [70097-40-4] #49
2,6-DMePEA [76935-78-9] see #43 a-[ ' 4C]-DMPEA [79563-88-5] #49


a, f3,N-[d6]-DMPEA [85226-30-8] #49 3,5-DMPEA [3213-28-3] #50
f3-[ d2]-DMPEA [85479-74-9] #49 3,5-DMPEA [ 6461 0-35-1] #50
DMPEA [87059-72-1] #49 3,5-DMPEA [87059-73-2] #50
3-(C [d ]0)-DMPEA [88204-74-4] #49 3,5-DMPEA [93023-05-3] #50
3
a-[ 3H]-DMPEA [95864-24-7] #49 2,4-DNNA [102145-22-2] see #35
f3-[ 3H]-DMPEA [95864-22-5] #49 2,5-DNNA [67707-78-2] see #36
DMPEA [99275-26-0] #49 2,6-DNNA [ 1 05363-36-8] see #37
DMPEA [ 107326-31-8] #49 3,5-DNNA [ 1 05363-38-0 l see #39
[ 1 3N] -DMPEA [111045-19-3] #49 DOAA [42203-87-2] see #61
a- [1 3 C]-DMPEA [123283-21-6] #49 DOAC [ 222022-54-0 l see #55
DMPEA [124154-09-2] #49 DOAM [54975-72-3] #51
f3-[1 3 C]-DMPEA [157333-16-9] #49 DOAM [ 63779-90-8] #51
a-[ 1 3C]-DMPEA [157333-18-1] #49 R-DOAM [64813-1 7-8] #51
DMPEA [265323-73-7] #49 DOB [29705-96-2] #52
DMPEA [ 440124-92-5] #49 DOB [52432-70-9] #52
DMPEA [ 639806-99-8] #49 DOB [53581 -53-6] #52
a-[ 3H]-DMPEA [732945-89-0] #49 R-DOB [53581-79-6] #52
f3-[ 3H] -DMPEA [740759-57-3] #49 S-DOB [53581 -80-9] #52
a-[11C]-DMPEA [765846-80-8] #49 DOB [ 53581-90-3] #52
f3,4-DMPEA [31367-42-7] see #102 DOB [53581-91 -4] #52
2,3-DMPEA [669-36-3] #46 [ 77Br] -DOB [55181-90-3] #52
2
2,3-DMPEA [3166-89-0] #46 [ 8 Br]-DOB [55181-91-4] #52
2,3-DMPEA [3213-29-4] #46 DOB [ 64638-07-9] #52
2,3-DMPEA [ 14480-1 0-5] #46 R-(-)-DOB [1141 67-06-5] #52
2,3-DMPEA [64610-31 -7] #46 a, f3-[ 3Hli-DOB [770733-79-4] #52
2,3-DMPEA [ 87059-68-5] #46 m-DOB [6091 7-67-1] see #52
see
2,4-DMPEA [2039-55-6] #47 a-DOB [32156-25-5] #52
see
2,4-DMPEA [15806-29-8] #47
a-DOB [371 62-72-4] #52
2,4-DMPEA [64610-32-8] #47
R-(-)-DOB [ 43061-15-0] #52
2,4-DMPEA [ 87059-69-6] #47
R-DOB [50505-92-5] #52
4-(C [d p)-2,4-
3 [88204-73-3] #47 S-(+)-DOB [43061-16-1] #52
DMPEA
2,6-DMPEA [486-95-3] #48 S-DOB [ 50505-93-6] #52
3-DOB [72739-13-0] see #52
2,6-DMPEA [3167-06-4] #48
2,6-DMPEA [87059-71-0] #48 2,3,5-DOB [204776-50-1 ] see #52
2,6-DMPEA [861 039-93-2] #48 3,2,6-DOB [60887-75-4] see #52
3,5-DMPEA [637-26-3] #50 3,4,5-DOB [321 56-34-6] see #52


4,2,6-DOB [82789-71-7] see #52 DOHE [ 125903-45-9] see #60
4,3,5-DOB [ 64778-79-6] see #52 DOHM [29907-74-2] see #60
6,2,3-DOB [60887-73-2] see #52 DOI [42203-78-1 ] #58
DOB-Ac [42203-75-8] see #52 a,f3-[ d2 ]-DOI [ 64584-31-2] #58
DOBU [54749-54-1 ] #53 DOI [ 64584-34-5] #58
DOBU [ 63779-89-5] #53 [1 3 11]-DOI [65756-98-1 ] #58
R-DOBU [64813-16-7] #53 [1 231]-DOI [ 65 756-99-2] #58
DOBZ [1 58721-63-2] see #60 [1 23 1 ) -DOI [72299-69-5] #58
DOC [42203-77-0] #54 DOI [99632-42-5] #58
R-DOC [53626-23-6] #54 S-DOI [ 99665-05-1 ] #58
S-DOC [53626-24-7] #54 [1 25 1]-DOI [111381-00-1] #58
DOC [123431-31-2] #54 [1 25 1]-DOI [111381-06-7] #58
S-DOC [75641 8-21-0] #54 R-[1 25 1]-DOI [1221 67-34-4] #58
R-DOC [773790-50-4] #54 S-[1 25 1]-DOI [122167-35-5] #58
DOC-Ac [ 42203-74-7] see #54 R-[1 23 1]-DOI [ 122419-39-0] #58
DOCA [29907-75-3] see #55 S-[1 23 1]-DOI [ 122419-40-3] #58
DOCEB [ 125903-53-9] see #55 DOI [1 88576-64-9] #58
DOCEP [125903-50-6] see #55 R-(-)-DOI [ 82864-06-0 l #58
DOCN [125903-49-3] #55 S-(+)-DOI [ 99665-04-0 l #58
DOCN [ 125903-74-4] #55 DOI-Ac [82830-50-0] see #58
DOC OE [125926-18-3] see #55 DOIB [89556-64-9] see #60
DOCONHPr [ 125903-56-2] see #55 DOIP [ 42306-96-7] #59
DOEF [121649-01-2] see #60 DOIP [ 53581-56-9] #59
DOEH [121649-04-5] see #60 DOM [1 5588-95-1] #60
DOET [22139-65-7] #56 DOM [ 15589-00-1 ] #60
DOET [22702-1 8-7] #56 DOM [22702-23-4] #60
DOET [30100-54-0] #56 R-(-)-DOM [ 50505-88-9] #60
R-(-)-DOET [42011 -76-7] #56 S-(+)-DOM [ 50505-89-0 l #60
S-(+)-DOET [50505-91-4] #56 f3-[1 4C]-DOM [531 97-60-7] #60
S-(+)-DOET [53305-83-2] #56 R-(C[d3 ]0\-DOM [ 59262-02-5] #60
R-(-)-DOET [57116-37-7] #56 S-(C[d3]0\-DOM [ 59262-03-6] #60
DOET [22004-32-6] #56 R-a,f3-[ d2 ]-DOM [ 59262-04-7] #60
2,4,5-DOET [910382-26-2] see #56 S-a, f3-[ d2 ]-DOM [58262-05-8] #60
(+)-DOF [ 82830-43-1 ] #57 (C[d3 ]0\-DOM [ 60124-80-3] #60
DOF [ 125903-69-7] #57 (C[d3 ]0) 2-DOM [601 24-87-0] #60
(+)-DOF [ 697731-15-4] #57 S-a, f3-[ d2 ]-DOM [61471-46-3] #60
DOFM [260810-05-7] see #60 4-C[d3 ]-DOM [61552-35-0] #60
CAS Registry Numbers Index 37 1

Name CAS # Entry# CAS # Entry#

�
f3,f3-[ 3HJ-a-C[ 3Hk m-DOT [79440-52-1 ] see #3

[70097-3 7-9] #60
DOM
a-DOT [79440-51-0] see #3
f3, f3-[ 3Hlz-DOM [343323-59-1] #60
DOTB [53581 -57-0] see #60
4-C[d3 ]-DOM [736876-81-6] #60
DOTFM [ 1 59277-07-3] #63
R-(-)-DOM [43061-13-8] #60
DOTFM [ 159277-12-0] #63
S-(+)-DOM [43061-14-9] #60
DOYN [ 633290-70-7] see #60
m-DOM [79440-50-9] see #60
Escaline [3166-82-3] #64
R-DOM [754921-26-1] #60
Escaline [39201 -82-6] #64
3-DOM [72739-11-8] see #60
Escaline [39477-30-0] #64
homo-DOM [3891 0-34-8] see #60
Escaline [ 40275-08-9] #64
DOM-2,5-DIEtO [22702-1 5-4] see #60
Escaline [54110-93-9] #64
DOM-DFLY [260809-96-9] see #32
2-EA [39590-27-7] see #74
DOM-FLY [ 1 78557-22-7] see #68
3-EA [135014-86-7] #75
f3-Me-DOM [53581 -76-3] see #60
4-EA [ 129476-58-0] see #110
f3, f3-Me-DOM [53582-16-4] see #60
EAP [ 1 8259-37-5] see #40
'ljJ-DOM [ 80888-36-4] see #60
EBDB [167394-39-0] see #77
DOMAD [77886-58-9] see #60
2,3-EBDB [337464-38-7] see #77
DOMAI [51806-87-2] see #60
EDA [ 15033-67-7] #65
DOMAT [ 51806-86-1 ] see #60
EDA [ 15033-71-3] #65
DON [ 42203-79-2] #61
EDEA [ 1 5033-73-5] see #65
R-DON [64778-74-1 ] #61
EDMA [133787-66-3] see #65
DON [67460-68-8] #61
ED-mor-A [ 1 5057-45-1] see #65
R-(-)-DON [ 82830-45-3] #61
ED-mor-PEA [ 1 0554-60-6] see #65
a-DON [142893-52-5] see #61
ED-ND MA [ 1 5057-44-0] see #65
3-DON [ 146269-9 5-6] see #61
ED PEA [2231 0-84-5] see #65
DON-Ac [42203-72-5] see #61
ED-pyr-A [15147-05-4] see #65
DONH [ 42203-80-5] see #61
ED-pyr-PEA [13015-25-3] see #65
DONH-Ac [42203-73-6] see #61
EEAT [87394-83-0] see # 1 05
DON MM [88753-12-2] see #61 EEE [ 1 7231-83-3] see #118
DOOC [ 125903-46-0] see #60 EEM [ 1 7231-81-1] see #118
DOOH [ 125903-57-3] see #118 EHAT [87394-70-5] see # 1 05
homo-Dopamine [52336-30-8] see #38 EMA [872810-48-5] see #38
DOPh3 [ 125903-47-1] see #60 EME [ 1 7231-79-7] see #118
DOPR [ 53581-55-8] #62 EMM [ 1 7231-77-5] see #118
DOPR [ 63 779-88-4] #62 EMPEA [86456-97-5] see #49
R-DOPR [64813-15-6] #62 2,3-EMPEA [87790-87-2] see #46
DOSB [89556-69-4] see #60 2,4-EMPEA [ 1 09036-67-1 ] see #35


[3-HO-EMPEA [ 861 078-09-3] see #49 N-Et-3-TFMPEA [125236-62-6] see #63
a-EMTPEA [634607-21-9] see #103 F [99355-77-8] #66
4-EPEA [ 62885-82-9] see #102 F [ 99355-78-9] #66
ETA [201407-47-8] see #103 F-2 [85258-13-5] see #66
N-Et-3-BA [54947-21-6] see #75 F-22 [952016-51-2] see #66
N-Et-3-CA [54947-20-5] see #75 2-FA [ 1716-60-5] see #74
N-Et-DHPEA [21987-94-0] see #49 3-FA [1626-71-7] see #75
N-Et-DMPEA [1 3078-77-8] see #49 F2 -BDB [914800-78-5] see #9
i-----
N-Et-DOM [53581 -78-5] see #11 2-F-4,5-DMA [155831-43-9] see #118
N-Et-3-FA [ 54982-43-3] see #75 5-F-2,4-DMA [155831-44-0] see #118
N-Et-3-HA [ 50623-68-2] see #75 2,4-FDNNA [105466-93-1] see #118
[3,3,4-HO-a-Et-PEA [3198-07-0] see #33 F2 EM [501 700-02-3] see #29
�--
[3,3,4-HO-N-Et-PEA [51 79-72-6] see #49 F 3EM [501 700-03-4] see #29
a-Et-4-HPEA [100131-85-9] see #110 FEA [1121-46-6] #67
N-Et-3-IA [54947-22-7] see #75 FEA [ 53356-38-0 l #67
a-Et-Lophophine [ 1 7251 8-54-6] see #73 FEA [86423-58-7] #67
N-Et-2-MA [91553-50-3] see #74 FEA [856943-52-7] #67
N,N-Et-2-MA [ 100966-45-8] see #74 FEM [501 700-01 -2] see #29
N-Et-3-MA [ 50623-66-0 l see #75 [3,[3-F-PCA [38473-95-9] see #106
N,N-Et-3-MA [71250-21-0] see #75 FLEA [214414-88-7] see #84
a-Et-MD A [ 627876-91-9] see #77 FLORENCE [22702-19-8] see #60
N-Et-MDPEA [133011-30-0] see #85 (±)-FLY [1 78557-11-4] #68
N-Et-2,3-MDPEA [301 642-49-9] see #77 (±)-FLY [219986-80-8] #68
a-Et-MPEA [78108-1 8-6] see #110 R-(-)-FLY [332012-16-5] #68
homo-N-Et-3-MPEA [71250-30-1] see #101 S-(+)-FLY [332012-1 7-6] #68
homo-N,N-Et-3- S-(+)-FLY [769911-33-3] #68
[71250-28-7] see #101
MPEA
R-(-)-FLY [780028-3 7-7] #68
4-EtO-a-EtPEA [827611-21-2] see #110
F2-MBDB [914800-83-2] see #76
4-EtO-METH [827611-1 8-7] see #110 4-F-MCAT [447-40-5] see #92
a-Et-MPEA [78108-1 8-6] see #110 F2-MDA [91 0393-51 -0] see #77
N-Et-3-MPEA [727732-11-8] see #101 2-F-4,5-MDA [1 53506-1 8-4] see #98
N-Et-3-N02-A [54947-52-3] see #75 F2-MDE [914800-82-1 ] see #81
EtONE [19191 6-42-4] see #93 F2-MDMA [914800-81-0] see #82
N-Et-PCA [2275-67-4] see #106 F2-MDPEA [2781 83-65-6] see #85
N-Et-PEA [22002-68-2] see # 1 07 F2 -MDPEA [885067-88-9] see #85
4-Et-PEA [ 31 66-88-9] see # 1 02 4-FPEA [1583-88-6] see #102
N-Et-PMA [14367-46-5] see #110 4-FPP [2252-63-3] see #24
-- -·--�-.�-- -..--

Name CAS # Entry# Name -

CAS # Entry#
N-fur-2-MA [101104-91-0] see #74 2,3-HMeA [1 88852-11-1] see #34
G [207740-37-2] see #113 3,4-HMeA [2161 8-99-5] see #96
G-3 [ 207740-36-1 ] see #113 3,4-HMeA [29440-90-2] see #96
G-5 [1 33787-68-5] see #113 3,4-HMeA [ 64829-34-1 ] see #96
G-N [477904-62-4] see #113 a-HMe-M [49557-38-2] see #117
GEA [554-52-9] #69 2,3-HMeMA [ 1 88852-12-2] see #34
GEA [1477-68-5] #69 2,3-HMeMMA [ 188852-13-3] see #34
a, f3-[ 3H] 2-GEA [27954-87-6] #69 2,3-HMeMMPEA [ 188852-01 -9] see #34
GEA [52532-94-2] #69 2,3-HMeMPEA [1 88852-00-8] see #34
2,5,6-[ d3 ]-GEA [53587-31-8] #69 HMePEA
[370-98-9] #70
(N-Methyltyramine)
GEA [ 53 799-05-6] #69
HMePEA [241 9-58-1] #70
a,[3-[ d ]-GEA [74719-64-5] #69
4
5-[d]-GEA [81587-01-1] #69 HMePEA [ 13062-76-5] #70
2,5,6,a, [3-[ d5 ]-GEA [ 83008-35-9] #69 HMePEA [611 86-07-0] #70
GEA [94001-1 7-9] #69 HMePEA [923587-27-3] #70
GEA [ 97289-40-2] #69 HM-a-EPEA [ 221 73-84-8] see #96
GEA [1 00098-95-1] #69 HMMA [11 7652-27-4] see #33

GEA [ 129111-14-4] #69 HMMA [352422-1 5-2] see #33
[1 4C]-GEA [131 889-58-2] #69 HMMC [9161 77-15-6] see #92
GEA [144576-58-9] #69 HMPEA [645-33-0] see #49
a, f3-[ 3 HkGEA [801201 -30-9] #69 HMPEA [3213-30-7] see #49
GEA [851222-90-7] #69 3-HMPEA [51 674-33-0] see #71
GEA [892247-47-1] #69 2,3-HMPEA [1 986-12-5] see #34
GEA-f3k [13062-63-0] see #49 2,3-HMPEA [2074-95-5] see #34
2-HA [69271 -67-6] see #74 2,5-HMPEA [7451 6-48-6] see #22
3-HA [ 1075-61 -2] see #75 2,5-HMPEA [1 25438-42-8] see #22
N-He-2-MA [101425-96-1 ] see #74 HMPEA-f3k [13061 -68-5] see #49
4-HePEA [ 100874-90-6] see # 1 02 2,4-H0-5-AA [ 106868-44-4] see #118
HHAT [11 8298-09-2] see #105
4,5-H0-2-AA [ 168699-63-6] see #118
HMA [52336-47-7] see #33
[3-H0-2-APEA [ 13078-83-6] see # 1 00
2-HMA [61 866-77-1 ] see #74
2,4-H0-5-APEA [41241-41-2] see #124
2,5-HMA [74516-49-7] see #36 2,5-H0-4-APEA [41241 -40-1] see #124
HME [1 3062-56-1 ] see #49 4,5-H0-2-APEA [38411-80-2] see #124
HME [ 13062-62-9] see #49 HOBDB [167394-41 -4] see #77
HME [32655-70-2] see #49 N-H0-2C-D [ 42203-91 -8] see #20
HMEA [210708-1 5-9] see #33 [3-H0-2,5-DEA [1 05652-59-3] see #36


j)-H0-2,5-DEPEA [854168-07-3] see #22 j)-HO-N,N-Me-2,5-
[3489-99-4] see #36
DMA
j)-HO-DESMETHYL [24131 -22-4] see #29
j)-HO,Me-2,5-
j)-HO-DHA [ 6539-57-7] see #33 [63991-1 8-4] see #22
DMPEA
j)-HO-DHMA [13032-27-4] see #33
j)-HO-N-Me-2,5-
j)-H0-2,5-DMA [25351-11-5] see #36 [63991-1 7-3] see #22
DMPEA
j),2-H0-5,N-DMeA [857542-51-9] see #36 j)-HO-N-Me-2,6-
[3490-10-6] see #48
j),5-HO-DMPEA [241 59-01-1] see #30 DMPEA
j)-H0-2,5-DMPEA [ 60407-53-6] see #22 j)-HO-N-Me-3,5-

[582-31-0] see #50
DMPEA
j)-H0-2,6-DMPEA [145412-89-1] see #48
j)-HO-j),N-Me-2,5-
j)-H0-3,5-DMPEA [91252-41-4] see #50 [ 69766-13-8] see #22
DMPEA
j)-HO-DOB [ 677277-49-5] see #13 j)-HO-N,N-Me-2,5-
[ 63991-16-2] see #22
N-HO-DOM [43022-01-1] see #60 DMPEA
j)-HO-DHA [ 6539-57-7] see #33 j)-H O-N,N-Me-3,5-

[1 00252-59-3] see #50
DMPEA
j)-HO-DMA [3046-92-2] see #38
j),2-HO-N-Me-5-EA [108746-20-9] see #36
j),2-H0-5,N-DMeA [ 110556-08-6] see #36
2-HO-N-Me-5-EA-j)k [857983-04-1 ] see #22
j)-H0-3,5-DMPEA [91252-41-4] see #50
2-HO-N-Me-5-EPEA-
j),2-H0-5-EA [11 0492-83-6] see #36 [857566-16-6] see #22
j)k
j),2-H0-5-EPEA [857755-64-7] see #22
j),2-HO-N-Me-5-
[86051 0-57-2] see #22
2-H0-5-EPEA-j)k [ 85 7560-64-6] see #22 EPEA
j)-H0-3-HA [54-49-9] see #75 j)-HO-N-Me-HPEA [94-07-5] see #71
j)-HO-HMA [365-26-4] see #109 j)-HO-N-Me-3-HPEA [ 1477-63-0] see #71
j)-HO-Hordenine [2039-58-9] see #71 j),2-HO-N-Me-5-MA [110492-80-3] see #36
j)-HO-HPEA [104-14-3] see #71 2-H0-5,N-MePEA-
[857618-30-5] see #22
j)k
j)-H0-2-HPEA [2234-25-5] see #71
j),2-HO-N-Me-5-
j)-H0-3-HPEA [536-21 -0] see #71 [ 11 7342-28-6] see #22
MPEA
j)-HO-N-iPr-DHPEA [7683-59-2] see #49
j),5-HO-N-Me-2-
j)-HOM [ 13079-1 8-0 l see #91 [8541 79-26-3] see #22
MPEA
j),2-H0-5-MA [14722-93-1 ] see #36 5-HO-N-Me-2-
[ 85 7566-48-4] see #22
HO-mCPP [85474-76-6] see #24 MPEA-j)k
j)-HO-MDA [ 61555-32-6] see #77 j),2-H0-5-MePEA [857542-53-1 ] see #22
j),2-H0-5-MeA [857543-23-8] see #36 j),2-H0-5,N-MePEA [ 11 7886-34-7] see #22

j),3,4-HO-N,N-
j)-HO-N-Me-2,5- [554-99-4] see #49
[3489-98-3] see #36 MePEA
DEA
j)-HO-N,N-Me-PEA [1 797-76-8] see # 1 07
j)-HO-N-Me-2,5-
[8541 78-50-0] see #22 j)-H0-3,4-MePEA [100131-59-7] see #43
DEPEA
j)-HO-N-Me-2,5- j)-H0-3,4,N-MePEA [40807-91-8] see #43

[1 08746-19-6] see #36
DMA 2-H0-5-MePEA-j)k [ 860538-08-5] see #22

�·
Name CAS #
- �-· -·-·---
Entry# Name CAS # Entry#
�-I-I()-2-M-N-Me- 2-I-IPEA [2039-66-9] see #71
[7171 08-44-6] see #36
MeA
3-I-IPEA [588-05-6] see #71
f--
�-I-I()-2-M-5-MePEA [855271 -83-9] see #22
2,6-I-IPEA [54942-65-3] see #48
�-I-I ()-4-MPEA [55275-61-1] see # 1 02
3,5-I-IPEA [29866-11 -3] see #50
�,2-I-I()-5-MPEA [860511-14-4] see #22
IBF5AP [201407-57-0] see #77
2,5-I-I()-MPEA [1 3062-74-3] see #124
IBF5MAP [201407-56-9] see #77
2-I-I()-5-MPEA-�k [857560-60-2] see #22
N-iBu-DI-IPEA [ 65341 -01-7] see #49
2,5-I-I()-PAA [ 168699-64-7] see #118
N-iBu-2-MA [93721 -06-3] see #74
�-I-I()-PEA [7568-93-6] see # 1 07
iBu()NE [ 186028-82-0] see #93
2,4,5-I-I()-PEA [28094-15-7] see #124
2,5-1 3 1 IN CNMA [90064-61 -2] see #58
�-I-I()-PI-IA [552-85-2] see #109
IDA [71203-59-3] see #77
�-I-I ()-PMA [50802-67-0] see #110
I-DFLY [260809-95-8] see #32
N-I-I()-PMA [1454-68-8] see #110
2-I-3,5-DMA [159432-50-5] see #120
I-I()PP [ 56621 -48-8] see #88
3-I-2,6-DMA [159432-48-1 ] see #121
5-I-I()-PPAT [ 68593-96-4] see #34
5-I-2,4-DMA [159432-47-0] see #118
6-I-I()-PPAT [7501 7-01-5] see #35
2,5-1 3 1IDMAPA [90064-62-3] see #58
7-I-I()-PPAT [74938-11-7] see #36
2,5-1 3 1IDMNiPrNMeA [90064-64-5] see #58
�-I-I ()-N-Pr-PMA [1 08873-47-8] see #110
2,5-IDNA [ 844888-63-7] see #58
I-Iordenine [539-15-1 ] #71
2,5-1 3 1 1DNA [90064-53-2] see #58
I-Iordenine [622-64-0] #71
2,4-IDNNA [ 1 053 71 -59-3] see #118
I-Iordenine [5990-96-5] #71
2,5-IDNNA [85563-10-6] see #58
I-Iordenine [ 6027-23-2] #71
2,6-IDNNA [ 1 05363-46-0 l see #121
I-Iordenine [6027-24-3] #71
3,5-IDNNA-2 [1 05363-47-1] see #120
I-Iordenine [6202-1 7-1] #71 2,4-1 22IDNNA [102145-23-3] see #118
I-Iordenine [ 6209-35-4] #71
2,5_ 1 22IDNNA [85563-11 -7] see #58
I-Iordenine [ 1 7350-73-1] #71
2,6 1 22 IDNNA
- [ 105363-44-8] see #121
I-Iordenine [ 60411-16-7] #71 2,4-1 2s mNNA [ 1 05363-41-5] see #118
I-Iordenine [ 62493-39-4] #71
2,6-1 2slDNNA [ 105363-42-6] see #121
I-Iordenine [113038-79-2] #71
2,5-1 3 1IDNNA [90064-52-1 ] see #58
I-Iordenine [ 123830-49-9] #71
3,5-1 22 IDNNA-2 [ 105363-45-9] see #120
I-Iordenine [ 123830-50-2] #71
3,5_1 22 IDNNA-4 [ 109421 -50-3] see #117
I-Iordenine acetate [857767-21 -6] see #71
3,5-1 2slDNNA-2 [ 105363-43-7] see #120
I-I()T-2 [207740-38-3] see #25
2,5-1 3 1INNEA [ 90064-63-4] see #58
I-I()T-7 [ 207740-39-4] see #25 IM [31 66-75-4] see #72
I-I()T-17 [ 207740-40-7] see #25 IM [3937-1 6-4] #72
�-I-I()-TMA [771 58-46-4] see #117 IM [ 4668-10-4] #72
N-I-I()-TMA [149607-37-4] see #117 IM [87059-74-3] #72


IM [1 00009-75-4] #72 IPTA [201407-50-3] see # 1 03
2-1-5-MA [ 99254-51 -0 l see #36 IRIS [95201 6-59-0] see #60
4-1-2-MA [1 66820-02-6] see #35 I-SF [ 184473-66-3] see # 1 7
5-1-2-MA [ 159432-44-7] see #36 I-TRIS [876486-72-5] see #72
INBMDO [919797-25-4] see #58 K [220491-69-0] see #77
INBMeO [919797-19-6] --
see #58
-·�·-----�
Leptodactyline [ 13957-33-0] see #71
2-1-4,5-MDA [1 88852-25-7] see #98 Lophophine [23693-38-1 ] #73
2-1-4,5-MDDMA [1 88852-29-1 ] see #98 Lophophine [771 58-52-2] #73
2-1-4,5-MDMA [ 188852-27-9] see #98 2-MA [15402-84-3] #74
2-1-4,5-MDPEA [ 188852-35-9] see #98 2-MA [52850-79-0] #74
2,5-1 31INMeOEtA [90064-67-8] see #58 2-MA [59291 -68-8] #74
2,5-1 3 1INAA [90064-59-8] see #58 2-MA [ 64610-39-5] #74
2,5-1 3 1INCPMA [ 90064-55-4] see #58 2-MA [72739-03-8] #74
2,5-1 3 'INDoA [90064-57-6] see #58 S-2-MA [73495-53-1] #74
2,5-1 3 1INHA [ 90064-60-1 ] see #58 2-MA [87059-52-7] #74
2,5-1 3 1INHeA [90064-56-5] see #58 R-2-MA [ 11 7772-42-6] #74
2,5-1 3 'INHeNMeA [90083-1 8-4] see #58 R-2-MA [223930-67-4] #74
2,5-1 3 1INiPrA [90064-54-3] see #58 S-2-MA [223930-70-9] #74
IP [61367-70-2] see #91 3-MA [1 7862-85-0] #75
IPBDB [337464-41-2] see #77 3-MA [35294-10-1] #75
4-1-PEA [7391 8-57-7] see # 1 02 3-MA [52850-80-3] #75
iPHAT [811 85-35-5] see # 1 05
---------·�-
3-MA [59291-69-9] #75
�
3-1-PMA [159432-45-8] see #38 3-MA [ 64610-40-8] #75

4-iPPEA [61035-87-8] see # 1 02 R-3-MA [66033-00-9] #75
4-iPrA [32560-62-6] see #111 S-3-MA [ 66033-04-3] #75
N-iPr-4-Cl-PEA [2275-69-6] see #102 3-MA [87059-54-9] #75
DESMETHYL-iPr [ 42973-59-1 ] see #29 MAA [35534-19-1] see #40
N-iPr-2-MA [22331 -67-5] see #74 MADAM-6 [ 207740-46-3] see #77
iPrONE [ 1 86028-81-9] see #93 MAL [207740-41-8] see #91
�-HO-N-iPr-GEA [1420-27-5] see #49 MAPEA [39201 -81-5] see #90
N-iPr-DHA-�k [530-10-9] see #33 R-(-)-MBDB [ 103882-49-1 ] #76
N-iPr-DHPEA-�k [1 3076-1 0-3] see #49 S-(+)-MBDB [ 103882-50-4] #76
a-iPr-MDPEA [ 627876-89-5] see #77 R-(-)-MBDB [ 103882-53-7] #76
N-iPr-MDPEA [10631 0-52-5] see #85 S-(+)-MBDB [ 103882-54-8] #76
N-iPr-PCA [65114-99-0] see #106 MBDB [128767-12-4] #76
N-iPr-PMA [124206-65-1] see #110 MBDB [135795-90-3] #76
N-iPr-PEA [52007-97-3] see #107 2,3-MBDB [337464-37-6] see #77


4-M-Benzylarnine [2393-23-9] see # 1 07 5,6-MDAT [124399-99-1] see #77
2,3,6-MBM [ 200264-68-2] see #18 6,7-MDAT [101625-35-8] see #77
3,4,5-MBM [64778-73-0] see #18 MDBA [74698-49-0] see #77
MBZM [207740-08-7] see #118 a-Me-MDBA [121 734-64-3] see #45
MCPA [ 1 7061-21-1] see #41 MDBP [32231-06-4] #79
rnCPP [ 6640-24-0 l #24 MDBP [ 38063-96-6] #79
rnCPP [ 13078-15-4] #24 MDBP [130313-17-6] #79
rnCPP [51639-49-7] #24 MDBU [74698-38-7] see #77
rnCPP [ 65369-76-8] #24 MDBVP [1 7763-10-9] see #93
3-[1 4C]-rnCPP [11 5923-74-5] #24 MDBZ [2980-08-7] see #77
rnCPP [135014-37-8] #24 MDCM [74698-42-3] see #77
rnCPP [135014-38-9] #24 MDCPA [ 54719-10-7] see #41
rnCPP [ 1 71415-32-0] #24 MDCPM [74341-84-7] see #77
rnCPP [913701-64-1] #24 MD DEA [74698-51 -4] see #77
MDA [4764-1 7-4] #77 MDDEHP [1 7763-1 7-6] see #93
MDA [ 6292-91 -7] #77 MDDEVP [1 7763-15-4] see #93
MDA [56440-59-6] #77 MDDMA [74341-79-0] #80
R-(-)-MDA [61614-60-6] #77 MDDMA [74698-50-3] #80
R-MDA [61614-61 -7] #77 R-MDDMA [872679-98-6] #80
MDA [6461 0-47-5] #77 5-MDDMA [872679-99-7] #80
5-(+)-MDA [ 65620-66-8] #77 2,3-MDDMA [ 1 68968-03-4] see #77
MDA [65955-47-7] #77 horno-MDDMA
[ 125559-67-3] see #78
(HMDDMA)
MDA [64610-61-7] #77
MDDMBP [1 7763-12-1] see #93
R-MDA [70745-96-9] #77
MDDMHP [ 1 7763-16-5] see #93
5-MDA [70745-97-0] #77
MDDMVP [1 7763-13-2] see #93
MDA [91012-27-0] #77
MDE [74341 -78-9] #81
MDA [95172-73-9] #77
MDE [82801-81-8] #81
MDA [590346-12-6] #77
5-MDE [114612-26-9] #81
homo-MDA [40742-32-3] #78
R-MDE [114612-27-0] #81
homo-MD A [53581 -65-0] #78
5-(+)-MDE [197787-15-8] #81
R-horno-MDA [ 103664-98-8] #78
R-horno-MDA [ 103664-99-9] #78 R-(-)-MDE [328529-93-7] #81
2,3-MDA [86029-48-3] see #77 2,3-MDE [ 168968-00-1 ] see #77
4,5-MDAI [1 82634-37-3] see #77 horno-MDE (HMDE) [125559-68-4] see #78

5,6-MDAI [ 155344-90-4] see #77 MDEBP [ 1 7764-1 8-0] see #93
MDAL [74341 -75-6] see #77 [3-M -3,4 -
[ 197504-48-6] see #29
MDAM [74698-40-1 ] see #77 DESMETHYL


MOEVP [1 7763-02-9] see #93 MOOH [74341-83-6] #84
MOHE [74698-41-2] see #77 MOOH [74698-47-8] #84
MOHOET [74341 -74-5] see #77 R-MOOH [1 9801 7-93-5] #84
MOIB [74341 -85-8] see #77 S-MOOH [19801 7-94-6] #84
MDIP [74698-37-6] see #77 6-MOOH [145284-65-7] see #82
MDIPBP -
[1 7762-92-4] see #93 homo-MOOH [1 67394-42-5] see #78
MDIPVP [ 1 7763-03-0 l see #93 MOPBP [ 1 7762-91 -3] see #93
MOMA [ 42542-10-9] #82 MO PEA [1484-85-1 ] #85
MOMA [ 64057-70-1 ] #82 MO PEA [ 1 653-64-1 ] #85
S-(+)-MOMA [66142-89-0] #82 MOPEA [ 36406-68-5] #85
R-(-)-MOMA [69558-31-2] #82 MO PEA [58738-59-3] #85
S-(+)-MOMA [69558-32-3] #82 MO PEA [6461 0-36-2] #85
R-(-)-MOMA [81262-70-6] #82 MO PEA [ 1 09442-31-1] #85
N-CH2 [ 3H]-MOMA [1 28671 -19-2] #82 a,[3-[ d2 ]-MOPEA [ 152089-63-9] #85
[d5 ]-MOMA [ 136765-43-0] #82 a-[d]-MOPEA [ 152089-67-3] #85
N-[11C]-Me-MOMA [153506-20-8] #82 a,a-[ d2 ]-MOPEA [ 152089-68-4] #85
R-N-[11C]-Me- MO PEA [8491 86-61-4] #85
[1651 72-59-8] #82
MOMA
MOPEA [8491 86-62-5] #85
2,3-MOMA [168967-99-5] see #77
MO PEA [859932-61-9] #85
homo-MOMA [92279-85-1] #83
2,3-MOPEA [ 33542-90-4] see #77
homo-MOMA [108248-08-4] #83
homo-MO PEA [33543-11-2] see #78
4,5-MOMAI [ 1 82634-38-4] see #77
MOPH [39235-63-7] see #77
5,6-MOMAI [ 132741-82-3] see #77
MOPL [74341 -81-4] see #77
6,7-MOMAT [34620-52-5] see #77
MO PPP [24698-57-5] see #93
MOMBP [ 17762-90-2] see #93
MOPR [74341-77-8] #86
MOMEA [129819-63-2] see #77
MOPR [74698-36-5] #86
MO MEO [74698-48-9] see #77
homo-MOPR [ 125559-69-5] see #78
MOMEOET [74341-80-3] see #77
R-MOPR [ 150200-06-9] #86
MOMIPA [12981 9-64-3] see #77
S-MOPR [ 1 50200-07-0] #86
2-MOMOH [138556-75-9] see #82
MOPVP [ 1 7764-20-4] see #93
5-MOMOH [138537-66-3] see #82
MOSB [11 3527-37-0] see #77
6-MOMOH [ 138808-79-4] see #82
MOSBVP [1 7763-05-2] see #93
MOMP [81262-69-3] see #77
ME [901 32-31 -3] see #91
MO MPA [129819-65-4] see #77 MEA [32560-70-6] see #38
2,3-MOMPEA [ 33543-05-4] see #44 2-MeA [5580-32-5] see #111
MO MVP [ 1 7763-01-8] see #93 3-MeA [588-06-7] see #111
-
MOOC [25070-60-4] see #77 N-Me-ALEPH [849919-88-6] see #3


N-Me-ALEPH-2 [ 849919-89-7] see #3 N,N-Me-DHA [52370-69-1 ] see #33
N-Me-ALEPH-7 [849919-90-0] see #3 N,N-Me-DHA
[52370-70-4] see #33
diacetate
a,N-Me-FEA [ 63825-18-3] see #67
N-Me-DHPEA [501-15-5] see #49
a-Me-Benzylamine [61 8-36-0] see #107
N-Me-DHPEA-AA [ 13075-96-2] see #49
13-Me-2C-2 [83329-24-2] see #98
N,N-Me-DHPEA [21581 -37-3] see #49
N-Me-2C-3a [33543-06-5] see #99
N,N-Me-DHPEA-AA [5471 9-11-8] see #49
13-Me-2C-D [53581 -74-1] see #20
N,N-Me-2,3-DHPEA [ 13075-89-3] see #34
13,13-Me-2C-D [53581 -75-2] see #20
N-Me-DHPEA-13k [62-13-5] see #49
N-Me-2C-D [25505-67-3] see #20
N,N-Me-DMA [58993-77-4] see #38
N,N-Me-2C-D [24286-42-8] see #20
N-Me-2,3-DMA [93675-26-4] see #34
N-Me-2C-DMMDA [ 33543-08-7] see #44
N-Me-2,6-DMA [93675-28-6] see #37
N-Me-2C-
[ 33543-09-8] see #44
DMMDA-2 N-Me-3,5-DMA [93675-30-0] see #39
N-Me-2C- N-Me-DME [5653-66-7] see #49
[ 33543-10-1] see #44
DMMDA-3
N,N-Me-DME [ 1 9751-75-8] see #49
N-Me,CHO-DME [41688-37-3] see #49
N-Me-DMeA [1 05254-13-5] see #42
N-Me-3-Cl-MPEA [7569-59-7] see #49
N,N-Me-2,5-DMeA [ 105466-90-8] see #42
13-Me-4-Cl-PEA [ 4806-79-5] see #102
13-Me-DMPEA [55174-61 -3] see #49
N-Me-4C-T [849919-91-1] see #3
13-Me-2,5-DMPEA [3490-01 -5] see #22
N-Me-4C-T-2 [84991 9-92-2] see #3
13,N-Me-2,5-DMPEA [ 3490-03-7] see #22
N-Me-4C-T-7 [849919-93-3] see #3
j),N,N-Me-2,5-
[3490-04-8] see #22
MEDA [23693-25-6] see #97 DMPEA
N-Me-DCA [32633-68-4] see #38 N-Me-DMPEA [3490-06-0] see #49
N-Me-DEPEA [21581-36-2] see #49 N,N-Me-DMPEA [3490-05-9] see #49
N,N-Me-DEPEA [854908-22-8] see #49 N-Me-2,5-DMPEA [3489-95-0] see #22
N-Me-2,5-DEPEA- N-Me-3,5-DMPEA [75689-33-7] see #50
[855942-20-0] see #22 �-
13k
N,N-Me-2,5-DMPEA [ 64057-69-8] see #22
6-Me-2,4-DEPEA [101 863-62-1 ] see #122
N,N-Me-3,5-DMPEA [371 08-92-2] see #50
a-Me-DESMETHYL [ 146285-46-3] see #117
homo-N-Me-2,5-
[ 66997-06-6] see #22
a-Me-3- DMPEA
[146285-47-4] see #117
DES METHYL
N-Me-DMPEA-2 [3490-09-3] see #46
DESMETHYL-M [24131-1 7-7] see #29
N-Me-DMPEA-3 [3600-89-3] see #47
N-Me-3-
[241 31-16-6] see #30 N,N-Me-DMPEA-2 [3494-01-7] see #46
DESMETHYL
4-Me-2,6-DMPEA [1 09035-91-8] see #122
DESMETHYL-MM [26138-1 3-6] see #29
6-Me-2,4-DMPEA [ 109036-65-9] see #122
N,N-Me-3-
[381 84-65-5] see #30 3,4,6-Me-2,5-DMPEA [861 007-05-8] see # 1 08
DES METHYL
N-Me-3,4,5- N,N-Me-2,5-DMPEA-
[7391 7-91-6] see #29 [85761 8-59-8] see #22
DESMETHYL 13k
-- - -

----- ---�------

N-Me-DOB [1 55638-80-5] see #52 N-Me-HME [29866-04-4] see #49
N,N-Me-DOB [1 07271 -31-8] see #52 N,N-Me-HME [ 63504-04-1 ] see #49
N,N-Me-3,2,6-DOB [1 05466-92-0] see #52 N,N-Me-2,5-
[74516-50-0] see #22
HMPEA
[) -Me-DOM [53581 -76-3] see #60
N-Me-HMPEA-f3k [1 3062-69-6] see #49
f3,f3-Me-DOM [53582-1 6-4] see #60
f3-Me-HPEA [90765-58-5] see #71
N,N-Me-DOM [26070-49-5] see #11
N,N-Me-2-HPEA [94-54-2] see #71
N,N-Me-DOMAI [52428-22-5] see #60
N,N-Me-3-HPEA [ 601 89-30-2] see #71
2-Me-4,5-DOM
[ 56966-33-7] see #60
(a-DOM) N-Me-N-iPr-
[57303-11 -4] see #49
DHPEA
3-Me-2,4-DOM [25068-97-7] see #60
a-Me-N-iPr-MDBA [121734-68-7] see #45
MEE [ 1 7231-82-2] see #11 8
N-Me-Lophophine [ 33543-07-6] see #73
N-Me-3-EA [959219-61 -5] see #75
MEM [161 28-88-4] #87
N-Me-EMPEA [21581-47-5] see #49
MEM [ 1 7231-80-0] #87
N-Me-2,3-EMPEA [ 105339-86-4] see #46
R-MEM [6731 3-99-9] #87
N,N-Me-2,3-EMPEA [4981 8-52-2] see #46
N,N-Me-2-MA [71861-16-0] see #74
N,N-Me-3,4-EMPEA [861008-11-9] see #49
N,N-Me-3-MA [99540-1 4-4] see #75
N,N-Me-4,3-EMPEA [861 008-09-5] see #49
4,N-Me-2-MA [1 66820-00-4] see #35
6-Me-2,4-EMPEA [101 787-06-8] see # 1 22
5-Me-MDA [20491 6-89-2] see #77
N-Me-2-EPEA [21 629-1 6-3] see # 1 00
6-Me-MDA [855635-29-9] see #77
N-Me-3-EPEA [21581-46-4] see #101
7-Me-MDA [71203-56-0] see #77
N-Me-4-EPEA [21581-35-1] see # 1 02
f3-Me-MDPEA [56311-97-8] see #85
N,N-Me-2-EPEA [861006-97-5] see # 1 00 ---
N,N-Me-MDPEA [ 65953-87-9] see #85

N,N-Me-3-EPEA [861 006-98-5] see #101
a,a-Me-2,3-MDPEA [301 642-50-2] see #77
N,N-Me-4-EPEA [777-86-6] see # 1 02
N,N-Me-2,3-
2,6-Me-4-EPEA [1 09469-29-6] see # 1 22 [301 642-48-8] see #77
MD PEA
4,6-Me-2-EPEA [ 109471-03-6 J see # 1 22
4-Me-2,6-MEA [22702-1 6-5] see # 1 22
N-Me-a-Et-GEA [181485-31 -4] see #49
f3-Me-2-MMA [21900-1 0-7] see #74
a-Me-N-Et-MDBA [121734-66-5] see #45
-·- --------
f)-Me-3-MMA [827611-28-9] see #75
N-Me-N-Et-MDPEA [ 627876-88-4] see #85
-�- -�-� N-Me-MMDA-2 [108925-34-4] see #98
f3-Me-N-E t-4-MPEA [861 007-58-1 ] see # 1 02 a,a,3-Me-MPEA [ 198226-60-7] see #38
---
3-Me-a-Et-MPEA [827611 -24-5] see #38 f3-Me-3-MPEA [5090-33-5] see #101

f3-Me-N-Et-PEA [91339-14-9] see # 1 07 f3-Me-4-MPEA [1 3062-93-6] see # 1 02
N-Me-FEA [1 4497-54-2] see #67 f3,N-Me-2-MPEA [5414-92-6] see # 1 00
Me-3,5-IFLY [ 497239-34-6] see #68 f),N-Me-4-MPEA [725735-35-3] see # 102
f3-Me-GEA [ 69478-40-6] see #49 f3,N,N-Me-4-MPEA [ 1 33302-86-0 l see # 1 02
N-Me-GEA-f3k [13062-64-1 ] see #49 f),N,N-Me-3-MPEA [ 1 77339-29-6] see #101
------
N,N-Me-2,5-HMA [74516-5 1 - 1 ] see #36 f),N,N-Me-4-MPEA [133302-86-0] see # 1 02

--


N-Me-2-MPEA [1 04338-26-3] see # 1 00 4-MePEA [3261 -62-9] see # 1 02
N-Me-3-MPEA [ 33543-62-3] see #101 4-N,N-MePEA [52632-05-0] see # 1 02
N-Me-4-MPEA [409 1-50-3] see # 1 02 N,N-Me-PMA [26070-48-4] see # 1 1 0
N,N-Me-2-MPEA [861007-85-4] see # 1 00 B-Me-PMMA [ 827611-30-3] see # 1 1 2
N,N-Me-3-MPEA [601 89-31-3] see #101 3-Me-PMMA [827611-22-3] see #38
N,N-Me-4-MPEA [50822-98-5] see # 1 02 a,a-Me-PMPEA [56490-94-9] see #110
2,6-Me-MPEA [52670-1 2-9] see # 1 22 N-Me-PNA [4302-88-9] see # 1 06
2,6-Me-MPEA [52670-12-9] see # 1 22 a-Me-N-Pr-MDBA [ 1 2 1 734-67-6] see #45
3,5-Me-4-MPEA [52670-14-1] see #91 Mescaline [54-04-6] #91
4,6-Me-2-MPEA [ 109036-63-7] see # 1 22 Mescaline [642-73-9] #91
Me0-2C-2,6-IFLY [ 194787-78-5] see #68 Mescaline [832-92-8] #91
Me0-2C-ISF [194787-61-6] see # 1 7 Mescaline [11 52-76-7] #91
B-MeO-DOB [ 6 77277-53-1] see #13 Mescaline [5967-42-0] #91
B-MeO-HMePEA [25006-35-3] see #71 Mescaline [5967-44-2] #91
MeOPP [38212-30-5] #88 Mescaline [6043-76-1 ] #91
MeOPP [38869-47-5] #88 Mescaline [13338-64-2] #91
MeOPP [70849-64-8] #88 a,B-[ d2 ] -Mescaline [27954-94-5] #91
MeOPP [84145-43-7] #88 2,6-[ 3H] 2-Mescaline [27954-95-6] #91
MeOPP [11 7208-67-0] #88 a, B-[ 3H] 2-Mescaline [28008-37-9] #91
MeOPP [154306-45-3] #88 Mescaline [ 41 885-48-7] #91
MeOPP [876132-12-6] #88 Mescaline [51 749-33-8] #91
2-MeOPP [35386-24-4] see #88 Mescaline [51 749-34-9] #91
3-MeOPP [1601 5-71 -7] see #88 Mescaline [87059-78-7] #91
MeOPPP [478243-09-3] see #92 a,a-[ d2 ] -Mescaline [87096-79-5] #91
MePAA [88753-19-9] see # 1 06 a-[14C]-Mescaline [ 94600-00-7] #91
N,N-Me-PCAI [73536-81 -9] see # 1 06 ( C[ d3 ] ) 3-Mescaline [ 152477-93-5] #91
ME PEA [36377-59-0] #90 Mescaline [856823-11-5] #91
ME PEA [ 39201 -83-7] #90 homo-Mescaline [31 66-94-7] see #91
ME PEA [39697-37-5] #90 METHCATH [ 5650-44-2] #92
ME PEA [ 109035-92-9] #90 METHCATH [ 49656-78-2] #92
B,N-MePEA [ 5969-39-1] see #107 METHCATH [ 58623-25-9] #92
homo-B,N-MePEA [1041 78-02-1 ] see # 1 07 5-METHCATH [66514-93-0] #92
N-MePEA [589-08-2] #89 METHCATH [ 92502-36-8] #92
N-MePEA [ 4104-43-2] #89 METHCATH [ 1 07778-20-1 ] #92
N,N-MePEA [1126-71-2] see #107 METHCATH [ 1 22117-24-5] #92
2-MePEA [55755-18-5] see #100 R-METHCATH [15261 0-69-0] #92
3-MePEA [5470-40-6] see #101 R-METHCATH [ 1 60977-88-8] #92


METHCATH [21 7635-05-7] #92 2,5-MH-MMA [61866-76-0] see #36
5-METHCATH [ 625454-70-8] #92 B-H0-2-M-5-MeA [110612-15-2] see #36
METHCATH [ 860409-50-3] #92 HM-a-Et-PEA [181485-30-3] see #33
5-METHCATH [869277-00-9] #92 2,4-MHPEA [ 34536-1 5-7] see #47
5-METHCATH [869277-04-3] #92 B,2-MHPEA-3 [91252-21-0] see #47
5-METHCATH [871228-31-8] #92 M-Bk [13079-1 9-1 ] see #91
5-METHCATH [871228-33-0] #92 M-M [ 4383-96-4] #95
5-METHCATH [871228-34-1 ] #92 M-M [ 6308-81-2] #95
5-METHCATH [871228-35-2] #92 2-MMA [93-30-1 ] see #74
a-Me-ThEA [ 30433-93-3] see #67 2-MMA-Bk [882302-55-8] see #74
a,B-Me-ThEA [53387-69-2] see #67 3-MMA [93675-25-3] see #75
a,N-Me-ThEA [7464-94-0] see #67 2,4-MMA [ 53581 -59-2] see #35
N-Me-ThEA [7404-71-9] see #67 3,4-MMA [241 60-29-0] #96
N-Me-3-ThEA [857361 -89-8] see #67 3,4-MMA [25068-95-5] #96
a,N-Me-3-ThEA [857361 -90- 1 ] see #67 R-3,4-MMA [ 133097-26-4] #96
N-Me-TH-FEA [71259-74-0 l see #67 5-3,4-MMA [133097-27-5] #96
a,N-Me-TH-FEA [98486-68-1 ] see #67 5-3,4-MMA [133097-28-6] #96
METHYLONE [1 86028-79-5] #93 R-3,4-MMA [133097-29-7] #96
METHYLONE [ 1 86028-80-8] #93 MMAI [ 136468-1 9-4] see #96
5-METHYLONE [19191 6-41-3] #93 MMAT [87394-81-8] see # 1 05
N-Me-TMA [93675-34-4] see # 1 1 7 7,6-MMAT [ 32828-83-4] see #96
N-Me-TMA-2 [93675-32-2] see #118 2,3,5-MMB [2074-96-6] see # 1 8
N-Me-TMA-3 [93675-31 - 1 ] see # 1 1 9 2,3,6-MMB [200264-65-9] see # 1 8
N-Me-TMA-6 [93675-33-3] see #122 2,4,5-MMB [200264-66-0] see # 1 8
N-Me-B,3,4-TMPEA [56120-35-5] see #49 MMBDB [ 16 7394-40-3 J see #77
N,N-Me-B,3,4- 2,3-MMBDB [337464-39-8] see #77
[52910-84-6] see #49
TMPEA
MMDA [ 60676-84-8] #97
MHA [ 13026-44-3] #94
MMDA [62319-20-4] #97
R-MHA [1 3062-61 -8] #94
R-MMDA [ 67225-70-1 ] #97
R-MHA [150200-02-5] #94
MMDA [13674-05-0] #97
5-MHA [150200-03-6] #94 MMDA-2 [23693-1 8-7] #98
MHAOH [674368-62-8] see #33 MMDA-2 [ 64778-82-1 ] #98
MHAT [78950-80-8] see # 1 05 R-MMDA-2 [ 67225-69-8] #98
MHEA [ 69389-97-5] see #94 MMDA-3a [23693-19-8] #99
MHMA [11 7652-28-5] see #94 MMDA-3a [33298-29-2] #99
MHMAOH [674368-63-9] see #33 R-MMDA-3a [ 67225-68-7] #99
MHMC [91 81 9-04-4] see #92 MMDA-3b [23693-20-1 ] see #97


J23693-21-2]
--· -- -- - ·-
MMDA-4 see #97 0-[ d2 ]-4-MPEA [95864-31-6] # 1 02

....
MMDA-5 [23693-22-3] see #97 4-MPEA [ 97289-45-7] # 1 02
N-MMDBA [15205-27-3] see #45 a-[1 4C]-4-MPEA [11 8828-79-8] # 1 02
N-MMDPEA [451 -77-4] ___.,_____
see #85
-----�
0-[1 4C]-4-MPEA [136476-77-2] # 1 02
MME [ 1 7231 -78-6] see # 1 1 8 4-MPEA [301 650-55-5] # 1 02
2,5-MMeA [1 88852-10-0] see #34 4-MPEA [330795-82-9] # 1 02
. -- --
2,3-MMeMA [ 1 05338-61-2] see #34 4-MPEA [330795-83-0] # 1 02

2,3-MMeMMA [1 07410-19-5] see #34 4-MPEA
-- ------- --
[330795-84-1] # 1 02
2-M-5-MePEA-0k [ 860538-07-4] see #22 4-MPEA [330795-85-2] # 1 02
a-MM-M [4340-07-2] see #117 4-C[d2 ]H-4-MPEA [484024-82-0] # 1 02
-�---
2,4-MMPEA [1391 02-20-8] see #47 4-C[ d3 ]-4-MPEA [ 484024-83-1] # 1 02

MMTA [91341 -37-6] see #1 03 _;@j d2t4-M P_]j_�� . [757899-75-5] # 1 02
M(20P)M [1 46724-77-8] see #118 4-MPEA [ 855388-59-9] # 1 02
M(30P)M [ 146724-76-7] see #11 8 4-MPEA [ 855388-60-2] # 1 02
N-mor-2-MA [ 92322-94-6] see #74 a- [1 4C]-4-MPEA [855632-40-5] # 1 02
MP [901 32-33-5] see #91 4-MPEA [ 856822-70-3 J # 1 02
·�
2-MPEA [2045-79-6] #1 00 a,a-[ d2 ]-4-MPEA [884329-98-0] # 1 02

2-MPEA [3167-07-5] # 1 00 3,5-Me-PHA [24973-31-7] see # 1 1 7
2-MPEA [ 64610-28-2] # 1 00 3,5-Me-PMA [24973-30-6] see #91
2-MPEA [69587-06-0] #1 00 MPHP [ 34138-58-4] see #92
- -------·
--
a, 0-[ d2 ]-2-MPEA [147702-21-4] #1 00 MPM [1 23643-24-3] see #118

2-MPEA [288864-48-2] # 1 00 MPPP [2811 7-80-8] see #92
-�
2-MPEA [ 856822-73-6] # 1 00 MTA [1411 6-06-4] # 1 03

3-MPEA [2039-54-5] # 1 01 MTA [94784-92-6] # 1 03
3-MPEA [2039-67-0] #101 MTA [557768-72-6] # 103
3-MPEA [ 601 89-29-9] #101 (+)-MTA [ 634607-22-0] # 1 03
· ---------
3-MPEA [6461 0-29-3] #101 (-)-MTA [ 634607-23-1] # 1 03

3-MPEA [87059-66-3] # 1 01 (-)-MTA [75681 6-57-6] #103
- -------·- --- '--· ·--..�---�
a,a-[d 2 ]-3-MPEA [108089-01-6] # 1 01 (+)-MTA [765898-09-7] # 1 03

a, 0-[dJ-3-MPEA [147702-22-5] # 1 01 5-MTA [943744-15-8] #103
[d 3 ]-Me0-3-MPEA [484024-84-2] #101 5-MTA [943816-6 1 -3] #103
3-MPEA [855395-37-8] - - -- - -
#101
- ------------
2-MTA [92286-71 -0] see # 1 03
4-MPEA [55-81 -2] #102 3-MTA [91330-07-3] see # 1 03
4-MPEA ------- - -- -
[645-58-9] #102 MTAI [73536-80-8] see # 1 03
------
4-MPEA [ 61035-86-7] # 1 02 MTALA [ 634607-19-5] see # 1 03

--I---
4-MPEA [ 64610-30-6] # 1 02 MTC [138889-33-5] see # 103

----·---··---- ------ --
4-MPEA [87059-67-4] # 1 02 MTDALA [ 634607-20-8] see # 103

·----
-
Name CAS # _!_L1try#

·----
Name CAS # Entry#
MTDEA [ 634607-15-1] see #103 Proscaline [39201 -79-1] # 1 04
MTDMA [ 634607-13-9] see #103 Proscaline [40275-09-0] # 1 04
MTDPA [634607-1 7-3] see # 1 03 Proscaline [ 61367-69-9] # 1 04
MTEA [376580-97-1 ] see # 1 03 4-PA [ 1 29476-60-4] see # 1 1 0
mTFMPP [2394-89-0] #116 PAA [57736-33-1 ] see # 1 06
mTFMPP [15532-74-8] #116 PAMA [4302-87-8] see # 1 06
mTFMPP [1 5532-75-9] # 116 PAP [52597-14-5] see #40
mTFMPP [1601 5-69-3] #116 i-PAP [52597-15-6] see #40
mTFMPP [76835-14-8] #116 PAPEA [ 13078-82-5] see # 1 02
mTFMPP [78056-41 -4] #116 PAT [76135-31-4] # 1 05
[1 8F]-mTFMPP [132785-03-6] #116 R-PAT [78095-19-9] # 1 05
mTFMPP [135014-39-0] #116 S-PAT [78095-20-2] # 1 05
mTFMPP [135014-40-3] #116 PAT [78950-78-4] # 1 05
mTFMPP [378758-87-3] #116 R-PAT [ 80300-09-0 l # 1 05
2,3,5,6-[ d ]- S-PAT [ 80300-10-3] # 1 05
4 [859843-14-4] #116
mTFMPP
R-PAT [11 9273-42-6] # 1 05
MTMA [547736-90-3] see # 1 03
S-PAT [ 119273-43-7] # 1 05
MTPA [634607-1 6-2] see #103
PAT [ 1 34331-05-8] # 1 05
2-MTPEA [69587-07-1 ] see #103
7-[ 3H]-PAT [ 136696-23-6] # 1 05
a-M,V-M [ 4340-08-3] see # 1 1 7
R-7-[ 3H]-PAT [ 136779-03-8] # 1 05
NEA [ 40808-62-6] see #67
S-7-[ 3H]-PAT [136779-04-9] # 1 05
3-NEA [73625-1 0-2] see #67
PAT [14121 5-27-2] # 1 05
2-NH2-4,5-DMA [ 92058-62-3] see # 1 1 8
R-PAT [149097-87-0] # 1 05
5-NH2-2,4-DMA [168699-72-7] see #118
S-PAT [ 149097-88-1 ] # 1 05
5-NH2-2,4-DMPEA [ 168699-69-2] see #124
S-7-[ 3H]-PAT [736109-11 -8] # 1 05
NMEA [83732-75-6] see #67
7-[ 3H]-PAT [737729-40-7] # 1 05
3-N02-HPEA [49607-1 5-0] see #49
R-7-[ 3H]-PAT [762209-1 9-8] # 1 05
6-N02-IBF5AP [201407-54-7] see #77
PBAI [73536-88-6] see # 1 06
2-N02-4,5-MDA [ 1 51 920-04-6] see #98 PBDB [ 33 7464-40-1 ] see #77
2-N02-HPEA [2419-60-5] see #47 PCA [64-12-0] # 1 06
1-NP [57536-86-4] see #24 S-(+)-PCA [405-46-9] # 1 06
4-NPEA [861 007-76-3] see #102 R-(-)-PCA [405-47-0] # 1 06
oCPP [135014-36-7] see #24 PCA [3706-38-5] # 1 06
ONE [ 80535-73-5] see #93 S-(+)-PCA [ 1 6064-30-5] # 1 06
4-0PEA [861 007-75-2] see # 1 02 R-(-)-PCA [16064-31 -6] # 1 06
oTFMPP [ 30645-73-9] see # 1 1 6 PCA [22490-82-0] # 1 06
-
Proscaline [39201 -78-0] # 1 04 S-PCA [2411 6-85-6] # 1 06


S-PCA [2411 6-86-7] # 1 06 a, �-[d2 ] -PEA [81 541 -03-9] # 1 07
PCA [2411 6-87-8] # 1 06 a-[14C]-PEA [85336-78-3] # 1 07
S-PCA [28357-54-2] # 1 06 a,�-[ d ]-PEA [87620-08-4] # 1 07
4
S-PCA [33423-88-0l # 1 06 �-[d2 ]-PEA [95864-27-0] # 1 07
PCA [341 76-59-5] # 1 06 �-[d2 ] -PEA [1011 53-74-6] # 1 07
PCA [341 76-60-8] # 1 06 [1 3N]-PEA [ 1 0241 5-94-1] # 1 07
PCA [341 76-61 -9] # 1 06 a-[1 4C]-PEA [114307-16-3] # 1 07
PCA [34203-22-0] # 1 06 PEA [120375-47-5] # 1 07
PCA [34622-16-7] # 1 06 PEA [127755-12-8] # 1 07
PCA [34622-1 7-8] # 1 06 PEA [151 059-43-7] # 1 07
PCA [51395-1 6-5] # 1 06 [1 5N]-PEA [155755-37-6] # 1 07
PCA [59963-26-7] # 1 06 PEA [209064-25-5] # 1 07
�-[1 4C]-PCA [ 61 040-64-0 l # 1 06 PEA [344948-61-4] # 1 07
�-[14C]-PCA [61040-91 -3] #106 PEA [855383-01-6] # 1 07
S-PCA [141725-81 -7] # 1 06 PEA [855383-02-7] # 1 07
R-PCA [141 725-82-8] # 1 06 Ring [d 5 ]-PEA [912627-99-7] # 1 07
homo-PCA [53896-12-1] see # 1 06 homo-PEA [2038-57-5] see # 1 07
PCAI [73536-86-4] see # 1 06 PEAT [811 85-37-7] see # 1 05
PCAT [ 60480-00-4] see # 1 06 PeMA [23693-29-0] see # 1 08
PCBA [ 3886-69-9] see # 1 06 PeMeA [32156-2 1 - 1 ] see # 1 08
PCMA [1199-85-5] see # 1 06 PeMePEA [31 67-13-3] see # 1 08
pCPP [934991 -33-0] see #24 PFA [459-02-9] see # 1 06
PE [207740-42-9] see #91 PFAI [2340-06-9] see # 1 06
PEA [60-19-5] #107 PFMA [861007-48-9] see # 1 06
PEA [64-04-0] # 1 07 PHA [1 03-86-6] # 1 09
PEA [5471 -08-9] # 1 07 PHA [306-21-8] # 1 09
PEA [24722-38-1] # 1 07 PHA [876-26-6] # 1 09
PEA [25566-62-5] # 1 07 S-PHA [151 8-87-2] # 1 09
PEA [3221 8-88-5] #107 R-PHA [151 8-88-3] # 1 09
[1 5N] -PEA [41498-55-9] #107 R-PHA [ 1 51 8-89-4] # 1 09
�-[1 4C]-PEA [42006-59-7] #107 S-PHA [151 8-90-7] # 1 09
PEA [5391 6-94-2] #107 R-PHA [1518-91-8] # 1 09
a-[1 3C]-PEA [67519- 1 9-1] #107 S-PHA [1 693-66-9] # 1 09
PEA [71 750-39-5] # 1 07 PHA [ 61 70-28-1 J # 1 09
�-[14 C]-PEA [77956-20-8] # 1 07 R-PHA [ 1 3990-47-1 ] # 1 09
a,a-[d2 ]-PEA [77970-78-6] # 1 07 PHA [23771 -48-4] # 1 09
�-
a-[11C]-PEA [79482-02-3] # 1 07 PHA [33462-22-5] # 1 09


a,f:\-[ d2 ]-PHA [38875-32-0] # 1 09 S-PMeA [81 601 -11-8] #111
R-PHA [41509-97-1] # 1 09 R-PMeA [81601-1 2-9] #111
S-PHA [41509-98-2] #109 S-PMeA [81601-14-1] #111
j3-[ 3H] -PHA [58278-83-4] # 1 09 a, f:\-[ d2 ]-PMeA [147702-23-6] #111
j3-[14 C]-PHA [ 60756-93-6] # 1 09 R-PMeA [788775-45-1] #111
a, j3-[d2 ]-PHA [64357-23-9] # 1 09 --
PMeA [878794-34-4] #111
R-PHA [ 67323-60-8] # 1 09 PMeMA [11 3358-79-5] see # 1 1 1
S-PHA [71295-78-8] # 1 09 PMMA [3398-68-3] #112
PHA [94753-97-6] # 1 09 PMMA [2233 1 -70-0] #112
PHAT [ 811 85-33-3] see # 1 05 S-PMMA [11 3429-54-2] #112
PHEA [ 69389-96-4] see #110 R-PMMA [25 1 321 -76-3] #112
PHMMA [ 69792-61 -6] see #110 PMMA-f:\k [530-54-1 ] see # 1 1 2
Pholedrine [370-1 4-9] see #109 2-PmP [20980-22-7] see #24
PIAP [58759-28-7] see #40 PNA [ 1 3026-03-4] see # 1 06
pip-2C-B [155639-27-3] see # 1 8 PNAI [73536-87-5] see # 1 06
N-pip-2-MA [132912-56-2] see #74 pp [92-54-6] see #24
pip-PEA [ 1135-33-7] see #107 4-PPEA [57224-67-6] see # 1 02
PLY [502924-27-8] see #68 PPhA [32560-67-1] see # 1 1 0
PMA [64-13-1] #110 PPP [19134-50-0] see #40
PMA [3706-26-1 ] #110 4-PrA [139102-1 8-4] see # 111
PMA [23239-32-9] #110 N-Pr-DOB [99632-47-0] see #52
R-a, j3-[ d2 ] -PMA [38875-30-8] #110 N-Pr-M [ 62028-43-7] see #91
R-(-)-PMA [ 50505-80-1 ] #110 N-Pr-MDPEA [ 627876-90-8] see #85
S-(+)-PMA [50505-81-2] #110 N-Pr-PMA [93309-51-4] see #111
PMA [52740-56-4] #110 PRONE [ 1 86028-86-4] see #93
S-(+)-PMA [58993-78-5] #110 PrONE [201474-93-3] see #93
�-----
R-(-)-PMA [58993-79-6] #110 PROPYNYL [95201 7-05-9] see #91

j3-[1 4C] -PMA [ 60756-92-5]
-------
#110 4-Pr-PEA [31 66-99-2] - - �-
see # 1 02
PMA [ 6461 0-41-9] #110 pTFMPP [30459-1 7-7] see #116
�-
R-(-)-PMA [ 67346-52-5] #110 PZAP [ 93865-44-2] see #40

�-
S-(+)-PMA [ 67346-53-6] #110 Quipazine [4774-24-7] see #24

1-----
--- --�
_
PMA [87059-53-8] #110
. --· - - - ---- ------- - �-----
Salicifoline [ 6882-07-1 ] see #49
----- r--- -- -- --- - -- -
homo-PMA [51062-15-8] see #110 SB [901 09-62-9] see #91
I
PMA-f:\k
_,, ______
[ 42416-75-1 ] see #110 sBuONE
------- ------- - --
[ 186028-83-1 ] see #93
::: : -�=
PMeA [64-11-9] #111 SF [ 130933-03-81_ see # 1 7
--� �-----
PMeA [ 41632-56-8] 4-SPEA

--- - -- -- --·---
[57224-69-8] see # 1 02
PMeA [50650-74-3] TAP [3160-20-1 ] see #42

------- - -- ------ ---- -- -

Name CAS # Entry#
---.----------·- -
Name -- · ----- -
CAS # Entry#
3-TASB [901 32-49-3] see #91 TH-FEA [98277-97-5] see #67
4-TASB [901 09-52-7] see #91 THMA-2 [136706-32-6] see # 1 1 8
5-TASB [901 32-48-2] see #91 TH-NMEA [ 422545-96-8] see #67
- -------------- -- - ·· -- - -- ------ �·
TB
----- -�- --- ---·--- --- -
[901 09-57-2] see #91 2-TIM [7551 0-74-6] see #72
tBuONE [1 86028-84-2] see #93 3-TIM [78335-86-1] see # 72
-·
4-tBuPEA [91552-82-8] see # 1 02 4-TIM [78335-87-2] see #72
-·
TE [901 09-50-5] see #91 TM [71 539-35-0] see #91
3-TE [90132-38-0] see #91 3-TM [78335-85-0] see #91
3-ThEA [ 34843-84-0 l see #67 TMA [1 082-88-8] #117
TeMA [23693-26-7] #113 TMA [5688-80-2] #117
S-TeMA [ 6 7225-65-4] #113 TMA [1 3071-39-1 ] #117
R-TeMA [ 67225-66-5] #113 S-TMA [1 9065-1 4-6] #117
TeMA-2 [23693-27-8] see #115 dl-TMA [221 99-1 7-3] #117
TeMA-3 [23693-28-9] see # 1 1 5 R-TMA [ 50505-86-7] #11 7
r-------
TeMeA [321 56-18-6] see #114 TMA [ 6461 0-48-6] #117
TeMeA-2 [321 56-19-7] see # 1 1 4 R-TMA [ 64778-77-4] #117
TeMeA-3 [321 56-20-0] see # 1 1 4 TMA [87059-65-2] #117
TeMePEA [3166-72-1 ] see # 1 1 4 S-TMA [7081 98-43-0] #117
TeMePEA-2 [3167-11-1] see #114 TMA [ 856823-05-7] #117
-- .
TeMePEA-3 [3167-12-2] see #114 TMA-2 [ 1 083-09-6 J #118
TeMPEA [3166-91-4] #114 TMA-2 [1 5995-72-9] #118
TeMPEA [13022-03-2] #114 S-(+)-TMA-2 [1 9065-13-5] #118
TeMPEA-2 [3166-92-5] see # 1 1 5 R-(-)-TMA-2 [53626-22-5] #118
TeMPEA-3 [15806-33-4] #115 R-TMA-2 [ 64778-76-3] #118
TeMPEA-3 [3167-08-6] #115 TMA-2 [ 65955-48-8] #118
TEtPEA-6 [1081 23-62-2] see # 1 23 S-TMA-2 [ 671 73-94-8] #118
2-TFMA [670-03-1 ] see #63 TMA-2 [87059-63-0] #118
3-TFMA [673-18-7] see #63 homo-TMA-2 [3891 0-36-0] see # 9 1
TFM-DFLY [260809-99-2] see #32 TMA-3 [1 082-23-1] #119
3-TFMDMAP [74626-42-9] see #92 dl-TMA-3 [1 5995-73-0] #119
TFM-FLY [733730-70-6] see #68 (+)-TMA-3 [1 9065-15-7] #119
TFMA [882-00-8] see #63 dl-TMA-3 [221 99-12-8] #119
3-TFMMPEA [52516-31-1 ] see #63 TMA-3 [601 0-77-1] #119
3-TFMPEA [141029-17-6] see #63
�·
TMA-3 [52850-84-7] #119
THA [91240-37-8] see # 1 1 7 R-TMA-3 [ 64838-26-2] #119
THA-2 [41241 -36-5] see #118 TMA-3 [ 87059-60-7] #119
Th EA [861 88-24-1 ] see #67 homo-TMA-3 [3891 0-35-9] see #91

�-------·-·--···-�·----�-- ---·------·---
Name CAS # EntfJ'.li'__ Name

' --
CAS # Entry#
TMA-4 [5556-74-1 ] # 120 TMePEA-6 [31 67-10-0] see # 123
dl-TMA-4 [22199-1 3-9] # 120 TMMDA [22969-85-3] see # 1 08
TMA-4 [23693-1 4-3] # 120 4T-MMDA-2 [ 133787-69-6] see #98
TMA-4 [52948-32-0] # 1 20 a,N,N-TMMDBA [112101-18-5] see #45
R-TMA-4 [6731 3-95-5] # 120 TMPEA-2 [31 66-78-7] # 1 24
dl-TMA-4 [72739-09-4] # 120 TMPEA-2 [1 5394-83-9] # 1 24
dl-TMA-4 [79002-10-1 J # 1 20 TMPEA-2 [6461 0-37-3] # 1 24
TMA-4 [ 87059-61-8] # 1 20 13,13-[ 3HkTMPEA-2 [70097-42-6] # 124
TMA-5 [20513-1 6-0] #121 13-[d]-TMPEA-2 [ 82698-36-0 l # 1 24
TMA-5 [5556-75-2] #121 a,a-[d 2 ]-TMPEA-2 [82698-37-1] # 1 24
dl-TMA-5 [22199-14-0] #121 a,a, 13-[ d3]-
[ 82698-38-2] # 1 24
TMPEA-2
dl-TMA-5 [52948-33-1] # 1 21
a,13-[ d2 ]-TMPEA-2 [ 82698-39-3] # 1 24
R-TMA-5 [67313-96-6] #121
a,13-[ d2 ]-TMPEA-2 [ 82698-45-1] # 1 24
TMA-5 [87059-62-9] #121
13,13-[ d2] -TMPEA-2 [8691 7-28-4] # 1 24
TMA-6 [15402-79-6] # 1 22
3,6-[d2 ]-TMPEA-2 [8691 7-32-0] # 1 24
dl-TMA-6 [22199-1 6-2] # 1 22
TMPEA-2 [87059-76-5] # 1 24
TMA-6 [23815-74-9] # 1 22
TMPEA-4 [31 66-77-6] see # 1 20
TMA-6 [6461 0-49-7] #122
TMPEA-5 [3166-84-5] see #121
R-TMA-6 [ 6 7225-64-3] #122
TMPEA-6 [ 3166-90-3] see #122
dl-TMA-6 [72739-10-7] # 1 22
13,3,4-TMPEA [ 4722-08-1] see #49
TMA-6 [87059-64-1 ] # 1 22
2-TOET [779279-63-9] see #56
homo-TMA-6 [3891 0-37-1] see #91
5-TOET [84910-93-0] see #56
TMAT [33446-12-7] see # 1 1 7
2-TOM [84910-90-7] see #3
TM CPA [773 790-48-0 l see #41
5-TOM [207740-45-2] see #3
3-TME [90132-35-7] see #91
5-TOMSO [84910-95-2] see #60
4-TME [90109-47-0] see #91
TP [901 09-55-0] see #27
5-TME [90132-40-4] see #91
Trichocereine [529-91 -9] # 1 25
TMeA [32156-1 7-5] see # 1 23
Trichocereine [54547-01-2] # 1 25
TMeA-2 [ 91 0404-30-7] see # 1 23
TRIS [901 09-63-0] see #91
TMeA-6 [24973-32-8] see #123
2,4,6-TRIS [ 1 08013-35-0 l see # 122
T-Mel [6308-78-7] see #91
3-TSB [90132-52-8] see #91
TMePEA [31 66-71-0] # 1 23
4-TSB [901 09-46-9] see #91
TMePEA [76935-66-5] #123
TMePEA-2 [31 67-03-1] see # 123 3-T-TRIS [90132-54-0] see #91
TMePEA-3 [76935-62-1 ] see # 1 23 4-T-TRIS [901 09-53-8] see #91

Tyramine [51-67-2] # 1 26
�·-----
TMePEA-4 [76935-63-2] --
see # 1 23
TMePEA-5 [76935-64-3] see #123 Tyramine [60-19-5] # 126

Name CAS # Entry#

a-[1 4C]-Tyramine [ 13822-1 2-3] # 126
Tyramine [ 1 7605-58-2] # 1 26
R-a-[1 4C]-13-[ 3H]-
[39236-1 0-7] # 1 26
Tyramine
S-a, 13,13-[ d3 ]-
[52009-73-1] # 126
Tyramine
-�· F-
R-a,13,13-[ d3 ]-
[52009-74-2] # 126
Tyramine
2-[ 3H]-Tyramine [60745-26-8] # 126
Tyramine [ 62722-95-6] # 126
S-a- [ 3H]-Tyramine [74447-55-5] # 126
R-a-[ 3H]-Tyramine [74447-59-9] # 1 26
Tyramine [78569-00-3] # 126
a- [14C] -Tyramine [80787-62-8] # 1 26
a,a-[ d2 ]-Tyramine [81 541 -01-7] # 1 26
a, 13-[ d2 ]-Tyramine [81541 -02-8] # 1 26
Tyramine [84713-35-9] # 1 26
13,13-[ d2 ] -Tyramine [92400-90-3] # 1 26
13,13-[ d2 ]-Tyramine [95864-32-7] # 1 26
[1 5N] -Tyramine [ 98985-53-6] # 1 26
a,a, 13,13-[ d ]-
4 [1 05233-20-3] # 126
Tyramine
13-[ d ]-Tyramine [ 1 08748-74-9] # 126
a,a,13,2,3,5,6-[ d7]-
[ 11 4076-86-7] # 126
Tyramine
R-a-[ d ]-Tyramine [1 24454-73-5] # 126
S-a- [d]-Tyramine [ 124454-75-7] # 126
a-[1 3C]-Tyramine [151459-88-0] # 1 26
a-[11C]-Tyramine [151560-60-0] # 1 26
-·----·-·- ·-·-
Tyramine [21991 9-55-8] # 1 26

Tyramine [308271 -86-5] # 1 26
- - --- - - -
2,3,5,6-[ d ]-Tyrami_IL� [94�136_-:_6 3-4]

Tyramine [924281 -00-5] # 126
# 126
4 -

CAS Index (Numerical)
Table lOb. Chemical Abstracts Service (CAS) Registry Numb ers;

Numerical Index.
�- · ·· · ·--- -
CAS # Name Entry# CAS # Name Entry#

[51-67-2] Tyramine #126 [499-61-6] DHPEA-Bk see #49
[54-04-6] Mescaline #91 �1-15-5] N-Me-DHPEA see #49
[54-49-9] B-H0-3-HA see #75 [529-91-9] Trichocereine #125
[55-81-2] 4-MPEA # 1 02 [530-1 0-9] N-iPr-DHA-Bk see #33
[60-19-5] PEA # 1 07 [530-54-1 ] PMMA-Bk see #112
[60-19-5] Tyramine #126 [536-21-0] B-H0-3-HPEA see #71
[ 62-13-5] N-Me-DHPEA-Bk see #49 [539-15-1] Hordenine #71
[64-04-0] PEA # 1 07 [552-85-2] B-HO-PHA see # 1 09
[64-11-9] PMeA #111 [554-52-9] GEA #69
[64-12-0] PCA # 1 06 [554-99-4] B,3,4-HO-N,N-MePEA see #49
[64-13-1 ] PMA #110 [555-64-6] DHA #33
[90-84-6] DEAP see #40 B-HO-N-Me-3,5-
[582-31-0] see #50
DMPEA
[92-54-6] pp see #24
[588-05-6] 3-HPEA see #71
[93-30-1 ] 2-MMA see #74
[588-06-7] 3-MeA see # 111
[94- 07-5 ] B-HO-N-Me-HPEA see #71
[589-08-2] N-MePEA #89
[94-54-2] N,N-Me-2-HPEA see #71
[61 8-36-0] a-Me-Benzylamine see # 1 07
[ 100-46-9] Benzylamine see # 1 07
[622-64-0] Hordenine #71
[1 02-31-8] DMeA #42
[635-85-8] DMPEA #49
[ 103-86-6] PHA # 1 09
[637-26-3] 3,5-DMPEA #50
[1 04-14-3] B-HO-HPEA see #71
[642-73-9] Mescaline #91
[ 120-20-7] DMPEA #49
[645-33-0] HMPEA see #49
[120-26-3] DMA #38
[645-58-9] 4-MPEA #102
[151-06-4] 4-Cl-a,a-MePEA see #1 06
[669-36-3] 2,3-DMPEA #46
[ 156-41-2] 4-Cl-PEA see # 1 02
[670-03-1] 2-TFMA see #63
[306-21 -8] PHA #109
[673-1 8-7] 3-TFMA see #63
[365-26-4] B-HO-HMA see # 1 09
[777-86-6] N,N-Me-4-EPEA see # 102
[370-14-9] Pholedrine see #109
[828-06-8] DHA #33
HMePEA
[370-98-9] #70
(N-Methyltyramine) [832-92-8] Mescaline #91
[405-46-9] S-(+)-PCA #106 [876-26-6] PHA # 1 09
[405-47-0] R-(-)-PCA # 1 06 [882-00-8] TFMA see #63
[447-40-5] 4-F-MCAT see #92 [1 075-61-2] 3-HA see #75
[451-77-4] N-MMDPEA see #85 [ 1082-23-1] TMA-3 #119
[459-02-9] PFA see # 1 06 [1082-88-8] TMA #117
[486-95-3] 2,6-DMPEA #48 [ 1083-09-6] TMA-2 #118


[1121-46-6] FEA #67 [21 76-14-9] DESMETHYL #29
[1124-40-9] DHBA see #49 --
[2176-16-1] BZ see #91
[1126-71-2] N,N-MePEA see # 1 07 [2220-19-1 ] 2C-3a see #99
[11 35-33-7] pip-PEA see # 1 07 [2234-25-5] f3-H0-2-HPEA see #71
[11 52-76-7] Mescaline #91 [2252-63-3] 4-FPP see #24
[1199-85-5] PCMA see # 1 06 [2275-64-1 ] CAB see # 1 06
[1420-27-5] N-iPr-f3-HO-GEA see #49 [2275-67-4] N-Et-PCA see # 1 06
[ 1454-68-8] N-HO-PMA see #110 [2275-69-6] N-iPr-4-Cl-PEA see # 1 02
[1477-63-0] f3-HO-N-Me-3-HPEA see #71 [2340-06-9] PFAI see # 1 06
[1477-68-5] GEA #69 [2393-23-9] 4-M-Benzylamine see # 1 07
[ 1484-85-1 ] MDPEA #85 [2394-89-0] mTFMPP #116
[151 8-87-2] S-PHA # 1 09 [2413-00-5] DESMETHYL #29
[151 8-88-3] R-PHA # 1 09 [2419-58-1] HMePEA #70
[151 8-89-4] R-PHA # 1 09 [2419-60-5] 2-N02-HPEA see #47
[151 8-90-7] S-PHA # 1 09 [2656-14-6] R-(-)-DMA #38
[1518-91 -8] R-PHA #1 09 [2743-78-4] R-DHA #33
[ 1 583-88-6] 4-FPEA see # 1 02 [2801-68-5] 2,5-DMA #36
[1 626-71-7] 3-FA see #75 [2811-24-7] S-(+)-DMA #38
[ 1653-64-1 ] MDPEA #85 [2980-07-6] DMBZ see #38
[ 1693-66-9] S-PHA #109 [2980-08-7] MDBZ see #77
[1716-60-5] 2-FA see #74 [3046-92-2] f3-HO-DMA see #38
[1 797-76-8] f3-HO-N,N-Me-PEA see # 1 07 [31 60-20-1 ] TAP see #42
[1 892-59-7] R-DHA #33 [3166-71-0] TMePEA #123
[1 972-58-3] 2,3-DHPEA see #34 [3166-72-1] TeMePEA see # 114
[ 1986-12-5] 2,3-HMPEA see #34 [3166-74-3] 2C-H #22
[2014-52-0] DH-a-Et-PEA see #33 [3166-75-4] IM see #72
[2021-64-9] 2,4-DFA see #35 [3166-76-5] 4-BuPEA see # 102
[2038-57-5] homo-PEA see # 1 07 [3166-77-6] TMPEA-4 see #120
[2039-54-5] 3-MPEA #101 [3166-78-7] TMPEA-2 #124
[2039-55-6] 2,4-DMPEA #47 [3166-82-3] Escaline #64
[2039-58-9] f3-HO-Hordenine see #71 [3166-84-5] TMPEA-5 see # 121
[2039-62-5] 2,4-DHPEA see #47 [3166-88-9] 4-Et-PEA see # 102
[2039-66-9] 2-HPEA see #71 [3166-89-0] 2,3-DMPEA #46
[2039-67-0] 3-MPEA #101 [3166-90-3] TMPEA-6 see # 122
[2045-79-6] 2-MPEA # 1 00 [3166-91 -4] TeMPEA #114
[2074-95-5] 2,3-HMPEA see #34 [3166-92-5] TeMPEA-2 see #115
[2074-96-6] 2,3,5-MMB see #18 [3166-94-7] homo-Mescaline see #91


[3166-99-2] 4-Pr-PEA see # 1 02 [4091-50-3] N-Me-4-MPEA see # 1 02
[3167-03-1] TMePEA-2 see # 123 [4104-43-2] N-MePEA #89
[3167-06-4] 2,6-DMPEA #48 [4302-87-8] PAMA see # 1 06
[3167-07-5] 2-MPEA # 1 00 [4302-88-9] N-Me-PNA see # 1 06
[3167-08-6] TeMPEA-3 # 115 [4302-93-6] 2-CMA see #74
[3167-1 0-0] TMePEA-6 see #123 [4340-07-2] a-MM-M see #117
[3167-11-1] TeMePEA-2 see #114 [4340-08-3] a-M,V-M see #117
[3167-1 2-2] TeMePEA-3 see #114 [ 4383-96-4] M-M #95
[3167-1 3-3] PeMePEA see # 1 08 [4395-23-7] DESOXY #31
[3198-07-0] f3,3,4-HO-a-Et-PEA see #33 [ 4668-10-4] IM #72
[3213-28-3] 3,5-DMPEA #50 [4722-08-1] f3,3,4-TMPEA see #49
[3213-29-4] 2,3-DMPEA #46 [4764-1 7-4] MDA #77
[3213-30-7] HMPEA see #49 [4774-24-7] Quipazine see #24
[3261 -62-9] 4-MePEA see #102 [ 4806-79-5] f3-Me-4-Cl-PEA see # 1 02
[3398-68-3] PMMA # 112 [ 4806-87-5] DCA see #38
[3489-95-0] N-Me-2,5-DMPEA see #22 [4998-74-7] S-DHA #33
[3489-98-3] f3-HO-N-Me-2,5-DEA see #36 [ 5006-63-3] DMPEA #49
f3-H0-N,N-Me-2,5- [5090-25-5] 3,4-DESMETHYL see #29
[3489-99-4] see #36
DMA
[5090-32-4] 3,5-DESMETHYL see #30
[3490-01-5] f3-Me-2,5-DMPEA see #22
[5090-33-5] f3-Me-3-MPEA see #101
[3490-03-7] f3,N-Me-2,5-DMPEA see #22
[51 79-72-6] f3,3,4-HO-N-Et-PEA see #49
f3,N,N-Me-2,5-
[3490-04-8] see #22 [5414-92-6] f3,N-Me-2-MPEA see # 1 00
DMPEA
[5470-35-9] DMePEA #43
[3490-05-9] N,N-Me-DMPEA see #49
[5470-40-6] 3-MePEA see #101
[3490-06-0] N-Me-DMPEA see #49
[5471-08-9] PEA # 107
[3490-09-3] N-Me-DMPEA-2 see #46
[5556-74-1] TMA-4 # 120
f3-HO-N-Me-2,6-
[3490-10-6] see #48 [5556-75-2] TMA-5 #121
DMPEA
[3459-15-2] DHA #33 [5580-32-5] 2-MeA see # 111
[3494-01-7] N,N-Me-DMPEA-2 see #46 [5650-44-2] METHCATH #92

[3600-86-0] 2C-H #22 [5653-66-7] N-Me-DME see #49
[3600-89-3] N-Me-DMPEA-3 see #47 [5688-80-2] TMA #117
[3706-26-1 ] PMA #110 [5720-26-3] 3,4,5-DESMETHYL see #29
[3706-38-5] PCA # 1 06 [5934-00-9] a-Et-ThEA see #67
[3721 -28-6] cPr-PEA see #107 [5967-42-0] Mescaline #91
[3886-69-9] PCBA see # 1 06 [5967-44-2] Mescaline #91
[3904-11-8] 2,6-DMA #37 [5969-39-1 ] f3,N-MePEA see # 1 07
___,. --------
-- --- - -------�·----
[3937-1 6-4] IM #72 [5973-70-6] DMeA #42

----- �- -- '-.-----


[5990-96-5] Hordenine #71 [ 13062-62-9] HME see #49
[ 6009-73-0 l DMeA #42 [13062-63-0] GEA-Bk see #49
[601 0-77-1] TMA-3 # 119 [ 13062-64-1] N-Me-GEA-Bk see #49
[6027-23-2] Hordenine #71 [13062-69-6] N-Me-HMPEA-Bk see #49
[6027-24-3] Hordenine #71 [ 13062-71-0] 3-DESMETHYL #30
[6043-76-1] Mescaline #91 [13062-74-3] 2,5-HO-MPEA see # 124
[61 70-28-1 ] PHA # 1 09 [1 3062-76-5] HMePEA #70
[6202-17-1] Hordenine #71 [1 3062-88-9] 3,5-Br-DESMETHYL see #29
[ 6209-35-4] Hordenine #71 [1 3062-93-6] B-Me-4-MPEA see # 1 02
[6292-91 -7] MDA #77 [ 13062-96-9] 2C-2 see #98
[ 6308-78-7] T-Mel see #91 [ 13071 -39-1] TMA #117
[6308-81-2] M-M #95 [ 13075-89-3] N,N-Me-2,3-DHPEA see #34
[6539-57-7] B-HO-DHA see #33 [ 13075-96-2] N-Me-DHPEA-AA see #49
[6632-31-1] 3,5-DMePEA see #43 [ 13076-06-7] N-Bu-DHPEA see #49
[6632-32-2] 2,5-DMePEA see #43 [1 3076-10-3] N-iPr-DHPEA-Bk see #49
[ 6640-24-0] mCPP #24 [1 3078-1 5-4] mCPP #24
[6882-07-1] Salicifoline see #49 [ 13078-75-6] DMA #38
[ 6924-15-8] DME see #49 [13078-77-8] N-Et-DMPEA see #49
[71 76-39-8] 4-BzA see #110 [ 13078-80-3] 2-Cl-PEA see # 1 00
[7224-66-0] Coryneine see #49 [13078-82-5] PAPEA see # 1 02
[7404-71 -9] N-Me-ThEA see #67 [1 3078-83-6] B-H0-2-APEA see # 1 00
[7437-51-6] DMeA #42 [ 13078-85-8] 2-APEA-Bk see # 1 00
[7464-94-0 l a,N-Me-ThEA see #67 [1 3079-18-0] B-HOM see #91
[7568-93-6] B-HO-PEA see # 1 07 [ 13079-19-1] M-Bk see #91
[7569-59-7] N-Me-3-Cl-MPEA see #49 [ 13338-64-2] Mescaline #91
[7683-59-2] B-HO-N-iPr-DHPEA see #49 [ 13662-98-1 ] DHAOH see #33
[101 05-90-5] DMAP #40 [13674-05-0] MMDA #97
[1 0389-72-7] 2-Cl-a,a-MePEA see #74 [13822-12-3] a-[1 4C] -Tyramine #126
[ 10554-60-6] ED-mor-PEA see #65 [ 13957-33-0] Leptodactyline see #71
[1301 5-25-3] ED-pyr-PEA see #65 [13990-47-1] R-PHA # 109
[13022-03-2] TeMPEA #114 [1411 6-06-4] MTA # 103
[1 3026-03-4] PNA see # 1 06 [14367-46-5] N-Et-PMA see #110
[1 3026-44-3] MHA #94 [ 14456-33-8] DMPEA #49
[1 3032-27-4] B-HO-DHMA see #33 [14457-28-4] DMPEA #49
[1 3061-68-5] HMPEA-Bk see #49 [14480-10-5] 2,3-DMPEA #46
[ 13062-56-1 ] HME see #49 [14497-54-2] N-Me-FEA see #67
[ 13062-61-8] R-MHA #94 [14513-20-3] S-DHA #33


[14543-76-1 ] DMeA #42 [ 1 7231-77-5] EMM see #118
[14722-93-1] B,2-H0-5-MA see #36 [ 1 7231-78-6] MME see #118
[ 15033-67-7] EDA #65 [1 7231-79-7] EME see #118
[1 5033-71 -3] EDA #65 [ 1 7231-80-0] MEM #87
[ 1 5033-73-5] EDEA see #65 [ 1 7231-81-1] EEM see #118
[15057-44-0] ED-ND MA see #65 [ 1 7231-82-2] MEE see # 1 1 8
[1 5057-45-1] ED-mor-A see #65 [ 1 7231-83-3] EEE see #118
[15147-05-4] ED-pyr-A see #65 [1 7279-41-3] S-(+)-DMA #38
[15183-13-8] DMMDA #44 [ 1 7283-14-6] DMePEA #43
[15183-24-1 ] DMMDA #44 [ 1 7283-15-7] DMePEA #43
[151 83-25-2] DMMDA-2 see #44 [ 1 7350-73-1] Hordenine #71
[ 15205-27-3] N-MMDBA see #45 [ 1 7605-58-2] Tyramine # 126
[ 15257-73-5] N-CCCl-M see #91 [ 1 7762-90-2] MDMBP see #93
[15351-09-4] DMAP #40 [ 1 7762-91-3] MDPBP see #93
[1 5394-83-9] TMPEA-2 #124 [1 7762-92-4] MDIPBP see #93
[ 15398-87-5] DHMA see #33 [1 7763-01-8] MDMVP see #93
[ 15402-79-6] TMA-6 # 122 [1 7763-02-9] MDEVP see #93
[15402-81-0] 2,3-DMA #34 [ 17763-03-0 l MDIPVP see #93
[1 5402-82-1 ] 3,5-DMA #39 [1 7763-05-2] MDSBVP see #93
[1 5402-84-3] 2-MA #74 [ 1 7763-10-9] MDBVP see #93
[ 15532-74-8] mTFMPP #116 [1 7763-12-1 ] MDDMBP see #93
[1 5532-75-9] mTFMPP # 116 [1 7763-13-2] MDDMVP see #93
[1 5588-95-1] DOM #60 [ 17763-15-4] MDDEVP see #93
[ 15589-00-1 ] DOM #60 [ 1 7763-1 6-5] MDDMHP see #93
[15806-29-8] 2,4-DMPEA #47 [ 1 7763-1 7-6] MDDEHP see #93
[ 15806-33-4] TeMPEA-3 #115 [1 7764-1 8-0] MDEBP see #93
[1 5886-81-4] ABM see #117 [1 7764-20-4] MDPVP see #93
[1 5995-72-9] TMA-2 #118 [ 1 7862-85-0 l 3-MA #75
[ 15995-73-0] dl-TMA-3 #119 [ 18259-37-5] EAP see #40
[ 1601 5-69-3] mTFMPP #116 [ 18620-27-4] a-A-ThEA see #67
[16015-71 -7] 3-MeOPP see #88 [ 19064-48-3] 2,5-DMeA see #42
--------
[1 6046-07-4] 3-DESMETHYL #30 -----·---
[19065-13-5] S-(+)-TMA-2 #118
[1 6064-30-5] S-(+)-PCA # 106 [1 9065-14-6] S-TMA #117
[ 16064-31-6] R-(-)-PCA # 1 06 [1 9065-15-7] (+)-TMA-3 # 119
e----
[16128-88-4] MEM #87 [19134-50-0] PPP see #40

[ 1 7061-21 -1] MCPA see #41 [1 9523-16-1 ] a, B,B-[ 3HkDHA #33
[1 7097-73-3] AEM #1 [ 19751 -75-8] N,N-Me-DME see #49

CAS # Name
-
Entry# CAS # Name Entry#
[20513-16-0] TMA-5 # 121 [23582-55-0] B03MM see #101
[20980-22-7] 2-PmP see #24--··-·--·�-
[23642-63-9]
--�..--·------·-
--
B03EE see #101
�
[211 93-23-7] 2-CA see #74 [23690-13-3] 2,4-DMA #35

[21581-35-1] N-Me-4-EPEA see #102 [23690-14-4] 2,6-DMA #37
[21581-36-2] N-Me-DEPEA see #49 [23693-14-3] TMA-4 #120
[21581 -37-3] N,N-Me-DHPEA see #49 [23693-1 8-7] MMDA-2 #98
[21581-45-3] DC PEA see #49 [23693-19-8] MMDA-3a #99
[21581-46-4] N-Me-3-EPEA see #101 [ 23693-20-1] MMDA-3b see #97
[21581 -47-5] N-Me-EMPEA see #49 [23693-21-2] MMDA-4 see #97
[2161 8-99-5] 3,4-HMeA see #96 [ 23693-22-3] MMDA-5 see #97
[21 629-16-3] N-Me-2-EPEA see # 100 [23693-25-6] MEDA see #97
[21 900-10-7] f3-Me-2-MMA see #74 [23693-26-7] TeMA # 113
[21987-94-0] N-Et-DHPEA see #49 [23693-27-8] TeMA-2 see #115
[22002-68-2] N-Et-PEA see # 1 07 [23693-28-9] TeMA-3 see # 115
[22004-32-6] DOET #56 [23693-29-0] PeMA see # 1 08
[22139-65-7] DOET #56 [23693-38-1] Lophophine #73
[221 73-84-8] HM-a-EPEA see #96 [23693-39-2] 4C-3a see #99
[22199-1 2-8] dl-TMA-3 #119 [23771-48-4] PHA # 1 09
[22199-13-9] dl-TMA-4 #120 [23815-74-9] TMA-6 # 122
[22199-14-0] dl-TMA-5 #121 [2411 6-85-6] S-PCA # 1 06
[22199-1 6-2] dl-TMA-6 # 122 [2411 6-86-7] S-PCA #106
[22199-1 7-3] dl-TMA #117 [2411 6-87-8] PCA # 106
[2231 0-84-5] ED PEA see #65 N-Me-3-
[24131-1 6-6] see #30
DES METHYL
[22331 -67-5] N-iPr-2-MA see #74
[24131-17-7] DESMETHYL-M see #29
[22331 -70-0] PMMA #112
[24131 -22-4] f3-HO-DESMETHYL see #29
[22490-82-0] PCA # 1 06
[22702-15-4] DOM-2,5-DIEtO see #60 [24159-01-1] f3,5-HO-DMPEA see #30
[22702-16-5] 4-Me-2,6-MEA see #122 [241 60-29-0] 3,4-MMA #96
[22702-1 8-7] DOET #56 [24286-42-8] N,N-Me-2C-D see #20
[22702-19-8] FLORENCE see #60 [24333-1 9-5] 2C-D #20
[22702-21-2] BHB see #60 [24550-13-8] B03M2C see #46
[22702-22-3] '¢-BBB see #122 [24550-16-1] B03MIP see #101
[ 22702-23-4] DOM #60 [24550-1 7-2] B03MB see #101
[22969-85-3] TMMDA see #108 [24550-1 8-3] B03MDM see #101
[23239-32-9] PMA #110 [24550-20-7] B03MEA see #101
[23582-49-2] B03ME see #101 [24550-23-0] B03A see #101

[23582-50-5] B03E see #101 [24550-24-1 ] B03P see #101

- ---- -

[24566-01-6] B03M see #101 a-[1 4 C]-
[27954-82-1] #29
DESMETHYL
[24578-46-9] B03MA see #101
[27954-87-6] a, B-[ 3HJi-GEA #69
[24698-57-5] MDPPP see #93 ---··---�-� -
a, B-[3 HJi-
[24722-38-1 ] PEA #107 [27954-91-2] #29
DESMETHYL
[24973-25-9] 2,5-DMA #36
[27954-94-5] a, B-[ d2 ]-Mescaline #91
[24973-29-3] 3,5-DMA #39
-� ··--·- -
[27954-95-6] 2,6-[ 3 H] 2-Mescaline #91
[24973-30-6] 3,5-Me-PMA see #91
[28008-37-9] a, B-[3 HJi-Mescal�ne #91
[24973-31-7] 3,5-Me-PHA see #117 .
[28094-15-7] 2,4,5-HO-PEA see # 1 24
[24973-32-8] TMeA-6 see # 123
[2811 7-80-8] MPPP see #92
[ 25006-35-3] B-MeO-HMePEA see #71
[28357-54-2] 5-PCA # 1 06
[25068-95-5] 3,4-MMA #96
[29401-05-6] 3-Cl-4,5-MDPEA see #73
[ 25068-96-6] dl-2,3-DMA #34
[29440-90-2] 3,4-HMeA see #96
[25068-97-7] 3-Me-2,4-DOM see #60
[29440-91-3] HM-a-EPEA see #96
[25070-60-4] MDOC see #77
[29705-96-2] DOB #52
[25351-11-5] B-H0-2,5-DMA see #36
[29866-04-4] N-Me-HME see #49
[ 25505-65-1 ] 2C-D #20
[29866-11-3] 3,5-HPEA see #so
[25505-67-3] N-Me-2C-D see #20
[29907-74-2] DOHM see #60
[ 25505-68-4] BEATRICE #11
[29907-75-3] DOCA see #55
[25566-62-5] PEA #107
[30100-54-0] DOET #56
[ 26070-48-4] N,N-Me-PMA see # 110
[30433-93-3] a-Me-ThEA see #67
[26070-49-5] N,N-Me-DOM see #11
[30459-17-7] pTFMPP see #116
[26138-13-6] DESMETHYL-MM see #29
[30543-88-5] AEPEA see # 1 07
[26568-24-1 ] BCPA see #41
[30645-73-9] oTFMPP see #116
[26568-25-2] CCPA see #41
[31338-31-5] 3-Cl-PHA see #38
[27160-05-0] B-[ d2 ]-DMPEA #49
[31338-32-6] DFA see #38
[27164-1 8-7] 3,5-Cl-4-MPEA see #19
[31367-42-7] B,4-DMPEA see # 1 02
[27164-23-4] 3,5-Cl-4-BPEA see #19
[32156-1 6-4] 3,5-DMeA see #42
[27164-25-6] 3,5-Cl-4-ALPEA see #19
[32156-17-5] TMeA see #123
[27164-26-7] 3,5-Cl-4-MA see # 1 9
[32156-1 8-6] TeMeA see # 114
[27164-28-9] 3-Cl-4,5-DMPEA see # 1 9
[32156-1 9-7] TeMeA-2 see # 114
[27164-29-0] 2-Cl-4,5-MDA see #98
[ 32156-20-0 l TeMeA-3 see # 114
[27164-30-3] 3-Cl-4,5-DMA see #91
[32156-21-1] PeMeA see # 1 08
[27164-31-4] 2-Cl-4,5-DMPEA see #19
[32156-22-2] 3-Br-PMA see #38
[27167-81-3] B-[ d]-DMPEA #49
[32156-23-3] 4-Br-3-MA see #38
[27487-78-1 ] homo-DMA see #38
[27572-11-8] 4-Cl-3-MA see #38 [32156-24-4] 2-Br-5-MA see #36
[27906-91-8] N-PrPEA see #1 07 [32156-25-5] a-DOB see #52

- �.


[321 56-34-6] 3,4,5-DOB see #52 [341 38-58-4] MPHP see #92
[3221 8-88-5] PEA # 1 07 [341 76-59-5] PCA # 1 06
[32231 -06-4] MDBP #79 [341 76-60-8] PCA # 1 06
[32560-53-5] 3-Cl-4-HPEA see #49 [341 76-61-9] PCA # 1 06
[32560-59-1] 3-CA see #75 [ 34203-22-0 l PCA # 1 06
[ 32560-60-9] 2,4-DMeA see #42 [34332-74-2] 2,3-DMeA see #42
[ 32560-62-6] 4-iPrA see # 111 [ 34509-36-9] t-BAP see #40
[32560-67-1] PPhA see # 110 [34536-15-7] 2,4-MHPEA see #47
[32560-70-6] MEA see #38 [34620-52-5] 6,7-MDMAT see #77
[32560-72-8] 3-Br-PHA see #38 [34622-16-7] PCA # 1 06
[32560-77-3] 2,4-DCA see #35 [34622-1 7-8] PCA # 1 06
[32560-78-4] 2,5-DFA see #36 [34843-84-0] 3-ThEA see #67
[32560-79-5] 2,6-DCA see #37 [34911 -55-2] Bupropion see #92
[ 32633-68-4] N-Me-DCA see #38 [35026-77-8] 5-DMAP #40
[32655-70-2] HME see #49 [35026-78-9] 5-DMAP #40
[ 32828-83-4] 7,6-MMAT see #96 [ 35026-79-0 l 5-DMAP #40
[ 331 89-36-5] 2,4-DMA #35 [35026-80-3] R-DMAP #40
[33236-61-2] DMMA see #38 [35149-78-1] 4C-3-MPEA see #101
[33236-63-3] DMEA see #38 [ 35294-10-1 ] 3-MA #75
[33236-63-4] DMPA see #38 [35386-24-4] 2-MeOPP see #88
[33286-27-0] DIME TH see #107 [35534-19-1] MAA see #40
[33298-29-2] MMDA-3a #99 [36377-59-0] MEPEA #90
[ 33423-88-0 l 5-PCA #1 06 [36406-68-5] MD PEA #85
[33446-12-7] TMAT see #117 [37015-19-3] 2-BM see # 114
[33462-22-5] PHA # 1 09 [37108-92-2] N,N-Me-3,5-DMPEA see #50
[33542-90-4] 2,3-MDPEA see #77 [37162-72-4] a-DOB see #52
[ 33542-94-8] 2C-DMMDA see #44 [37699-47-1] a-[d2]-DMPEA #49
[33542-95-9] 2C-DMMDA-2 see #44 [37852-37-2] DMPEA #49
[33542-96-0] 2C-DMMDA-3 see #44 [ 38063-96-6] MDBP #79
[ 33543-05-4] 2,3-MDMPEA see #44 N,N-Me-3-
[38184-65-5] see #30
DESMETHYL
[33543-06-5] N-Me-2C-3a see #99 ·- - --·-
[38212-30-5] MeOPP #88

[33543-07-6] N-Me-Lophophine -----
see #73
------
--
[ 33543-08-7] N-Me-2C-DMMDA see #44 [38411-80-2] 4,5-H0-2-APEA see #124
[33543-09-8] N-Me-2C-DMMDA-2 see #44 [38473-95-9] f3, f3-F-PCA see # 1 06
[33543-10-1] N-Me-2C-DMMDA-3 see #44 [38869-47-5] MeOPP #88
[33543-11-2] homo-MD PEA see #78 [38875-30-8] R-a, f3-[dJ -PMA #110
[33543-62-3] N-Me-3-MPEA see #101 [38875-32-0] a,f3-[ d2 ]-PHA # 109


[3891 0-34-8] homo-DOM see #60 [42047-49-4] DMPEA #49
[38910-35-9] homo-TMA-3 see #91 [42203-72-5] DON-Ac see #61
[38910-36-0] homo-TMA-2 see #91 [42203-73-6] DONH-Ac see #61
[38910-37-1] homo-TMA-6 see #91 [42203-74-7] DOC-Ac see #54
[39201 -75-7] AL #2 [ 42203-75-8] DOB-Ac see #52
[39201 -76-8] AL #2 [42203-77-0] DOC #54
[39201 -78-0] Proscaline #104 [ 42203-78-1 ] DOI #58
[39201 -79-1] Proscaline # 1 04 [42203-79-2] DON #61
[39201-81-5] MAP EA see #90 [42203-80-5] DONH see #61
[39201 -82-6] Escaline #64 [42203-87-2] DOAA see #61
[39201 -83-7] ME PEA #90 [42203-91-8] N-H0-2C-D see #20
[ 39235-63-7] MDPH see #77 [42311-16-0] 2,5-DMA-Ac see #36
R-a-[1 4C]-j)-[3 H]- [42416-75-1] PMA-j)k see #110
[39236-10-7] #1 26
Tyramine
[ 42542-07-4] BOB #9
[39477-28-6] AL #2
[42542-1 0-9] MOMA #82
[39477-30-0] Escaline #64
[ 42973-59-1 ] DESMETHYL-iPr see #29
[39590-27-7] 2-EA see #74
[43022-01-1] N-HO-DOM see #60
[39697-36-4] AL #2
[43061-13-8] R-(-)-DOM #60
[39697-37-5] ME PEA #90
[43061-14-9] S-(+)-DOM #60
[ 40275-08-9] Escaline #64
[43061-15-0] R-(-)-DOB #52
[ 40275-09-0] Proscaline #104
[43061-16-1 ] S-(+)-DOB #52
[ 40393-68-8] AEM #1
[ 42306-96-7] DOIP #59
[40393-73-5] 2,6-BM see #1 08
[49557-34-8] a-CMe-M see #117
[40742-32-3] homo-MDA #78
[49557-38-2] a-HMe-M see #117
[40807-91-8] j)-H0-3,4,N-MePEA see #43
[49607-15-0] 3-N02-HPEA see #49
[ 40808-62-6] NEA see #67
[ 49656-78-2] METHCATH #92
[ 41241 -36-5] THA-2 see #118
[49818-52-2] N,N-Me-2,3-EMPEA see #46
[41241 -40-1] 2,5-H0-4-APEA see #124
[50505-80-1 ] R-(-)-PMA #110
[ 41241-41-2] 2,4-H0-5-APEA see #124 [50505-81-2] S-(+)-PMA #110
[41498-55-9] [1 5N] -PEA #1 07 [ 50505-82-3] R-2,3-DMA #34
[41509-97-1] R-PHA #109 [50505-83-4] S-2,3-DMA #34
[41 509-98-2] S-PHA #109 [ 50505-84-5] R-2,5-DMA #36
[41 632-56-8] PMeA #111 [ 50505-85-6] S-2,5-DMA #36
[41 688-37-3] N-Me,CHO-DME see #49 [ 50505-86-7] R-TMA #117
[ 41 885-48-7] Mescaline #91 [ 50505-88-9] R-(-)-DOM #60
[ 42006-59-7] j)-[1 4 C] -PEA # 1 07 [ 50505-89-0 l S-(+)-DOM #60
[42011-76-7] R-(-)-DOET #56 [50505-91-4] S-(+)-DOET #56

-�--
CAS # Name Entry# CAS #

�----- -
Name Entry#
[50505-92-5] R-DOB #52 [52670-14-1] 3,5-Me-4-MPEA see #91
[50505-93-6] S-DOB #52 [52740-56-4] PMA #110
[50623-66-0] N-Et-3-MA see #75 [52842-58-7] ARIADNE #7
[50623-68-2] N-Et-3-HA see #75 [ 52842-59-8] R-(-)-ARIADNE #7
[50650-74-3] PMeA # 111 [52842-60-1 ] R-(-)-ARIADNE #7
[50802-67-0] B-HO-PMA see #110 [52850-79-0] 2-MA #74
[50822-98-5] N,N-Me-4-MPEA see #102 [52850-80-3] 3-MA #75
[51 062-15-8] homo-PMA see #110 [ 52850-84-7] TMA-3 #119
[51 080-00-3] DHA #33 [ 52881-88-6] S-(+)-ARIADNE #7
[51395-16-5] PCA #1 06 [52881-89-7] S-(+)-ARIADNE #7
[51 639-49-7] mCPP #24 [52910-84-6] N,N-Me-B,3,4-TMPEA see #49
[51 674-33-0] 3-HMPEA see #71 [52918-31 -7] ARIADNE #7
[51749-33-8] Mescaline #91 [52948-31-9] 2,5-DMA #36
[51 749-34-9] Mescaline #91 [52948-32-0] TMA-4 # 120
[51 806-86-1] DOMAT see #60 [52948-33-1] dl-TMA-5 #121
[ 51 806-87-2] DOMAI see #60 [53197-60-7] B-(1 4 C]-DOM #60
[52007-97-3] N-iPr-PEA see # 1 07 [53305-83-2] S-(+)-DOET #56
S-a, B,B-[ d 3 ]- [ 53356-38-0 l FEA #67
[52009-73-1] # 126
Tyramine
[53387-69-2] a, B-Me-ThEA see #67
R-a,B,B-[d3] -
[52009-74-2] #1 26 [ 53581 -53-6] DOB #52
Tyramine
[53581-55-8] DOPR #62
[52336-29-5] 2,5-DES-Me-DOM see #60
[53581-56-9] DOIP #59
[52336-30-8] homo-Dopamine see #38
[53581-57-0] DOTB see #60
[52336-47-7] HMA see #33
[53581-59-2] 2,4-MMA see #35
[52336-49-9] 2-DES-Me-DOM see #60
[53581-61-6] 4-Cl-2-MA see #35
[52370-69-1 ] N,N-Me-DHA see #33
[53581 -65-0] homo-MDA #78
N,N-Me-DHA
[52370-70-4] see #33 [53581-71-8] R,S-trans-(-)-DMCPA #41
diacetate
[52428-22-5] N,N-Me-DOMAI see #60 [53581 -74-1] B-Me-2C-D see #20
[52432-70-9] DOB #52 [53581 -75-2] B,B-Me-2C-D see #20

[52516-31-1] 3-TFMMPEA see #63 [53581 -76-3] B-Me-DOM see #60
[52532-94-2] GEA #69 [53581 -78-5] N-Et-DOM see #11
[52597-14-5] PAP see #40 [53581-79-6] R-DOB #52
[52597-15-6] i-PAP see #40 [ 53581 -80-9] S-DOB #52
[52597-1 6-7] BAP see #40 [ 53581-90-3] DOB #52
[52632-05-0] 4-N,N-MePEA see #102 [53581-91-4] DOB #52
[52663-86-2] R-(-)-ARIADNE #7 [53582-1 6-4] B,B-Me-DOM see #60

[52670-12-9] 2,6-Me-MPEA see #122 [53587-31-8] 2,5,6-[ d3 ]-GEA #69

-�--

[53626-22-5] R-(-)-TMA-2 #118 [56621-48-8] HOPP see #88
[ 53626-23-6] R-DOC #54 [56966-33-7] a-DOM see #60
[53626-24-7] S-DOC #54 [57116-37-7] R-(-)-DOET #56
[53799-05-6] GEA #69 [57224-67-6] 4-PPEA see # 1 02
[53896-12-1] homo-PCA see # 1 06 [57224-68-7] 4-APEA see # 1 02
[5391 6-94-2] PEA # 1 07 .�
[57224-69-8] 4-SPEA see # 1 02
[5411 0-93-9] Escaline #64 [57294-60-7] DMePAA see # 1 06
[5411 0-94-0] AL -
#2 [57303-11-4] N-Me-N-iPr-DHPEA see #49
[54373-56-7] DMPEA #49 [57536-86-4] 1-NP see #24
[54373-57-8] DMPEA #49 [57580-64-0] a-Me-FEA see #67
[54547-01-2] Trichocereine #125 [57736-33-1] PAA see # 1 06
[54687-43-3] 2,5-DMMA see #36
---�- --
[ 58262-05-8] S-a,13-[ d 2 ]-DOM #60
[54690-19-6] ARIADNE #7 [58278-83-4] 13-[3H]-PHA # 1 09
[54713-06-3] S-( +)-ARIADNE #7 [58379-90-1] DMA #38
[ 54719-1 0-7] MDCPA see #41 [ 583 79-99-0 l DMMAOH see #38
[5471 9-11-8] N,N-Me-DHPEA-AA see #49 [ 58380-00-0 l DMAOH see #38
[54749-54-1 ] DOBU #53 [ 58623-25-9] METHCATH #92
[54942-65-3] 2,6-HPEA see #48 [ 58738-59-3] MD PEA #85
[54947-20-5] N-Et-3-CA see #75 [ 58759-28-7] PIAP see #40
[54947-21-6] N-Et-3-BA see #75 [58993-77-4] N,N-Me-DMA see #38
[54947-22-7] N-Et-3-IA see #75 [58993-78-5] S-(+)-PMA #110
[54947-52-3] N-Et-3-N02-A see #75 [58993-79-6] R-(-)-PMA #110
[54975-72-3] DOAM #51 [58993-80-9] S-( + )-2,5-DMA #36
[54982-43-3] N-Et-3-FA see #75 [58993-81-0] R-(-)-2,5-DMA #36
[55174-55-5] 4C-DMPEA see #38 [58995-64-5] N,N-DMMDBA see #45
[55174-61-3] 13-Me-DMPEA see #49 [59262-02-5] R-(C[d 3 ]0) 2-DOM #60
[551 81-90-3] [ 77Br]-DOB see #52 [ 59262-03-6] S-(C[d3 ]0) 2-DOM #60
2
[551 81-91-4] [ 8 Br]-DOB #52 [ 59262-04-7] R-a, 13-[ d2 ]-DOM #60
[55275-61-1] 13-H0-4-MPEA see # 1 02 [59291 -68-8] 2-MA #74
[55323-11-0] 13-[1 4C]-DMPEA #49 [59291 -69-9] 3-MA #75
[55755-18-5] 2-MePEA see # 1 00 [ 59963-26-7] PCA # 1 06
[55875-51-9] Amiflamine see #42 [ 60124-80-3] (C[d3 ]0) 2-DOM #60
[56120-35-5] N-Me-13,3,4-TMPEA see #49 [60124-87-0] (C[d3 ]0) 2-DOM #60
[56281-37-9] 2C-B #18 [ 601 89-29-9] 3-MPEA #101
[56311-97-8] 13-Me-MDPEA see #85 [ 601 89-30-2] N,N-Me-3-HPEA see #71
[56440-59-6] MDA #77 [ 601 89-31-3] N,N-Me-3-MPEA see #101
[56490-94-9] a,a-Me-PMPEA see #110 [ 60407-53-6] 13-H0-2,5-DMPEA see #22


[60411-1 6-7] Hordenine #71 [ 62493-39-4] Hordenine #71
[ 60480-00-4] PCAT see # 1 06 [62722-95-6] Tyramine # 1 26
[60676-84-8] MMDA #97 [ 62885-82-9] 4-EPEA see # 1 02
[ 60745-26-8] 2-[3H]-Tyramine #126 [63037-49-0] DESOXY #31
[ 60756-92-5] j3-[14 C]-PMA #110 [63223-62-1] 2,6-DMeA see #42
[ 60756-93-6] j3-[1 4C]-PHA # 1 09 [ 63286-43-1] DMPEA #49
[60887-73-2] 6,2,3-DOB see #52 [ 63375-81-5] 2,4,5-BMM see # 1 8
[60887-75-4] 3,2,6-DOB see #52 [ 63504-04-1] N,N-Me-HME see #49
[60887-76-5] 2,3,5,6-BMMBA see #115 [ 63 779-88-4] DOPR #62
[6091 7-67-1] m-DOB see #52 [ 63779-89-5] DOBU #53
[ 61 035-86-7] 4-MPEA # 1 02 [ 63 779-90-8] DOAM #51
[61035-87-8] 4-iPPEA see # 1 02 [ 63825-18-3] a,N-Me-FEA see #67
[ 61 040-64-0 l j3-[14C]-PCA # 1 06 [6391 8-08-1] ASB #8
[ 61040-91-3] j3-[14 C]-PCA # 1 06 j)-HO-N,N-Me-2,5-
[63991-16-2] see #22
DMPEA
[61 079-92-3] DMeA #42
j)-HO-N-Me-2,5-
[61114-45-2] 3,4-DMCPA see #41 [63991-17-3] see #22
DMPEA
[611 86-07-0] HMePEA #70
j)-HO,Me-2,5-
[61 367-69-9] Proscaline # 1 04 [ 63991-1 8-4] see #22
DMPEA
[61 367-70-2] IP see #91 [64057-69-8] N,N-Me-2,5-DMPEA see #22
[61381 -04-2] DE PEA see #49 [64057-70-1] MDMA #82
[61471-46-3] S-a,j)-[ d2 ]-DOM #60 [64357-23-9] a, j)-[ d2 ]-PHA # 1 09
[61552-35-0] 4-C[d3 ]-DOM #60 [64584-31-2] a, j)-[ d2 ]-DOI #58
[61 555-32-6] j)-HO-MDA see #77 [ 64584-32-3] 2C-I #23
[61614-60-6] R-(-)-MDA #77 [ 64584-33-4] 4C-I see #58
[61614-61-7] 1-MDA #77 [ 64584-34-5] DOI #58
[61 638-07-1] ALEPH #3 [64610-28-2] 2-MPEA # 1 00
[61 638-08-2] ALEPH #3 [64610-29-3] 3-MPEA #101
[ 61 638-09-3] 2C-T #25 [ 64610-30-6] 4-MPEA # 1 02
[61638-10-6] 2C-T #25 [64610-31 -7] 2,3-DMPEA #46
[61 866-76-0] 2,5-MH-MMA see #36 [64610-32-8] 2,4-DMPEA #47
[61 866-77-1] 2-HMA see #74 [ 64610-33-9] 2C-H #22
[ 62028-43-7] N-Pr-M see #91 [64610-34-0] DMPEA #49
[ 62028-44-8] N-CPM-M see #91 [64610-35-1] 3,5-DMPEA #50
[ 62028-46-0l N-AL-M see #91 [ 6461 0-36-2] MD PEA #85
[ 62028-47-1 ] N,N-Butenyl-M see #91 [64610-37-3] TMPEA-2 #124
[ 62028-50-6] a,N-Butenyl-M see #117 [6461 0-39-5] 2-MA #74
[62319-20-4] MMDA #97 [ 64610-40-8] 3-MA #75


[64610-41-9] PMA #110 [ 65995-43-9] 2-CM see #114
[ 6461 0-42-0l 2,3-DMA #34 [ 65995-44-0] 2,6-CM see # 1 08
[ 6461 0-43-1] 2,4-DMA #35 [ 66033-00-9] R-3-MA #75
[ 64610-44-2] 2,5-DMA #36 [ 66033-04-3] S-3-MA #75
[ 6461 0-45-3] OMA #38 [66142-81 -2] 2C-B #18
[ 6461 0-46-4] 3,5-DMA #39 [66142-89-0] S-(+)-MDMA #82
[6461 0-47-5] MDA #77 [ 66432-25-5] f3-Me-DHPEA see #49
[ 6461 0-48-6] TMA #117 [66514-93-0] S-METHCATH #92
[ 6461 0-49-7] TMA-6 #122 homo-N-Me-2,5-
[ 66997-06-6] see #22
DMPEA
[6461 0-61 -7] MDA #77
[671 73-94-8] S-TMA-2 #118
[ 64638-07-9] DOB #52
[ 67225-64-3] R-TMA-6 #122
[ 64778-73-0 l 3,4,5-MBM see # 1 8
[ 67225-65-4] S-TeMA #113
[64778-74-1 ] R-DON #61
[ 67225-66-5] R-TeMA #113
[ 64778-75-2] B see #91
[ 67225-68-7] R-MMDA-3a #99
[ 64778-76-3] R-TMA-2 #118
[ 67225-69-8] R-MMDA-2 #98
[64778-77-4] R-TMA #117
[ 67225-70-1] R-MMDA #97
[64778-78-5] R-(-)-DMA #38
[67287-36-9] 2-Cl-3,4-DMPEA see # 1 9
[64778-79-6] 4,3,5-DOB see #52
[ 67293-51-0] ASM see # 1 1 7
[64778-82-1] MMDA-2 #98
[67293-52-1] AHM see # 1 1 7
[64813-14-5] R-ALEPH #3
[ 67293-56-5] ANM see # 1 1 7
[ 64813-15-6] R-DOPR #62
[67293-57-6] AAM see # 1 1 7
[64813-16-7] R-DOBU #53
[ 67293-58-7] APM see # 1 1 7
[64813-17-8] R-DOAM #51
[67313-94-4] R-2,4-DMA #35
[ 64829-34-1] 3,4-HMeA see #96
[ 67313-95-5] R-TMA-4 # 120
[ 64838-26-2] R-TMA-3 #119
[ 67313-96-6] R-TMA-5 #121
[ 65114-99-0] N-iPr-PCA see # 1 06
[ 67313-98-8] R-DMMDA #44
[65341-01 -7] N-iBu-DHPEA see #49
[ 67313-99-9] R-MEM #87
[65369-76-8] mCPP #24
[ 67323-60-8] R-PHA # 1 09
[65423-11-2] 4-BPEA see # 1 02
[ 67346-52-5] R-(-)-PMA #110
[65528-82-7] R-DMAP #40
[ 67346-53-6] S-(+)-PMA #110
[65615-1 7-0] BOH #15
[ 6 7460-68-8] DON #61
[ 65620-66-8] S-(+)-MDA #77
[67482-58-0] 5-Cl-a-Me-ThEA see #67
[ 65756-98-1 ] [1 3 11]-DOI #58
2 [67482-59-1] 3-Cl-a-Me-ThEA see #67
[ 65756-99-2] [1 31]-DOI #58
[65953-87-9] N,N-Me-MDPEA see #85 [67482-60-4] 4-Cl-a-Me-ThEA see #67
[65955-47-7] MDA #77 [67482-61-5] 3,4-Cl-a-Me-ThEA see #67

[ 65955-48-8] TMA-2 #118 [67482-62-6] 4,5-Cl-a-Me-ThEA see #67

----·

[67482-63-7] 3,5-Cl-a-Me-ThEA see #67 [71203-56-0] 7-Me-MDA see #77
[67519-19-1] a-[1 3C]-PEA # 1 07 [71203-59-3] IDA see #77
[ 67685-71-6] 2,3-DMePEA see #43 [71250-1 9-6] N-Bu-3-MA see #75
[ 67707-78-2] 2,5-DNNA see #36 [71250-21-0] N,N-Et-3-MA see #75
[67890-16-8] R,S-trans-(-)-DMCPA #41 [71250-28-7] homo-N,N-Et-3-MPEA see #101
[67890-1 7-9] R,S-trans-( + )-DMCPA #41 [71250-30-1] homo-N-Et-3-MPEA see #101
[ 68593-96-4] 5-HO-PPAT see #34 [71259-74-0] N-Me-TH-FEA see #67
[69271 -67-6] 2-HA see #74 [71295-78-8] S-PHA # 1 09
[ 69294-22-0 l 4C-Cl see #54 [71539-34-9] 2C-E #21
[ 69294-23-1 ] 4C-DOB see #52 [71 539-35-0] TM see #91
[ 69294-24-2] 4C-HM see #118 [71 750-39-5] PEA # 1 07
[ 69294-25-3] 4C-HE see #118 [71832-30-9] 2,5-DMA #36
[ 69321 -45-5] 2,5-DMA #36 [71861 -16-0] N,N-Me-2-MA see #74
2
[ 69389-96-4] PHEA see #110 [72299-69-5] [1 3J]-DOI #58
[ 69389-97-5] MHEA see #94 [72667-79-9] 4C-E see #7
[ 69478-40-6] j)-Me-GEA see #49 [72667-80-2] 4C-iP see #7
[ 69501-21-9] 4C-T see #3 [72667-81-3] 4C-P see #7
[ 69558-31-2] R-(-)-MDMA #82 [72667-82-4] 4C-Bu see #7
[69558-32-3] S-(+)-MDMA #82 [72667-83-5] 4C-HO see # 1 1 8
[ 69587-06-0] 2-MPEA # 1 00 [72667-84-6] 4C-Et0 see # 1 1 8
[69587-07-1] 2-MTPEA see # 1 03 [72667-85-7] 4C-Pr0 see #118
[69587-09-3] 2-BPEA see # 1 00 [72667-86-8] 4C-iPrO see #118
[69587-11-7] 2C-I #23 [72667-87-9] 4C-NO see #61
j)-HO-j),N-Me-2,5- [72667-88-0] 4C-NH see #61
[ 69766-13-8] see #22
DMPEA
[72739-03-8] 2-MA #74
[69792-61 -6] PHMMA see #110
[72739-09-4] dl-TMA-4 #120
[ 69854-49-5] DMCPA #41
[72739-1 0-7] dl-TMA-6 #122
[ 69980-34-3] R,S-trans-(-)-DMCPA #41
[72739-11 -8] 3-DOM see #60
[ 69980-35-4] R,S-trans-(-)-DMCPA #41
[72739-13-0] 3-DOB see #52
[ 69980-36-5] S,R-trans-( + )-DMCPA #41
[72739-1 6-3] 2,4-DMA-j)k see #35
[69980-37-6] S,R-trans-( + )-DMCPA #41
[72912-40-4] 2,3,4-BMM see # 1 8
[70097-37-9] f3,f3-[3H]-a-C[3H] -DOM #60
3
[70097-40-4] j3-3H2-DMPEA #49 [73304-06-0] BOH #15
[70097-42-6] j3, j3-[ 3H] 2 -TMPEA-2 #124 [73495-53-1] S-2-MA #74
[70745-96-9] R-MDA #77 [73536-80-8] MTAI see # 1 03

[70745-97-0] S-MDA #77 [73536-81-9] N,N-Me-PCAI see # 1 06
[70849-64-8] MeOPP ----·�-
#88 [73536-86-4] PCAI see # 1 06


[73536-87-5] PNAI see # 1 06 [7501 7-01-5] 6-HO-PPAT see #35
[73536-88-6] PBAI see # 1 06--
[75510-74-6] 2-TIM see #72
[73625-10-2] 3-NEA see #67 [75689-33-7] N-Me-3,5-DMPEA see #50
N-Me-3,4,5- [76135-31-4] PAT # 1 05
[7391 7-91-6] see #29
DES METHYL
[76381-67-4] a, f3-[ d2 ]-DHA #33
[7391 8-56-6] 4-Br-PEA see # 1 02
[7 6835-14-8] mTFMPP #116
[7391 8-57-7] 4-1-PEA see # 1 02
[76935-60-9] 2,4-DMePEA see #43
[74341 -74-5] MDHOET see #77
[76935-62-1 ] TMePEA-3 see # 1 23
[74341 -75-6] MDAL see #77
[76935-63-2] TMePEA-4 see # 1 23
[74341 -77-8] MDPR #86
[76935-64-3] TMePEA-5 see # 1 23
[74341-78-9] MDE #81
[76935-66-5] TMePEA # 123
[74341 -79-0] MDDMA #80
[76935-78-9] 2,6-DMePEA see #43
[74341-80-3] MD MEOET see #77
[77158-46-4] f3-HO-TMA see # 1 1 7
[74341-81-4] MDPL see #77
[771 58-52-2] Lophophine #73
[74341 -83-6] MDOH #84
[77886-58-9] DO MAD see #60
[74341-84-7] MDCPM see #77
[77956-20-8] f3-[1 4C] -PEA # 1 07
[74341 -85-8] MDIB see #77
[77970-78-6] a,a-[d2 ]-PEA # 1 07
[74447-55-5] S-a-[ 3H] -Tyramine #126
[78056-41-4] mTFMPP #116
[74447-59-9] R-a-[ 3 H]-Tyramine #126
[78095-19-9] R-PAT # 1 05
[7451 6-48-6] 2,5-HMPEA see #22
[78095-20-2] S-PAT # 1 05
[7451 6-49-7] 2,5-HMA see #36
[78108-18-6] a-Et-MPEA see #110
[7451 6-50-0] N,N-Me-2,5-HMPEA see #22
[78335-85-0] 3-TM see #91
[74516-51-1] N,N-Me-2,5-HMA see #36
[78335-86-1] 3-TIM see #72
[74626-42-9] 3-TFMDMAP see #92
[78335-87-2] 4-TIM see #72
[74698-36-5] MDPR #86
[78569-00-3] Tyramine # 126
[74698-37-6] MDIP see #77
[78950-78-4] PAT # 1 05
[74698-38-7] MDBU see #77
[78950-80-8] MHAT see # 1 05
[74698-40-1 ] MDAM see #77
[79002-10-1] dl-TMA-4 # 1 20
[74698-41-2] MDHE see #77
[79440-50-9] m-DOM see #60
[74698-42-3] MDCM see #77
[79440-51-0 l a-DOT see #3
[74698-47-8] MDOH #84
[79440-52-1 ] m-DOT see #3
[74698-48-9] MD MEO see #77 [79482-02-3] a-[11C]-PEA # 1 07
[74698-49-0] MDBA see #77 [79563-88-5] a-[1 4C]-DMPEA #49
[74698-50-3] MDDMA #80 [ 80300-09-0l R-PAT # 1 05
[74698-51-4] MDDEA see #77 [ 80300-10-3] S-PAT # 1 05
[74719-64-5] a,f3-[ d ]-GEA #69 [80535-73-5] ONE see #93
4
[74938-11-7] 7-HO-PPAT see #36 [80787-62-8] a-[1 4C]-Tyramine # 1 26


[ 80888-36-4] 'ljJ-DOM see #60 [85226-30-8] a, f3,N-[ d6]-DMPEA #49
[811 29-32-0] DMMCPA see #41 [85258-13-5] F-2 see #66
[811 77-1 0-8] DMMCPA see #41 [ 85336-78-3] a-[1 4C]-PEA # 1 07
[ 811 85-33-3] PHAT see # 1 05 [85474-76-6] HO-mCPP see #24
[811 85-34-4] BHAT see # 1 05 [85479-74-9] f3-[ d2 ]-DMPEA #49
[811 85-35-5] iPHAT see # 1 05 [ 85563-10-6] 2,5-IDNNA see #58
22
[811 85-37-7] PEAT see # 1 05 [85563-11-7] 2,5-1 IDNNA see #58
[ 811 85-39-9] BBAT see # 1 05 [86029-48-3] 2,3-MDA see #77
[81262-69-3] MDMP see #77 [86188-24-1 ] ThEA see #67
[81262-70-6] R-(-)-MDMA #82 [86188-25-2] a-Me-3-ThEA see #67
[81541-01 -7] a,a-[ d2 ]-Tyramine #126 [ 86423-58-7] FEA #67
[81541 -02-8] a, f3-[ d2 ]-Tyramine #126 [86456-97-5] EMPEA see #49
[81541-03-9] a, f3-[ d2 ]-PEA # 1 07 [86917-28-4] f3, f3-[ d2 ] -TMPEA-2 #124
[81587-01-1] 5-[d]-GEA #69 [86917-32-0] 3,6-[ d2 ]-TMPEA-2 #124
[81601-11-8] S-PMeA #111 [87059-52-7] 2-MA #74
[81601-12-9] R-PMeA #111 [87059-53-8] PMA #110
[81601-14-1] S-PMeA #111 [87059-54-9] 3-MA #75
[82698-36-0] f3-[ d]-TMPEA-2 #124 [87059-55-0] 2,3-DMA #34
[82698-37-1 ] a,a-[d2 ]-TMPEA-2 #124 [87059-56-1] 2,4-DMA #35
[82698-38-2] a,a, f3-[ d3]-TMPEA-2 # 124 [87059-57-2] 2,5-DMA #36
[82698-39-3] a,f3-[d2 ]-TMPEA-2 #124 [ 87059-58-3] 2,6-DMA #37
[82698-45-1] a,f3-[ d2 ]-TMPEA-2 #124 [87059-59-4] DMA #38
[82789-71 -7] 4,2,6-DOB see #52 [ 87059-60-7] TMA-3 #119
[82801-81 -8] MDE #81 [87059-61-8] TMA-4 # 1 20
[ 82830-43-1] (+)-DOF #57 [ 87059-62-9] TMA-5 #121
[ 82830-45-3] R-(-)-DON #61 [87059-63-0] TMA-2 #118
[82830-50-0] DOI-Ac see #58 [87059-64-1 ] TMA-6 #122
[ 82864-06-0 l R-(-)-DOI #58 [ 87059-65-2] TMA #117
[ 83008-35-9] 2,5,6,a,f3-[ d5 ]-GEA #69 [87059-66-3] 3-MPEA #101
[83329-24-2] f3-Me-2C-2 see #98 [87059-67-4] 4-MPEA # 1 02
[83732-75-6] NMEA see #67 [87059-68-5] 2,3-DMPEA #46
[ 84055-86-7] 4C-Me0 see #118 [87059-69-6] 2,4-DMPEA #47
[84145-43-7] MeOPP #88 [87059-70-9] 2C-H #22
[84713-35-9] Tyramine # 126 [87059-71 -0] 2,6-DMPEA #48
[84910-90-7] 2-TOM see #3 [87059-72-1] DMPEA #49
[84910-93-0] 5-TOET see #56 [87059-73-2] 3,5-DMPEA #50
[84910-95-2] 5-TOMSO see #60 [87059-74-3] IM #72


[87059-76-5] TMPEA-2 #124 [90109-46-9] 4-TSB see #91
[ 87059-78-7] Mescaline #91 [90109-47-0] 4-TME see #91
[87096-79-5] a,a- [ d2 ]-Mescaline #91 [90109-50-5] TE see #91
[87258-67-1 ] [d ] -DMAP #40 [90109-52-7] 4-TASB see #91
5
[87394-70-5] EHAT see # 1 05 [90109-53-8] 4-T-TRIS see #91
[87394-81-8] MMAT see # 1 05 [ 90109-55-0 l TP see #27
[ 87394-83-0 l EEAT see # 1 05 [90109-57-2] TB see #91
[87620-08-4] a,13-[ d ]-PEA # 1 07 [90109-62-9] SB see #91
4
[87790-87-2] 2,3-EMPEA see #46 [90109-63-0] TRIS see #91
[87920-96-5] 3,5-DMA #39 [90132-30-2] ASB #8
4-(C[dJ 0)-2,4- [90132-31-3] ME see #91
[88204-73-3] #47
DMPEA
[90132-33-5] MP see #91
[88204-74-4] 3-(C[d3 ]0)-DMPEA #49 [90132-35-7] 3-TME see #91
[88441-07-0] 2C-CN see #55 [90132-38-0] 3-TE see #91
[88441-11-6] 2C-CA see #55 [90132-40-4] 5-TME see #91
[88441-14-9] 2C-C #19 [90132-48-2] 5-TASB see #91
[88441-15-0] 2C-C #19 [90132-49-3] 3-TASB see #91
[88753-12-2] DONMM see #61 [90132-52-8] 3-TSB see #91
[88753-19-9] MePAA see # 1 06 [90132-54-0] 3-T-TRIS see #91
[89556-64-9] DOIB see #60 [90485-24-8] 5-Br-DESMETHYL see #29
[89556-69-4] DOSB see #60 [90765-58-5] 13-Me-HPEA see #71
[ 90000-40-1 ] a-Me-NEA see #67 [91012-27-0] MDA #77
[90064-52-1 ] 2,5-1 3 1IDNNA see #58 [91240-37-8] THA see #117
[ 90064-53-2] 2,5-1 3 1IDNA see #58 [91252-21-0] 13,2-MHPEA-3 see #47
[ 90064-54-3] 2,5-1 3 1INiPrA see #58 [91252-41-4] 13-H0-3,5-DMPEA see #50
[ 90064-55-4] 2,5-1 3 1INCPMA see #58 [91252-61-8] DES-TMPEA-6 see #122
[90064-56-5] 2,5-1 3 1INHeA see #58 [91330-07-3] 3-MTA see # 1 03
[90064-57-6] 2,5-1 3 1INDoA see #58 [91339-14-9] 13-Me-N-Et-PEA see # 1 07
[ 90064-59-8] 2,5-1 3 1INAA see #58 [91340-28-2] DMA #38
[ 90064-60-1 ] 2,5-1 3 1INHA see #58 [91341 -37-6] MMTA see # 1 03

[91552-82-8] 4-tBuPEA see # 1 02
[90064-61-2] 2,5-1 3 1INCNMA see #58
[91553-50-3] N-Et-2-MA see #74
[ 90064-62-3] 2,5-1 3 1IDMAPA see #58
[9181 9-04-4] MHMC see #92
[ 90064-63-4] 2,5-1 3 1INNEA see #58
[92015-18-4] 3,4,5-BMM see # 1 8
[90064-64-5] 2,5-1 3 1IDMNiPrNMeA see #58 [ 92058-62-3] 2-NH2-4,5-DMA see #118
[90064-67-8] 2,5-1 3 1INMeOEtA see #58 [92206-37-6] BEATRICE #11
[90083-1 8-4] 2,5-1 3 1INHeNMeA see #58 [ 92279-85-1] homo-MD MA #83


[ 92282-59-2] R-BEATRICE #11 [98537-37-2] BOH #15
[92286-71-0] 2-MTA see # 1 03 [98537-38-3] BOD #14
[92322-94-6] N-mor-2-MA see #74 [98537-39-4] BOB #13
[92330-91-1] N-Bu-2-MA see #74 [98537-40-7] BOM #16
[92400-90-3] 13, 13-[ d2 ]-Tyramine #126 [98537-41-8] BOD #14
[ 92502-36-8] METHCATH #92 [98537-42-9] BOB #13
[ 93023-05-3] 3,5-DMPEA #50 [98985-53-6] [1 5N]-Tyramine # 126
[93309-51-4] N-Pr-PMA see #111 [99180-14-0] 3,5-Br-4-MPEA see #91
[93675-25-3] 3-MMA see #75 [99254-51-0] 2-1-5-MA see #36
[93675-26-4] N-Me-2,3-DMA see #34 [99275-26-0] DMPEA #49
[93675-27-5] 2,4-DMMA see #35 [99355-77-8] F #66
[93675-28-6] N-Me-2,6-DMA see #37 [99355-78-9] F #66
[93675-30-0] N-Me-3,5-DMA see #39 [99540-14-4] N,N-Me-3-MA see #75
[93675-31-1] N-Me-TMA-3 see #119 [99632-42-5] DOI #58
[93675-32-2] N-Me-TMA-2 see #118 [99632-47-0] N-Pr-DOB see #52
[ 936 75-33-3] N-Me-TMA-6 see #122 [99632-51-6] 4-Br-2-MA see #35
[93675-34-4] N-Me-TMA see #117 [ 99665-04-0 l S-(+)-DOI #58
[93721-06-3] N-iBu-2-MA see #74 [ 99665-05-1] S-DOI #58
[93865-44-2] PZAP see #40 [ 99985-96-3] AcO-MePEA see #71
[94001-1 7-9] GEA #69 [ 100009-75-4] IM #72
[ 94600-00-7] a-[14C]-Mescaline #91 [ 100098-95-1] GEA #69
[ 94640-33-2] DEA see #38 [ 1 00131-59-7] 13-H0-3,4-MePEA see #43
[94753-97-6] PHA # 1 09 [ 1 00131-85-9] a-Et-4-HPEA see #110
[94783-21 -8] DESMETHYL #29 13-HO-N,N-Me-3,5-
[1 00252-59-3] see #50
DMPEA
[94784-92-6] MTA # 1 03
[ 100868-39-1 ] a-Me-TH-FEA see #67
[951 72-73-9] MDA #77
[1 00874-90-6] 4-HePEA see # 1 02
[95864-22-5] 13-[3H]-DMPEA #49
13-[dJ -PEA
[ 100966-45-8] N,N-Et-2-MA see #74
[95864-24-7] a-[ 3H]-DMPEA #49
[101104-91-0] N-fur-2-MA see #74
[95864-27-0] # 1 07
[95864-31-6] 13-[ d2 ]-4-MPEA # 1 02 [101153-74-6] 13-[ d2 ]-PEA # 1 07
[95864-32-7] 13, 13-[ d2 ]-Tyramine # 1 26 [101425-96-1] N-He-2-MA see #74
[97289-40-2] GEA #69 [101468-37-5] R,R-cis-DMCPA #41
[ 97289-45-7] 4-MPEA # 1 02 [ 101625-35-8] 6,7-MDAT see #77
[97561-43-8] a-Me-3-NEA see #67 [101 787-05-7] 2,4-DEPEA see #47

[98277-97-5] TH-FEA see #67 [101 787-06-8] 6-Me-2,4-EMPEA see #122
[98486-68-1 ] a,N-Me-TH-FEA see #67 [101 863-62-1 ] 6-Me-2,4-DEPEA see #122
[98537-36-1] BOM #16 [102145-22-2] 2,4-DNNA see #35

-

22
[ 1 02145-23-3] 2,4-1 IDNNA see #118 [ 1 0631 0-52-5] N-iPr-MDPEA see #85
[1 02321 -77-7] DMAP #40 [ 106868-44-4] 2,4-H0-5-AA see #118
[1 02415-94-1] [1 3N] -PEA # 1 07 [1 07271-31-8] N,N-Me-DOB see #52
[ 103664-98-8] homo-MD A #78 [1 07326-31-8] DMPEA #49
[ 103664-99-9] homo-MD A #78 [1 0741 0-1 9-5] 2,3-MMeMMA see #34
[1 03882-47-9] R-BDB -�---,·--- -�--·--
#9
·--------·-
[107447-03-0]
---�- ·----··--
BDB #9
[ 1 03882-48-0 l S-BDB #9 [1 07778-20-1 ] METHCATH #92
[ 103882-49-1 ] R-(-)-MBDB #76 [1 08013-35-0] 2,4,6-TRIS see #122
[ 103882-50-4] S-(+)-MBDB #76 [ 108089-01-6] a,a-[ d2 ]-3-MPEA #101
[1 03882-51-5] R-(-)-BDB #9 [108123-62-2] TEtPEA-6 see # 1 23
[1 03882-52-6] S-(+)-BDB #9 [1 08248-08-4] homo-MD MA #83
[1 03882-53-7] R-(-)-MBDB #76 [ 108479-33-0 l DMAP #40
[ 1 03882-54-8] S-(+)-MBDB #76 [3-HO-N-Me-2,5-
[1 08746-19-6] see #36
DMA
[ 1 04178-02-1] homo-f3,N-MePEA see # 1 07
[108746-20-9] f3 ,2-H 0-N-Me-5-EA see #36
[ 104338-26-3] N-Me-2-MPEA see # 1 00
[1 08748-74-9] f3-[ d]-Tyramine # 1 26
[1 04371 -22-4] S-( + )-3,5-DMA #39
[1 08774-13-6] 2C-H #22
[1 04371-23-5] S-( + )-3,5-DMA #39
[1 08774-54-5] DES METHYL #29
[ 1 04958-31-8] 2C-3b see #99
[1 08873-47-8] f3-HO-N-Pr-PMA see #110
a,a,f3,f3-[ d ]-
[1 05233-20-3] 4 #126
Tyramine [ 1 08925-34-4] N-Me-MMDA-2 see #98
[1 05254-13-5] N-Me-DMeA see #42 [ 1 09035-91-8] 4-Me-2,6-DMPEA see # 1 22
[1 05338-61-2] 2,3-MMeMA see #34 [ 109035-92-9] MEPEA #90
[ 105339-86-4] N-Me-2,3-EMPEA see #46 [ 109036-63-7] 4,6-Me-2-MPEA see # 122
[ 105363-36-8] 2,6-DNNA see #37 [ 109036-65-9] 6-Me-2,4-DMPEA see # 122
[ 105363-38-0 l 3,5-DNNA see #39 [1 09036-67-1 ] 2,4-EMPEA see #35
2 22
[1 05363-41-5] 2,4-1 5IDNNA see #118 [ 109421 -50-3] 3,5-1 IDNNA-4 see # 1 1 7
2
[ 1 05363-42-6] 2,6-1 5lDNNA see #121 [109442-31-1] MD PEA #85
2
[ 105363-43-7] 3,5-1 5IDNNA-2 see # 120 [ 1 09469-29-6] 2,6-Me-4-EPEA see #122
22
[ 105363-44-8] 2,6-1 IDNNA see #121 [ 1 09471-03-6] 4,6-Me-2-EPEA see #122
22
[ 105363-45-9] 3,5-1 IDNNA-2 see # 120 [109881-35-8] (-)-a,N-DMMDBA #45
[ 105363-46-0l 2,6-IDNNA see #121 [1 09922-33-0] ( + )-a,N-DMMDBA #45
[1 05363-47-1] 3,5-IDNNA-2 see # 120 [110492-80-3] f3,2-HO-N-Me-5-MA see #36
[1 05371 -59-3] 2,4-IDNNA see #118 [11 0492-83-6] f3,2-H0-5-EA see #36
[ 1 05466-90-8] N,N-Me-2,5-DMeA see #42 [ 110556-08-6] f3,2-H0-5,N-DMeA see #36
[ 105466-92-0 l N,N-Me-3,2,6-DOB see #52 [110612-15-2] f3-H0-2-M-5-MeA
f---·
see #36
[ 105466-93-1 ] 2,4-FDNNA see #118 [111045-19-3] [1 3N]-DMPEA #49
2
[ 105652-59-3] f3-H0-2,5-DEA see #36 [111381-00-1] [1 51]-DOI #58


2 23
[111381-06-7] [1 s l]-DOI #58 [122419-40-3] 5-[1 1]-DOI #58
[112101-18-5] a,N,N-TMMDBA see #45 [123283-21-6] a-[1 3C]-DMPEA #49
[113038-79-2] Hordenine #71 [123431-31-2] DOC #54
[11 3358-79-5] PMeMA see #111 [123643-24-3] MPM see # 1 1 8
[113429-54-2] 5-PMMA #112 [1 23643-26-5] ALEPH-4 #5
[113527-37-0] MDSB see #77 [1 23830-49-9] Hordenine #71
a,a, j),2,3,5,6-[ d7] - [123830-50-2] Hordenine #71
[114076-86-7] # 126
Tyramine
[1241 54-09-2] DMPEA #49
[1141 67-06-5] R-(-)-DOB #52
[124206-65-1] N-iPr-PMA see #110
[114307-16-3] a-[14 C]-PEA # 1 07
[124399-99-1 ] 5,6-MDAT see #77
[114562-60-6] AMPH-OH see # 1 07
[124454-73-5] R-a-[d]-Tyramine #126
[114612-26-9] 5-MDE #81
[1 24454-75-7] 5-a- [d] -Tyramine #126
[11461 2-27-0] R-MDE #81
[1 24866-26-8] (+)-DMeA #42
[115121-90-9] DMAP #40
[ 124866-27-9] (-)-DMeA #42
[11 5923-74-5] 3-[1 4C]-mCPP #24
[125236-62-6] N-Et-3-TFMPEA see #63
[11 7208-67-0] MeOPP #88
[ 125438-42-8] 2,5-HMPEA see #22
[11 7652-27-4] HMMA see #33
homo-MDDMA
[ 125559-67-3] see #78
[11 7652-28-5] MHMA see #94 (HMDDMA)
[11 7772-42-6] R-2-MA #74 [ 125559-68-4] homo-MOE (HMDE) see #78
[ 11 7886-34-7] j),2-H0-5,N-MePEA see #22 [125559-69-5] homo-MD PR see #78
[ 11 8298-09-2] HHAT see # 1 05 [1 25903-45-9] DOHE see #60
[ 11 8828-79-8] a- [1 4C]-4-MPEA # 1 02 [125903-46-0] DOOC see #60
[119273-42-6] R-PAT # 1 05 [125903-47-1] DOPh3 see #60
[119273-43-7] 5-PAT # 1 05 [125903-49-3] DOCN #55
[1 20375-47-5] PEA # 1 07 [ 125903-50-6] DOCEP see #55
[121316-76-5] 5-(-)-DMAP #40 [ 125903-53-9] DOCEB see #55
[121649-01-2] DOEF see #60 [125903-56-2] DOCONHPr see #55
[121 649-04-5] DOEH see #60 [125903-57-3] DOOH see #118
[121 734-64-3] a-Me-MDBA see #45 [1 25903-69-7] DOF #57
[ 121 734-65-4] a,N-DMMDBA #45 [1 25903-74-4] DOCN #55
[121 734-66-5] a-Me-N-Et-MDBA see #45 [125926-1 8-3] DOCOE see #55
2
[121 734-67-6] a-Me-N-Pr-MDBA see #45 [12621 0-33-1 ] [1 s1]-2C-I #23
[121734-68-7] a-Me-N-iPr-MDBA see #45 [127755-12-8] PEA # 1 07
[12211 7-24-5] METHCATH #92 [ 128671 -19-2] N-CH2 [ 3 H] -MDMA #82
2
[1221 67-34-4] R-[1 5 1]-DOI #58 [128767-12-4] MBDB #76
2
[1221 67-35-5] 5-[1 5 1]-DOI #58 [129111-14-4] GEA #69
2
[ 12241 9-39-0] R-[1 3 1]-DOI #58 [129476-58-0] 4-EA see #110


[ 129476-60-4] 4-PA see # 110 [ 138556-75-9] 2-MDMOH see #82
[ 129556-97-4] 4C-3,5-DMPEA see #39 [ 138808-79-4] 6-MDMOH see #82
[ 129819-63-2] MDMEA see #77 [ 138889-33-5] MTC see # 103
[129819-64-3] MDMIPA see #77 [139102-1 8-4] 4-PrA see # 111
[129819-65-4] MD MPA see #77 [ 139102-20-8] 2,4-MMPEA see #47
[130313-17-6] MDBP #79 [ 139102-26-4] 4-Br-2-MPEA see #47
[ 130933-03-8] SF see # 1 7 [ 1 39102-29-7] 6-Br-2-MA see #37
[ 130933-09-4] B-SF #17 [ 141029-17-6] 3-TFMPEA see #63
[131889-58-2] [1 4C]-GEA #69 [141215-27-2] PAT # 105
[ 1 32741-82-3] 5,6-MDMAI see #77 [141725-81-7] 5-PCA # 106
[ 132785-03-6] [1 8F]-mTFMPP #116 [ 141 725-82-8] R-PCA # 106
[ 1 32912-56-2] N-pip-2-MA see #74 [ 142893-52-5] a-DON see #61
[133011-30-0] N-Et-MDPEA see #85 [144576-58-9] GEA #69
[ 133097-26-4] R-3,4-MMA #96 [ 145284-65-7] 6-MDOH see #82
[ 133097-27-5] 5-3,4-MMA #96 [145412-89-1 ] f)-H0-2,6-DMPEA see #48
[ 133097-28-6] 5-3,4-MMA #96 [ 146269-95-6] 3-DON see #61
[ 133097-29-7] R-3,4-MMA #96 [ 146285-46-3] a-Me-DESMETHYL see # 1 1 7
[ 133302-86-0] f),N,N-Me-4-MPEA see # 1 02 a-Me-3-
[ 146285-47-4] see # 1 1 7
DESMETHYL
[ 133787-66-3] EDMA see #65
[146724-75-6] ALEPH sulfone see #3
[ 133787-68-5] G-5 see #113
[ 146724-76-7] M(30P)M see # 11 8
[ 133787-69-6] 4T-MMDA-2 see #98
[ 134331 -05-8] PAT # 105 [ 146724-77-8] M(20P)M see # 118
[135014-36-7] oCPP see #24 [146849-92-5] 3C-E see # 1 1 7
[135014-37-8] mCPP #24 [ 147702-21 -4] a,f)-[ d2 ]-2-MPEA # 100
[ 135014-38-9] mCPP #24 [147702-22-5] a, f)-[ d2 ]-3-MPEA #101
[ 1 35014-39-0] mTFMPP #116 [ 147702-23-6] a, f)-[ d2 ]-PMeA # 111

[135014-40-3] mTFMPP #116 [147947-26-0] 3C-BZ see # 11 7
[135014-86-7] 3-EA #75 [149097-87-0] R-PAT # 1 05
[ 135795-90-3] MBDB #76 [149097-88-1] 5-PAT # 105
[ 136468-19-4] MMAI see #96 [ 149607-37-4] N-HO-TMA see #117
[ 136476-77-2] f)-[14C]-4-MPEA # 102 [150200-02-5] R-MHA #94
[ 136696-23-6] 7-[ 3H]-PAT # 105 [ 150200-03-6] 5-MHA #94
[ 136706-32-6] THMA-2 see # 11 8 [ 150200-06-9] R-MDPR #86
[ 136765-43-0] [d5 ]-MDMA #82 [ 150200-07-0] 5-MDPR #86
[ 136779-03-8] R-7-[ 3H]-PAT # 105 [151059-43-7] PEA # 107
[136779-04-9] 5-7-[ 3H]-PAT # 1 05 [ 151459-88-0l a-[1 3C]-Tyramine # 126
[ 138537-66-3] 5-MDMOH see #82 [151560-60-0] a-[11C]-Tyramine # 126


[151 920-03-5] 2-Br-4,5-MDA see #98 R-N-[11C]-Me-
[1651 72-59-8] #82
MDMA
[151920-04-6] 2-N02 -4,5-MDA see #98
[ 166820-00-4] 4,N-Me-2-MA see #35
[152089-63-9] a, j3-[ d2] -MDPEA #85
[166820-02-6] 4-1-2-MA see #35
[152089-67-3] a-[d]-MDPEA #85
[ 167394-39-0] EBDB see #77
[ 152089-68-4] a,a-[ d2 ]-MDPEA #85
[167394-40-3] MMBDB see #77
[152477-93-5] (C[ d ] ) -Mescaline #91
3 3
[167394-41-4] HOBDB see #77
[152610-69-0] R-METHCATH #92
[167394-42-5] homo-MDOH see #78
[ 152623-93-3] BF6AP see #77
[ 168699-63-6] 4,5-H0-2-AA see #118
[152624-03-8] BF5AP see #77
[168699-64-7] 2,5-HO-PAA see # 118
[153379-46-5] R-(-)-3,5-DMA #39
[ 168699-66-9] 2C-NH see # 124
[ 153506-18-4] 2-F-4,5-MDA see #98
[ 168699-69-2] 5-NH2-2,4-DMPEA see # 124
[153506-20-8] N-[11C]-Me-MDMA #82
[168699-72-7] 5-NH2-2,4-DMA see #118
[ 154306-45-3] MeOPP #88
[1 68783-21-9] BODM see #14
[ 1 55344-90-4] 5,6-MDAI see #77
[168783-22-0] BOBE see #14
[ 155638-80-5] N-Me-DOB see #52
[168783-23-1] BOPS see #14
[ 155638-82-7] 2C-B-M see #18
[168783-25-3] BOT see #14
[ 155639-23-9] 2C-B-MM see #18
[168783-26-4] BOI see #14
[155639-24-0] 2C-B-E see # 1 8
[168783-27-5] BON see #14
[155639-27-3] pip-2C-B see #18
[168783-38-8] BOE see #14
[155755-37-6] [1 5N]-PEA # 107
[168967-99-5] 2,3-MDMA see #77
[155831-43-9] 2-F-4,5-DMA see #118
[ 168968-00-1] 2,3-MDE see #77
[155831-44-0] 5-F-2,4-DMA see #118
[168968-03-4] 2,3-MDDMA see #77
[157333-16-9] j3-[1 3C]-DMPEA #49
[171415-32-0] mCPP #24
[157333-18-1] a-[1 3C]-DMPEA #49
[ 1 72518-54-6] a-Et-Lophophine see #73
[158721-63-2] DOBZ see #60
[1 72967-65-6] R-DHA #33
[159277-07-3] DOTFM #63
[159277-08-4] 2C-TFM #28 [1 77339-29-6] j),N,N-Me-3-MPEA see #101
[159277-12-0] DOTFM #63 [1 77971-34-5] R-(-)-3,5-DMA #39

[159277-13-1] 2C-TFM #28 [1 78485-02-4] ALEPH-2 #4
[159432-44-7] 5-1-2-MA see #36 [178557-10-3] B-SF #17
[ 159432-45-8] 3-1-PMA see #38
[178557-11-4] (±)-FLY #68
[ 159432-47-0] 5-1-2,4-DMA see #118
[178557-19-2] B-FLY #12
[159432-48-1 ] 3-1-2,6-DMA see #121
[1 78557-20-5] 2C-FLY see #68
[159432-50-5] 2-1-3,5-DMA see # 120
[160977-87-7] N-(C[d ] ) 2-DMAP #40 [1 78557-22-7] DOM-FLY see #68
3
[160977-88-8] R-METHCATH #92 [181425-74-1 ] DHEA see #33
---
[161121-04-6] R-DMA #38 [ 1 81485-30-3] HM-a-Et-PEA see #33


[ 1 81485-31-4] N-Me-a-Et-GEA see #49 [198226-60-7] a,a,3-Me-MPEA see #38
[ 1 821 89-03-3 J 2,5-DMA #36 [198821-67-9] Candi cine see #71
[ 1 82634-37-3] 4,5-MDAI see #77 [199527-10-1] R-DMA #38
[ 1 82634-38-4] 4,5-MDMAI see #77 [ 199527-11-2] S-DMA #38
[ 1 84473-66-3] I-SF see # 1 7 [200264-65-9] 2,3,6-MMB see # 1 8
[ 185562-00-9] ALEPH-2 #4 [ 200264-66-0 l 2,4,5-MMB see # 1 8
[ 186028-79-5] METHYLONE #93 [200264-67-1] 2,3,5-BMM see # 1 8
[1 86028-80-8] METHYLONE #93 [200264-68-2] 2,3,6-MBM see # 1 8
[ 1 86028-81-9] iPrONE see #93 [200264-69-3] 2,3,5,6-BMMB see # 115
[ 1 86028-82-0 l iBuONE see #93 [201162-24-5] [11C]-BEATRICE #11
[ 1 86028-83-1] sBuONE see #93 [201407-47-8] ETA see # 1 03
--
[ 1 86028-84-2] tBuONE see #93 [201407-50-3] IPTA see # 103
[ 1 86028-85-3] ALONE see #93 [201407-53-6] 6-B-IBF5AP see #77
[ 1 86028-86-4] PRONE see #93 [201407-54-7] 6-N02 -IBF5AP see --
#77
[ 186028-87-5] cPrONE see #93 [201407-55-8] 6-C-IBF5AP see #77
[ 188576-64-9] DOI #58 [201407-56-9] IBF5MAP see #77
[ 188852-00-8] 2,3-HMeMPEA see #34 [201407-57-0] IBF5AP see #77
[ 1 88852-01 -9] 2,3-HMeMMPEA see #34 [201474-93-3] PrONE see #93
[ 1 88852-10-0] 2,5-MMeA see #34 [204776-50-1] 2,3,5-DOB see #52
[1 88852-11-1] 2,3-HMeA see #34 [204916-89-2] 5-Me-MDA see #77
[1 88852-12-2] 2,3-HMeMA see #34 [ 207740-08-7] MBZM see # 11 8
[ 188852-13-3] 2,3-HMeMMA see #34 [207740-1 5-6] 2C-F see #20
[ 188852-25-7] 2-1-4,5-MDA see #98 [207740-16-7] ALEPH-7 #6
[ 188852-27-9] 2-1-4,5-MDMA see #98 [207740-17-8] 2C-B-2-Et0 see # 1 8
[ 188852-29-1 ] 2-1-4,5-MDDMA see #98 [207740-18-9] 2C-G see #114
------
[1 88852-35-9] 2-1-4,5-MDPEA see #98 [207740-1 9-0] 2C-G-3 see # 114
r-------..- -- f----
[191916-41-3] S-METHYLONE #93 [207740-20-3] 2C-G-5 see #114

[19191 6-42-4] EtONE see #93
f--
------�
[207740-21 -4] 2C-G-N see #114
[191916-43-5] DMONE see #93 [207740-22-5] 2C-P see #20
[191916-44-6] DEONE see-
#93
--
[207740-23-6] CPM see #91
1--
--- ·--- -
[194787-61-6] Me0-2C-ISF see # 1 7

[207740-24-7] 2C-T-2 #26
[ 194787-78-5] Me0-2C-2,6-IFLY see #68
[207740-25-8] 2C-T-4 see #25
f)-M-3,4-
[ 197504-48-6] see #29 [207740-26-9] 2C-T-7 #27
DESMETHYL
[ 197787-15-8] S-(+)-MDE #81 [207740-27-0] 2C-T-8 see #25
----·---- -
---------·
[207740-28-1] 2C-T-9 see #25
J!��9! ��4=-�L
[19801 7-93-5] R-MDOH #84 �-----·-- -··--
--
--- ---- �---- -

S-MDOH #84 [207740-30-5] 2C-T-13 see #25
___ -·---- - - ---- --·


[207740-32-7] 2C-T-17 see #25 [265323-73-7] DMPEA #49
[207740-33-8] 2C-T-21 see #25 [278183-65-6] F2-MDPEA see #85
[207740-36-1 J G-3 see #113 [ 288864-48-2] 2-MPEA # 100
[207740-37-2] G see #113 N,N-Me-2,3-
[301642-48-8] see #77
MD PEA
[207740-38-3] HOT-2 see #25
[301642-49-9] N-Et-2,3-MDPEA see #77
[207740-39-4] HOT-7 see #25
[301642-50-2] a,a-Me-2,3-MDPEA see #77
[207740-40-7] HOT-17 see #25
[301650-55-5] 4-MPEA # 102
[207740-41-8] MAL see #91
[308271 -86-5] Tyramine # 126
[207740-42-9] PE see #91
[319920-71-3] 2-Cl-4,5-MDMA see #98
[207740-45-2] 5-TOM see #3
[328529-93-7] R-(-)-MDE #81
[207740-46-3] MADAM-6 see #77
[330795-82-9] 4-MPEA # 1 02
[209064-25-5] PEA # 107
[330795-83-0] 4-MPEA # 1 02
[210708-1 5-9] HMEA see #33
[330795-84-1 ] 4-MPEA # 102
[214414-87-6] 3C-Al see #117
[ 330795-85-2] 4-MPEA # 102
[214414-88-7] FLEA see #84
[332012-16-5] R-(-)-FLY #68
[21 7635-05-7] METHCATH #92
[332012-1 7-6] S-(+)-FLY #68
[219919-55-8] Tyramine # 126
[332012-1 8-7] R-(-)-B-FLY #12
[219986-75-1 ] B-FLY #12
[332012-19-8] S-(+)-B-FLY #12
[219986-78-4] dl-B-DFLY #10
[332012-22-3] R-(-)-DFLY #32
[219986-80-8] (±)-FLY #68
[332012-23-4] S-(+)-DFLY #32
[219986-94-4] dl-B-DFLY #10
[332012-24-5] R-(-)-B-DFLY #10
[220491-69-0] K see #77
[332012-25-6] S-(+)-B-DFLY #10
[222022-54-0] DOAC see #55
[337464-36-5] 2,3-BDB see #77
[223923-44-2] 4C-2-MPEA see #74
[337464-37-6] 2,3-MBDB see #77
[223930-67-4] R-2-MA #74
[337464-38-7] 2,3-EBDB see #77
[223930-70-9] S-2-MA #74
[337464-39-8] 2,3-MMBDB see #77
[251321-76-3] R-PMMA # 112
[ 337464-40-1 ] PBDB see #77
[255732-51-5] R-ALEPH-2 #4
[337464-41-2] IPBDB see #77
[255732-52-6] R-ALEPH-4 #4
[343323-59-1] f3, f3-[3Hlz-DOM #60
[260809-94-7] dl-DFLY #32
[260809-95-8] 1-DFLY see #32 [344948-61-4] PEA # 107
[ 260809-96-9] DOM-DFLY see #32 [352422-1 5-2] HMMA see #33
[260809-97-0] 2C-DFLY see #32 [376580-97-1 ] MTEA see # 103
[260809-98-1] 2C-B-DFLY see #32 [378758-87-3] mTFMPP # 116
[260809-99-2] TFM-DFLY see #32 [ 422545-96-8] TH-NMEA see #67
[260810-05-7] DOFM see #60 [ 440124-92-5] DMPEA #49
[261 789-00-8] 2C-N see #20 [444289-41-2] 5-(-)-DMAP #40


[477904-62-4] G-N see #113 [634607-19-5] MTALA see # 1 03
[ 478243-09-3] MeOPPP see #92 [634607-20-8] MTDALA see # 1 03
[484024-82-0] 4-C[ d2 ]H-4-MPEA # 1 02 [634607-21-9] a-EMTPEA see # 103
[ 484024-83-1] 4-C[d3 ]-4-MPEA # 1 02 [634607-22-0] (+)-MTA # 1 03
[484024-84-2] [ d3 ]-Me0-3-MPEA #101 [ 634607-23-1] (-)-MTA # 1 03
[486459-02-3] 3-BMAP see #92 [ 639806-99-8] DMPEA #49
[ 486459-03-4] 4-BMAP see #92 [648957-40-8] 2C-T-3 see #25
[497239-34-6] Me-3,5-IFLY see #68 [648957-42-0] 2C-T-16 see #25
[501700-01-2] FEM see #29 [648957-44-2] 2C-T-19 see #25
[501700-02-3] F2 EM see #29 [648957-46-4] 2C-T-21 . 5 see #25
[ 501 700-03-4] F3EM see #29 [648957-48-6] 2C-T-22 see #25
[501700-06-7] 3C-FEM see #117 [648957-50-0] 2C-T-25 see #25
[501 700-07-8] 3C-F2EM see # 11 7 [648957-54-4] 2C-T-28 see #25
[501 700-08-9] 3C-F3EM see # 11 7 [648957-56-6] 2C-T-30 see #25
[501700-10-3] 3C-IB see # 117 [674368-62-8] MHAOH see #33
[501 700-11-4] 3C-P see #117 [674368-63-9] MHMAOH see #33
[501 700-12-5] 3C-IP see # 11 7 [ 674368-64-0 l DHMAOH see #33
[502659-23-6] B-PLY see #68 [ 677277-49-5] f3-HO-DOB see # 1 3
[ 502659-24-7] 2C-B-PLY see #68 [677277-53-1] f3-Me0-DOB see # 1 3
[502759-67-3] R-(-)-B-DFLY #10 [681160-71-4] 2C-T-2 #26
[502924-26-7] 2C-PLY see #68 [697731-15-4] (+)-DOF #57
[502924-27-8] PLY see #68 [708198-43-0] 5-TMA #117
[547736-90-3] MTMA see # 1 03 [714903-64-7] R,5-trans-(-)-DMCPA #41
[ 556053-68-0 l a,a-DMMDBA see #45 f3-H0-2-M-N-Me-
[717108-44-6] see #36
MeA
[557768-72-6] MTA # 103
[722550-56-3] 4C-2,3-DMPEA see #34
[590346-12-6] MDA #77
[ 625454-70-8] 5-METHCATH #92 [722550-57-4] 4C-2,4-DMPEA see #35
[627876-88-4] N-Me-N-Et-MDPEA see #85 [722550-58-5] 4C-2CH see #7
[ 627876-89-5] a-iPr-MDPEA see #77 [722550-59-6] 4C-TMPEA-3 see # 119
[ 627876-90-8] N-Pr-MDPEA see #85 [722550-60-9] 4C-TMPEA-6 see # 122
[627876-91-9] a-Et-MDA see #77 [725735-35-3] f3,N-Me-4-MPEA see # 102
[ 633290-70-7] DOYN see #60 [727732-11-8] N-Et-3-MPEA see #101
[ 633290-73-0] 2C-YN see #20 [730933-68-3] R-(-)-DFLY #32
[ 634607-13-9] MTDMA see # 1 03 [732945-89-0] a-[3H]-DMPEA #49
[ 634607-15-1] MTDEA see # 1 03 [733720-95-1] 2C-B-FLY see #68
[634607-16-2] MTPA see # 1 03 [733730-70-6] TFM-FLY see #68

[634607-1 7-3] MTDPA see # 1 03 [736109-11-8] 5-7-[ 3 H]-PAT # 1 05

-�·---- - --- -·- --

[736876-81-6] 4-C[d ]-DOM #60 [84901 0-80-8] 4C-T-7 see #3
3 -------
[737729-40-7] 7-[ 3H]-PAT # 105 [849186-61-4] MDPEA #85

[740759-57-3] j3-[ 3H]-DMPEA #49 [8491 86-62-5] MD PEA #85
[740790-11-8] --�
R-B-FLY #12 [84991 9-74-0] ALEPH-7 #6
[741616-71-7] S-2,3-DMA #34 [849919-75-1] ALEPH-19 see #3
[744974-27-4] R-2,3-DMA #34 [84991 9-76-2] ALEPH-S-amyl see #3
[754921-26-1 ] R-DOM #60 [849919-77-3] ALEPH-4 #5
[756225-27-2] BIS-TOM see #3 __@_4_9_9�7� 8-4] ALEPH-S-PhEt see #3
[756418-21-0] S-DOC #54 [849919-79-5] 4C-T-2 see #3
[756816-57-6] (-)-MTA # 1 03 [849919-88-6] N-Me-ALEPH see #3
[757899-75-5] BAH d2 ]-4-MPEA # 1 02 [84991 9-89-7] N-Me-ALEPH-2 see #3
[762209-19-8] R-7-[ 3H]-PAT # 1 05 [84991 9-90-0] N-Me-ALEPH-7 see #3
[765846-80-8] a-[11C]-DMPEA #49 [849919-91-1] N-Me-4C-T see #3
[765898-09-7] (+)-MTA # 1 03 [849919-92-2] N-Me-4C-T-2 see #3
[766498-58-2] S-B-FLY #12 [849919-93-3] N-Me-4C-T-7 see #3
[769911-33-3] S-(+)-FLY #68 [850140-15-7] 2C-T-7 #27
[770733-79-4] a, f)-[3 HkDOB #52 [851222-90-7] GEA #69
[773790-48-0] TMCPA see #41 [854168-07-3] f)-H0-2,5-DEPEA see #22
[773790-50-4] R-DOC #54 f)-HO-N-Me-2,5-
[8541 78-50-0] see #22
DEPEA
[779279-63-9] 2-TOET see #56
f),5-HO-N-Me-2-
[780028-37-7] R-(-)-FLY #68 [8541 79-26-3] see #22
MPEA
[787538-82-3] S-(+)-DFLY #32
[854685-37-3] 2,5-DMA-f)k see #36
[788100-96-9] 5-DES-Me-DOM see #60
[ 854685-49-7] 2,5-DMMA-f)k see #36
[788775-45-1] R-PMeA # 111
[854908-22-8] N,N-Me-DEPEA see #49
[801201 -30-9] a, f)-[ 3HkGEA #69
[855271-83-9] f)-H0-2-M-5-MePEA see #22
a-[ 14C]-
[802035-74-1 ] #29 [855383-01-6] PEA # 1 07
DES METHYL
a, f)-[3Hk [ 855383-02-7] PEA # 107
[ 802035-75-2] #29
DESMETHYL [855388-59-9] 4-MPEA # 1 02
[827611-18-7] 4-EtO-METH ·-
see # 110 [ 855388-60-2] 4-MPEA # 102
[827611-21-2] 4-EtO-a-EtPEA see # 110 [855395-37-8] 3-MPEA #101
[827611-22-3] 3-Me-PMMA see #38 [ 855400-90-7] N-Bu-PHA see #110
[827611 -24-5] 3-Me-a-Et-MPEA see #38 [855632-40-5] a-[ 14C] -4-MPEA # 102
[827611-28-9] f)-Me-3-MMA see #75 [855635-29-9] 6-Me-MDA see #77
[827611 -30-3] f)-Me-PMMA see #112 N-Me-2,5-DEPEA-
[855942-20-0] see #22
[844888-61-5] 2,5-1'CIDNA see #58 f)k
[ 844888-62-6] 2,5-11CIDNNA see #58 [856814-48-7] 2,5-DEA-f)k see #36
[ 844888-63-7] 2,5-IDNA see #58 [ 856822-70-3] 4-MPEA # 1 02

--

[ 856822-73-6] 2-MPEA # 1 00 [861006-97-5] N,N-Me-2-EPEA see # 100
[ 856823-05-7] TMA #117 [ 861006-98-5] N,N-Me-3-EPEA see #101
[856823-11-5] Mescaline #91 [ 861007-05-8] 3,4,6-Me-2,5-DMPEA see # 1 08
[856943-52-7] FEA #67 [861007-48-9] PFMA see # 106
[857361-89-8] N-Me-3-ThEA see #67 [ 861007-58-1 ] f3-Me-N-E t-4-MPEA see # 102
[857361-90-1] a,N-Me-3-ThEA see #67 [861007-60-5] DMeA #42
[857542-51-9] f3,2-H0-5,N-DMeA see #36 [861007-75-2] 4-0PEA see # 1 02
[857542-53-1] f3,2-H0-5-MePEA see #22 [861007-76-3] 4-NPEA see # 102
[857543-23-8] f3,2-H0-5-MeA see #36 [ 861007-85-4] N,N-Me-2-MPEA see # 100
[857560-60-2] 2-H0-5-MPEA-f3k see #22 [861008-09-5] N,N-Me-4,3-EMPEA see #49
[857560-64-6] 2-H0-5-EPEA-f3k see #22 [861008-11-9] N,N-Me-3,4-EMPEA see #49
2-HO-N-Me-5-EPEA- [861039-93-2] 2,6-DMPEA #48
[857566-16-6] see #22
f3k
[861078-07-1] DEE see #49
5-HO-N-Me-2-
[857566-48-4] see #22 [ 861078-09-3] f3-HO-EMPEA see #49
MPEA-f3k
[869277-00-9] S-METHCATH #92
[85761 8-30-5] 2-H0-5,N-MePEA-f3k see #22
[869277-04-3] S-METHCATH #92
N,N-Me-2,5-DMPEA-
[857618-59-8] see #22 [871228-31-8] S-METHCATH #92
f3k
[857755-64-7] f3,2-H0-5-EPEA see #22 [871228-33-0] S-METHCATH #92
[857767-21-6] Hordenine acetate see #71 [871228-34-1 ] S-METHCATH #92
[857982-44-6] DMAP #40 [871228-35-2] S-METHCATH #92
[857983-04-1] 2-HO-N-Me-5-EA-f3k see #22 [872679-98-6] R-MDDMA #80
[859843-14-4] 2,3,5,6-[ d ] -mTFMPP #116 [872679-99-7] S-MDDMA #80

4
[859932-61-9] MD PEA #85 [872810-48-5] EMA see #38
[860003-91-4] BEDA see #97 [876132-12-6] MeOPP #88

[ 860003-93-6] a-Me-3-FEA see #67 [876486-72-5] I-TRIS see #72
[860003-94-7] 4-Br-a-Me-ThEA see #67 [878794-34-4] PMeA #111

[860003-95-8] 5-Br-a-Me-ThEA see #67 [882302-55-8] 2-MMA-f3k see #74
[ 860003-96-9] 5-Br-a-Me-FEA see #67 [884329-98-0] a,a-[ d2 ]-4-MPEA # 1 02

[860409-50-3] METHCATH #92 [885067-88-9] F2 -MDPEA see #85
f3,2-HO-N-Me-5- [892247-47-1] GEA #69
[860510-57-2] see #22
EPEA
[910382-26-2] 2,4,5-DOET see #56
f3,2-HO-N-Me-5-
[117342-28-6] see #22 [910393-51-0] F2-MDA see #77
MPEA
[910404-30-7] TMeA-2 see # 1 23
[860511-14-4] f3,2-H0-5-MPEA see #22
see #22 [912627-99-7] Ring [d5 ]-PEA # 1 07
[860538-07-4] 2-M-5-MePEA-f3k
[860538-08-5] 2-H0-5-MePEA-f3k see #22 [913701-64-1] mCPP #24
�
[ 860538-19-8] 2,5-DMPEA-f3k see #22 [914800-78-5] F2-BDB see #9
[861006-36-2] 2-BA see #74 [914800-81 -0] F2 -MDMA see #82

-- --- ·- -------� --

CAS # Name Entry#

[914800-82-1 ] F2-MDE see #81
[914800-83-2] F2-MBDB see #76
[916177-15-6] HMMC see #92
[919797-19-6] INBMeO see #58
[919797-25-4] INBMDO see #58
[923013-67-6] 2C-E #21
[923587-27-3] HMePEA #70
[924281-00-5] Tyramine # 126
[934991-33-0] pCPP see #24
[943744-15-8] S-MTA # 1 03
[ 943816-61-3] S-MTA # 1 03
[ 944386-63-4] 2,3,5,6-[ d ]-Tyramine # 126
4
[952006-71-2] 1.11-2C-T-4 see #25
[952006-95-0] 2C-T-15 see #25
[952016-51-2] F-22 see #66
[952016-59-0] IRIS see #60
[952017-05-9] PROPYNYL see #91
[959219-61-5] N-Me-3-EA see #75

419
" . . . there are some researchers - doctors - who are giving this
kind of drug to volunteers, to see what the effects are, and
they're doing it the proper scientific way, in clean white hospital
rooms, away from trees and flowers and the wind, and they 're
surprised at how many of the experiments turn sour. They 've
never taken any sort of psychedelic themselves, needless to
say. Their volunteers - they're called 'subjects, ' of course - are
given mescaline or LSD and they 're all opened up to their
surroundings, very sensitive to color and light and other
people's emotions, and what are they given to react to ? Metal
bed-frames and plaster walls, and an occasional white coat
carrying a clipboard. Sterility. Most of them say afterward that
they 'll never do it again. "
- Alexander Shulgin
A PPENDIX A
ADDITIONAL NOTES ON
IU PAC NOMENCL ATURE
Additional notes on IUPAC nomenclature,
Appendix A
with s p ecial reference to novel ring structures.
The IUPAC approach t o naming o f organic compounds assures a unique, unambigu

ous name for every chemical structure, and a single structure for every name. However,
since these unique names arise from very general rules, relationships between allied com
pounds, and the actual structures arising from some names, may at times create some
consternation. This becomes particularly acute when minor modifications create structures
with different levels of nomenclatural precedence, and in the creation of novel ring sys
tems. The following examples are offered for illustration, in the hope that they can guide
interpretation.
As shown in the Introduction, phenethylamines and amphetamines are generally named

as phenyl derivitives of ethanamine or propanamine; numerical location of substituents
on the ring is indicated relative to the position of the side-chain attachment, in most cases
labeled as the "l" carbon of the ring (Figure A.la) . Changes in the substituent groups,
however, may create a new functional group, with higher nomenclatural precedence in
the IUPAC system, as shown in Figure A.lb. Here, removal of the 5-methoxy methyl from
DOM to create the metabolite 5-DES-Me-DOM also creates a phenol moiety. The IUPAC
0}: O}:
name primarily stems from this structure, and the numerical location of the remaining
funtional groups shifts accordingly.
6 6
H 3C0 1 N H2 HO NH2
I
s
�
1
� b. 5-Des-Me-DOM
a. DOM ,,,;::. 4 CH3
4 CH3 2
:-
2 (see DOM,
( #60) H 3C OCH3
H3C OCH3 #60) 3
1 -(2,5-dimethoxy-4-methylphenyl) 5-(2-aminopropy 1)-4-methoxy-2-

propan-2-amine methylphenol
Figure A . 1 . Demethylation converts a phenylaminopropane to an aminopropyl phenol.

Note the direction of substituent numbering in 5-DES-Me-DOM.
Numerous phenethylamines with additional carbon rings fused to the aromatic phenyl
group are known, and include both simple alkyl rings and bridged rings (Figure A.2);
substituent numbering procedes such that each has the lowest number possible, and func
tional groups are addressed alphabetically.
a. DOMAD
H 3 CO
(see DOM, b. G-6
8
#60) (seeTeMA,
# 1 13)
2
OCH 3
3
5,8-dimethoxy-6-methy1-1,2-dihydro 1 -(5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-
naphthalen-2-amine ethanonaphthalen-6-yl)propan-2-amine
Figure A.2. Polycyclic phenethylamine derivitives with (a.) simple fused,

and (b. ) fused and bridged rings.
Appendix A 423
Additional Notes on IUPAC Nomenclature
Rings with dissimilar atoms are termed heterocyclic, and introduce new names derived
from their fusion with the phenyl group (Figure A.3) . Ring numbering starts with a
heterocyclic atom, and procedes so that substituents have the lowest possible numbers
(Figure A.4).
1,3-dioxole benzene benzo[d] [l,3] dioxole
tetrahydrofuran benzene 2,3,6,7-tetrahydrobenzo

[ l ,2-b:4,5-b' ] difur an
Figure A.3. Terminology associated with fused heterocyclic rings.
MDA
( # 77 )
�CH3NH2
I
6
'-':: 5
� 4
}-- 0 3
lo
�CH3NH2
1 -(benzo[ d] [ l,3 ]dioxol-5-yl) l -( 7-bromo-5-methoxy-2,3-dihydrobenzo
propan-2-amine furan-4-yl )propan-2-amine
7 OCH3 2
EDA '-':: 6
I
( #6 5)
NH2
� 5
l
o
2 � 04
3 Br
3
1 -(2,3-dihydrobenzo[b] [ l,4 ] dioxin- l -(5-methoxy-2,3-dihydrobenzofuran- l -(8-bromobenzo[l,2-b:4,5-b '] difuran-
6 -yl)propan-2-amine 6-yl)propan-2-amine 4-yl)propan-2-amine
Figure A.4. Amphetamine derivitives with fused oxygen heterocyclic rings.
Finally, rings may be formed by closure between the a-carbon of the side-chain and what
would otherwise be considered the "2" carbon of the phenyl ring (Figure A.4), with either
one (aminoindanes) or two carbons (amninotetralines) between the a-carbon and the ben
zene ring. Once again, ring numbering procedes from one of the heterocycle atoms, as in
the previous examples.

Additional Notes on IUPAC Nomenclature
a. 4,5-MDAI
� 5 6
N H2 b. 5,6-MDAI
�
4
bxn- s
3Q I ,,.:;::.
(see MDA,
<
(see MDA, 6
}-- 0 1
2
10
# 77) # 77) N H2
�
7
8
w
5
7,8-dihydro-6H-indeno[ 4,5-d] 6,7-dihydro-5H-indeno[5,6-d]
4
x;o
[l,3]dioxol-7-amine [l,3] dioxol-6-amine
6
c.
3
6,7-MDAT 7 N H2
I ,,.:;::.
(see MDA, d. 5,6-MDAT s N H2
Q 6
30 I
(see MDA,
<
# 77) 8
# 77) 2
}.- 0 1 01
9 7
,,.:;::.
9 8
6,7,8,9-tetrahydronaphtho[l,2-d] 5,6,7,8-tetrahydronaphtho [2,3-d]

[l,3] dioxol-7-amine [l,3] dioxol-6-amine
Figure A.4. MDA-like compounds with aminoindane (a,b)

or aminotetralin (c,d) rings.
Appendix A 425
"Psychedelic drugs don't change you - they don't
change your character - unless you want to be
changed. They enable change; they can't
impose it... "
- Alexander Shulgin
A PPENDIX B
STATE L AW ON THE WEB
App endix B
Web Addresses for State Statutes on
Phenethylamine Psychedelics
In the United States the Controlled Substances Act defines the status of psychoactive
materials subject to regulation at the federal level (FR, 2007) . However, the states (and
District of Columbia) also promulgate similar, but not identical, lists of scheduled
substances. This Appendix lists the Internet addresses of sites posted by state (and D.C.)
justice and health departments where relevant statutes were found, as of late 2008. It is
important for researchers and clinicians to appreciate the status of materials they might
work with, and we have surveyed the federal and state statutes for the main entry
compounds in this volume using these resources. We have not attempted interpretation of
the federal analog substance subchapter (Title 21, Chapter 13, Subchapter I, Part B, § 813),
but suggest readers may need to research additional legal opinions on this ancillary code.
State URL
Alabama http: I I www.legislature.state.al.us I CodeofAlabama I 1975 I 50719 .htm
Alaska http: I I touchngo.com / lglcntr I akstats I Statutes / Titlell I Chapter71 I
Section1 50.htm
Arizona http: / / www.azleg.state.az.us / ars / 36 / 02512.htm
Arkansas http: I I www.arkleg.state.ar. us I NXT I gateway.dll I ARCode I title04016.htm I
subti tle04701 .htm I chapter04770.htm ?f=templates$fn=document-frameset.
htm$q=controlled % 20substances$x=Advanced #LPHit 1
California http: I I www.leginfo.ca.gov I cgi-bin / displaycode?section=hsc&group=llOOl-
12000&file=ll053-11058
Colorado http: / / www.michie.com / colorado / lpext.dll / cocode / 2c8c9 / 30e87 / 30£55 / 30£
62?f=templates&fn=document-frame.htm&2.0#JD_18-1 8-203
Connecticut http: I / law.justia.com / connecticut / codes / title2 l a / sec21 a-243.html (see
paragraph '£')
Delaware http: I I delcode.delaware.gov I title 16 I c047 I sc02 I index.shtml
Washington D.C. http: / / weblinks.westlaw.com / signon / default.wl?db=DC% 2DST&itemkey=
DCCODES48%2D902%2E04&newdoor=true&path=%2Ftoc%2Fdefault%2Ewl
&RS=WEBL8%2ElO&SP=DCC%2DlOOO&strRecreate=no&VR=2%2EO
Florida http: I I www.leg.state.fl.us / statutes I index.cfm?App_mode=Display_
Statute&Search_String=&URL=Ch0893 / SEC03.HTM&Title=-%3E2008-
%3ECh0893-%3ESection%2003 #0893.03
Georgia http: I I www.lawskills.com I code I ga I 1 6 I 13 I 25 I
Hawaii http: I I www.capitol.hawaii.gov I hrscurrent I Vol06_Ch0321-0344 I HRS0329 I
HRS_0329-0014.htm
Idaho http: / / www3.state.id. us / ids tat / TOC / 3702702KTOC.html
Illinois http: I I www.ilga.gov I legislation I ilcs I ilcs4.asp?DocN ame=072005700HArt%
2E+ Il&ActlD= 1941 &ChapAct=720&ChapterlD=53&ChapterName=CRIMIN
AL+OFFENSES&SectionlD=61078&SeqStart=2400&SeqEnd=4900&ActName
= Illinois+Controlled +Substances+ Act
Appendix B 429
Indiana http: I I www.state.in. us I legislative I ic I code I title35 I ar48 I ch2.html
Iowa http: I I www.legis.state.ia.us I, then use "Quick find" + "124.204 Schedule I"
to go to pdf
Kansas http: I I www.kslegislature.org I legsrv-statutes I getStatute.do ?number=2641 l
Kentucky http: I I www.lrc.state.ky.us / KRS I 218AOO I CHAPTER.HTM
Lousiana http: I I www.legis.state.la. us I lss_doc I lss_house I RS% SC40% SC Copy% 20
of%20RS% 2040% 20964% 20(rev%205).html
Maine http: I I www.mainelegislature.org / legis I statutes I 1 7-A / title17-Ach45sec0.
html
Maryland http: I I mlis.state.md.us / asp / web_statutes.asp?gcr&S-402
Masachusetts http: I I www.mass.gov I legis I laws I mg! I 94c-1 .htm
Michigan http: I I www.legislature.mi.gov I (S(az3pxyr2hetjjq45qejoc045)) I mileg.aspx?p
age=getobject&objectname=mcl-333-7212
Minnesota https: I I www.revisor.leg.state.mn.us I statutes I ?id=1 52.02
Missisippi http: / I www.mscode.com / free / statutes / 41 / 029 I 0113.htm
Missouri http: I I www.moga.mo.gov I statutes I cl00-199 I 195000001 7.htm
Montana http: I I data.opi.state.mt.us / bills I mea l 50 I 32 / 50-32-222.htm
Nebraska http: I I uniweb.legislature.ne.gov I laws I statutes.php?statute=s2804005000
Nevada http: / / www.leg.state.nv.us / nac / NAC-453.html #NAC453Sec510
New Hampshire http: I I www.gencourt.state.nh.us I rsa / html I xxx I 318-b I 31 8-b-mrg.htm
--see also--
http: I I www.dhhs.state.nh.us I DHHS I ATOD I controlled-substance.htm
New Jersey Legal status data provided by a correspondant
New Mexico http: I I law.justia.com I newmexico I codes I nmrc I jd_30-31-6-ca97.html
New York http: I I law.justia.com / newyork / codes I public-health / pbh03306_3306.html
North Carolina http: I I law.justia.com / northcarolina / codes I chapter_90 I gs_90-89.html
North Dakota http: / / www.legis.nd.gov / cencode / t19c03 1 . pdf
Ohio http: I I codes.ohio.gov I ore I 3719
Oklahoma http: I I oklegal.onenet.net / oklegal-cgi / get_statute?99 / Title.63 I 63-2-204.html
Oregon http: / / www.leg.state.or.us / ors / 475.html
Pennsylvania http: I I www.pacode.com I secure I data I 028 I chapter25 I s25.72.html
Rhode Island http: / / www.rilin.state.ri.us / Statutes / TITLE21 / 21-28 / 21-28-2.08.HTM
South Carolina http: / / www.scstatehouse.gov / code / t44c053.htm
South Dakota http: I I legis.state.sd. us I statutes I DisplayStatute.aspx?Statute=34-
20B&Type=Statute
Tennessee http: I I health.state.tn.us I Boards I Controlledsubstance I faq .shtml #Q2
Texas http: I I tlo2. tic.state. tx.us I statutes I docs I HS I content I htm I
hs.006.00.000481 .00.htm
Utah http: I I www.dopl.utah.gov I laws I 58-37. pdf
Vermont http: I I www.leg.state.vt.us I statutes I fullsection.cfm?Title=1 8&Chapter=084&
Section=04201

Virginia http: I / legl.state.va.us I cgi-bin / legp504.exe?OOO+cod+54. 1-3446
Washington http: / / search.leg.wa.gov I wslrcw I RCW%20% 2069% 20%20TITLE I RCW%20
%2069%20. %2050%20%20CHAPTER / RCW% 20%2069%20. % 2050%20%20
chapter.htm
West Virginia http: / / www.legis.state.wv.us / WV CODE I Code.cfm ?chap=60a&art=2 #02
Wisconsin http: / / www.legis.state.wi.us I Statutes / Stat0961 .pdf
Wyoming http: / / legisweb.state.wy.us I statutes I statutes.aspx?file=titles I Title35 /
T35CH7ARlO.htm
Appendix B 43 1
"There is a wealth of information built into us ...
tucked away in the genetic material in every one
of our cells ... without some means of access, there
is no way even to begin to guess at the extent and
quality of what is there. The psychedelic drugs
allow exploration of this interior world, and
insights into its nature. "
-Alexander T. Shulgin
A PPENDIX C
MASS S PECTR A
C.1

Appendix C
Phenethylamine Mass Spectra
Mass spectrometry, particularly when coupled to separation systems like gas or liquid
chromatography (GC / MS, LC / MS), has become one of the premier modern analytical
technologies. Compounds are vaporized into a high vacuum system, where a variety of
ionization methods can be used to break molecules into charged pieces, and detect these
unique fragmentation products to provide complimentary information on chemical struc
ture, molecular weight, and sample purity. The results very often allow unambiguous
identification with very small sample sizes. This has fostered the use of GC / MS and LC /
MS in clinical and forensic environments throughout the world. However, until the devel
opment of desktop computers in the 1980s, the organization and retrieval of spectral data
was often a manual process, and methods for comparing spectra were left to the individual
researcher.
Dr. Shulgin quickly adopted GC / MS and collected the mass spectra of many of the com
pounds he created, largely during his lengthy association with the Clinical Pharmacology
and Experimental Therapeutics Division of the University of California at San Francis
co. In this Appendix we have assembled 229 mass spectra from the Shulgin Laboratory,
photographically reproducing the majority from a binder affectionately referred to as the
"Spectral Atlas" (Figure C.l). This oversized album contained overlapped, taped-down
arrays of spectra, usually one hundred per page, arranged so that names could be quickly
scanned, and the columns folded back to reveal individual plots (Figure C.2). Large num
bers of infrared and NMR spectra were also included, that we hope to reproduce in the
future.
Previously unpublished spectra are indicated in each figure; early spectra photographed
from the "Atlas" are identifiable by the dot-matrix graphics of their plots. Thirty spec
tra were prepared for this volume from samples in the Shulgin reference collection; their
spectra can be discerned by the use of vector graphics. All spectra were collected with
detectors) with 70 eV electron impact ionization, with data collection utilizing HP I Agilent
Hewlett-Packard or Agilent benchtop GC / MS systems (with 5970 and 5972 mass selective
MSD Chemstation software. Some compounds in this appendix are not otherwise covered
(n.o.c.) in this book.
HP MS 8fll� . d;"scan··5ae;..10'&.e
u •ti '• .,.,..,_,.....,_c_.
.11.1;n"'""
�1� MS 9111J0.29a . d� Sc.ttn 1·211

HP MS -��d.. Seen. "'48; «..�
C .2
Appendix C 435
Mass Spectra Appendix
List of Mass Sp ectra of Selected

Psychedelic Phenethylamines and Related Com p ounds
# Code/Trivial Name IUPAC Name

1. A-2 1-(2,3,6-trimethoxyphenyl)butan-2-amine
2. N-Acetyl DMPEA N-(3,4-dimethoxyphenethyl)acetamide
3. N-Acetyl MDPEA N-(2-(benzo[d] [l,3]dioxol-5-yl)ethyl)acetamide
4. 2-AI 2,3-dihydro-lH-inden-2-amine
5. AL 2-(4-(allyloxy)-3,5-dimethoxyphenyl)ethanamine
6. ALEPH 1-(2,5-dimethoxy-4-(methylthio )phenyl)propan-2-amine
7. m-ALEPH (META-DOT) 1-(2,4-dimethoxy-5-( methylthio )phenyl)propan-2-amine
8. a-ALEPH (ORTHO-DOT) 1-(4,5-dimethoxy-2-(methylthio )phenyl)propan-2-amine
9. ALEPH-2 1-( 4-( ethyl thio )-2,5-dimethoxyphenyl)propan-2-amine
10. ALEPH-4 1-(4-(isopropylthio )-2,5-dimethoxyphenyl)propan-2-amine
11. ALEPH-6 1-(2,5-dimethoxy-4-(phenylthio )phenyl)propan-2-amine
12. ALEPH-7 1-(2,5-dimethoxy-4-(propylthio )phenyl)propan-2-amine
13. ALEPH-21 1-( 4-( (2-fluoroethyl)thio )-2,5-dimethoxyphenyl)propan-2-amine
14. Amphetmine 1-phenylpropan-2-amine
15. ARIADNE 1-(2,5-dimethoxy-4-methylphenyl)bu tan-2-amine
16. Asarone (E)-1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene
1 7. ASB 2-(3,4-diethoxy-5-methoxyphenyl)ethanamine
18. B 2-(4-butoxy-3,5-dimethoxyphenyl)ethanamine
19. BDB 1-(benzo[ d] [ 1,3]dioxol-5-yl)butan-2-amine
20. BEATRICE 1-(2,5-dimethoxy-4-methylphenyl)-N-methylpropan-2-amine
21. BIS-TOM 1-( 4-methyl-2,5-bis(methylthio )phenyl)propan-2-amine
22. BMA N-benzyl-N-methyl-1-phenylpropan-2-amine
23. BZP 1 -benzylpiperazine
24. 2C-B 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine
25. 2C-B-FLY 2-( 8-bromo-2,3,6, 7-tetrahydrobenzo[ l,2-b:4,5-b ' ]difuran-
4-yl)ethanamine
26. 2C-BIS-TOM 2-(4-methyl-2,5-bis(methylthio )phenyl)ethanamine
27. 2C-B-M 2-(4-bromo-2,5-dimethoxyphenyl)-N-methylethanamine
28. 2C-C 2-(4-chloro-2,5-dimethoxyphenyl)ethanamine
29. 2C-D 2-(2,5-dimethoxy-4-methylphenyl)ethanamine
30. CD3-DOM 1-(2,5-dimethoxy-4-trideuteromethylphenyl)propan-2-amine
31. 2C-D-5-ETO 2-(5-ethoxy-2-methoxy-4-methylphenyl)ethanamine
32. 2C-E 2-(4-ethyl-2,5-dimethoxyphenyl)ethanamine
33. 2C-E-5-ETO 2-(5-ethoxy-4-ethyl-2-methoxyphenyl)ethanamine
34. 3C-E 1-(4-ethoxy-3,5-dimethoxyphenyl)propan-2-amine
35. 2C-G 2-(2,5-dimethoxy-3,4-dimethylphenyl)ethanamine
36. 2C-G-3 2-(4,7-dimethoxy-2,3-dihydro-lH-inden-5-yl)ethanamine
37. 2C-G-5 2-(5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-6-
yl)ethanamine
38. 2C-G-N 2-(1,4-dimethoxynaphthalen-2-yl)ethanamine
39. 2C-H 2-(2,5-dimethoxyphenyl)ethanamine
40. 2C-I 2-(4-iodo-2,5-dimethoxyphenyl)ethanamine
41 . 2C-N 2-(2,5-dimethoxy-4-nitrophenyl)ethanamine
42. 2C-0-4 2-(4-isopropoxy-2,5-dimethoxyphenyl)ethanamine
43. 2C-P 2-(2,5-dimethoxy-4-propylphenyl)ethanamine
44. 3C-P 1-(3,5-dimethoxy-4-propoxyphenyl)propan-2-amine
45. CPM 2-(4-(cyclopropylmethoxy)-3,5-dimethoxyphenyl)ethanamine
46. 2C-Se 2-(2,5-dimethoxy-4-propylphenyl)ethanamine
47. 2C-T 2-(2,5-dimethoxy-4-(methylthio)phenyl)ethanamine

# Code/Triv. Name IUPAC Name

48. m-2C-T 2-(2,4-dimethoxy-5-(methylthio)phenyl)ethanamine
49. o-2C-T 2-(4,5-dimethoxy-2-(methylthio)phenyl)ethanamine
50. ip-2C-T 2-(2,6-dimethoxy-4-(methylthio)phenyl)ethanamine
51. 2C-T-2 2-(4-(ethyl thio )-2,5-dimethoxyphenyl)ethanamine
52. ip-2C-T-2 2-(4-(ethylthio )-2,6-dimethoxyphenyl)ethanamine
53. 2C-T-4 1-(4-(isopropylthio )-2,5-dimethoxyphenyl)propan-2-amine
54. ip-2C-T-4 2-( 4-(isopropylthio )-2,6-dimethoxyphenyl)ethanamine
55. 2C-T-7 2-(2,5-dimethoxy-4-(propylthio)phenyl)ethanamine
56. 2C-T-8 2-( 4-( ( cyclopropylmethyl)thio )-2,5-dimethoxyphenyl)ethanamine
57. 2C-T-9 2-( 4-( tert-butylthio )-2,5-dimethoxyphenyl)ethanamine
58. 2C-T-13 2-(2,5-dimethoxy-4-( (2-methoxyethyl)thio )phenyl)ethanamine
59. 2C-T-14 2-(2,5-dimethoxy-4-((2-(methylthio)ethyl)thio)phenyl)ethanamine
60. 2C-T-15 2-(4-( cyclopropylthio )-2,5-dimethoxyphenyl)ethanamine
61. 2C-T-16 2-(4-( allyl thio )-2,5-dimethoxyphenyl)ethanamine
62. 2C-T-17 2-(4-(sec-butylthio )-2,5-dimethoxyphenyl)ethanamine
63. R-2C-T-17 (R)-2-(4-(sec-butylthio)-2,5-dimethoxyphenyl)ethanamine
64. 2C-T-19 2-( 4-(butylthio )-2,5-dimethoxyphenyl)ethanamine
65. 2C-T-21 2-(4-((2-fluoroethyl)thio)-2,5-dimethoxyphenyl)ethanamine
66. 2C-TFM 2-(2,5-dimethoxy-4-(trifluoromethyl)phenyl)ethanamine
67. 4C-TMPEA-5 1-(2,3,6-trimethoxyphenyl) butan-2-amine
68. 4C-TMPEA-6 1-(2,4,6-trimethoxyphenyl)butan-2-amine
69. 2C-2-TOET 1-(4-ethyl-5-methoxy-2-(methylthio )phenyl)propan-2-amine
70. 2C-5-TOET 1 -(4-ethyl-2-methoxy-5-(methylthio)phenyl)propan-2-amine
71. 2C-2-TOM 1-(5-methoxy-4-methy1-2-(methylthio)phenyl)propan-2-amine
72. 2C-5-TOM 1-(2-methoxy-4-methy1-5-(methylthio )phenyl)propan-2-amine
73. Deprenyl N-methyl-N-(l-phenylpropan-2-yl)prop-2-yn-1-amine
74. DEONE 1-(benzo[ d] [ l,3]dioxol-5-yl)-2-( diethylamino )propan-1 -one
75. 2,4-DIPDMA 1-(2,4-diisopropoxyphenyl)-N,N-dimethylpropan-2-amine
76. 2,3-DMA 1 -(2,3-dimethoxyphenyl)propan-2-amine
77. 2,4-DMA 1 -(2,4-dimethoxyphenyl)propan-2-amine
78. 2,5-DMA 1-(2,5-dimethoxyphenyl)propan-2-amine
79. 3,4-DMA 1-( 3,4-dimethoxyphenyl)propan-2-amine
80. 3,5-DMA 1-( 3,5-dimethoxyphenyl)propan-2-amine
81. DMCPA 2-(2,5-dimethoxy-4-methylphenyl)cyclopropanamine
82. 2,6-DMDMA 1 -(2,6-dimethoxyphenyl)-N,N-dimethylpropan-2-amine
83. DMDMPEA 2-(3,4-dimethoxyphenyl)-N,N-dimethylethanamine
84. 2,4-DMEA 1 -(2,4-dimethoxyphenyl)-N-ethylpropan-2-amine
85. 2,4-DMHA N-(1-(2,4-dimethoxyphenyl)propan-2-yl)hexan-1-amine
86. 2,4-DMIPA 1-(2,4-dimethoxyphenyl)-N-isopropyl propan-2-amine
87. 2,4-DMMA 1-(2,4-dimethoxyphenyl)-N-methylpropan-2-amine
88. 2,5-DMMA 1 -(2,5-dimethoxyphenyl)-N-methylpropan-2-amine
89. 2,4-DM-5-MTA 1 -(2,4-dimethoxy-5-(methylthio )phenyl)propan-2-amine
90. 2,4-DMPA N-(1-(2,4-dimethoxyphenyl)propan-2-yl)propan-1-amine
91. DMPEA 2-(3,4-dimethoxyphenyl)ethanamine
92. DOAM 1 -(2,5-dimethoxy-4-pentylphenyl)propan-2-amine
93. DOB 1-(4-bromo-2,5-dimethoxyphenyl)propan-2-amine
94. DOBU 1-(4-butyl-2,5-dimethoxyphenyl)propan-2-amine
95. DOET 1-(4-ethyl-2,5-dimethoxyphenyl )propan-2-amine
96. DOI 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine
97. DOIB 1-(4-isobutyl-2,5-dimethoxyphenyl)propan-2-amine
98. DOIP 1-(4-isopropyl-2,5-dimethoxyphenyl)propan-2-amine
99. DOM 1-(2,5-dimethoxy-4-methylphenyl)propan-2-amine
100. ip-DOM 1 -(2,6-dimethoxy-4-methylphenyl)propan-2-amine
Appendix C 437

101. DOPR 1-(2,5-dimethoxy-4-propylphenyl)propan-2-amine
1 02. DOSB 1-( 4-(sec-butyl)-2,5-dimethoxyphenyl)propan-2-amine
103. 4-EA 1 -(4-ethoxyphenyl)propan-2-amine
1 04. EDMA 1-(2,3-dihydrobenzo[ b] [ 1,4 ]dioxin-6-yl)-N-methylpropan-2-amine
105. Escaline 2-(4-ethoxy-3,5-dimethoxyphenyl)ethanamine
106. ETHYL-J 1-(benzo[ d] [ 1,3] dioxol-5-yl)-N-ethy lbutan-2-amine
107. ETHYL-K 1-(benzo[ d] [ 1,3] dioxol-5-yl)-N-ethylpentan-2-amine
1 08. ETHYL-L 1-(benzo[d] [l,3]dioxol-5-yl)-N-ethylhexan-2-amine
1 09. 4-EtO-METH 1-(4-ethoxyphenyl)-N-methylpropan-2-amine
110. EtONE 1-(benzo[d] [l,3]dioxol-5-yl)-2-(ethylamino)propan-1-one
111 . FLEA N-(1-(benzo[d] [l,3]dioxol-5-yl)propan-2-yl)-N-methylhydroxylamine
112. N-Formyl DMPEA N-(3,4-dimethoxyphenethyl)formamide
113. N-Formyl MDPEA N-(2-(benzo[d] [l,3]dioxol-5-yl)ethyl)formamide
114. G-3 1-(4,7-dimethoxy-2,3-dihydro-lH-inden-5-yl)propan-2-amine
115. G-4 1-(1,4-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-yl)propan-2-amine
116. G-5 1-(5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-6-
yl)propan-2-amine
117. G-N 1-(1,4-dimethoxynaphthalen-2-yl)propan-2-amine
118. HO-DOPR 1-(4-(2-aminopropyl)-2,5-dimethoxyphenyl)propan-1-ol
119. Hordenine 4-(2-( dimethyI amino )ethy!)phenol
120. HOT-2 N-(4-( ethylthio )-2,5-dimethoxyphenethyl)hydroxylamine
121 . HOT-7 N-(2,5-dimethoxy-4-(propylthio)phenethyl)hydroxylamine
122. HOT-ARIADNE N-(1-(2,5-dimethoxy-4-methylphenyl)butan-2-yl)hydroxylamine
123. HOT-2C-E N-(4-ethyl-2,5-dimethoxyphenethyl)hydroxylamine
124. IDA 1-(2,2-dimethylbenzo[ d] [ 1,3 ] dioxol-5-yl)propan-2-amine
1 25. JUNO 1-(3,6-dimethoxy-2,4-dimethylphenyl)propan-2-amine
126. K 1-(benzo[ d] [ 1,3]dioxol-5-yl)pentan-2-amine
127. L 1 -(benzo[ d] [ l,3]dioxol-5-yl)hexan-2-amine
128. Lobivine 2-(benzo[ d] [ 1,3] dioxol-5-yl)-N,N-dimethylethanamine
129. Lophophine 2-(7-methoxybenzo[d] [l,3]dioxol-5-yl)ethanamine
130. 2-MA 1-(2-methoxyphenyl)propan-2-amine
131. 3-MA 1-(3-methoxyphenyl)propan-2-amine
132. MADAM-6 N-methyl-1-(6-methylbenzo[d] [1,3]dioxol-5-yl)propan-2-amine
133. MAL 2-(3,5-dimethoxy-4-((2-methylallyl)oxy)phenyl)ethanamine
134. MBDB 1-(benzo[ d] [ l,3 ]dioxol-5-yl)-N-methylbutan-2-amine
135. 3,4,5-MBM 2-(4-bromo-3,5-dimethoxyphenyl)ethanamine
136. MBzA 1-(4-(benzyloxy)-3-methoxyphenyl)propan-2-amine
137. MBzMA 1-(4-(benzyloxy)-3-methoxyphenyl)-N-methylpropan-2-amine
138. M-d2 2,2-dideutero-2-(3,4,5-trimethoxyphenyl)ethanamine
139. M-d3 2-(3,5-dimethoxy-4-(trideuteromethoxy)phenyl)ethanamine
140. MDA 1-(benzo[ d] [l,3] dioxol-5-yl)propan-2-amine
141. 2,3-MDA 1-(benzo[ d] [1,3]dioxol-4-yl)propan-2-amine
142. MDA-Formamide N-(1-(benzo[ d] [1,3]dioxol-5-yl)propan-2-yl)formamide
143. MDAM N-(1-(benzo[d] [l,3]dioxol-5-yl)propan-2-yl)pentan-1-amine
144. MDBU N-(1-(benzo[ d] [1,3]dioxol-5-yl)propan-2-yl)butan-1 -amine
145. MDCM 2-( ( 1-(benzo[ d] [ l,3 ]dioxol-5-yl)propan-2-yl)amino )acetonitrile
146. MDDMA 1-(benzo[d] [l,3]dioxol-5-yl)-N,N-dimethylpropan-2-amine
147. MDE 1-(benzo[d] [l,3]dioxol-5-yl)-N-ethylpropan-2-amine
148. MDIP 1-(benzo[d] [ l,3]dioxol-5-yl)-N-isopropylpropan-2-amine
149. MDMA 1-(benzo[ d] [1,3] dioxol-5-yl)-N-methylpropan-2-amine
150. homo-MDMA 4-(benzo[d] [l,3]dioxol-5-yl)-N-methylbutan-2-amine
151. MDMBP 1-(benzo[d] [l,3]dioxol-5-yl)-2-(methylamino)butan-1 -one
152. MDMP 1-(benzo[ d] [ 1,3] dioxol-5-y1)-N,2-dimethyl propan-2-amine


153. MDOH N-(1-(benzo[ d] [1,3]dioxol-5-yl)propan-2-yl)hydroxylamine
154. MDP(�)Cl 5-(2-chloroethyl)benzo[d] [l,3]dioxole
155. MDPEA 2-(benzo[d] [l,3] dioxol-5-yl)ethanamine
156. MDPEA-AA N-(2-(benzo[d] [l,3]dioxol-5-yl)ethyl)acetamide
157. MDP(�)OH 2-(benzo[ d] [l,3]dioxol-5-yl)ethanol
158. MDP(�)OH Acetate 2-(benzo[d] [l,3]dioxol-5-yl)ethyl acetate
159. ME 2-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine
160. MEDA 1-(8-methoxy-2,3-dihydrobenzo[b] [l,4] dioxin-6-yl)-propan-2-amine
161. N-Me-DMPEA 2-(3,4-dimethoxyphenyl)-N-methylethanamine
162. N,N-Me-2,5-HMA 3-(2-( dimethylamino )propyl)-4-methoxyphenol
163. N-Me-N-iPr-MDPEA N-(2-(benzo[d] [l,3]dioxol-5-yl)ethyl)-N-methylpropan-2-amine
164. 7-Me-MDA 1-(2-methylbenzo[ d] [ 1,3] dioxol-5-yl)propan-2-amine
165. a-Me-MDA 1-(benzo[d] [ l,3]dioxol-5-yl)-2-methylpropan-2-amine
166. N,N-Me-MDPEA 2-(benzo[d] [ l,3]dioxol-5-yl)-N,N-dimethylethanamine
167. N-Me-MMDA-2 1-( 6-methoxybenzo[ d] [ 1,3 ]dioxol-5-yl)-N-methylpropan-2-amine
168. 4-MeO-PEA 2-(4-methoxyphenyl)ethanamine
169. MEPEA 2-(4-ethoxy-3-methoxyphenyl)ethanamine
1 70. N,N-Me-PMA 1-(4-methoxyphenyl)-N,N-dimethylpropan-2-amine
171. Mescaline 2-(3,4,5-trimethoxyphenyl)ethanamine
1 72. Methcathinone 2-(methylamino)-1-phenylpropan-1-one
1 73. Methyl-DMMDA 1-(4,7-dimethoxybenzo[d] [l,3] dioxol-5-yl)-N-methylpropan-2-amine
1 74. METHYL-K 1-(benzo[ d] [ l,3 ]dioxol-5-yl)-N-methylpentan-2-amine
1 75. METHYL-L 1-(benzo[ d] [ 1,3] dioxol-5-yl)-N-methylhexan-2-amine
1 76. Methyl-MMDA-2 1-(6-methoxybenzo[d] [l,3]dioxol-5-yl)-N-methylpropan-2-amine
1 77. Methylone 1-(benzo[d] [l,3]dioxol-5-yl)-2-(methylamino)propan-1-one
1 78. MIP-MDPEA N-(2-(benzo[d] [l,3]dioxol-5-yl)ethyl)-N-methylpropan-2-amine
1 79. MIP-PEA N-methyl-N-phenethylpropan-2-amine
1 80. M-M N-methyl-2-(3,4,5-trimethoxyphenyl)ethanamine
181. 3-MMA 1-( 3-methoxy-4-methylphenyl)propan-2-amine
182. MMDA 1-(7-methoxybenzo[ d] [1,3]dioxol-5-yl)propan-2-amine
183. MMDA-2 1-( 6-methoxybenzo[ d] [ 1,3] dioxol-5-yl)propan-2-amine
184. MMDA-3a 1 -(4-methoxybenzo[d] [l,3] dioxol-5-yl)propan-2-amine
185. MMDA-3b 1-(7-methoxybenzo[d] [l,3]dioxol-4-yl)propan-2-amine
1 86. 4-MNNA 1-(4-methoxyphenyl)-N,N-dimethylpropan-2-amine
187. MP 2-(3,4-dimethoxy-5-propoxyphenyl)ethanamine
188. mTFMPP 1-(3-( trifluoromethoxy)phenyl)piperazine
189. 2-NH2-MDMA-TFAA N-(1-(6-aminobenzo[d] [ l,3]dioxol-5-yl)propan-2-yl)-2,2,2-
trifluoro-N-methylacetamide
190. p 2-(3,5-dimethoxy-4-propoxyphenyl)ethanamine
191. PE 2-(3,5-dimethoxy-4-phenethoxyphenyl)ethanamine
192. Phenmetrazine 3-methyl-2-phenylmorpholine
193. PMA 1-( 4-methoxyphenyl)propan-2-amine
194. PMMA 1-(4-methoxyphenyl)-N-methylpropan-2-amine
195. Propynyl 2-(3,5-dimethoxy-4-(prop-2-yn-1-yloxy)phenyl)ethanamine
196. SB 2-(3,5-diethoxy-4-methoxyphenyl)ethanamine
197. 3-TASB 2-(4-ethoxy-3-(ethylthio )-5-methoxyphenyI )ethanamine
198. 4-TASB 2-( 3-ethoxy-4-(ethylthio )-5-methoxyphenyl)ethanamine
199. 5-TASB 2-(3,4-diethoxy-5-(methylthio)phenyl)ethanamine
200. TB 2-(4-(butylthio )-3,5-dimethoxyphenyl)ethanamine
201 . TE 2-(4-( ethyl thio )-3,5-dimethoxyphenyl)ethanamine
202. 3-TE 2-( 4-ethoxy-3-methoxy-5-(methylthio )phenyl)ethanamine
203. THC-A 1-(5-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-6-yl)propan-2-
amine
Appendix C 439
Mass Spectra

204. 3-TIM 2-(2,4-dimethoxy-3-(methylthio)phenyl)ethanamine
205. TM 2-(3,5-dimethoxy-4-(methylthio)phenyl)ethanamine
206. 3-TM 2-(3,4-dimethoxy-5-(methylthio)phenyl)ethanamine
207. TMA 1-(3,4,5-trimethoxyphenyl)propan-2-amine
208. TMA-2 1-(2,4,5-trimethoxyphenyl)propan-2-amine
209. TMA-2-AA N-( 1-(2,4,5-trimethoxyphenyl)propan-2-yl)acetamide
211 . TMA-4 1-(2,3,5-trimethoxyphenyl)propan-2-amine
213. 3-TME 2-( 3-( ethylthio )-4,5-dimethoxyphenyl)ethanamine
214. 4-TME 2-(3-ethoxy-5-methoxy-4-(methylthio)phenyl)ethanamine
215. 5-TME 2-(3-ethoxy-4-methoxy-5-(methylthio)phenyl)ethanamine
1-(4-(methylthio )benzo [ d] [2-(2,5-dimethoxy-4-( trifluoromethyl)

216. 2,4,5-TMIPA 2-amino-1-(2,4,5-trimethoxyphenyl)propan-1 -ol
217. 2T-MMDA-3a
phenyl)ethanamine
218. TMPEA-2 2-(2,4,5-trimethoxyphenyl)ethanamine
219. 2-TOET 1 -(4-ethyl-5-methoxy-2-(methylthio)phenyl)propan-2-amine
220. 5-TOET 1-(4-ethyl-2-methoxy-5-(methylthio)phenyl)propan-2-amine
221 . 2-TOM 1-(5-methoxy-4-methyl-2-(methylthio)phenyl)propan-2-amine
222. 5-TOM 1-(2-methoxy-4-methy1-5-(methylthio )phenyl)propan-2-amine
223. TP 2-(3,5-dimethoxy-4-(propylthio )phenyl)ethanamine
224. Trichocereine N,N-dimethyl-2-(3,4,5-trimethoxyphenyl)ethanamine
225. TRIS 2-(3,4,5-triethoxyphenyl)ethanamine
226. 3-TSB 2-(3-ethoxy-5-( ethylthio )-4-methoxyphenyl)ethanamine
227. 4-TSB 2-(3,5-diethoxy-4-(methylthio)phenyl)ethanamine
228. 3-T-TRIS 1-(3,4-diethoxy-5-(ethylthio )phenyl)propan-2-amine
229. 4-T-TRIS 2-(3,5-diethoxy-4-(ethylthio)phenyl)ethanamine

Mass Spectra 1 - 3
�oc�CH3NH2
�
�. . 2
:--.. 1 82 A-2 (n.o.c)
5.0
4.8
OCH3
4.5
4.0
4.2
3.8
3.5
3.2
3.0 1-(2,3,6-trimethoxyphenyl)butan-2-amine
2.8
Chemical Formula: C13Hz1N03
2.5
>-
2.2
1.8
2.0
�
m / z: 239.1521 (100.0%), 240.1555 (14.1%)
1.5 Elemental Analysis: C, 65.25; H, 8.84; N, 5.85; 0, 20.06
16
1.2
Previously unpublished, no CAS #
�
...1:�J1L .i1 .
1.0
�c.�: ,JL ., JL
o.s
.1L
0.5 23
0 . 0 ..• J._
0.2
� Yo
1. ,.1•.. .1dd._ 1 .J
40 60 80 100 1 20 160 1 80 200
... . . ..... . .. ... . ......
mlz
1 40 220 24 0 260 280
8.5
1 64/'. N-acetyl-DMPEA(n.o.c)
H3CO OCH3 CH3

8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
N-(3,4-dimethoxyphenethyl)acetamide
4.0 43
Chemical Formula: C12H17N03
3.5
>-
/ Exact Mass: 223.1208
3.0
m / z: 223.1208 (100.0%), 224.1242 (13.0%)
2.5
22�
2.0
/1 0 7 CAS # 6275-29-2
�:� .L LJ,1. ' JI. . 1

1.5
l 1..
� Yo
,,Jt. 1. _ _
300
.. ... . .. .. . . .. . .. . . .... ..... .. ... ...... ... .. ... .. .. .... . . . . . . . . . . . . . . . .. . . . . . . . .. .
m/z
50 75 100 1 25 150 175 200 225 250 275 325 350
1.6 N-acetyl-MDPEA (n.o.c.)

1.5
\...-Y CH3
1.4
1.3
o
1.2
1.1
1.0
0
0.9
:0
0
<
N-(2-(benzo[d] [l,3]dioxol-5-yl)ethyl)acetamide
x
0.8
� Chemical Formula: C11H13N03
0.7 3
>-
/4 Exact Mass: 207.0895
0.6 Molecular Weight: 207.23
o.5 m / z: 207.0895 (100.0%), 208.0929 (11 .9%)
CAS # 58026-25-8
.-... . .. '·-· - ' ·

0.3
207"'
.J .11 1
0.2
/ 105
l.i . J.. . . .. ..
0.1
o.o .. ILlL 1
.. • . . ... . . . . ...... . . . .. .. . ... . . . .
mlz
50 75 1 00 1 25 1 50 1 75 200 225 250 275 300 325 350
Appendix C 441
Mass Spectra 4 - 6
2.1 2-AI (n.o.c.)

2.0
co-
1 .9
l.7
1.8
1.6
N H2
�
1.5
1.4 2,3-dihydro-lH-inden-2-amine
/91
1.3 11 Chemical Formula: C9H11N
.1
1.2 Exact Mass: 133.0891
0.9
1
1 .0
0.7
m / z: 133.0891 (100.0%), 134.0925 (9.7%)
>- 0.8
0.5
CAS# 2338-18-3
6�
0.6
0.4
/77
0 . 0 . II d i 1 . . 1 l i l , ,, . ini lL . .JI . 1 1 1 . .. .
I.. I I.
0.3
0.2
90 100 130 0
0.1
.. " 1. ... . 1
40 50 60 70 80 110 1 20 14 150
rn/z
�
6.4
AL ( # 2)
6,0
�
5.6 H3CO NH2
5.2
4,B H zC�
o
4,4
4.0 OCH3
3,6 2-(4-( allyloxy )-3 .5-dimethoxyphenyl)ethanamine
;;;
<
x
3.2 Chemical Formula: C13H19N03
�
s
2,B Exact Mass: 237 . 1 365
>- 2 . 4 168 Molecular Weight: 237.29
23
2.0 m/z: 237 . 1 3 65 ( 1 00.0%), 23 8 . 1 398 ( 1 4 . l %)
l
1.6 Elemental Analysis: C, 65 . 80 ; H, 8 . 07 ; N, 5 .90; 0, 20.23
L
1.2
ll- .ic_ . .i.... .Jtt........_...a. . -�-..J.uJLJ L�...__.....l-

0.8 123'
0. 4
/39 "'
o.o ·- . ..
m/z
50 75 100 1 25 1 50 175 200 225 250 275 300 325
3.2
19�
ALEPH ( # 3)
3.0
�
�
H 3 l,; U NH2
2.8
2.6 �H3
2.4
H3CS "
O"CH3
2.2
2.0
1-(2,5-dimethoxy-4-(methylthio )pheny l)propan-2-amine
1.8
Chemical Formula: C12H19N02S
1 .6
>-
1.4
m / z: 241.1136 (100.0%), 242.1170 (13.0%), 243.1094 (4.5%)
1 .2 Elemental Analysis: C, 59.72; H, 7.93; N, 5.80; 0, 13.26; S, 13.29
1.0 /44
o.s
0.6
0.4
250 275
0.2
o.o
m/z
50 75 1 00 1 25 150 175 200 225 300 325

Mass Spectra 7-9
9.0
198"" meta -DOT (see #3)
B.5
H3CS � NH2
H3CO M OCH3
B.O
fV' � H3
7.5
7.0
6.5
6.0 1-(2,4-dimethoxy-5-(methylthio)phenyl)propan-2-amine
5.5 Chemical Formula: C12H19N02S
(
Kl
0
5.0 Exact Mass: 241 .1 136
... 4 .5 Molecular Weight: 241 .35
� 4.0
>-
m / z: 241 .1 136 (100.0%), 242.1170 (13.0%), 243.1094 (4.5%)
3. 5 Elemental Analysis: C, 59.72; H, 7.93; N, 5.80; 0, 13.26; S, 13.29
3.0
2.5
2.0
241"'
1.5
1.0
.L
0.5
125
o . o .....
50 75 100 1 50 1 75 200 225 250 275 300 325
1 9EY"";
ortho-DOT (see # 3)
6.0
5.6
H3CO � NH2
H3CO M SCH3
5.2
4.B
�
4.4
4.0
C> f' H3
�
1-(4,5-dimethoxy-2-(methyJthio )phenyl)propan-2-amine
3.6
iD Chemical Formula: C12H19N02S
3.2
Exact Mass: 241 .1 136
� 2.B Molecular Weight: 241 .35
>- 2 . 4 m / z: 241 .1 136 (100.0%), 242.1170 (13.0%), 243.1094 (4.5%)
2.0 Elemental Analysis: C, 59.72; H, 7.93; N, 5.80; 0, 13.26; S, 13.29
/44
1 ""
1.6
1 .2
_L
O.B
241"
0.4
0.0 .. .._.w.....J... 1 .Ji ......IL..J11i..
50 75 1 00 1 25 150 1 75 200 225 250 275 300 325
m/z
"-21 2
4.0 ALEPH-2 ( # 4)
3.4
3.B
3.6
H3CO � NH2
3.2
3.0
2. B H3C � S
� OCH3
�"� H3
2.6
2.4 l -(4-(ethylthio)-2,5-dimethoxyphenyl)propan-2-amine
'f 2 . 2 Chemical Formula: C13H21N02S
;: 2 . 0
x 1 .8
Exact Mass: 255 . 1 293
>-
1 .6 m/z: 255 . 1 293 ( 1 00.0%), 256. 1 327 ( 1 4. 1 %), 257. 1 25 1 (4.5%)
1,4
Elemental Analysis: C, 6 1 . 1 4 ; H, 8.29; N, 5.48; 0, 1 2 . 5 3 ; S, 1 2.56
1 .2 /44
�:� j �-��::;L.L.j 200l.

19�
0.6
/255
�:� . . --�� . .. ��.. .l
75 250 275
m/z
50 1 00 125 1 50 175 225 300 325
Appendix C 443
Mass Spectra 10 - 12
=---226
- ALEPH-4 ( #5)
. xx:f NH2
6,4
6.0
5 6 H3CO
CH3 I
5,2
4.8
CH 3
4.4
H3C,A__ S :::::-._ OCH3
4.0 1-(4-(isopropylthio)-2,5-dimethoxyphenyl)propan-2-amine
3.6 /184
<
u:; Exact Mass: 269.1449
3,2
/44
� Molecular Weight: 269.40
)( 2.8
m / z: 269.1449 (100.0%), 270.1483 (15.1%), 271 .1407 (4.5%),
)- 2 . 4 271 .1517 (1.1%)
2.0
l
Elemental Analysis: C, 62.42; H, 8.61; N, 5.20; 0, 1 1 .88; S, 1 1 .90
/269
l
1.6
1 .2
...�.�Li..k.u.6....h...."�
l.. 1..... J
0.8 "
121
0.4
. � __
225
o.o
200
Ill/ %
50 75 1 00 125 150 175 250 275 300 325
ALEPH-6 (see # 3)
� 3CO
5.2
� S � rv,
4 .8 NH2
�H3
OCH3:
4,4
4,0
3,6
h
1-(2,5-dimethoxy-4-(pheny1thio )phenyl)propan-2-amine
..
3.2 Chemical Formula: C17H21 N02S
2,8 Exact Mass: 303.1293
!! 2 . 4
/44
m / z: 303.1293 (100.0%), 304.1327 (18.4%), 305.1251 (4.5%),
>- 2 � 0 305.1360 (l .6%)
1 .6 Elemental Analysis: C, 67.29; H, 6.98; N, 4.62; 0,
J
10.55; S, 10.57
� 15� ,
1 .2
J
245'.
..... .....ML.,1.._....i....i...1..............i.......i.1....J.. .i.._L.l ...J. . .1

21
o.e "
0.4 10 /303
o.o . •. . _ L-
m/z
50 75 100 125 150 1 75 200 225 250 275 300 325
-:---.2
. 26
xx:f NH2
6.4
ALEPH-7 ( # 6)
6.0
5.6
5.2
H3CO
4.8
H3 �S
c :::::-...
I CH3
4.4 OCH3
4.0 1-(2,5-dimethoxy-4-(propylthio)phenyl)propan-2-amine
3,6
�)(
3.2
2.8
m/ z: 269.1449 (100.0%), 270. 1483 (15.1%), 271 .1407 (4.5%),
271 .1517 (1.1%)
Elemental Analysis: C, 62.42; H, 8.61; N, 5.20; 0,
1 1 .88; s, 1 1 .90
/269
50 75 100 125 175 200 225 250

� .. .l . 275 300 325
m/z
150
444 The Shulgin Index - Psychedelic Phenethylam ines and Related Compounds
Mass Spectra 13 - 1 5
� NH2
ALEPH-21 (n.o.c.)
M
450000 44.0
H3CO
400000
F� S H3
S ""
OCH3
350000 1
1-(4-((2-fluoroethyl)thio)-2,5-dimethoxyphenyl)
propan-2-amine
300000
Chemical Formula: C13H20FN02S
!
1
206.2
I
250000
1
191.1
m/ z: 273.1 199 (100.0%), 274.1232 (14.1%),
230.1
200000 275.1 157 (4.5%)
Elemental Analysis: C, 57.12; H, 7.37; F, 6.95;
150000
N, 5.12; 0,11 .71; S, 1 1 .73
Synthesis (Shulgin and Shulgin 1991);
100000
spectrum previouslyunpublished, no CAS#
1
91 . 1 1 7'· '
11
50000 1
I . , ,1,e. '.1l,�,. . 111 ..... 1.. 1 "'"'· 11l,,,1... l11,1.1i,,, ,11,l11.1.11,,,,;,�L.�11.Jl1,1 .. ,,1 .. 11 l . ... L.,1 I. . .. T. .' . Ii. I . '" �"�'1 '�
77.0
0•
105 . 0 1 1 5.0 1 28.1 1 60 . 1
1
mlz--> 40 50 60 70 80 90 1 00 1 1 0 1 20 130 140 150 160 1 70 1 80 1 90 200 2 1 0 220 230 240 250 260 270 280
. � .11 .• . . .
8.4
"44 Amphetamine (n.o.c.)
8,0
7.6
7.2
6.8
6,4
5,6
6,0
1-phenylpropan-2-amine
5.2
4.8
Chemical Formula: C9H13N
< 4,4
iO Exact Mass: 135.1048
x
� 4.0 Molecular Weight: 135.21
3,6 m / z: 135.1048 (100.0%), 136.1082 (9.7%)
,.. 3 . 2 Elemental Analysis: C, 79.95; H, 9.69; N, 10.36
2.8 CAS # 51-64-9
2.4
2.0 9 1"'
1 .6
1.2
..l.L
0.8
0
o .. o
4 ..LlI L.
mlz
40 60 80 1 00 120 140 160 180 200 220 240 260 280
2. 1 ARIADNE ( # 7)
2
�
,0
1 .9
1.8 H3CO N H2
::::,.... I
1.7
1 ,6
1.5 CH3
1 .4
1 .2
H3C OCH3
1.3
� 1.0
1 -(2,5-dimethoxy-4-methylpheny1) butan-2-amine
1.1
Chemical Formula: C 13H2 1N02
;Ji
Exact Mass: 223 . 1 572
Molecular Weight: 223 . 3 1
� 0.9
0,8
,.. m / z: 223. 1 572 ( 1 00.0%), 224. 1 606 ( 1 4. 1 %)
0.7
Elemental Analysis: C. 69.92; H, 9.48; N, 6.27 ; 0, 1 4.33
0.6
0,5
l ) /223
0.4
..i.JLJl/9 1 ..i11. _.l l 19�

0.3
0.2
0.1
o.o � ... .. . .d�1.. . ... _ -· _ j_ -·- -1
�
5o i5 100
150 175 200 12s 1225 250 275 300 325
mlz
Appendix C 445
Asarone (see # 118)

208.2
1000000
900000
H3CO xx:
� CH 3
I
1
800000 0
700000
H3CO O CH3
1
(E)-1,2,4-trimethoxy-5-(prop-l-en-l -yl)benzene
600000
Chemical Formula: C12H1603
500000, Molecular Weight: 208.25
ml z: 208.1099 (100.0%), 209.1 133 (13.0% )
Elemental Analysis: C, 69.21; H, 7.74; 0, 23.05
165. 1 CAS # 2883-98-9
I
160 170
177 . 1
.J I I r. dill, � '
180 190
I
. , -- I �
200 210
21 °"
� NH2
ASB ( # 8)
�153
2.1
2.0 H3CO
� I
1 .9
1.8 181"'
1.7
1 .6 H3C,.......,,_ 0 �
1.5
1.4 O '-.../ CH3
1.3
� Lt
2-(3,4-diethoxy-5-methoxyphenyl)ethanamine
23�
;;; 1 . 2
)( 1 . 0
0.9
>- o . B
0.7 m / z: 239.1521 (100.0%), 240.1555 (14.1%)
0.6
. . ,;�. . (:11,
13�
,
0.5
0.4
�'.! J
o.3
40 60 80
_ __
100
,11 .nl
120
1l1
140 160
I. IL
1 80 200 220
,__ .. l.
240 260 280
rn/z
H3CO � NH2
:--.- 1 59
3.0 B (see # 91)
2.8
H3C�O �
2.6
16
2,4
2.2
2.0 OCH3
1.8
(
�
' 2-(4-butoxy-3,5-dimethoxyphenyi)ethanamine
)( 1.4
>-
\ Molecular Weight: 253.34
1.2 /224 m / z: 253.1678 (100.0%), 254.1711 (15.1%), 255.1 745 (1.1%)
1 .0
'"--��--h-.��: .�l_J_J � .l. t

O.B /253
0,6
0.4
::� 1 ?s
12s
-� --
5o 7'5 100 150 225 250 275 300 325

rn/z
446 The Shulgin Index - Psychedelic Phenethylam ines and Related Compounds
5!YI
(YJ NH2
BDB ( # 9)
1.1
1 .0
13°"' � '-- cH3

0.9
o.8
o
0.7 \..- o
0.6
)-
1-(benzo [ d] [1,3] dioxol-5-y!)bu tan-2-amine
Chemical Formula: CnH15N02
0.5 Exact Mass: 193.1 103
0.4 m/ z: 193.1 103 (100.0%), 194.1136 (11 .9%)
16"-
0.3 /77
0.2
/193
.....J L.,. L_...!. . ...L . . .

0.1
JJIL..
220 240 280
o.o
60
.. .
m/z
40 80 1 00 1 20 140 1 60 180 200 260
6.4 51Y"i /166 BEATRICE ( # 11)
:ca: HN , CH3
s.o
5,6
5.2 H3CO ...,.
4.8
4.4
� I CH3
4.0
H3C OCH3
1-(2,5-dimethoxy-4-methylphenyl)-N-methylpropan-2-amine
3.6
3.2
)- 2 . 4 m / z: 223.1572 (100.0%), 224.1606 (14.1%)
1.6
/105
1.2
91"
IL . I
o.9
·"'. 1 1... 1.1 . 1,1ii. . 1 1. . .

/192
�:: .1.,11.
223
m/z
.. .. 1o 11o•••• ... 1.. . . . . .1.
/
iiL Al..
40 1 40 1 60 200 220 240
... ... . ... . .. . .
60 80 100 1 20 180
2.6 191Y"i
BIS-TOM (see # 60)
2 .4
H3CS � NH2
H3C � SCH3
2.2
2.0
1 .8 cr- �H3
1 .6 1-(4-methyl-2,5-bis(methylthio)phenyl)propan-2-amine
,..
<
w 1 .4 Chemical Formula: C12H19NS2
0 Exact Mass: 241 .0959
...
1.2
.?5 Molecular Weight: 241.42
1 .0 m / z: 241 .0959 (100.0%), 242.0992 (13.0%), 243.0917 (9.0%),
/134
o.8 242.0953 (1.6%), 244.0950 (1.2%)
Elemental Analysis: C, 59.70; H, 7.93; N, 5.80; S, 26.56
/91
o.6
L_(2�3
241"
L
0.4
.JL .&.. "

0.2
o . o .... _,___... . .. ...1... h ... i.JJ. .. � J• �- - ·-· __
75 30 0
..... . . ...
50
rn/z
1 00 125 150 1 75 200 225 250 275 325
Appendix C 447
-9 1 1 4s--; BMA (n.o.c.)

6.4
6,0
5.6
� � ::,,()
5.2
C
4.8
4.4
4.0
� H3
3.6 N-benzyl-N-methyl- l -phenylpropan-2-amine
<
\0
3.2 Chemical Formula: C17H21N
x
;:
2.8
>- 2.4
�
ml z: 239.1674 (100.0%), 240.1708 (18.4%), 241 .1741 (1.6%)
2.0
1 .6 CAS # 1085-42-3
6
20 �
il.
1.2
111....Ll J
0.8
0.4 /224
o.o . ..J.. . . .. .... w.
... _ J. ....• 1 ,, _ ,, __
1 25 1 75
m/z
50 75 100 15 0 200 225 250 275 300 325
3000000
BZP (n.o.c.)
2SOOOOO
134
2000000 1-benzylpiperazine
1 500000 Molecular Weight: 1 76.26
m l z: 176.1313 (100.0%), 177.1347 (11 .9%)
1 000000 CAS # 2759-28-6
500000 1 76
42 120
1 04 146
77 1 61
0
m/z-> "'° 50 oo 10 eo liO 1 00 1 1 0 1:io 1 30 140 11SO 160 110 1eo 100 200 210 220 230 240 250 260 710
6.4 "230
2C-B ( # 18)
6.0
5,6
H3CO � NH2
MrvOCH3
'u
5.2
4.8
4.4 Br
4.0
2-(4-bromo-2,5-dimethoxyphenyl)ethanamine
3,6
Chemical Formula: C10H14BrN02
3.2
\0
(
x
2.B
�
>- 2.4
/259
m l z: 259.0208 (100.0%), 261 .0187 (97.3%),
2.0 260.0241 (10.8%), 262.0221 (10.5%)
Elemental Analysis: C, 46.17; H, 5.42; Br,
201""'
1 ,6
30.72; N, 5.38; 0, 12.30
.JI. . - .11 L. "" . .. IL .

rn/z
50 75 1 00 1 25 1 50 1 75 200 225 250 275 300 325

1
253.9 2C-B-FLY (see # 68)
300000
J
2soooo :
2000
2-(8-bromo-2,3,6, 7-tetrahy drobenzo[ 1,2-b :4,5-b 1
difuran-4-yl)ethanamme
150000 I
I Exact Mass: 283.0208
m/ z: 283.0208 (100.0%), 285.0187 (97.3%),
1
283.o
115 1 1 74 . 1
284.0241 (13.0%), 286.0221 (12.6%)
Il I I
Elemental Analysis: C, 50.72; H, 4.97;
131.1
Br, 28.12; N, 4.93; 0, 1 1 .26
Il I I I
145 1 1 59 1
, � 1 1 11
I
18 7 .1
204.1 266.o
I
BO
225 9 238 9
mlz-->
1111 1 . 11 1 ,.111 , L r:i!l1- . . .. !
1 1 ,, 1 1 .. \
. 11p .1 _ ,..1:i. , . ll !!
1 1 :1 1 - � · ' ,l. r'T'"'" �i
40 50 60 70 90 100 1 1 0 120 1 30 140 1 50 160 170 1 80 1 90 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340
--. 1 e o
5.2
2C-BIS-TOM (n.o.c.)
5.0
H3CS � NH2
H3C �Cf'
SCH3U
4.8
4.5
4.2
4.0
3.8
3.5 2-(4-methyl-2,5-bis(methylthio)phenyl)ethanamine
3,2
3.0
Chemical Formula: C11H17NS2
<
;;; Exact Mass: 227.0802
2.8
x
� 2.5
>-
2.2 m / z: 227.0802 (100.0%), 228.0836 (11 .9%),
229.0760 (9.0%),228.0796 (1 .6%), 230.0794 (1.1%)
1 .8
2.0
1.5 N, 6.16; S, 28.20
Synthesis (Shulgin and Shulgin, 1991
1.0
1.2
/134
I _..iL .
spectrum previously unpublished, no CAS #
0.8 /91
7 7"
.LL�dhdt!d.�
0.5
0.2
o.o �..J., J.... Ju. .....L... ... . ..� L .!1 ··-" lh
275 300 325
m/z
50 75 100 125 1 50 1 75 200 225 250
4.0 23� 2C-B-M (see # 18)
XX::
3,8
3.6
H
3.4 H 3C O N,
I
3.2 CH3
3,0
2.8
Br
� OCH3
2.6
2,4
2-(4-bromo-2,5-dimethoxyphenyl)
2.2 /44 -N-methylethanamine
2.0
1.8
1 .6 Molecular Weight: 274.15
,..
1.4 m / z: 273.0364 (100.0%), 275.0344 (97.3%),
274.0398 (11 .9%), 276.0377 (11.6%)
1 .0
1.2
27�
Elemental Analysis: C, 48.19; H, 5.88; Br, 29.15;
0.8 N, 5.11; 0, 1 1 .67
U ,.1, J ...it L ('..:,'..J��.:�.u1. ,;A��Jt ..JL I l ,,,,

/77
. . i1.t... ,h .•. . . .• .. .. ... ... ... 1 JJ

40 60 80 100 120 1 40 160 180 200 220 240 260 280
mlz
Appendix C 449
3.0 ...... 186
H3CO � NH2
2C-C ( # 19)
2,8
2,6
2,4
2.2
2,0
Cl � OCH3
2-(4-chloro-2,5-dimethoxyphenyl)ethanamine
1,8 Chemical Formula: C10H14ClN02
1.6
<
;;; Exact Mass: 215.0713
x
8 l.4 Molecular Weight: 215.68
>-
m / z: 215.0713 (100.0%), 217.0684 (32.0%),
0.8
1.2
216.0747 (10.8%), 218.0717 (3.5%)
/215
1.0 171""'
Cl, 16.44; N , 6.49; 0, 14.84
111 / z
40 60 00 100 1 20 140 1 60 1ao 200 220 240 260 2ao
XX:: N H2
166"'1 2C-D ( # 20)
5.2
4.B H3CO
4,0
4.4
�
�
I
H3C OCH3
�0
3.6
2-(2,5-dimethoxy-4-methylphenyl)ethanamine
3.2
2.8
... Exact Mass: 195.1259
� 2.4
>-
2,0
13�
m / z: 195 . 1 259 (100.0%), 196.1293 ( 1 1 .9% )
195'.
91"'
1.6 "'- Elemental Analysis: C, 67.66; H, 8.78; N, 7 . 1 7; 0, 16.39
1. 2
J
0,8
0.4
o . o .J .... ..:.�.1.J
60 80
.. .. ...
120 140
Jfl1. ......1L. ... !. . ...... .
160
.... l. .. .
220 260
m/z
40 240 280
1
1 00 180 200
44.0
CD3-DOM (see # 60)
1500000
1 H3CO � NH2
1400000�
D3C M OCH3
1
1300000
�r S H3
1200000
11
1 1 00000
'
1000000
159 1 1-(2,5-dimethoxy-4-trideuteromethylphenyl)propan-2-amine
900000
Chemical Formula: C12H16D3N02
1
800000
1
1
7 00000
600000 ml z: 212.1604 (100.0%), 213.1638 (13.0%)
500000 Elemental Analysis: C, 67.89; H, 10.44; N, 6.60; 0, 15.07
i
400000 1
154.1
I
300000
o' � i1l 1 1��i�1, . •111 111 ,, . i1l11l1, , ,111 I 11. ..��j,·I�· I

200000
., I
M. 1 1 �. 1
, .1. ��2 . . . ,, ,11.

100000
. ' ' . I -. ,
79. 1
T " �-, I · .,...

67 _0
212.2
11/z-> ™ � m � m n m m m
181 . 1 1 97.1
,___, • �
40 50 60 70 80 90 100 110 120 1 30 140

Mass Spectra 3 1 - 33
1 .8 1ao----; 2C-D-5-ETO (see # 20)

1.7
H3C '-./ O � NH2
H3C �"f'U
1 .6
1.5
1 51'\.
1.4
1.3
OCH3 ·
1 .2 2-(5-ethoxy-2-methoxy-4-methylphenyl)ethanamine
LO Exact Mass: 209.1416
�
ml z: 209.1416 (100.0%), 210.1449 (13.0%)
13� 1
0,8
>- 0 . 7 Elemental Analysis: C, 68.87; H, 9.15; N, 6.69; 0, 15.29

20
0.6
�:;
0,5
/91
�:� .c..�9 . . . . .1 �7Jt L

40
.• . ,
60 80
. . . . . .
100
.. 1.1. t . . ...
120
.1111L .J . "·· ·
140
... 1.• 1.. . . ..
1 60
,,L
180 200
. . I..
:xx:: NH2
m/z
8,0 2C-E ( # 21)

7.6
7.2
6.8 H3C -:?
6.4
6.0 H 3C ::::.:,-. I
5.6
5.2
OCH3
4.8
2-(4-ethyl-2,5-dimethoxyphenyl)ethanamine
16�
<
ifi 4 . 4
4.0
x 3.6
;: Molecular Weight: 209.28
>-
3.2
m l z: 209.1416 (100.0%), 210. 1449 (13.0%)
2.8 Elemental Analysis: C, 68.87; H, 9. 15; N, 6.69; 0, 15.29
2.4 /209
2.0
1.6
11� 1 4�
/'
.J
1,2 9 h,
.lu Iii .
4
o.e
�:� !. .
"
. .1 . .. 1o1.... 1.1.1.1 11.t .1 L ...... l

140 160 1 80 200 220
.... . .... ....... . .... .. .. .. . .. .. .. ... . ..... ... ... . ... ... ... . ... . .
m/z
40 60 80 100 120
:cc: NH2
6.0 2C-E-5-ETO (see # 20)
5,6
5.2
H3C '-./ -;?
I
4.8
4,4
4,0
/165
H3C ::::.:,-. OCH3
3,6 2-(5-ethoxy-4-ethyl-2-methoxyphenyl)
3.2
ethanamine
2,8
/223
>- 2 . 4 Molecular Weight: 223.31
2.0 ml z: 223.1572 (100.0%), 224.1606 (14.1%)
1 ,6 Elemental Analysis: C, 69.92; H, 9.48; N, 6.27;
1.2
91 0, 14.33
"'
0.8
0,4
o . o .. !.�--·
40
. ,:�.1 . li . .
60
. . ..
BO
. .. �t i.(�,�: . JL
.
.. .. .
1 00 120
... . . .
140
mlz
.. ..... 11 1.
160 180 200
.. .. . L
220 240
Appendix C 451
�
6.0
3C-E (see # 117)
5.6
5.2 H3CO N H2
16� ::::::... I
4.8
CH3
4.4 /"'-...
H3C O
4.0
3.6
OCH3
1-(4-ethoxy-3,5-dimethoxyphenyl)propan-2-amine
'f' 3.2 Chemical Formula: C13H21N03
x 2.8
�
>- 2.4 /44 Molecular Weight: 239.31
2.0 m / z : 239.1521 (100.0%), 240.1555 (14. 1 % )
1 .6
� �
1 .2
ul. . �J
o.e 23
12
�:: , ,_ ..;..__J . .J.i . L ··- _..._ J ...
V:::
... � . . ..... ... ....... . ....
m/2
50 75 1 00 125 150 175 200 225 250 275 300 325
6.4
2C-G (see # 114)
6.0
5.6
H3CO N H2
::::::... I
5.2
4.6
H3C OCH3
4.4
4.0
CH3
b 3.2
3.6
2-(2,5-dimethoxy-3,4-dimethylphenyl)ethanamine
"'
B 2.e
�
20""
>- 2 . 4 m/ z: 209.1416 (100.0%), 210.1449 (13.0%)
1.6 11""
/134
2.0
1.2
91"
O.B
�:: J.1.1
40
.. ..
6�
1.L... 1.1.I
. .
60
..
IL
...
60
.. ..
100
J 120
II
L. ..1 11.. . 1.11 1 l . 1 1 liL .o1 1L
... .
m/z
140
I . ..
160
i11 L
160
........... ..... I. ..
200 220
... .
240
5.0
2C-G-3 (see # 114)
4.8
4.5
4.0
4.2
3.8
3.5
3.2
3.0
2.8 2-(4, 7-dimethoxy-2,3-dihydro-lH-inden-5-y l)ethanamine
2.0
2.2 Exact Mass: 221 .1416
1 >-
1.8
161"
m / z: 221 .1416 (100.0%), 222.1 449 (14.1%)
/22 1
1 .5
11�
1.2
1 .0
:�L-J... L.t.�1 1.
o.e
0.2
o.5
o.o ....• · .J
100 225 250 325
·'·-··� · ... .
m/z
50 75 125 150 1 75 200 275 300

2C-G-5 (see # 114)

6.0
5.6
5,2
4.B
4.4
17°"
4.0
3.6
<
ill 2-(5,8-dimethoxy-1,2,3,4-tetrahydro-1,4
0
24�
....
3.2
-methanonaphthalen-6-yl)ethanamine
� 2.e Chemical Formula: C1sH21N02
>-
/115
2.4 Exact Mass: 247.1572
;2 . 0
ml z: 247.1572 (100.0%), 248.1606 (16.2%),
1 .6
249.1639 (1.2%)
6°"
1 .2 Elemental Analysis: C, 72.84; H, 8.56;
o.a
• ILL ,J, __
N, 5.66; 0, 12.94
0.4
o . o .J••.. J.�• .
BO 100
m/z
60 100 i2o 200 220 240 260 200
�
40 140 1 60
4.8 1 87-""" 2C-G-N (see # 114)

4.5
4.2
4.0
N H,
3.8
3.5
2.8
3.2
3.0
OCH3
"'
<
0
2.5 2-(1,4-dimethoxynaphthalen-2-yl)ethanamine
.... 2.2
1.8
x
231"
,..
2.0
/128
1 1°"
1 .5
m / z: 231 .1259 (100.0%), 232. 1293 (15.1%),
1 .2
233.1326 ( 1 . 1 % )
1.0
Elemental Analysis: C , 72.70; H , 7.41; N , 6.06;
7�
, _J
0.8 0, 13.83
0.5
0.2
o.o _,__ ·-·"·-•k ....o L LJI�.- _ __ __ _ ..
m/z
50 75 100 125 150 175 200 225 250 275 300 325
:---.. 1 52
�
2C-H ( # 22)
6.8
6.4
6.0 H3CO NH2
5.6
5.2
� OCH3
13�
4.8
4 .4 2-(2,5-dimethoxyphenyl)ethanamine
Chemical Formula: C10H1sN02
<
4.0
3.6
iO
x
�
3.2 Molecular Weight: 181 .23
,... 2.6 m / z: 181.1 103 (100.0%), 182.1136 (10.8%)
121"
2.4 Elemental Analysis: C, 66.27; H, 8.34; N, 7.73;
181
2.0 / 0, 17.66
1.6
..J 11.
1.2
6
. J.1.1 .. , .1 .... . ....li... .1 . . Ju I IL . ..l1h I..
0.8
0.4
o;o °" .. . ..
/77 . . .. 11111ll .... .. ..•..• 1... .. ,! ...
m/z
40 60 80 1 00 1 20 1 40 160 160 200 220
Appendix C 453
'276 2C-I ( # 23)
X:C:
6. 4
6.0
5.6 H3CO N H2
5.2
4,8
Y" I
4.4
I � OCH3
2-(4-iodo-2,5-dimethoxyphenyl)ethanamine
4,0
Chemical Formula: C10H14IN02
u; 3,6 Exact Mass: 307.0069
�... 3.2
/3 1
/307 Molecular Weight: 307.13
� 2.B m / z: 307.0069 (100.0%}, 308.0103 (10.8%)
24�
,.. 2,4
Elemental Analysis: C, 39.11; H, 4.59; I, 41 .32;
I
2.0 N, 4.56; 0, 10.42
o.e
Jl_
1.6
JL
1 .2 /180
0,4
o.o . 1:1 I. . -..1. .. ....__

50
19Yt
mlz
75 100 125 150 175 200 225 250 275 300 325
2C-N (see # 20)

2.4
�
Mf'\r' U
2.2 H3CO N H2
2.0
1 ,8 02N OCH3
1 .6 2-(2,5-dimethoxy-4-nitrophenyl}ethanamine
1 .4
(
�
u;
0
1.0
....
0.8
�
>-
16
m/ z: 226.0954 (100.0%), 227.0987 (10.8%)
0,6
0,4
0.2 7�
Ji...,,l.
50 75 100 125 150 175 200 275 300
0 . 0 ...._ _JJ• .
,./z
225 250
:--... 1 67
6,4 2C-0-4 (see # 124)
6.0
5,6
5,2
4,B
21°"
4.4
4,0
3.6
2-(4-isopropoxy-2,5-dimethoxyphenyl}ethanamine
u; Chemical Formula: C13H21N03
<
;: 3,2 Exact Mass: 239.1521

� 2.B
,..
2.4 rn / z: 239.1521 (100.0%}, 240.1555 (14. 1%)
0, 20.06
o.e 6� 9""
1.6
1 .2
�:� 40 JU_ ,L,11L\�

60 80
.•
100 120
_, J
_,1LJ�, IL_.JL,,,. · ---'
140
mlz
-·- J• -----·-- -·-'
160 180 200 220 240 260 280
l. . ··-

�
19�
2C-P (see # 20)
2,6
2,4
NH,
2.2
2.0
H3C O CH3
1 .8
1.6
2-(2,5-dimethoxy-4-propylphenyl)ethanamine
<
u; 1 .4
x 1.2
16�
;: Molecular Weight: 223.31
>- 1.0
ml z: 223.1572 (100.0%), 224.1606 (14.1%)
0.8 /23
0.6
I l J 1. . .
9 1"' 13�
JIJ,,._ lddllL,.IJI L
0.4
.Jl 11.l .
0.2 6�
O.O ·' '"" '·" • ,,J,, . • . . Jo o. . . .•• . • .J L .. I. ·-
� � 00 UO HO ffiO 220 260

. . ... ..
m/z
100 180 200 240 280
1
m
1500000 44.1 3C-P (see # 117)
1400000
y
13000001
1200000
1 H3CO NH2
1100000 H3C � CH3

o
1000000
OCH3
900000 1 -(3,5-dimethoxy-4-propoxyphenyl)propan-2-amine
800000 Chemical Formula: C14H23N03
700000 Exact Mass: 253.1678
m/ z: 253.1678 (100.0%), 254.1711 (15.1%),
600000
210.2
300000 1
500000
255.1745 (1.1%)
I h 53 0 65.0 7� .0 91.1 107.0 1213. 1 137.1 l,,1 I ,

200000
100000 1 153.1
0 TTTT'" U I 11u Jil1i . ..,i 1 h1o • • 11111 .1 1 . i 1r11 •. · · l' i 1 . I 179.1 194. . ·0 . I 222 1 TTTT238
-;2"TT""'"T'""j ..,a. �
253.1
m/Z->
. . ..... .. . 11 i 11 ... . .1 .... . . . . . _ ,, . !'TT' , ""T""T'"" •
40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270
�
'167 CPM (see #91)
5.6
5.2 H3CO NH2
V
4.B
4.4
4,0
3.6
O
� O CH3
2-(4-(cydopropylmethoxy}-3,5-dimethoxyphenyl)
:
iii 3 . 2
2.8
( ethanamine
lC
2.4 Exact Mass: 251 .1521
/222
m/ z: 251 .1521 (100.0%), 252.1555 (15.1%), 253.1589 (1.1%)
2.
1 .6
/251
/55 � l�.
�
1.2
5
12 1
o.e
;
0.4 L ....1.L .1
.
o.o . ..1... .. ......_ ..... ..A... _ , _ll

50 75 100 1 25 150 175 200 225 250 275 300 325
. ... .
m/z
Appendix C 455
Mass Spectra 46-48
6,0
2C-Se (see # 124)
5.6
5.2 H3CO � NH2
I
4.4
4.8
H 3C
4 . 0-
'se � OCH3
�
/275
3.6
2-(2,5-dimethoxy-4-(methylselanyl)phenyl)ethanamine
30
Chemical Formula: C11H17N02Se
3,2
,_ 2 , 4 m / z: 275.0425 (100.0%), 273.0432 (47.9%), 271 .0451 (18.9%),
20°"
2.0
277.0426 (17.6%), 272.0458 (15.4% ), 276.0458 (11 .9%),
/9 1
274.0466 (5.7%), 272.0485 (2.2%), 278.0460 (2.1%),
::: .7�
�!��;
L
1.6 151'. 273.0492 (1 .8%), 269.0484 (1.8%)
I
Eleme lysis: C, 48.18; H, 6.25; N, 5.11; 0, 1 1 .67;
o .o .1-.11..
50
.11!...JL ·
75 100
. ..1 ·
125
1l1�l
150
.A.1
175
rnlz
200 225 250
_ --·-
275
.
300
..
325
6.4 19a--" 2C-T ( # 25)

/03
�
6.0
......
Mn0u
5.6 H3C O NH2
5.2
/227
4.8
H3CS OCH3
4.4
2-(2,5-dimethoxy-4-(methylthio)phenyl)ethanamine
4.0
167"' Chemical Formula: C11 H17N02S
3.6
.
3.2
,_
2 8 m / z: 227.0980 (100.0%), 228.1014 (11 .9%), 229.0938 (4.5% )
2.4 Elemental Analysis: C, 58.12; H, 7.54; N, 6.16; 0, 14.08; S, 14. 1 1
2.0
1 .6
1 .2
0.8
mlz
0.4
o.o .J
50 75 100 1 25 1 50 175 200 225 250 275 300 325
9 ,0 19ir; meta-2C-T (n.o.c.)

8.5
8.0
�
Mrv' LI
7.5
H3CS NH2
7.0
6.5
6,0
H3CO OCH3
5.5
2-(2,4-dimethoxy-5-(methylthio)phenyl)ethanamine
5.0
4.5
4.0
>- 3 . 5
m / z: 227.0980 (100.0%), 228.1014 (11 .9%), 229.0938 (4.5%)
16i\
2,5
0, 14.08; s, 14.1 1
2.0
Previously unpublished; n o CAS #
1.5
Iii
1.0
... I, Jii t . It .
6""' 9 1"
0,5
I I
o.o
I
40 W 00 � � � � � = m � B =
mlz

Mass Spectra 49 51 -
19s--"' ortho-2C-T (n.o.c.)
� NH2
9.5
� Cf'U
9,0
H3CO
8,5
8,0
7,5
H3CO SCH3
7.0
6,5
2-(4,5-dimethoxy-2-(methyJthio )phenyl)ethanamine
5.5 Exact Mass: 227.0980
4.5 m/ z: 227.0980 (100.0%), 228.1014 (11 .9%), 229.0938 (4.5%)
>-
4,0 Elemental Analysis: C, 58. 12; H, 7.54;
3.5 N, 6.16; 0, 14.08; S, 14.11
3,0 Previously unpublished; no CAS #
2.5 /227
1 3""' /1 5 1
2,0
1 .5
. l�1....JlL.
107'.
1.0
�:
6� '
O .. •··'···"····"""'•·'•k ... L.• Jl,1L. ... . L .
m/z
40 60 80 100 120 140 1 60 180 200 220 240 260 280
I
900000 1 198 0
'11 - 2C-T (see # 25)
800000
700000
600000
1I
500000 2-(2,6-dimethoxy-4-(methylthio)phenyl)ethanamine
400000 Exact Mass: 227.0980
3000001 ..
m / z: 227.0980 (100.0%), 228.1014 (11 .9%),
151 9 229.0938 (4.5%)
:: :
137 1 Elemental Analysis: C, 58.12; H, 7.54; N, 6.16;
:: : :
4.08; 14.
1 '"i ·0 o
ll
.
S,
I
•• ,
·"' I, , . 11,i,, ,,, JJ;� 1,, .. 1 1 1 . . I , . . ,I . - .. .. ' I 20 :1 . °' I ..

770
91 '
1il1 . . .l 1 .1 1... . 1 1 1 1 1 . ... .1 1 1 1 ..

..
45.. 0
""
1s3 ,
,,1 Ii,
mfz-->
... 1 .. ,� . .__....,
0 ... . . .. .. . . . . .. ., . . .. ! .
40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240
.
-...2
.. 1 2
3.8
2C-T-2 ( # 26)
� NH2
3,6
3,4
H3CO
M
3.2
3.0
2.8 �
H3C S OCH3
2.6
2.4 2-(4-(ethylthio ) ·2,5-dimethoxyphenyl)ethanamine
211
2.2
" Chemical Formula: C12H19N02S
<
in
0 2.0 Exact Mass: 241 .1 136
....
.:5
>-
1.6 24 1"
m/z: 241 . 1 136 (100.0%), 242.1170 (13.0%),
1.4
�
243.1094 (4.5%)
1 .2
Elemental Analysis: C, 59.72; H, 7.93; N, 5.80;
l
1.0 15 0, 13.26; S, 13.29
J
O.B
7�
0.6
0.4
121"
L . I
w..J..... .i....o. m...i • .I
0.2
0•0 ii..
75 100 1 75 275
.... . .
m/z
50 1 25 150 200 225 250 300 325
Appendix C 457
4QQQQQ I 212.1
ljJ-2C-T-2 (n.o.c.)
350000
� NH2
H3C � S JlA OCH3
300000 1
250000
2-(4-(ethylthio)-2,6-dimethoxyphenyl)ethanamine
1
200000
Exact Mass: 241 . 1 136
1
1
150000
m / z: 241 .1 136 (100.0%), 242.1170 (13.0%),
243.1094 (4.5%)
100000
151.1
0, 13.26; S, 13.29
1
1
1 66.0
l ,1L
1 84 . o
1 , 1 . Ii ..
1 38.1
1� I --�'�·��'I�
I.
50000 1 23. 1
�·"'J. ,l,l.1... L .. 1il11Ji1...11 1L.L, 11.111... .. ,�11111. . ..111111 t .1111 11..

"0 91 . 1
· 109 0
Ill ' .. �
45.0 65 . 0
,, 111 .. 19
m/z->
0 -
40 so 60 10 ao so 100 1
1 o do 130 140 1 50 6
1 0 1 10 180 1 90 200 210 220 230 240 250 260
2C-T-4 (see # 25)
XX:: NH2
1.1
1.0
H3CO
I
0.9
H3c A s
CH3
O.B ,&- OCH3
0.7 2-(4-(isopropy1 thio )-2,5-dimethoxypheny1 )ethanamine
0.6
<
ill 5 Exact Mass: 255.1293
2 �
x
� Molecular Weight: 255.38
0.5
>-
m/ z: 255.1293 (100.0%), 256.1327 (14. 1%), 257.1251 (4.5%)
0.4
/153
0, 12.53; S, 12.56
0.3
0.2 /4 1
l� .i.�1J�dl.
/91
0.1
o.o .
mh
50 75 100 125 150 175 200 225 250 275 300 325 350
....... 1 8 3
1 . 1 ljJ-2C-T-4 (see # 25)
�
1.0
0.9
NH2
H3C A S )lA OCH3
0,8
CH3
�
0.7
0.6 5 2-(4-(isopropylthio)-2,6-dimethoxyphenyl)ethanamine
2
0.5
>-
Exact Mass: 255.13
0,4
/153 m/ z: 255.1293 (100.0%), 256.1327 (14.1 %), 257.1251 (4.5%)
-- !&'i 0, 12.53; S, 12.56
/41
: : : l ��.i.1l�1..J,l�, .L,C��LJ J1,JJ

0.2
50 75 1 00
...
1 25 1 50
. ,;i I '
175
,J L..
200
..L. '·" I L
225
·-·- ·····-
250
L. .
275 300 325 350
m/z

Mass Spectra 55- 57
226"1 2C-T-7 (see # 27)

2.6
2.4 H3CO :cc: NH2

2.2
H3C �S :::::.-.. I
2.0 OCH3
1 .8 2-(2,5-dimethoxy-4-(propylthio)phenyl)ethanamine
"
1 .6
< 1.4
u; Exact Mass: 255.1293
1.2 25
�
ml z: 255.1293 (100.0%), 256.1327 (14.1%), 257.1251 (4.5% )
/153
�
>- Elemental Analysis: C, 61.14; H, 8.29; N, 5.48;
1.0
0, 12.53; S, 12.56
0.0
u
0.6
0.4
2 lliJ./
41
0 •.
0.0 .
50 75
m/z
1 00 1 25 150 175 200 225 250 275 300 325 350
T H3CO � NH2
2C-T-8 (see # 25)
500000
450000
400000 1
350000
�S�OCH3
1 2-(4-((cyclopropylmethyl)thio)-2,5-dimethoxyphenyl)
300000 ethanamine
Chemical Formula: C14Hz1N02S
250000 Exact Mass: 267.1293
"'·' ml z: 267.1293 (100.0%), 268.1327 (15.1 % ),
200000,
269. 1251 (4.5%), 269. 1360 (1.1%)
0, 1 1 .97; S, 1 1 .99
m/z->
:cc: NH2
2C-T-9 (see # 25)
184-'"'"'"
4.2
4.0 H3CO
3.8
H3C �CH3 �
:::::.-.. I
3.4
3.6
3.2
3.0
H3C S OCH3
2-(4-(tert-butylthio)-2,5-dimethoxyphenyl)ethanamine
2.0
Chemical Formula: C14Hz3N02S
....
2.6
2.4 Exact Mass: 269.1 449
< 2.2
u;
0 Molecular Weight: 269.40
ml z: 269.1449 (100.0%), 270.1483 (15.1%), 271 .1407 (4.5%),
1 .8
2.0
..'!
�
>- 1.6
271 .1517 (1.1%)
1.4
Elemental Analysis: C, 62.42; H, 8.61; N, 5.20; 0, 1 1 .88; S, 1 1 .90
1.2 26
1.0
o.a
0.6
300
Appendix C 459
242-" 2C-T-13 (see # 25)
:cc: NH2
7.2
6.8
6.4
6.0
H3CO
5.6 I
5.2
4.8
H3C,.. o �S ::::.,,_ OCH3
2-(2,5-dimethoxy-4-((2-methoxyethyl)thio)
(
4.4
phenyl)ethanamine
,...
ifi 4.0
0 3.6
25 3 . 2 /183 /271
>-
2.8
m / z: 271 .1242 (100.0%), 272.1276 (14.1%),
2.4
151"" 273.1200 (4.5%)
2,0 Elemental Analysis: C, 57.54; H, 7.80; N, 5.16;
1.6 0, 17.69; S, 1 1 .82
50 75
m/z
100 125 150 175 200 225 250 275 300 325
11 XX:: NH2
75.0
2C-T-14 (n.o.c.)
130000 H3CO
120000
1 I
1
s
1 1 0000
100000
H3C,.. �S .0 OCH3
2-(2,5-dimethoxy-4-((2-(methylthio)ethyl)thio)
]
90000 i phenyl)ethanamine
aoooo
Chemical Formula: C13H21 N02S2
70000
60000 m / z: 287.1014 (100.0%), 288.1047 (14.1%), 289.0972 (9.0%),
50000 288.1008 (1 .6%), 290.1005 (1 .3%)
Elemental Analysis: C, 54.32; H, 7.36; N, 4.87; 0, 1 1 .13; S, 22.31
40000
I
Synthesis (Shulgin and Shulgin 1991);
30000 spectrum previously unpublished, no CAS #
. � ·.'.1 � .1� "l'� .l��

20000
'\:1L,.�:., . . !,., '.t: , �:.r ' '.i: . :�.· J1.:

10000
.. ..
mtz-->
0 . . . '"· "" "" · .
4 0 50 60 7 0 80 9 0 100 1 1 0 120 130 140 1 50 160 1 70 180 1 90 200 210 220 230 240 250 260 270 280 290 300
'-224
4.2 2C-T-15 (see # 25)
H3CO � NH2
4.0
� S � OCH3
3.8
3.5
3.2
/253
3.0
2.8 2-(4-( cyclopropy1 thio )-2,5-dimethoxyphenyI)
(
2.5 ethanamine
2.2
iii
x
s
2.0 Exact Mass: 253.1 136
>-
191""
16�
1 .5 m / z: 253.1 136 (100.0%), 254.1170 (14.1%),
1 ,2 255.1094 (4.5%)
1.0
7�
0, 12.63; S, 12.66
. l1JM150L . l'
o.s
121""
0,5
iJ .i.Jilill11.Jli .
0.2
0.0 .11.1.••t....•.••i....•.• • • . L� --• " ··- .. L
125 200 225 250 275 300 325
m/z
50 75 100 , 1 75

1 224 . 1 2C-T-16 (see # 25)
1
110000
100000
90000 1
80000 1
183.0
60000 I
70000 2-(4-(allylthio)-2,5-dimethoxyphenyl)
1
ethanamine
50000 1
40000 1
m/ z: 253.1 136 (100.0%), 254.1170 (14.1%),
44.0 137.1 255.1094 (4.5%)
1 1
253· 1 Elemental Analysis: C, 61 .63; H, 7.56; N, 5.53;
: : :i 1
11 11 1
30000 152 9
1
I
I
121 , 0, 12.63; S, 12.66
I
91 . 1
1 , 1l1.,.,. rll11l1. I. 1, , c;-nl • )·�·�

65. 0 " · 0 19 1 0 206. 2
53 0 109.0
°'�40111 IJl50 ,1 1601 , l1ll170l 1 .1 1 l80, 1, l,.901 l 1 L100"1l1 110l l1,J120l1 , 1 , 13011,1 1 1 140 150
16? .0
I
mlz->
.. 1 . ....
160 170 180 190 200 210 220 230 240 250 260 270 280
6.0 1s:Y'
2C-T-17 (see # 25)
XJC:
5.6
5,2
24°" H3CO N H2
4,8
�S I
CH3
4.4 H3C :::::-..
4,0
OCH3
3.6
�
2-(4-(sec-butylthio)-2,5-dimethoxyphenyi)ethanamine
3,2
;o 26
0
( Exact Mass: 269.1449
.. 2 . 8
x
,_
m / z: 269.1449 (100.0%), 270.1483 (15.1%), 271 .1407 (4.5%),
153\_
2. 4
2.0
271 .1517 (1.1%)
1 ,6 0, 11 .88; S, 1 1 .90
J
1 .2
l
o .e
.Jl.uw-J.i...Jt.. d,L,wLlL�l.1
77'. 110-.
0.4 "- "-
O,O L�M l. ' -"--�L ...... L.
I
• - L -
250 275 300 325
m/z
50 75 100 125 150 175 200 225
1500000
183.0
H3CO � R-2C-T-17 (n. o.c.)
NH2
I
1400000 H CH3
1
1300000 <,
H 3C <-.../
1200000 �S 0 OCH3
1 1 00000 (R)-2-(4-(sec-butylthio)-2,5-dimethoxyphenyl)
ethanamine
1000000
900000 Exact Mass: 269.1449
700000 m / z: 269.1449 (100.0%), 270.1483 (15.1%),
600000 240 1 271 .1407 (4.5%), 271 .1517 (1.1%)
500000 0, 11 .88; S, 1 1 .90
400000 153.1 169 0 CAS# 207740-32-7
300000 269 . 1
Appendix C 461
1
240.1 2C-T-19 (see # 25)
1
260000
1
240000
220000'
183 0
200000
180000 1
i
2-{4-{butylthio)-2,5-dimethoxyphenyl)ethanamine
160000 Chemical Formula: C14H23N02S
1
140000
1
120000 m / z: 269.1449 (100.0%), 270.1483 (15. 1 % ),
1000 00
1 271 . 1407 (4.5%), 271 .1517 (1.1%)
1
153 1
40000 I
80000 269 1 0, 1 1 .88; S, 1 1 .90
169.0
20000 1
60000
I .1 1 1 11 .. ,,1,l 11 . i.I I, . �.�1° 2. 1 I I

44.1
Ll40, L 50 2'.r 1 I.
91.1 110.0 121.1 138.1
m/z->
; l l LJu11 L J�ll1 J1i1,, .11 1l 1 i
65 0 77.0
.1.l 1.1,, ,,,1 1 ,1,, 1 l 1 .. . . }� � -1
60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220 230 240 250 260 270 280 290
. . ..... . . .. �1 . l1 �
'230
9.0 2C-T-21 (see # 25)
B.
8.0 H3CO :cc:: N H2
I
7.5
�S
? .O
F
6.5 � OCH3
6.0
5.5
2-{4-{{2-fluoroethyl)thio)-2,5-dimethoxyphenyl)
5,0
ethanamine
iii
( Chemical Formula: C12H1sFN02S
� 4.5
� 4.0
,_
3.5
m / z : 259.1042 (100.0%), 260.1076 (13.0%),
3.0 /259
2.5
261.1000 (4.5%)
/183
2.0
Elemental Analysis: C, 55.58; H, 7.00; F, 7.33;
1 3�
N, 5.40; 0, 12.34; S, 12.36
1.5 /153
1,0
�:� �'.� {1 1IL ,�l. .L .

77
.• J••L .••111 J1i ,11k

•...• 11 �· .J.
40 60 80 100 120 140 160 180 220 240 260
....... .. ... . ... ..... .. ... ... ...
200
rn/z
280
4.2
22(}-"'; 2C-TFM (see # 28)
4,0
3.8
3.6 �
M�('LJ
H3CO N H2
3.4
3.2
3.0
2,6
j
F3C OCH3
2.6 2-(2,5-dimethoxy-4-{trifluoromethyl)phenyl)
2.4 ethanamine
24�
2.2 Chemical Formula: C11H14F3N02
2.0
1 .6
,_ 1 . 6
1,4
m/ z: 249.0977 {100.0%), 250.1010 (11 .9%)
1•2 Elemental Analysis: C , 53.01; H, 5.66; F , 22.87;
1 .0 N , 5.62; 0, 12.84
o.6
5\_
�:�"'·1=--""'�-=�,.,""'....""...."". ' "-"'·�"">"" i.1""1.i""l,,"".1l t
1 2 "' 189'.
14
0.6 '\. '\.
40
.. . ...
60 so
..."" ."'-
.1.. "· '-"
''""'
100
"'""
'1... ,,,
11i.�
..
120
•
.,,
.....!l"
140
111..J1.""
., '''"'
1.1."'
160
"''""
"'"""
""""
li,,1,,
.l .,,
,, .....""
..
ISO
...."""" l "". '""220
..1 .,
. 1"l
200
1.,""
,1
...j�'l. . . 240 �"""'
.. . ,,,_
'-"' .. 5
rn/2.

Mass Spectra 67- 69
4C-TMPEA-5 (n.o.c.)
5.2
�:::
5.0
4.8
4.5
4.2
4.0
3.8
3.5
3.2 OCH3
3.0
5�
< 2.B
;o 1-(2,3,6-trimethoxyphenyl)butan-2-amine
x
2.5
2.2 Exact Mass: 239.1521
)- 2.0 Molecular Weight: 239.31
16�
1 .B m/z: 239.1521 (100.0%), 240.1555 (14.1%)
1 .5
1 .2
23�
1 .0
Previously unpublished; no CAS #
. . . . .J1l... . . .1IIL."1llL
o.8
91
,/'123
�: � JL
0.5
.•• J•• _ .•�· u.� .111 "' ..• 1ll, _ _ __ __ L
111 /z
40 60 80 100 1 20 140 160 180 200 220 240 260 280
!
182.1
4C-TMPEA-6 (see # 122)
� NH2
350000
H3CO )lA OC � CH3

300000 1
250000 i
�M
1
1-(2,4,6-trimethoxyphenyl)butan-2-amine
58.0 Exact Mass: 239. 1521
m/ z: 239.1521 (100.0%), 240.1555 (14.1 % )
100000
I 41 .0
i
soooo 1
lo .J 1 1 1. l l 1
65.a no su
i
11111q ,11 11,l,, l1 . . . 111 •. • . 11111 1, .1111111.

108. 1
mfz.-> 40 so 60 70 80 90 100 1 1 0
:x x: NH2
6.4 1 7&-- 2C-2-TOET (see #56)
6.0
5.6
5.2
H3C �
4.8
H 3C I
4.4 SCH3
_,-:;:.
4.0 2-(4-ethyl-5-methoxy-2-(methylthio)phenyl)
3.6 ethanamine
3.2
� Chemical Formula: C12H19NOS
<
x 2.8
� Exact Mass: 225.1 187
>-
2.4 /225 m/ z: 225.1187 (100.0%), 226.1221 (13.0%),
2.0 227.1 145 (4.5% )
0, 7. 10; S, 14.23
40 60 80 100 1 20 140 160

'"" 1.
180 200
I . , Ir.
220 240 280 300
rn/z
260
Appendix C 463
:x x: NH2
:----. 1 95 2C-5-TOET (see #56)
6.0
5,6
5.2 H3C ':::::

4.B
4.4
H 3C I ...-::;. OCH3
/225
4,0
2-(4-ethyl-2-methoxy-5-(methylthio)phenyl)
3.6 ethanamine
Chemical Formula: C12H19NOS
3.2
2.B
2.4
m/ z: 225.1187 (100.0%), 226. 1221 (13.0%),
2.0 227.1 145 (4.5%)
::: ,, ' .:� .J::J.�JL. IL .iii.

1.6
1 2
/117 /149 0, 7.10; s, 14.23
. ·- �l Ji I - - L
140 160
mlz
40 60 BO 100 120 160 200 220 240 260 280
16"
5.0 :----.1 92 2C-2-TOM (see #56)
4.B
4.5
H3CO � NH2
3, 8
4.0
H3C � SCH3
CO /"'U _
4.2
3.5
3.2 2-(5-methoxy-4-methyl-2-(methylthio)phenyl)
2.8
3.0 ethanamine
2.5
2,2
>-
1 .8
2.0
m/ z: 211.1031 (100.0%), 212.1064 (11 .9%),
1 .5 213.0989 (4.5%)
1.2
13� /211
J(213
0, 7.57; S, 15.17
"
0.0
1,0
1��.,..Jt.1...J.J. J&l1 1 li\. ,j�L.,1 �1 IL L

91
0.5
0.2
.. 1 J
.. .... •. . • .J,
40 240
o.o
mlz
60 BO 100 1 20 140 160 180 2 00 220 260 280
6,0 :----. 1 e2
2C-5-TOM (see #56)
5.6
5.2
H3CS � NH2
H3C �l""\OCH3
/"' U_
4.8
4.4
4.0
2-(2-methoxy-4-methyl-5-(methylthio)phenyl)
3,6
ethanamine
<
;Ji 3 . 2 167"" Chemical Formula: C11H17NOS
x
� 2.B Exact Mass: 211. 1031
>- 2.4 Molecular Weight: 211 .32

m / z: 211. 1031 (100.0%), 212.1064 (11 .9%),
2,0
213.0989 (4.5%)
1 .6 Elemental Analysis: C, 62.52; H, 8.11; N, 6.63;
1.2 0, 7.57; S, 15.17
O.B
0.4
40 80
o.o
mlz
60 1 00 1 20 1 40 160 180 200 220 240 260 280

3.6 Deprenyl (n.o.c.)

3,4
3.2
3.0
2.8
2.6
2.4
2.2
N·methyl·N·(l ·phenylpropan-2-yl)prop-2-yn-1-amine
..
:0 2 . 0
h 1.8 Chemical Formula: C13H17N
! 1.6 Exact Mass: 187.1361
>- 1.4
6
1 .2 m/ z: 187.1361 (100.0%), 188.1395 (14. 1%)
1 .0 Elemental Analysis: C, 83.37; H, 9.15; N, 7.48
0.8
CAS # 2079-54-1
0.6
0.4
2
0.2 Iii
LI
1
o•o '
50 75 bo 125 150 1 75 260 2 5
mlz
6.4
:-... 1 00
DEONE (see # 93)
6.0
5.6
( CH3
¢� 1
5.2
O
4.8
.
4.4
4 0
H,
3.6
0
\.- o
3,2
2.8
1-(benzo[d] [1,3]dioxol-5-yl)-2-(diethylamino)propan-1 -one
>-
2.4
2.0
m/ z: 249.1365 (100.0%), 250.1398 (15.1%), 251.1432 (1.1%)
1 74 24
/ "'
50 125 1 50 175 300 325

m/z
75 1 00 200 225 250 275
6.0
2,4-DIPDMA (n.o.c.)
5.6
5.2
CH3 I
4.8
� N ' CH3
(H3C)2HCO � OCH(CH3)2
�,-��3
4.4
4.0
3,6
1-(2,4-diisopropoxyphenyl)-N,N-dimethylpropan-2-amine
3,2
2.8
2.0 /123 m / z: 279.2198 (100.0%), 280.2232 (18.4%), 281 .2265 (L6%)
1 .6 Elemental Analysis: C, 73.07; H, 10.46; N, 5.01; 0, 1 1 .45
/73
1.2
�:� 1.IL 1 ..,.,1 ll11..... ,{�::

0.8
....... . ..(1:�. ... �.3�. . :�

2
.• d1•• .•11 ••• •••11 _ . __ _ _ 1L . • .. . ..

40 60 80 100 120 1 40 160 1 80 200 220 240 260 280
m/z
Appendix C 465
2,3-DMA ( # 34)
NH2
H3
3
OCH3
1-(2,3-dimethoxyphenyl)propan-2-amine
m / z: 195.1259 (100.0%), 196.1293 ( 1 1 .9%)
/ 180
/195
_ .. 1 . MI.. . .. .
m/z
50 75 100 125 150 1 75 200 225 250 275 300 325
1 52""'
6.0 2,4-DMA ( # 35)
5.6
5.2 � NH2
4.8
H3CO� rv'
4.4
�H3
4.0
OCH3
3.6
1-(2,4-dimethoxyphenyl)propan-2-amine
3.2 Exact Mass: 195.1259
/44
>- 2.4 m / z: 195. 1259 (100.0%), 196.1293 (1 1 .9%)
2.0
::: . ..d"c.J.L
1 .6
1 .2
1, _
m/z
50 75 100 125 150 1 75 200 225 250 275 300 325
2.4 15:y-; 2,5-DMA ( # 36)

2.2
H3CO Y'i(Y NH2
� OCH3
2.0
1.8
1 .6
�0: H3
1 -(2,5-dimethoxyphenyl)propan-2-amine
1.4
�x 1 . 2
Chemical Formula: C 1 1 H 17N02
iO Exact Mass: 1 95 . 1 259
...
>-
1 .0 m / z: 1 95 . 1 259 ( 1 00.0%), 1 96. 1 293 ( 1 1 .9%)
Elemental Analysis: C, 67 .66; H, 8.78; N, 7 . 1 7 ; 0, 1 6.39
o.8
0,6
121"'
0.4
..lli. .J11 ..J

91"' /195
0.2
o.o ..1.,1, •. . .l11o1•• •
4o 60
.J
....
so
... .. _.11111
1 00
1
. . ...
120
JI . .....1..I L . . •
m/z
140
1 1 ! I 1601 1o� 8°'j_8 .
...
1 0 220 240

152"1 3,4-DMA ( # 38)

6,4
6.0
5.6 NH2
5.2
4,B
H3
4.4
H3CO
4.0
OCH3
3.6 1-(3,4-dimethoxyphenyl)propan-2-amine
>-
2.B
2.4
m/ z: 195.1259 (100.0%), 196.1293 ( 1 1 .9%)
2 .0
.1
1.6
1.2
�
. . . .J
O.B 91 /107
25
.Jl1l ��
0,4
"' B /195
o . o . .1 .. l. l. 1 .. .. . . . . ... 1 ..lh .11.,i.. 1
...... ••. ,,,L
4 60 120 140 1 60 220
.... . .. .. .. . .. . .. . ....
0 240
m/z
80 100 180 200
--152
H3CO m NH2
3,5-DMA ( # 39)
1 .6
1 .5
1.4
1.3
1 .2
CH3 y
1.1
1,0 OCH3
0.9 1-(3,5-dimethoxyphenyl)propan-2 -amine
0.8
0.7
>-
0.6
ml z: 195.1259 (100.0%), 196.1293 ( 1 1 .9%)
195"-
0.5
0,4
1
0.3
l 1..__,dl l. . i1.1 . . .
91"'
0.2 /121
0.1
o.o J,1 , .t....... 1L IL IL . ...L
40 220 260
. . .... ... ..... . . .
60
m/z
80 100 1 20 140 160 1 80 200 24Q 280
5.6
--176 DMCPA(#41)
5.2
4,8 H3CO � NH2

H3C ��f'L
OCH3J
4.4
4.0
3.6
2-(2,5-dimethoxy-4-methylphenyl)cyclopropanamine
<
"'
� 2.8
x
2.4
,.. m/ z: 207.1259 (100.0%), 208.1293 (13.0%)
1.6
1.2
o.8
0.4
0,0
50 75 100 125 150 200 225 250 275 300 325
m/z
175
Appendix C 467
:--72
2,6
2,6-DMDMA (see # 36)
�H3� ::H3
2.4
U OCH3
2.2
nr�
2.0
1.0
1 .4
1.6
1-(2,6-dimethoxyphenyl)-N,N-dimethylpropan-2-amine
<
;;;
1 .2
2 Exact Mass: 223.1572
�
,.
1 .0
m / z: 223.1572 (100.0%), 224.1606 (14.1 %)
o.e Elemental Analysis: C, 69.92; H, 9.48; N, 6.27; 0, 14.33
0.6
0.2 208"-.
0.4
0•Q ..• .J.L

40
.L�:J.J l.11 l 100JJI(.��.�
60 eo
. . . . ,. ,., ..
1 20
. M. . . ......
1 40
(��-l
160
· •"'•
160 200
.l.
220
/223
,L
240 260 280 .
m/z
N,N-Me-DMPEA (see #49)
1.1
� N ' CH3
1 .0
CH3 I
H3CO �
0.9
O.B
0.7
OCH3
�
x
0.6
0.5
2-(3,4-dimethoxyphenyl)-N,N-dimethylethanamine
>- Exact Mass: 209.1416
0.3 m/ z: 209.1416 (100.0%), 210. 1449 (13.0%)
20�
0.2
4=
1 07 151
0.1
· 5o is 100 12s 150 17s 200

0 0 ... ••-lh. . . ....... . !.��-----···� ---------··--"-··· - ·----- --- ----- ·
:---.7.. 2
22s 250 27s 300 325 350 ··
m/z
6.0
2,4-DMEA (see #42)
5.6
5.2
4.8 � NH '.../ CH3

4.4
4.0
� "" �H3
H3CO OCH3
152"-.
3.6
3.2
1-(2,4-dimethoxyphenyl)-N-ethylpropan-2-amine
2.8 Exact Mass: 223.1572
2.4
>-
1 .6
2.0
m / z: 223.1572 (100.0%), 224.1606 (14.1%)
/44
121"'
17� 20� /222

1 .2
0.4
J .l l. 1. . .
o.s
i.I. . . t
100 200
1
o . o ..1•• 1 1 "" ... J . .• .I..
80 1 20 140 1 60
.. ... ...... . ... . ··'"·
40 60 180 220 240

m/z

:--,. 1 28
4.2
2,4-DMHA (n.o.c.)
4.0
3.8
3.5
3.2
3.0
2.8
2.5
N-( 1-(2,4-dimethoxyphenyl)propan-2-yl)hexan-1-amine
( 2.2
;;; Chemical Formula: C17H29N02
x
� Exact Mass: 279.2198
2 .0
,_
La
1.5
m/ z: 279.2198 (100.0%), 280.2232 (18.4%), 281 .2265 (1 .6%)
Elemental Analysis: C, 73.07; H, 10.46; N, 5.01; 0, 1 1 .45
1.2 Synthesis (Shulgin and Shulgin, 1991); spectrum previously
1 .0 unpublished, no CAS #
�:� ·'(_·'- .._J

0.5
0.0
44 1 2 1"'
j�
/
179 /2 1 8 27�
... � •.1.• • L.... _ __ _ ..Ji..�-·.t.._._......._.H_....._W_ , __ H . ....._._ . ... _ H ·- •
50 75 100 125 150 175 200 225 250 275 300 325
lll / Z
5.0
2,4-DMIPA (n. o.c.)
4.5
4.8
NH CH3
4.2
H3 Y
3.8
OCH3 CH 3
4.0
3.5
H3CO
3.2 1-(2,4-dimethoxyphenyl)-N-isopropylpropan-2-amine
<
;;; 2.8
� 2.5
x
>-
2.2
m / z: 237.1729 (100.0%), 238.1762 (15.1%), 239.1796 (1.1%)
2.0
/44
/151
1.5 Synthesis (Shulgin and Shulgin, 1991); spectrum previously
1.2 unpublished, no CAS #
0.0
�:� J. J
1.0 /179
.J.I
40
• � .1•
. •
60
• 1
JJ.._, 1..,
80
.....1111 ••• i., L, _,..,.,J.. _ ..i11
1 00 120
m/z
140 . 1 60
···""'·- .•.
180
··-'·"·
200 220
/222
...J• . -•·-
240 260 280
�-- CH3
2,4-DMMA (see #35)
3.2
3.0
2.8 15�
2.6
2.4
H3
2.2
H3CO OCH3
2.0 1 -(2,4-dimethoxyphenyl)-N-methylpropan-2-amine
1.8 Chemical Formula: C12H19N02'
1 .6
>-
1 .4
1 .2
ml z: 209.1416 (100.0%), 210.1449 (13.0%)
1.0
0.8
1.
7�
0.6
/1 2 1
, .It , J1
/91
0.4
0.2
o.o .1 . .. . ,
40
,1 ,, . 1
1 i . 1 .I
60
,
80
... .
100
, ,,,11,1. ,.,J,
120
" 111, ,
140
ohl ..
1 60
. 111. 17�1,
180
. . . •
/
I
1�
200
11.
mtz
Appendix C 469
2,5-DMMA (see # 36)

1 .9
1.6
1 ,7 H3CO ,,.� HN , CH3
1.6
1 .5
I CH3
OCH3
�
1 ,4
1.3
1.2
15�
1-(2,5-dimethoxyphenyl)-N-methylpropan-2-amine
1.1
1.0
o.e ml z: 209.1416 (100.0%), 210.1449 (13.0%)
,_
0,7 Elemental Analysis: C, 68.87; H, 9.15; N, 6.69; 0, 15.29
o.6
0.5
0,4
0.3
0.2
0.1
.
/194
o.o . 1••li... _...I...
40 60 80 100 120 140 160 180 200 220 240
Ol/Z
44.1
2,4-DM-5-MTA (n.o.c.)
H3CS� NH2
� "OCH3
800000
" � H3
700000
198 0
600000 H3CO
1-(2,4-dimethoxy-5-(methylthio)pheny1)
I
5000001 propan-2-amine
400000 1 Exact Mass: 241 .1 136
ml z: 241 .1 136 (100.0%), 242.1170 (13.0%),
300000
!
243.1094 (4.5%)
200000 N, 5.80; 0, 13.26; S, 13.29
1 a3 o
1 1
1· I .
CAS # 69587-03-7
I 1 1 1•
100000
l J I J l , 1 1 1 1 .. l l l l l i J l l . . . o d J i ! l 1 1 . . . . . . . 1 J l i 1 J 1 ..... . . 1 ! 1 l l l 1 ,
1 52 . 1 167 .0 ·
69.0 77.1 91 . 1 1 37.1
Q-;-m
51 0 1 09 .0 121 . 1 241 .1
,II I 1 1 1.. , , , 1 , . I, � 1.�;�-• 2 �?�
m/z->
n. : l 1 l, , . . i 1 1 1 l 1 l 1 1 . . . . , . ,111 ·''"' j,j r .,11,I 11 "T --.r-rr
�
40 50 60 70 80 90 1 00 1 1 0 120 1 30 140 1 50 160 1 70 1 80 1 90 200 210 220 230 240 250 260
2,4-DMPA (n.o.c.)
� N �CH3
": H 3
H3CO � "OCH3
N-(1-(2,4-dimethoxyphenyl)propan-2-yl)
propan-1-amine
Chemical Formula: C14H23NOz
ml z: 237.1729 (100.0%), 238.1762 (15.1%),
239.1796 (1 . 1%)
0 /179
N, 5.90; 0, 13.48
0. 6 /44
,5 l l
Synthesis (Shulgin and Shulgin, 1991);
JL,LL...
120 160 80
spectrum previously unpublished, no CAS #
�. � .1.ll . . tao. .. .........i.. .....L . ..... .......

/222
1•• ·' 1•..•..1111•.. 1 1 111
1
...• L.. .�•- ..... 1 . .....
4o GO 100 140 200 220 240 260 280
111/z
•

Mass Spectra 91- 93
DMPEA ( # 49)
6.8
6.4
NH2
H3CO �
(Y'-'
6.0
5.6
5.2
4.8 OCH3
4.4 2-(3,4-dimethoxyphenyl)ethanarrtine
4,0
�
� Chemical Formula: C10H1sN02
3.6 Exact Mass: 181.1 103
� 3.2 Molecular Weight: 181 .23
2.8 m / z: 181.1103 (100.0%), 182.1136 (10.8%)
,..
/ 1 07
2.4 Elemental Analysis: C, 66.27; H, 8.34; N, 7.73; 0, 1 7.66
65'.... /181
2.0
. . ,L.i'JJl ......... .1
1 .6
1 .2
I
�:: .l,, .1•L1·
o.e
50 75 100 125 150 175

. ··. --'l"'-
m/z
200
DOAM ( # 51)
6.
5,6
H3CO � NH2
5.2 �
4.8 "� 3
H3C � nOCH3
.. . ..
1-(2,5-dimethoxy-4-pentylphenyl)
4.0
16�
3.6
propan-2-arrtine
Chemical Formula: C1�27NQi
3.2 Exact Mass: 265.2042
2. Molecular Weight: 265.39
m / z: 265.2042 (100.0%), 266.2075 (17.3%),
2. 267.2109 (1.4%)
/11 1 3�
Elemental Analysis: C, 72.41; H, 1 0.25
/265
N, 5.28; 0, 12.06
._.. .._.�.i.,...,.J=ii1,.04J"l11 1l..,l1 ,_.....,.i!='iL-F"""'l"• ...L .,

().u-o"'l..""r'd .
20 140
.,.,.
••
160
�-...
.1 �-....'l"
..
180
-·-·:::_..: :J.......lp:i.
200
....
..
220
...< ..:-':.· .IJ!>...-;. i_..,......,
..,, � 240 260 280
111/ z
40 60 80 100
:--..4 4
a.o DOB ( # 52)
7.6
H3CO � NH2
7.2
M n,.OCH3� �3
6.8
6.4
6.0
5.6
Br
5,2
4,8 1 -(4-bromo-2,5-dimethoxyphenyl)
4,4
<
;;:; propan-2-amine
x
4,0
� Chemical Formula: C11H16BrN02
3.6
>-
3.2 /230
2.8
2.4
m / z: 273.0364 (100.0%), 275.0344 (97.3%),
l
2.0
274.0398 (11.9%), 276.0377 (11 .6%)
1.6 Elemental Analysis: C , 48.19; H , 5.88; Br, 29.15;
1.2 2 1 9'. N, 5.11; 0, 1 1 .67
.L J ...
1 3 1""'
!.2 73
0.8 "-
�:� . �--·· �... ... J.. �:i._ ... _ .JJ. ... .J.iL . !.
2 75
.1l L · -· · - - -·· . . . . . .
1 75 200 225 300 325 350

.. ........ .. ... . . . . . .. .
m/z
50 75 100 125 150 250
Appendix C 471
Mass Spectra 9 4 - 9 6
DOBU ( # 53)
6.0 201Y1
5.6
5.2
4.8
4.4
4.0 1-(4-buty1-2,5-dimethoxyphenyl)propan-2-amine
3,6 Chemical Formula: C1sH2sN02
3.2 Exact Mass: 251 .1885
2.8 Molecular Weight: 251 .36
2,4
,..
m / z: 251 .1885 (100.0%), 252.1919 (16.2%), 253.1952 (1.2%)
.1
251"
-�
50 75 100 125 150 1 75 200 225 250 275 300 325
::ao:. CH3NH2
rolz
2.4 ,.._ 1 8 0 DOET ( # 56)

2.2
2.0
H3C �
1 .8 H3c ......
I
.......,_
.._ OCH3
1 .6
l-(4-ethyl-2,5-dimethoxyphenyl)propan-2-amine
1.4 /44
1 .2
1.0 m / z: 223.1572 (100.0%), 224.1606 (14. 1%)
0.8
50 75 100 125 150 1 75 200 225 250 275 300 325

rolz
D01 ( # 58)
H3CO Y"lrY NH2

5.6
M rv-OCH3�H3
5.2
4.8
4.4
4.0 I
3.6 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine
3.2
Chemical Formula: C11H16IN02
2.8
2.4
m / z: 321 .0226 (100.0%), 322.0259 (11 .9%)
2.0 Elemental Analysis: C, 41. 14; H, 5.02; I, 39.52;
1 .6
247"-.
N, 4.36; 0, 9.96
1.2
:::"�·�_,1,,L.'4'_.,, ,l""1. l
=/ ,.,JL"". "'-'- ..,,.("".."'i':�""'6JL _ . "'�----""-.k""" ""__l>=' l �l- --=-.=----'-"'!��
0.8 F.ll
/321
50
.. · ...
_,,, .. =,,,,...=-·=(_""1._.91""'
200 225
.. =
__
250
_
275 300 325
mlz
75 100 125 150 1 75

1£(JQ:
co CH3NH2
2.2
DOIB (see # 60)
2.0
1.0
CH3 Y" I
16�
1 .6
H3C :::::.... OCH3
1.4
1·(4-isobutyl-2,5-dimethoxyphenyl)
1.2
propan-2-amine
;;;
0
( Chemical Formula: C1sH2sN02
..
1.0 Exact Mass: 251 . 1 885
�
>-
0.0
m/ z: 251 .1885 (100.0%), 252.1919 (16.2%),
o •.6
253.1952 (l .2%)
�
Elemental Analysis: C, 71 .67; H, 10.02;
0.4 13
N, 5.57; 0, 12.73
�
91
L I
"
L
0.2
23
o.o "\" i
. ....... . . ...... .if. •... 1 il1 11�1 i••j •
• .•• •. . ••• ........ ... .i �-.11.,�. <#•�••._ . # ... J L . .... _ . . .... _ ...
40 60 BO 100 1 20 140 160 180 ibo 2 4 6 8

111 /:i:
2 0 2 0 2 0 2 0
3.6
�CH3NH2
3.6 :---.. 1 94 DOIP ( # 59)
c
3, 4
H3C Y"
I
3.2
3,0
2.B
2.6
H3 :::::.... OCH3
2.4
2.2
CH3
1 -(4-isopropyl-2,5-dimethoxyphenyl)
� 1,6
;;; 2 0 17� propan-2-amine
.
b 1.8
..
,. Exact Mass: 237.1729
1.4
1.2
1 .0
m / z: 237.1 729 (100.0%), 238.1762 (15.1 %),
' /115 16""'

0,8 239.1796 (1.1%)
9 1'.
0.6
N, 5.90; 0, 13.48
0.4 237"
0.2
o.o
40
JL L ..1t .•. . ll.1L..
120
1JJ. 11.L li..
•••
180
• . .... J. 1
260 280
.... . ..... . . ........ ...... . .. ... ....... .....
mh
60 80 100 140 160 200 220 240
6.0 DOM ( # 60)

5.6
5.2 H3CO Y'i(Y NH2

H3C � nr
4.8
OCH3�
4 4
H3
4.0
3.6 1-(2,5-dimethoxy-4-methylphenyl)
3.2
propan-2-amine
/44
2.8
>-
2.0 m / z: 209.1416 (100.0%),
1 .6
20�
210.1449 (13.0%)
1.2
91" Elemental Analysis: C, 68.87; H, 9.15;
1 .J,(�:�1IL 1. L
O.B
N, 6.69; 0, 15.29
1 00
0.4
o.o J,,1 111... . . . .l.1.... ..... . . •• 11!1�
160 240
.. .. .. . ..... ........ ...
160
m/z
40 60 80 120 1 40 200 220
Appendix C 473
6.0 'l!J-DOM (see # 60)

5.6
ro�
5.2
4.B H,
4.4
4.0
3.6
H3C OCH3
151"' 1-(2,6-dimethoxy-4-methylphenyl)
< 3.2
iii
0
propan-2-amine
....
/44
2.8
.:;
>-
2.4
2.0
ml z: 209.1416 (100.0%), 210. 1449 (13.0%)
1.6
20�
I,
91"'
1.2 N, 6.69; 0, 15.29
IL 1 ��: . .11. L._ ,J L 220

O.B
40 200 240
0.4
o.o ..Lili 1 . • . •111 .. . ...1.l,1
.. .. . . ... ... . .... _ .. . 1 , 1 1... . .
. . .. 11111
.. . ..• tlft�. ..... ti.. ...
60 BO 100 1 20 140 160 180
m/z
:-....1 94
6,0 DOPR ( # 62)
5.6
5.2 H3CO � NH2
H3C � OCH3
4.8
4.4 nr-�H3
4.0
�
1-(2,5-dimethoxy-4-propylphenyl)propan-2-amine
3.6 Chemical Formula: C14Hz3N02
<
iii
0
3.2 16 Exact Mass: 237.1729
2.8
....
.:; Molecular Weight: 237.34

>- 2,4 m l z : 237.1 729 (100.0%), 238.1762 (15.1%),
4 239.1796 (1.1%)
2.0 /4 Elemental Analysis: C, 70.85; H, 9.77;
23�
1,6 N, 5.90; 0, 13.48
�:: _,., .
.. ...... .. .. �
1
- ..I9t "'1 ...• 1 •• ..Jt .. 1•••
1L.3�,.1 •. .. 1,l. _ •• I
i1 ·---�· l ....., _ . ..... . . ••c . . J240
40 60 80 260 280
mlz
100 120 1 40 160 180 200 220
206""1 DOSB (see # 60)

5.6
5.2
4.B
H CO NH2
4.4 H3
4 .0 H3C
3.6 CH3
2.a
1-(4-(sec-butyl)-2,5-dimethoxyphenyl)
<
3.2
;;; propan-2-amine
x
2.0
� Chemical Formula: C15H2sN02
2.4
>-
Exact Mass: 251 . 1 885
1 .6
_/44
m l z: 251 .1885 (100.0%), 252.1919 (16.2%),
/25 1
253.1952 (1.2%)
/115 /149
1.2 Elemental Analysis: C, 71.67; H, 10.02;
�
o.a 91 N, 5.57; 0, 12.73
J1 11• 1
"
0.4 23
L 1
140 160
,,, lt I .I.
o.o ··"·· · ....... .........1iL. .. . . . ... . .
"'
lfl/Z
40 60 80 100 120 180 200 220 240 260 280

Mass Spectra 1 03- 1 05
1
44 0
4-EA (see # 110)
550000
500000
450000
400000
350000
1-(4-ethoxyphenyl)propan-2-amine
300000 Chemical Formula: C11H17NO
250000 Molecular Weight: 1 79.26
200000
m / z : 179.1310 (100.0%), 180.1344 (11 .9%)
150000 1 07 0 1 36,1
:L 1 !�,1,,�r 5,t, ,,, r-]�, . . . I, � ,

100000
. i,'i.'., _,,1 ,
5000
. " '.�?. .'')· � �'4� , � 6:' �� ... � · �

' 1
m/z.�>
"
35 40 45 50 55 60 65 70 75 80 85 90 95 100 1 05 1 1 0 1 1 5 1 20 1 25 1 30 1 35 140 145 1 50 1 55 160 1 65 1 70 1 75 180 185 1 90 195 200
1 .8
EDMA (see #82)
1.7
1.6
1 . !'i
1,4
1 .3
1.2
1.1
iO 1 ,0 /150 1-(2,3-dihydrobenzo[b J [1,4]dioxin-6-yl)
� 0.9 -N-methylpropan-2-amine
� 0.8
..
>- 0.7 Exact Mass: 207.1259
0,6 Molecular Weight: 207.27
0.5 m/ z: 207.1259 (100.0%), 208.1293 (13.0 % )
0.4 Elemental Analysis: C , 69.54; H , 8.27;
IJ
0.3 /77 /123 N, 6.76; 0, 15.44
L ....... J..
0.2 /192
�: � LI. ..l..I Lli
40
••. ...... 1.IL 1J1 1
.. ........ .. Jodl.. ·-'' .. 1l . . 1IL
111 / z
60 60 100 120 140 1 60 1 60 200 220 2 40 260 260
H3CO � NH2
6.0 16Yo Escaline ( # 64)
!'i . 6
19�
!'i . 2
H3C /'-.. O �
4.6
4.4
4.0
3,6
OCH3
<
iO 3.2
2-(4-ethoxy-3,5-dimethoxyphenyl)
2.8
ethanamine
"
2
2.4
> Exact Mass: 225.1365
1,6 m/ z: 225.1365 (100.0%), 226.1398 (13.0%)
1 .2
o.e
N, 6.22; 0, 21 .31
0,4
o.o
200
ml;:
50 75 1 00 125 150 175 225 2!10 275 300 325
Appendix C 475
H
m N'-./CH3
5.6 Ethyl-J (see # 77)
5.2
JY '-cH3
4.8
4.4
4.0 0
3.6 \- o
3.2 1-(benzo[d] [l,3]dioxol-5-yl)-N-ethylbutan-2-amine
2 .8
>-
2.4
2.0 ,/'135 m/ z: 221 .1416 (100.0%), 222.1449 (14. 1%)
1 .2
0.8
.L
,/'1 92
1
58'. ,/'163
,/'105
0.4
"
J... 1.l.. . . L.rl. . , l.1.I. . L ...1 . ..
..
. 1.1 ... J1!1.......J.1u.- .. ... 1 ..1 .. ....!1o..

222
.
.• i.11,.... . .. . . . ..
240
o.o
40 60 100 140 160 180
111 / Z
80 1 20 200 220
H
N'-./CH3
Ethyl-K (see # 77)
3.2
�100
CH3
3.0
2.8
2,6
2.4
0
2.2
2.0
\- o
! .8
1-(benzo[d] [l,3]dioxol-5-yl)-N-ethylpentan-2-amine
1.6
1.4
,_
1.2 m/ z: 235.1572 (100.0%), 236.1606 (15.1 % ), 237.1639 (1.1%)
1.0 Elemental Analysis: C, 71 .46; H, 8.99; N, 5.95; 0, 13.60
0.8
5�
0,6
/77 /192
/
.
0.4
/163
J . .lii L.1i . ....L..
0.2 23
. . 1.... . ...... . ....... . . ... . . ..... . . .. . .. ........ ........ 1.. .. ..... 1... . ..
�
0.0
rn/z
40 80 100 1 20 140 160 180 200 220
m�'-./CH3
6,4 Ethyl-L (see # 77)
6,0
5.6
O� �CH3
5.2
4,8
4,4
4.0 \- o
3.6 l-(benzo[d] [l,3]dioxol-5-yl)-N-ethylhexan-2-amine
3.2 Chemical Formula: C1sH23N02
2.8 Exact Mass: 249.1729
,_ 2 . 4 Molecular Weight: 249.35
2.0
5�
m / z: 249.1729 (100.0%), 250.1762 (16.2%), 251 . 1 796 (1 .2%)
1 .6 Elemental Analysis: C, 72.25; H, 9.30; N, 5.62; 0, 12.83
1 .2
...1 . . .
0,8
/192
�1�...
16�
--··"1........
0.4
o.o -"�L ,J,.. !,L.. 1 ...... I ll.l ....-.J1J L.-.• ,.tlU... ,., .... .
ro/z
40 60 80 100 120 140 160 180 200 220 240 260 280

Mass Spectra 1 09- 111
1
58.0
4-EtO-METH (see # 110)
900000
H
800000 :
� N 'CH3
� CH3
I
i
700000 /"-..
0
H3C
600000 1-(4-ethoxyphenyl)-N-methylpropan-2-amine
Chemical Formula: C12H19NO
I
soooool Exact Mass: 193.1467
1
1
400000 m I z: 193.1467 (100.0%), 194.1500 (13.0%)
300000
1
200000
1l11 111 . . .
1 00000 1 07.0
I
77.0
, 1.
.1
. . , . . . 'T",,. .
42 0
. ��f
5 · 1 �p. 1 1
��
" ,1 ii� ,] I . ?� ? T:t � . , 1 48 1 163 �,..,,., .. 1 7� ·�, -,-�J 93.1
mfz-->
0 1,.-mrT r--i
,_ .-
35 40 45 50 55 60 65 70 75 80 85 90 95 1 00 1 05 1 1 0 1 1 5 1 20 125 1 30 1 35 1 40 145 1 50 1 55 1 60 1 65 1 70 1 75 180 185 1 90 1 95 200
I
EtONE (see #93)
500000 1 72.0
!
I
y
450000
400000
350000 I 0
CH3 CH3
300000
\..- o
1-(benzo[d][l,3]dioxol-5-yl)-2-(ethylamino )propan-1-one
I
200000 Molecular Weight: 221 .2524
I ml z: 221 .1052 (100.0%), 222.1085 (13.0%)
1soooo 1 44.0
Elemental Analysis: C, 65. 14; H, 6.83; N, 6.33; 0, 21 .69
100000 1
1
I .1IL 1 1. J
65 0
1 1 .,..-.,-160---, �-�?�-r
50000 149.1
121.1
..�P- 1_
9 1 .0
o ----r-r-- 1 1 " ,n.�. ,1 � 3t �-
mfz-->
• . _,,,?.� -a ,_,, .
1 ?�· 0--,-,-1 9� . � 206.,2 _r_3 1 � · � .-
-.,-r --r
40 50 60 70 80 90 100 110 120 1 30 140 150 1 70 180 1 90 200 210 220
1.5 5V, FLEA (see # 84)

1.4
1 .3
OH
I
1.1
1.2
N , CH3
H3
1,0 0
0.9
\..- o
<
Ui Q . B N-(l-(benzo[d] [l,3]dioxol-5-y\)propan-2-yl)
s o.7 -N-methylhydroxylamine
>- 0 . 6
;; Chemical Formula: CnH15N03
/135 Exact Mass: 209.1052
0.4 m / z: 209.1052 (100.0%), 210.1085 ( 1 1 .9%)
/77
0.3
17�
N, 6.69; 0, 22.94
�: � 1 1••.
. 410
.. .. J.Ju,
GO
1 ..... . 11 IL
BO
.. 1.1, . . .
100
(��: 1 J.
..
120
.. . .....
111/z
140
... IL ... ...111..
160
.. .•1..
160
. .• ii..
/1 93
200 220 240
Appendix C 477
� To
N-formyl-DMPEA (n.o.c.)
�
H3co y
1.2
OCH3
1.0
N-(3,4-dimethoxyphenethyl)formamide
m / z: 209.1052 (100.0%), 210.1085 (11 .9%)
0.6
0.4 /43 107

/
CAS # 14301-36-1
0.2
)-
o.o .iJJ.Jr,.LtJJL�-1,k . .
50 75 100 125 150 175 200 225 250 275 300 325 350
m/z
YoH
....... 148 N-formyl-MDPEA (n.o.c.)
2.2
\.-Y �
2.0
1.B
o
1 .6 0
1 .4
1.2 N-(2-(benzo(d] [l,3]dioxol-5-yl}ethyl}formamide
1 .0 Exact Mass: 193.0739
0.8 77"'-.. Molecular Weight: 193.20
0.6 m / z: 193.0739 (100.0%), 194.0772 (10.8%)
Elemental Analysis: C, 62.1 7; H, 5.74; N, 7.25; 0, 24.84
.L
0,4 /193 CAS # 33542-98-2
::: L.50UJL75
/105
. JL.. L.<k . , , I· . . · - -----·· · ·
m/z
100 125 150 175 200 225 250 275 300 325 350
,...__ 1 36 G-3 (see # 113)

1.8
1 .7
1 .6
1.5
1.4
1.3
1 .2
1.1
1.0 1-(4,7-dimethoxy-2,3-dihydro-lH-inden-5-yl)
0.9 propan-2-amine
o.s Chemical Formula: C14H21N02
>- o. 7 Exact Mass: 235. 1572
o . e; Molecular Weight: 235.32
m / z: 235.1572 (100.0%), 236.1606 (15.1%), 237.1639 (1.1%}
/1 05
0.5
0.4 Elemental Analysis: C, 71 .46; H, 8.99; N, 5.95; 0, 13.60
0.3
I
1 79'
" /191
� :�.�.l"".11:...I11 "'-.:= I. ""'.11.,"'"_,,,1'"'f1 li.,_i =. ··'""'""". ""'"lt... .. 1 .,__,,.I"'"

0.2
.. .. ...
l 00
...,
....T- . '"=il..-=1.'--'
, ·"·--=
. ... ..""'
' "t"--".,,
.. ,
! BO
.. ....�
.-- ..,..._
.. .,..... ....,,
240
Jll/ Z
40 60 80 120 140 160 200 220

2400000 1
i 44.0
G-4 (see # 113)
1
2200000
2000000
1800000
1600000
1400000 206.2
1200000 1-(1,4-dimethoxy-5,6,7,8-
tetrahydronaphthalen-2-yl)propan-2-amine
1000000 Chemical Formula: C15Hz3N02
800000 1
191.1
600000 m/ z: 249.1729 (100.0%), 250.1762 (16.2%),
251 .1796 (1.2%)
400000 1 Elemental Analysis: C, 72.25; H, 9.30;
oL�_.401 I. 50.171�:�60. ��;�.70 .. 1;801.. . . 90'L 1001,�,[:1�1 0. l1L1120. �li1 30L, .140�.��i.150� . 1.:n160i:. 170.. iii.180. . 190I.. 200 210
I' . 2�2201r.�23023� �240}4250� 2�260 270
! N, 5.62; 0, 12.83
200000 1 91.0 1 1 5.0 1 175.1
77 0
mlz->
... ... . .. ... .��
. � ·�
:--.2.. 10
280
/190
6,4
6.0
5,6
5.2
4.B
4.4
4.0 1-(5,8-dimethoxy-1,2,3,4-tetrahydro-1,4
3.6
2.8
-methanonaphthalen-6-yl)propan-2-amine
1 7�
3.2
u;
( Chemical Formula: C16H23N02
x
;: Exact Mass: 261 .1729
>-
2.4
m / z: 261.1729 (100.0%), 262.1762 (17.3% ),
2.0
263.1796 (1.4%)
� /261
1.2 N, 5.36; 0, 12.24
.JIL.,fil j .J
O.B
il�.-- i�L 1� ..J. .. �

10
0.4
o.o .J.i
40 60
.., • • • . . �IL . .... ••...•
J
80 100 120
.•. • ...
140
.....
160
1 1 •••• �lj 1 ••
1 80
...1 200 220
'·· ·•·-· L....
240 260
.
280
G-N (see # 113)
18�
4.8
5.6
5,2
4.4
4.0
3.6
<
u; 3 . 2
0
2.4
1-(1,4-dimethoxynaphthalen-2-yl)
propan-2-amine
20
... 2.8
1
.?! Chemical Formula: C15H 19N02
1 1� /128
,.. Exact Mass: 245.1416
/245
.
A4
1 .6 / m/ z: 245.1416 (100.0%), 246.1449 (16.2%),
1.2
247.1483 (1.2%)
.J
0.0 N, 5.71; 0, 13.04
80 '120 200 280 300

0.4
o.o .i.J .. __ ... Lt... .. __ .L ____ _ . .. _
40
. . .. . .
m/:i:
60 100 140 160 180 220 240 260
Appendix C 479
Mass Spectra 1 1 8 - 120
1.7 :--.. 1 92 HO-DOPR (n.o.c.)

1.6
H CO NH2
1.3
1 .5
1.4
H3
1 .2
H3C
1.1 OH
1 .0
�
1-(4-{2-aminopropyl)-2,5-dimethoxyphenyl)propan-1-ol
o ... 9 Chemical Formula: C14H23N03
17 Exact Mass: 253.1678
0.6
>-
0,7
m l z: 253.1678 (100.0%), 254.1711 (15.1%), 255.1745 (1.1%)
0.6
/44 Elemental Analysis: C, 66.37; H, 9.15; N, 5.53; 0, 18.95
0.5
/121 /253
0.4
0.3
/227
0.2
91
""
J1 J 1ll1LLM1�L,.1�j,I J
0.1
o . o -Mh . ..... t ..•1 •• ... ..... ... . ..
..... � .... . • . 1. ....
40 BO
m/z
60 100 1 20 1 40 160 1 60 200 220 240 260 280
3.2
:--..59 Hordenine ( # 71)
3.0
2.8
CH3 I
2.6
2.4
� N ' CH3
2.2
2.0
HO �
4-(2-( dimethylamino )ethyl)phenol
;o 1 . 8
( Chemical Formula: C10H15NO
x
1.6
� Exact Mass: 165.1 154
1.4
>-
1.2 ml z: 165.1 154 (100.0%), 166.1187 (10.8%)
o.a
5"'-.
0.6
�:� J� L-.L�:\.�•-·
0.4
16
m/z
50 75 1 00 1 25 1 50 175 200 225 250 275 300 325 350
21Y
4.2 HOT-2 (see # 25)
4.0
3.8
(disproportionates to 2C-T-2)
3,6
3.4
3,2
H3CO XX: HN ....._ OH
3,0
2.6
I
2,6 H3C /'-.. S � OCH3
2.4
N-(4-(ethylthio)-2,5-dimethoxyphenethyl)
2.2
hydroxylamine
2.0
1 .6 241"" Chemical Formula: C12H19N03S
>- 1.6 Exact Mass: 257.1086
1.2
1.0
ml z: 257.1086 (100.0%), 258. 1119 (13.0%),
0,8 /15 3 259.1044 (4.5% )
�: � ,h:.�J, 1:.��1
I L . . ..
0.6
N, 5.44; 0, 18.65; S, 12.46
_, _..
40
.�.� 60
....
80
.... .. 1,11\h . ....
100 1 20 1 40
... ,,,Jl 1, •.•••••11 ... L_. __ .. l..
·· ····
1 60 1 80 200 220 240 260 280

m/z

Mass Spectra 1 2 1 - 123
2,6 HOT-7 (see # 25)
XX:: NH -..., OH
2.4
(disproportionates to 2C-T-7)
2.2
2.0
H3CO
1 .8 H3C � S ::::-.. I
1 .6
OCH3
1.4
N-(2,5-dimethoxy-4-(propylthio)phenethyl)
hydroxylamine
1 .2
/183 /255 Chemical Formula: C13H21N03S
>- 1,0 Exact Mass: 271 .1242
0,
8 m / z: 271 .1242 (100.0%), 272.1276 (14. 1%),
0.6 273.1200 (4.5%)
N, 5.16; 0, 17.69; S, 1 1 .82
50 75 100 1 25 150 175 300

rn/z
200 225 250 275 325
5.6 16V.
:oc: HN ,OH
HOT-ARIADNE ( # 7)
5,2
4.8 H3CO
4.4
I
4.0
H3C ::::-.. OCH3 CH3
3.6 N-(1-(2,5-dimethoxy-4-methylphenyl)
3,2
butan-2-yl)hydroxylamine
2.8
2.4
,_
2.0 m/ z: 239. 1521 (100.0%), 240.1555 (14. 1%)
1.6
N, 5.85; 0, 20.06
1 .2 /123 Previously unpublished, no CAS #
91
0.8
1 I. . . .
207""
""
,J
/223
0.4
/252
.LIL . '''"' . ... .I.Li. .JL 11l1h �L . . . .• 1111 I ..Id . .J. L J .L
60 80 140 1 60 1 80 200 220 240 280
o.o . .. ... . . . . .. . . . .. . . . . . . . .... .
120 260
rn/z
19Yi
40 1 00
:xc: HN -...,OH
3.8
HOT-2C-E (n.o.c.)
3.2
3.6
3,0
3.4 H3C
�
H3C ::::-.. I
2.8
2.6
OCH3
2.4 N-(4-ethyl-2,5-dimethoxyphenethyl)hydroxylamine
<
0 2.0
iii
1.6
1.4
.....
�
1.2
,_
13�
m / z: 225.1365 (100.0%), 226.1398 (13.0%)
1.0
16�
/225
Previously unpubvlished; no CAS #
0.4
0,8
0.2
. i:�J.. J. J
0.6
0.0 ..�.� J_ k.J ,

40 180 200
rn/z
J.hll. 11 1....•• .•. .J
220
... . ... ... . .. .
60 80 100 1 20 140 160 240 260 280
Appendix C 481
Mass Spectra 124 - 1 2 6
3,0 IDA (see # 77)

2,B
��
2.6 H,
2,4
2.2
2.0 O
1.B
H3c )r-CH3o
<
;o 1,6
� 1.4 1 -(2,2-dimethylbenzo [ d][ 1,3] dioxol-5-yl)

)(
�
propan-2-amine
>-
1 .0 12
'"-. - �--· 20"'

0.6 m/ z: 207.1259 (100.0%), 208.1293 (13.0%)
0,4
N, 6.76; 0, 15.44
.L.. . .. l
0.2
o.o I -·· . ..l. .
50 75 100 125 150 175 200 250 275 300 325

111/z
225
1
44.0 JUNO (n.o.c. )
2200000
OCH3
W
2000000
NHz
1
1800000
H3
1
1600000
H3C
1
1400000
1 80.1
OCH3
:::::: 1
1200000
1 -(3,6-dimethoxy-2,4-dimethylphenyl)
1 propan-2-amine
1
1 65.1 Exact Mass: 223.1572
!
600000
m / z: 223.1572 (100.0%), 224.1606 (14.1%)
1
400000 Elemental Analysis: C, 69.92; H, 9.48;
. I 1L . . . . , I ,1,. .
91 .0 N, 6.27; 0, 14.33
,-� . .. l., T ·r ' i • r I , ,,,1 �f .,O

.
200000 77.0 121.1
. 1 , 1 1 1 , . 1 1 3 1� 1111., 1 • 1 • 1 1 ! I J 1 , 1 r • t ' l ' l l l ' t'J'I'
53.0 65.0 1 05.1 1 35. 1 149.1
0 1.,_ 1 1 1 I 1 , 1 , , , . ,,1,, 208 � - - �� - �T"
m/z--> 40 50 60 70 80 90 1 00 1 1 0 120 1 30 140 1 50 1 60 1 70 1 80 1 90 200 210 220 230
ql:cH,
:---.7. 2 K (see # 77)
2.2
2.0
13�
1 .8
1.6
0
\-. o
1.4
1-(benzo[ d] [1,3]dioxol-5-yl)pentan-2-amine
<
;.o
1 .2 Exact Mass: 207. 1259
x
�
>-
""
m/ z: 207.1259 (100.0%), 208.1293 (13.0%)
5 1"
0,8 Elemental Analysis: C, 69.54; H, 8.27; N, 6.76; 0, 15.4
/207
J ... ..... .
0.6 16
/106
ti .
0.4
0.2
o.o
40
li
..i.1111. . .11. JI,,... lul
60 BO 100 120
mlz
140
. ......11 ....
160
I
· �80
20�
20�·· L

Mass Spectra 1 2 7- 129
m N H2
6.0
L (see # 77)
y �cH3
5.6
\-o
5.2
4.8
4 .4
0
4.0
3.6
1-(benzo [ d] r 1,3] dioxol-5-yl)hexan-2-amine
<
13�
;n 3 . 2
x
2 2.0
)-
2.0
m / z: 221 .1416 (100.0%), 222.1449 (14.1 % )
16""'
/51 /221
1. 6
1 .2
J .1.
0.8
i.11 _1.t .1.1.L., l.1. lL . ...

0.4 /190
o.o J.1.. .... .... i.. _ ___ .. . . ..._ ...... . .
CH3N
m/7
40 60 80 100 120 140 160 180 200 220 240 260 280
l'"'-58
6.4 Lobivine (see #85)
y 'cH,
6.0
5,6
I
\-o
5.2
4.8
.4 . 4
4.0 0
<
3,6
:.0
x
3.2 2-(benzo[d] [l,3]dioxol-5-yl)-N,N-dimethylethanamine
5.!
2.8 Chemical Formula: C11H1sN02
,_ Exact Mass: 193.1103
2.4
1.6
m / z: 193.1 103 (100.0%), 194.1 136 (11 .9%)
1.2
0.0
/91 /135 / 193
1-iL__.__..._J.
125
0.4
.. _ ..._ ._ .. ...1.•.•.• ••
50 75
o.o '
o � N H2
m/z
100 150 175 200 225 250 275 300 325 350
1 66.1
j1
Lophophine ( # 73)
400000
OCH3�
I
I1 (
350000
0
1
300000
250000
2-(7-methoxybenzo[d][l,3] dioxol-5-yl)
ethanamme
200000 1 Chemical Formula: C10H13N03

1
1 50000 ! m/ z: 195.0895 (100.0%), 196.0929 (10.8%)
1
Elemental Analysis: C, 61 .53; H, 6.71;
100000 I N, 7.18; 0, 24.59
.
I,
77.0 195 1
�;�!�; I II,,, ; I
50000 64 · 0
51 .0
:,�fr� �,,,, 1111,, :,�ii,'� 111

92.0
l J I , )! i i , , · .)
120. 1 151 .1
o� ,,, , , ' · -�
.
• · 11! • 1 � crrn r ' ��7� 1 ·- � r
mfz--> 35 40 45 50 55 60 65 70 75 80 85 90 95 1 00 1 05 1 1 0 1 1 5 120 1 25 1 30 1 35 140 145 1 50 1 55 1 60 1 65 1 70 175 1 80 1 85 1 90 1 95 200 205
Appendix C 483
1 .4 :"--.44 9 1" 2-MA ( # 74)

1. 3
1. 2 NH z
1.1 �3
/122
1.0 �n0��
OCH3
0.9
1-(2-methoxyphenyl)propan-2-amine
0.0 Chemical Formula: C10H1sNO
iii
0 0.7
(
....
!; 0.6
0.5
,.. ml z: 165.1 154 (100.0%), 166.1187 (10.8%)
0,4
1 6�
0.3
0.2
..J
0. 1
o.o •• I.
60 80 1 00 120 140 160 180 200 220 240 260 280
m/z
40
�4
1.8
3-MA ( # 75)
1 .7
1 .6
y �H3
1 .5
NH2
1 .4
1 .3
�
1 .2
1.1
iii 1 . 0
OCH3
0 0.9
. 1-(3-methoxyphenyi)propan-2-amine
/121
(
.... Chemical Formula: C10H1sNO

� 0,8 Exact Mass: 165.1 154
,.. 0 . 7 Molecular Weight: 165.23
0.6 m l z: 165.1 154 (100.0%), 166.1187 (10.8%)
0,5 /165 Elemental Analysis: C, 72.69; H, 9.15;
0.4 N, 8.48; 0, 9.68
.il.1I11. .1li . . tI J1 li..

0.3
1�
111!1..
0.2
0.1
o.o .
. ..
60
... Ill I. . .. . . 1 1 �1.. _1.1 1 II ...• .. ... i i. · - ... 11 L
40 80 100 120 1 40
m/z
160 180 200
5.6 5Y, MADAM-6 (see # 77)

� ....
5.2
4.8
CH3
\.-o
4.4 CH3
4,0 H3
1 5°"
3.6 0
3.2
<
iii N-methyl-1-(6-methylbenzo[d] [1,3]dioxol-5-yl)
2,8
x
� propan-2-amine
,..
2.0 Exact Mass: 207.1259
1 .6
ml z: 207.1259 (100.0%), 208.1293 (13.0%)
1.2 91"' Elemental Analysis: C, 69.54; H, 8.27;
LJ. J1 �t., 1�.�-� n�-�7J.

0,8 N, 6.76; 0, 15.44
..l.!11 .il.1.I L . ��J,180

0.4
..... . .1...
o.o .. .... . . .... ... J1
. .. . . .. . . . . ...
4o 6o so 100 120 140 160 200 220 240

m/z

H3CO � NH2
4,2
1 6 Yi MAL (see # 91)
4.0
H zC� o y
3.8
3.5
3.2
3.0
2,8 CH3 OCH3
.5 2-(3,5-dimethoxy-4-((2-methylallyl)oxy)phenyl)ethanamine
2
< 2.2
;;;
0
.....
�
2.0 Exact Mass: 251 .1521
1 ,8
>- Molecular Weight: 251.32
1 .5 m / z: 251 . 1521 (100.0%), 252.1555 (15.1%), 253.1589 (1.1%)
1.0
O.B
251"'
0.5
-�: .L
12�
0,2 /55
0.0 _1 -· .
50 75 1 25 175 225 275 300 325
m/z
100 150 200 250
72""1 MBDB ( # 76)

5.6
5.2
4 .8
�-- CH3
4.4
4.0 0 CH3
3.6 \..- o
3.2
1-(benzo[d] [l,3]dioxol-5-yl)-N-methylbutan-2-amine
2.8
13�
,..
2.0 m/ z: 207.1259 (100.0%), 208.1293 (13.0%)
�
1 .6 Elemental Analysis: C, 69.54; H, 8.27; N, 6.76; 0, 15.44
/77
1 ,2 17
J180
0.8
: : : .J.H LJl.J.L.J
40
. ..
60
I
. IL.J.L. ._.iJ1L .
1 0
,,,L...,,,
120
.. ..... d..
140
• -·•'· .•. . ..
2
0
200
�.-
240 260 280
� NH2
m/z
80 0 160 220
5.6 3,4,5-MBM (see # 18)

5.2
4.8
H3CO
4.4
:::c.... I
Br
4,0
3.6
OCH3
2-(4-bromo-3,5-dimethoxyphenyl)
3.2
<
ethanamine
2.8
"'
x
8
2.4
>-
2.0
m / z: 259.0208 (100.0%), 261 .0187 (97.3%),
1 .6 260.0241 (10.8%), 262.0221 (10.5%)
Br, 30.72; N, 5.38; 0, 12.30
BO
m/z
40 60 100 120 140 160 1 80 200 220 240 260 280
Appendix C 485
44. 1
1
1 600000 ' MBzA (n.o.c.)
1500000 i
1400000
1
1 300000 :
1200000 1
1
1 1 00000
1 000000
91 .1
900000 1-(4-(benzyloxy)-3-methoxyphenyl)
800000 propan-2-amine
600000 228.2
1I
500000
m/ z: 271 .1572 (100.0%), 272.1606 (18.4%),
400000 273.1639 (1 .6%)
300000 137.1 Elemental Analysis: C, 75.25; H, 7.80;
I
N, 5.16; 0, 1 1 . 79
I
200000 65·°
CAS # 89356-56-9
1 00000 107.1
0 �,11 1. ,I, ... .. . . 1 1.. .. 111 .. . . . I !,,.. .. 1 1 ! ,,1 ·--�-� f ... 1 1. 1 4�•.1 � � . r � ,-� � '9 s o �
77.0 1 1s 1 11 �5�-�21 !. - �. -rrr·
mlz-->
. �.
40 50 60 70 80 90 100 1 1 0 120 1 30 140 1 50 160 1 70 1 80 1 90 200 2 1 0 220 230 240 250 260 270 280 290
58. 1
I
2000000 1 MBzMA (n.o.c.)
i
1 800000
!
1
1600000
1400000
1200000 1
J
1000000
1-(4-(benzyloxy)-3-methoxyphenyl)-N-methylpropan-2-amine
1
Chemical Formula: C1sH23N02
1I
80oooo
600000 m / z: 285.1729 (100.0%), 286.1762 (19.5%), 287.1 796 (1.8%)
!
91.1 Elemental Analysis: C, 75.76; H, 8.12; N, 4.91; 0, 1 1 .21
40oooo 1 Previously unpublished; no CAS #
i J J J. I'- �- ��
200000 228.1
0 = .� ;, .1... _�;, _ _ 1 1 .. �[_ !�2 1 _ �,T 1 5p 1 1 63 1 J 7� 1 � 9i ' 1 c r-""

4 1 7 0 1 1 1 1
�84.1
m/z-->
�� -
30 40 50 60 70 80 90 1 00 1 1 0 1 20 1 30 140 1 50 1 60 1 70 1 80 1 90 200 210 220 230 240 250 260 270 280 290 300 3 1 0 320 330 340 350
5,2 :--... 1 84 M-d2 (see # 91)

5.0
4,8
4.5
4.2
H3CO � D D
NH2
H3co A/
4.0
3.8
3.2
3,5
3.0
169'.._
OCH3
;;; 2 . 8 2,2-dideutero-2-(3,4,5-trimethoxyphenyl)
� 2.5
(
x
ethanamine
Chemical Formula: C11H1sD2N03
2.0
2.2
,.. /21 3 Exact Mass: 213.1334
1 . !'i
m / z: 213. 1334 (100.0%), 214.1368 (11 .9%)
1.2
1 .0
0.8
UJ,,,,,. .�,,�_,,,, =· · ·.!' (1"'!!!1 .!!!J.{a.11. �.!l l1,,!J! "",. . .:!J!1 l!!c!1I ""'. ·.!il!!1!!! ""!.\"' """""
1 5°'-. N, 6.57; 0, 22.51
'\,
0 0
.. .. ...:!!!1ll1"'"
. ! ...."".!!!J ,..
,,11,!k
...• ... .. ""
= ! ""
••. ..••
'"'!1J!
Uil,. . ••.
••
=� .... .. ""'...""
:!.!!'�..,J!!!�'""'-
!J ....,w
. '"'-
·· ...._
... ....
m/z
40 60 80 100 120 140 160 180 200 220

Mass Spectra 139- 141
18Y.
H3CO � NH2
3.6 M-d3 (see # 91)
3.4
3.0
2.8
3.2
2.6 03co y
2.0
2.4
2.2 OCH3
2-(3,5-dimethoxy-4-(trideuteromethoxy)
1 .8
::ii phenyl)ethanamine
1.4 21�
(
s Chemical Formula: C11H14D3N03
1.2
� 1.6 Exact Mass: 214.1397
0,8
m / z: 214.1397 (100.0%), 215. 1430 (11.9%)
0.6
0.4 /107 "'

/60
N, 6.54; 0, 22.40
6�
l.L.
154'.
�: � 1 .luL. .l.IU .
00 100 200 220
. ...... .11ho......!li1.........11 1o1., •.••1d11.... ....1111..... ..... ........11
� � � � � �
· · '······--••II
m/:i:
240
MDA ( # 77)
C-...4 4
��
2 . 2" H,
2.0
1.8
O
1 .6 \-- o
1-(benzo[d] [l,3]dioxol-5-yi)propan-2-amine
1 .2
0.8
m / z: 179.0946 (100.0%), 180.0980 (10.8%)
/1 36 Elemental Analysis: C, 67.02; H, 7.31;
Lj""
0.6 N, 7.82; 0, 1 7.85
L.11.. 1 /91
0.4
0.2
0.0 .J.J . ....1..._._.__
m/z
50 75 1 00 125 1 50 175 200 225 250 275 300 325 350
1,3
:--...4 4 2,3-MDA (see # 77)
1 .2
w
H,
/135
1.1
1 .0
o__/ �
0.9
0,8
0.7
1-(benzo[d] [l,3]dioxol-4-yl)propan-2-amine
Chemical Formula: C10H1 3N02
0.6
>- 0,5 Molecular Weight: 179.22
0.4
m / z: 179.0946 (100.0%), 180.0980 (10.8%)
0.3
/105
N, 7.82; 0, 1 7.85
0.2
0.1
o.o .il.1!1 1. .l 1 r. 1l,1.
40
. ..
60
Ii
80
1.1.•
100
,, .• �l1h •• ·-'�' I.. · ··"'···
120 140 160 2 00 220 240
m/z
1 80
Appendix C 487
'-- 1 4 8
{Y):': �Yo
1.4
vH3 H
MDA- formamide (see # 77)
1.3
1.2
o\.-o
/'f
1.1
1 .0
0.9
0,8
N-( 1 -(benzo[ d] [ l,3 ]dioxol-5-yl)propan-2-yl)formamide
(
iD
0 0,7
x Exact Mass: 207.0895
0.5
-
>-
0,5 m / z: 207.0895 (100.0%), 208.0929 (11 .9%)
0.4
/44 CAS # 67669-00-5
0,3
�: � ,Ll1. t �l.1 \"

50
1
.. ..
75
11.. .. ll"""(��
100 1 25
l J � .. . ...
150
- · �-�l��-1.
1 75 200 225
..... -···-- ·.- "·
250 275 300

. .. . .... .. . .. ...
325
. .. . ... ··· - .. .. . .. . .
350
H
m/z
y.H3N �CH3
1 1.v-;
5.4 MDAM (see # 77)
6.0
5.6
5.2
\.-o
4,8
4.4 0
4.0
3,6
"'
N-(1-(benzo[d] [1,3]dioxol-5-yl)propan-2-yl)pentan-1 -amine
< Chemical Formula: C15H23N02
3.2
x
�
2,8
2.4
m / z: 249.1729 (100.0%), 250.1 762 (16.2%), 251 . 1 796 (1.2%)
2.0
1.6
23�
1 .2
0.8
0.4
o.o ·-· -L.
1 00 1 25 275 300 325
1
50 75 150 1 75 200 225 250
100 . 1
1400000 MDBU (see # 77)
1 300000
I
1200000:
1 100000
1000000
900000 1 1
800000
700000
N-(1-(benzo[d] [1,3]dioxol-5-yl)propan-2-yl)butan-1-amine
600000 Exact Mass: 235.1572
500000 44.0 Molecular Weight: 235.32
400000
m/ z: 235.1572 (100.0%), 236.1606 (15.1%), 237.1639 (1.1%}
300000
200000
I
135 1
58.0 77.0
10000
m/z-->
: �,11 , ..
40 50
l , . 1 160
. . . . �r.q .
70
. 1 801 , l.1,1,.
� 1• 0 , ,
163·1
.1 �! 1� 1 • �14;: 1 " 1 ' 1 1 · 1 176.1
· ,,,,-1-..-- 92.0
90 100 1 1 0 120 130 140 150 160 1 70 180 190 200 210 220 230 240
� , 1 �,
220.2 234.2
� · � ,,...,.,.---.--

---83
/136 MDCM (see # 77)
2.6
2.4
2.2
2.0
1 .8
1 .6
1 .4 2-((l-(benzo[d] [l,3]dioxol-5-yl)propan-2-yl)amino)acetonitrile
1.2
>-
l.O 6
/5
0,8
m/ z: 218.1055 (100.0%), 219.1089 (13.0%)
0.
0.46
'"'�"'-��1""",,,,L""... =··'-(..,.-"'" _2. 1_8_r--....---,.--�-

I
·
:::_,J""�'"'""50jr',""'·""'Li=·�,.,75"'k.,_, �·· ='l""."""·'"'·'·-r··"""""" [""

.. ""
11.1,,,
.•• ..."'
J' ."'
. · ··
""
'"'"'
....
175
. ..
200
..•
""
225 250 275 300 325

rn/z
100 1 25 1 50
MDDMA ( # 80)
CH3 I
N , CH3
\.-- o
3.0 7Y, H3
2.8 0
2.5
2.2 1-(benzo[ d] [ 1,3] dioxol-5-y1)-N,N-dimethylpropan-2-amine
2 0 .
ID
1.8 Exact Mass: 207.1259
<
0
1 5 . Molecular Weight: 207.27
x
.....
1 .2 m/ z: 207.1259 (100.0%), 208.1293 (13.0%)
>-
1.0
t ?/•
0.8
/91 /� �
0.5
21
0,2
o.o 1.11 1
. .. . .. ..1....r•·'· L 1 1
... .. . ..... . .. . ... ...... ..... .. 1 ........ 1 .. .1........ .......... .. . . . . . . . . . ...................................... ............................. . ............. .................. .... ....... ........... ........... .................... .,.....
50 75 100 1 25 1 50 1 75 200 225 250 275 300 325 350

rn/z
:--....7
2 MDE ( # 81)
2.8
2.6
2.4
H ....- C H3
N....
\.-- o
2.2
2.0
H3
0
1.8
1.6 1-(benzo[d] [l,3] dioxol-5-yl)-N

-ethylpropan-2-amine
1 .2
/135
>-
0.8
m / z: 207.1259 (100.0%), 208.1293 (13.0% )
N, 6.76; 0, 15.44
�
220 240
Appendix C 489
86.1
1 1 00000 MDIP (see # 77)
1000000
NH CH3
H3 Y
900000 j
aooooo l CH3
ll .. . o
O
1ooooo \.-0
600000 1 1 -(benzo[d][l,3]dioxol-5-yl)-N-isopropyl
500000 1
propan-2-amine
400000 1
300000
m/ z: 221 .1416 (100.0%), 222. 1449 (14.1%)
L J' .
200000 N, 6.33; 0, 14.46
m/z->
, ,. : 40
1 . J.50 �:60. � �.701 . I
•
BO
, 1 .,M'
90 100
:,r1 1 0 . .
120
· ''·' ·"
130 140
"'·' �
1 50
:�. :�
160
···,�·�·· �""'�
170 180 1 90 200 210 220 230
6.0 5Yo
MDMA ( # 82)
y. � --
5.6
5.2
4.8 CH3
4.4 H3
4.0 0
3.6 \-- o
1-(benzo[ d] [l,3]dioxol-5-yl)-N
<
u; 3.2
0
-methylpropan-2-amine
... 2.8 Chemical Formula: C11H1sN02
�
,_
2.4 Exact Mass: 1 93.1 1 03
/135
ml z: 193.1 1 03 (100.0%), 194.1 136 (11.9%)
1.2 N, 7.25; 0, 16.56
JLIJ
O.B 1� 19�
l
0.4
l•..• ! ·- tl. .._J '- ......... . J L • .JL_ ..... l . ,l . ....
175 200
o.o
50 75 100 125 150 225 250 275 300 325
m/z
��
5Yo homo-MOMA ( # 83)
6.0
5.6 / 135
5.2
/CH,
4.B
4.4 /207
4.0
O
3.6
\-- o
< 3.2
u; 4-(benzo[d] [l,3]dioxol-5-yl)-N
x
� -methylbutan-2-amine
2.B Chemical Formula: C12H17N02
,_ 2.4 Exact Mass: 207.1259
17�
1 ,6 /77 m / z: 207.1259 (100.0%),
1.2
208.1293 (13.0%)
�:: .40l;il1L .L..l1601f1l.l. . 1il .1 BOll; · 'l...l1I1. 100;.JJ1, I•:r..l l i. I

o.e
/105
1.l.
/i92 N, 6.76; 0, 15.44
. ... . . . . . 1.lllfL.
120
.,. 1,
140
. . .1 1 .. . . ..
160
1 !,
. . 1BO
. . . . . . rn • •
200
L 22�
m/z

800000 72.0
MDMBP (see # 93)
750000
700000
0
H
650000 N ,CH3
\-o
600000
550000 0
CH3
500000
450000 1-(benzo[d] [l,3]dioxol-5-yl)-2-(methylamino )butan-1-one
400000 Chemical Formula: C12H1sN03
350000 Exact Mass: 221 .1052
300000 Molecular Weight: 221 .25
250000 m / z: 221 .1052 (100.0%), 222.1085 (13.0%)
200000
150000
100000
.1IL J. ).I . . 1 1 . . . . �' 6

57.0
10�·.9 p-.· . . . ..,...,...) .3 � .1,,. . I . ..,....,- 1 _6f-,�r-. 1 7?-9-,...., 1 �f· �04� 221 . �
42.0 121 .1 149 . 1
50000
m/z-->
1 ••
40 50 60 70 80
91 .0
90
.. I. J
100 110 120 1 30 140 1 50 160 1 70 1 80 1 90 200 210 220
I
2.4 MDMP (n.o.c)

H
� n3v CH3
� N 'CH3
2.2
\-o
2.0
1.6
1.6
O
1 .4 1-(benzo [ d] [ 1,3] dioxol-5-y 1)-N,2-dimethyIpropan-2-amine
;;;
( Chemical Formula: C12H17N02
x
� 1 .2
1.0
�

0.8
m / z: 207.1259 (100.0%), 208.1293 (13.0%)
0.6 CAS # 81262-69-3
0.4
0.2
111/z
o.o .u... U ..-1
50 75 100 125 150 1 75 200 225 250 275 300 325
:---...1 36
MDOH ( # 84)
N OH
2.4
(disproportionates to MDA)
�H3
2.2
2.0 H
\-o
1.8 '
1 .6
1.4
/44
O� �
1 .2
"'
(
x
� N-( 1-(benzo [ d] [ 1,3] dioxol-5-yl)propan-2-y!)hydroxy !amine
1 .0 Chemical Formula: C10H13N03
,... Exact Mass: 195.0895
17�
o.e Molecular Weight: 195.22
/105
0.6
m/ z: 195.0895 (100.0%), 196.0929 (10.8%)
0.4
i. l,, .J u....).1.. " IL .1IL .

220
o.2
0•0 .• ... ... u• . .... 1L•• ...1 1•.

40 60 80 100 120 140 1 80 20 0 240
m/ :z
Appendix C 491
)7�_,CI
1.1 --.. 1 3 5 MDP(j))Cl (n.o.c)
1 .0
0.9
\..-- o
0,8
0.7
5-(2-chloroethyl)benzo[d] [ l,3]dioxole
<
;;:; 0.6 Chemical Formula: C9H9CI02
x 0,5
>- m / z: 184.0291 (100.0%), 186.0262 (32.0%),
0.4
185.0325 (9.7%), 187.0295 (3.1%)
0.3 /184 Elemental Analysis: C, 58.55; H, 4.91;
77"'
0.2
Cl, 19.20; 0, 17.33
I
CAS # 23808-46-0
.L.,LJL1,. L :L ..J.. .. . .1.•• •. • .... 1ir.... .... .. ......

/91
0.1
.. 1L . .. .. . ........ .. . . --. .. . .. ... .. _.._ _ _ _

_ . .. .... . . .. . ... . . .. . . . .
100
o.o
50 75 125 1 50 175 200 225 250 275 300 325 350
rn/z
2.0 "'-136 MDPEA ( # 85)
1.9
OY ""'
1.8
1 ,7
1.6
\..-- o
1.5
1.4
1.3
1.2
2-(benzo[d] [l,3]dioxol-5-yl)ethanamine
<
1.1
1.0
:;;
x 0.9 Exact Mass: 165.0790
o.a
0.7 m / z: 165.0790 (100.0%), 166.0823 (9.7%)
o.5 N, 8.48; 0, 19.37
0.4
0.3 106
/
i ,,
I I
0.2
0.1
o.o I I
" .J '� _i.. _ . . .. -"---
800000 1
50 l5 100 125 150 l l5 200 225 300 325 350
rn/z
148.1
1
o
MDPEA-AA (n.o.c)
750000
CH3
1
�Y
700000
650000 1
600000 1
\..-- o
550000 1
i
0
sooooo
450000 1
4000001
N-(2-(benzo[d] [ l,3]dioxol-5-yl)ethyl)acetamide
1
350000
1
300000 1 35.1 Molecular Weight: 207.23
250000 m/ z: 207.0895 (100.0%), 208.0929 (11 .9%)
200000 Elemental Analysis: C, 63.76; H, 6.32;
lr
1 5oooo
N, 6.76; 0, 23.16
1. . . ��
CAS# 58026-25-8
::1 .I ' '.'' 1.

·
mfz-> 40 50
;ir 70
60 80
Ji� . . "' ' ·
90 100 1 1 0 120 130 140 150 160 170 180 190 200 210 220 230 240 250
,, " " · � � . �

1,5 :--.. 1 35
MDP(�)OH (n.o.c)
1,4
Y
1.3
1.2
OH
1.1
1 .0 O
0.9
\.-o
2-(benzo[d] [l,3]dioxol-5-yl)ethanol
0.8
(
;;; Chemical Formula: C9H1003
x
� 0.7 Exact Mass: 166.0630
>-
m / z: 166.0630 (100.0%), 167.0663 (9.7%)
0,5
77"" lb� Elemental Analysis: C, 65.05; H, 6.07; 0, 28.88
0,4
CAS # 6006-82-2
0.3
- 1. _.1.1.1.. L
0.2 1 05
/
L t. . .... .. .... ... ......

0.1
o.o __ .. ... .. . .. . . . . . ........ .-.. .• . L .... -"' ····-··- -·�· � ...... .. ..

50 75 1 00 1 25 175 200 225 250 275 300 325 350
111 / z
1 50
--- 1 48
1.7 MDP(�)OH-acetate (n.o.c)
1.6
1.5
1 .4
oyo
1.3 CH3
1.2 0
1.1
1.0
/4 3 \.-o
2-(benzo[d] [l,3]dioxol-5-yl)ethyl acetate
0.9 Chemical Formula: C11H1204
0.8 Exact Mass: 208.0736
>-
0.6 m / z: 208.0736 (100.0%), 209.0769 (11.9%)
0.5 Elemental Analysis: C, 63.45; H, 5.81; 0, 30.74
0.4
CAS# 85263-29-2
0.3
1
0.2 /9 20
�
0.1
0,0 J, ·- IL . 1�1... .r. L_iL_ .. L

• ...l.L ...
125 150 1 75 200
I
225 300 325 350
111 / z
50 75 100 250 275
196"'1 ME (see # 91)

1.1
1.0
0.9
0.8
0.7
f
...
0,6 2-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine
15� �
� 0.5 Chemical Formula: C12H19N03
>- Exact Mass: 225.1365
22
0.3
m / z: 225.1365 (100.0%), 226.1398 (13.0%)
_J J
0.2 N, 6.22; 0, 21.31
, , - .�J.::J. �Lil
0.1
50 75 100 1 25 150 1 75 200 225 250 275 300 325

1'1/Z
Appendix C 493
�CH3NH2
'-180
2.1
MEDA (see # 99)
2.0
1 .9 H3CO
:::::,... I
1.8
1.7
1 .6
1 .5
0
1.4
1.3
�o
1.2 1-(8-methoxy-2,3-dihydrobenzo[b] [1,4]
1.1 dioxin-6-yl)propan-2-amine
1.0
0.9
>-
0.0
0.7
0,6 m / z: 223.1208 (100.0%), 224.1242 (13.0%)
�
0.4 N, 6.27; 0, 21 .50
. . 1.
0.3 /124
. . . . .,C.: . . . . . .J. .
0.2 16
77 /223
... .oh . . . . .... . . ,,�, I .. . . . .... .r. . .. .. ...l.
0.1
0,0 .,,!, . L,L . 1 "'"· . ......
40 60 120 180 200 220 240 260 280

....
80 100 140 160

rn/z
N,N-Me-DMPEA (see #49)
� N ' CH3
H
2.4
:---. 4 4 H3co y
2.2 OCH3
2.0
2-(3,4-dimethoxyphenyl)-N-methylethanamine
1 .8
1 .6
/ 1 52
1.4
1 .2
m / z: 195.1259 (100.0%), 196.1293 (11.9%)
l
1 .0
0 .8
0.6
�o : �o
. ,-J
..::'!
..J· :::;
;'.:
-A
50
�L .:::
'·:::
--� ,-;::: .li.1.. :�
"'.
::;:
:: -
: :::::::::
75
· t1..
.::: :::
100
::;·::.:
: -;:::
""- · L.
=;
· ·:::: ..::::
: -·::=::
125
--::::
· -:;::;::-
:
150
= -:
::;:::;:
� ::: : 9�
175
;;..:-
::;:::·::::
:: ··::::
- ::::;:
-·-
200
= :: ··:::
·-:;::.::
· =-:::- ::-
225
: -
:;:
=::::=
:::; =;::.:=
250
::;
275 300 325 350

mlz
:----. 7 2
3.6 N,N-Me-2,5-HMA (see # 36)
3.4
3.2
3.0
2.8
HO 'lX}: I
CH3
N .._
I
CH3
2.6 ,.lj CH3
2.4 OCH3
2.2
2.0
3-(2-(dimethylamino)propyl)-4-methoxyphenol
<
0 1.B
"' Chemical Formula: C12H19N02
x 1.6
>- 1.4
1.2
m / z: 209.1416 (100.0%), 210.1449 (13.0%)
Elemental Analysis: C, 68.87; H, 9. 15; N, 6.69; 0, 15 .29
1.0
5� / 107
0.8
/ 150 1 9""
0.6
.
_,,IJ.. ,,.i\.. _,,11,..!1 1. 'L1,,, J...
0,4
/209
o.o
0.2
1.L ,.,.,!, ... • n i l . . ... .. � � � - , . ,. ..I�.
1 80 280
.. ..
rn/z
40 60 80 1 00 1 20 140 1 60 200 220 240 260

86.1
N-Me-N-iPr-MDPEA (n.o.c.)
1800000
CH3
N YCH3
I
1600000
1
1400000
CH3
44.1
1200000
\-o
0
1000000 ,
800000 1
I N-(2-(benzo[d] [l,3]dioxol-5-yl)ethyl)-N-
methylpropan-2-amine
I
600000: Exact Mass: 221 .1416
400000j
I
200000 1
m/ z: 221.1416 (100.0%), 222.1449 (14.1 % )
1 911 .0
Elemental Analysis: C , 70.56; H , 8.65;
77 . 0
1 � . .. ,, .� . f,",� -,---,-
1 56J.0 . 65.0l 1
135.1 149.1
�l I
N, 6.33; 0, 14.46
m/z-->
o
I
40
1 � 1 ,,
50
.
60
1 1 1•... 11...
70 BO
, , ... • 1 ...
90
1 0 .o 1
100 1 1 0 1 20 130 140 150
.... 11.,,, l
. 1i .
� ��-!__r� 1 ?�-1..--rJ.9 �·�,-r-3.0?·2�
160 1 70 180 1 90 200 210 220 230
.
� . 221 .1
7-Me-MDA (see # 77)

5.2 15CVi
5 .0
4.B
4.5
4,2
4,0
3.5
3,B
3.2
3.0
2.B
1 -(2-methylbenzo[ d] [ 1,3] dioxol-5-yl)propan-2-amine
2.5 /44
2.2
0�
2.0 Exact Mass: 193.1103
1 .B Molecular Weight: 193.24
1.2
1.5
m / z: 193.1 103 (100.0%), 194.1 136 (11 .9%)
1 �
1.0
19
�:: .ll
�:� l
. ... ..i. i... Jl 1. .1.i._l.J.-� · -� -�� A• . J
200 225 250 275 300 325
m/z
50 75 100 125 150 1 75
a-Me-MDA (see # 77)

:---5
- s
3,B
3.6
3.4
3.2
3,0
2.6
2.6
2.4
1.4
;:;; 2 . 2
1.6
2.0 1-(benzo[ d] [ 1,3 ]dioxol-5-yl)-2-methylpropan-2-amine
x
>- 1.6
1
1 l
�:� 1/ 35
m / z: 193.1 103 (100.0%), 194.1 136 (11 .9%)
0,6
O.B Elemental Analysis: C, 68.37; H, 7.82; N, 7.25; 0, 16.56
/176
0.4 /66 /193
�:� 1LL '"·· JJ.. _.� ---- -L -· . _. . .1. _
50 75 250 275 325

m/z
100 1 25 1 50 1 75 200 225 300
Appendix C 495
�B
N,N-Me-MDPEA (see # 85)
� N , CH,
6,0
A.f"
5.6 CH3 I
5.2
4.8
4.4
4,0 o\-
3.6 o
3. 2 2-(benzo[d] [l,3]dioxol-5-yl}-N,N-
2.8 dimethylethanamine
>-
Chemical Formula: CnH1sN02
2.4
Exact Mass: 193.1 1 03
2.0
1.6 m / z: 193.1103 (100.0%), 194.1136 ( 1 1 .9%)
.1 L
0.8 N, 7.25; 0, 16.56
0.4 /91 /135 /1 93
o.o L.u....J....... 1.L. .... �.. ....1 � - - - l-·--···----···-·-- .-1. ...-..... ..
50 1
75 100 125 150 75 200 225 250 275 300 325 350
m/z
3.3 16&"1 N-Me-MMDA-2 (see # 98)
=ccf
3.6
NH , CH3
3.4
3.2
o
< I
3.0
2.8
2.6 0
CH3 -...;
2.4
° OCH3
2,2 1-(6-methoxybenzo[d] [1,3]dioxol-5-yl)-N
2.0 5� -methylpropan-2-amine
1 .8 Chemical Formula: C12H17N03
1.6 Exact Mass: 223.1208
>- 1 .4 Molecular Weight: 223.27
1 .2 m/ z: 223.1208 (100.0%), 224.1242 (13.0%)
1.0 Elemental Analysis: C, 64.55; H, 7.67
O.B N, 6.27; 0, 21 .50
0.6
0,4 /77 13�
222
0.2 /253�
/193
/
0 . 0 .•. Ji.. . • 1J.l.t.Jli.1...
40 60 100 120 140 160 180 200 220 240 260 280
m/z
80
3 .• 0 12r 4-MeO-PEA (n.o.c. )

2.8
2.6
2,4
� NH2
2.2
2.0
H3CO �
1.8 2-(4-methoxyphenyl)ethanamine
3
<
"' 1 . 6
0 Exact Mass: 151 .0997
1.4
>- 1 .2 m / z: 151 .0997 (100.0%), 152.1031 (9.7%)
7�
1 .0 Elemental Analysis: C, 71 .49; H, 8.67;
N, 9.26; 0, 10.58
1JLL
0,8
CAS #55-81-2
0.6
�l ..
0,4
/151
1.
0.2
o.o .. LL .. L . ·-- �------ ....... . :. . . ... ..

50 75 100 1 25 1 50 175 200 225 250 275 300 325 350
m/z

9. 5 MEPEA ( # 90)
9.0
/166
6.5
6.o
7.5
7.0
6.5
6,0
� 5. 5
5.0
2-(4-ethoxy-3-methoxyphenyl)ethanamine
x
5
4 .. 0 Exact Mass: 195.1259
...
>-
3,5
4 ,0
3 ml z: 195.1259 (100.0%), 196.1293 (11.9%)
2 5 Elemental Analysis: C, 67.66; H, 8.78;
l L
/195 N, 7.17; 0, 16.39
2 .. 0
J
1 5
• �• .1 .I�/94 .J '
1 .0 "'
�:�
.
.1•• . J. • 77' . • • .. .I. .
1
150
m/z
50 75 100 125 175 200 225 250 275 300 325
72.0
N,N-Me-PMA (see # 102)
1 CH3
6000000
I
1 � N ' CH3
5500000
H3CO � C H3
5000000
4500000 ,
4000000 1
1-(4-methoxyphenyl)-N,N-dimethylpropan-2-amine
3500000
3000000 Exact Mass: 193.1467
1
2500000
m / z: 193.1467 (100.0%), 194.1500 (13.0%)
1500000 1
1000000
0 i m� · J I . ,L. 1 .?�·-�. I I i 11.i . ��:? . . .

I
I
500000' 42.0 121.1
56.0 76.2
r . 1 1 .. . �.t� . , i " , .. ,,
..1 .��:\,;il. 9 �.��: �. 1.6f; 1 � 1 ?� ·�
m/z-->
' �.1.9�,. 1 TTTTTTTTl
35 40 45 50 55 60 65 70 75 80 85 90 95 100 1 05 1 1 0 1 1 5 120 125 1 30 1 35 1 40 145 1 50 1 55 1 60 1 65 1 70 175 1 80 1 85 190 195 200
:-.....182
H3CO � NH2
Mescaline ( # 91)
6.8
6.4
H3co y
6,0
5.6
�
5.2
4.8
16 OCH3
4 .4
4.0
2-(3,4,5-trimethoxyphenyl)ethanamine
(
3.6
x 3.2
� Exact Mass: 211.1208
,.. 2.6
2.4
m / z: 211.1208 (100.0%), 212.1242 (11.9%)
2.0
1.6
N, 6.63; 0, 22.72
1.2
o.6
0,4
3So
o.o �--•™1 I
so 75 1 oo 125 150 1 ?s 200 22s 25o 275 300 325

m/z
Appendix C 497
5. 6 5Y, Methcathinone ( # 92)

5.2
0
H
� N ' CH3
4.B
v CH3
4.4
4.0
3.6 2-(methylamino)-1-phenylpropan-1-one
3,2 Chemical Formula: C10H13NO
2,8
>-
2.4
m/ z: 163.0997 (100.0%), 164.1031 (10.8%)
N, 8.58; 0, 9.80
1 .6
l '"'
1.2
14�
0 , fl
.�l jj L�-- l.
0.4
/ 163
M __ ,... ___ ___ � --�'- -···· "
225
o.o
50 75 100 125 15 0 1 75 200 250 275 300 325
�CH3N,CH3
mlz
196"'
5.6 Methyl-DMMDA (see # 44)
5.2 H
4,8
H3CO .,,
4.4
5� :::::.... I
OCH3
\.-o
4.0 0
3.6
<
u; 3 , 2
0 2.8 1-(4,7-dimethoxybenzo[ d)[l,3] dioxol-5-yl)-N
...
2.4
� -methylpropan-2-amine
>-
2.0
m / z: 253.1314 (100.0%), 254.1348 (14.1%)
223"-.
1 .2
o.a
/79 151" N, 5.53; 0, 25.27
0.4 /252
mlz
0. 0 .Lii... ..1J ..1fLL.J�" JllL-•�L..lli . JL ..it ��- - "
50 75 1 00 1 25 1 50 1 75 200 225 250 275 300 325
Methyl-K (see # 77)

3,2
3.0
2,8
2.6
2.4
2.2
2.0
1-(benzo[d] [l,3]dioxol-5-yl)-N
1 .B
\ 1 -methy!pentan-2-amine
1 .6
>-
1 .4
1 .2
/4 4 /135 Molecular Weight: 221.30
1 7�
1 .0 ml z: 221 .1416 (100.0%), 222.1449 (14.1%)
1..
.180J. /190
0.6 N, 6.33; 0, 14.46
1 .1. 111...1.1
0.4
h.L 1 !1
/ 105
0.2 /221
0.0 .1 . 1 , , ... ... .1 ... .. . . . . .• ... . . I. .. ....11.. _ ..
........ . ... .. .
40 60 80 1 00 120 140 160 200 220 240

mlz

:--... 1 0 0
Methyl-L (see # 77)
(Yl � 'CH3
1 .7
1 ,6
o� �CH3
1 ,5
1 .4
1.3
1 .2
1.1 \.-o
1-(benzo[d] [1,3]dioxol-5-yl)-N
<
1.0
ifi -methylhexan-2-amine
0.9
x
0,6
>-
0,7
0,6
m/ z: 235.1572 (100.0%), 236.1606 (15.1%),
0.5
17�
237.1639 (1.1%)
0.4
/1 35 Elemental Analysis: C, 71 .46; H, 8.99;
�
0,3 N, 5.95; 0, 13.60
0.2
..1 11.. . .• .1(179 23
100 120 1 40 160 180 200 220

rn/z
3.8 Methyl-MMDA-2 (see # 98)
m
3.6
H
o N , CH3,
3.4
3.2
< I
3.0
2.8 CH3
2.6
2,4
0
,,.,.:; OCH3
2.2
1-(6-methoxybenzo[d] [l,3]dioxol-5-yl)-N
<
;;; 2.0
-methylpropan-2-amine
x
� 1 .8 Chemical Formula: C12H17N03
1 .6 Exact Mass: 223.1208
,.. 1 ,4 Molecular Weight: 223.27
1 .2 m / z: 223.1208 (100.0%), 224.1242 (13.0%)
�1��L J . I l .
0.8 N, 6.27; 0, 21.50
.li.. .
0.6
0.4
/77
o . o .•.Ji. .. 1••
0.2
,,u t.lll.1 •.. . . ,.1. .. . Ji••• • .. .. ... ..
260
rn/z
40 60 80 1 00 1 20 1 40 160 180 200 220 240 280
¢-
6.4 Methylone ( # 93)
6.0 0
5.6
5.2 �'CH3
4.8 H3
\.-o
4.4 0
4,0
3.6
3.2 1-(benzo[d] [1,3]dioxol-5-yl)-2-(methylamino)
propan-1-one
2.8
,.. 2.4 /149
2.0 /121
1 .6 m/ z: 207.0895 (100.0%), 208.0929 ( 1 1 .9%)
20�
J. . . . .
91
... .
"' N, 6.76; 0, 23.16
0.8
0.4
o.o J.i.1•• . .• . ......L l.. 1

. .• •• • .. ...1 .. • • ••• J..
111 / �
40 60 80 100 120 140 1 60 180 200 220 240 260 280
Appendix C 499
MIP-MDPEA (n.o.c.)
6.0
CH3
I
Y
5.6
N CH3
Y
5,2
4.6
4.4 0
CH3
4.0
3.6
\.-o
N-(2-(benzo[d][l,3]dioxol-5-yi)ethyl}-N
3,2 -methylpropan-2-amine
>- 2.4 44
�
/
2.0
13 /149 m / z: 221 .1416 (100.0%), 222.1449 (14.1%)
1.6
20� /22:
1.2
N, 6.33; 0, 14.46
0.0
--�t. . ._U� _,.l._

_.1L..J._ i
0.4
o.o .
. . -···· L.. t. . ·-····- ·-·""·· _
40 60 BO 100 160 220 240 260 260

rn/z
120 140 160 200
3.6 MIP-PEA (n.o.c.)

3.4
3.2
3,0
2.0
2.6
2.4
2.2
N-methyl-N-phenethylpropan-2-amine
2.0
<
;'ii
0
Chemical Formula: C12H19N
....
1 .6
1.6
.:::
>-
1.4
m l z: 177.1517 (100.0%), 178.1551 (13.0%)
1.2
4 Elemental Analysis: C, 81 .30; H, 10.80; N, 7.90
1 .0 / 4
CAS # 70160-93-9
0.0
0.6
.1 !1 . ,1,J.. .1L.1 . L.
0.4
0.2
. ..
o.o
BO 1 60 1 80 200 220 2 0
4
rn/z
40 60 100 1 20 140
� NH -.....CH3
2.2 "--4 4
M-M ( # 95)
2.0
1 .6 H3CO
1.6 I
H3CO 0
1 .2
1.4
OCH3
1.0
;;;
/162
N-methyl-2-(3,4,5-trimethoxyphenyl)
b
... ethanamine
�
>-
0.0 Exact Mass: 225.1365
16�
0.6 m / z: 225.1365 (100.0%), 226.1398 (13.0%}
/225
,jft.l..bl.Ji..1- :� ,....l.OL . Lk.J

0.4
N, 6.22; 0, 21.31
2
0.2
.. . .� · - ..·""-·-·- �-·- l·-- .. ··-· -·

1 75 200 2 5 275 300 325
o.o
50 75 1 00 125 150 250 350
rn/z

1 .9 /136
"'-44
1 .8
2.0 3-MMA (see # 75)
1.7
1 .5
1.6
1.4
1.3
1.1
1.2
ill
0
(
1-(3-methoxy-4-methylphenyl)propan-2-amine
1 .0
x 0.9
>-
0.8 /31
iU1 _ul�
0.6 m/ z: 179.1310 (100.0%), 180. 1344 (11.9%)
/179
0.4 N, 7.81; 0, 8.93
0.3
0.1
0.2
_l
75 125 �00 25 2l5 300 325
11 L L ._.i
50 100
o.o I I I
1 50 1l5 250
'
m/z
2
1.0
-166 MMDA ( # 97)
OCH3 �"'
(:�Jb:
0.9
0.8
0,7
0.6
1-(7-methoxybenzo[d] [1,3]dioxol-5-yl)
/44
0,5
propan-2-amine
>- 0.4 Exact Mass: 209.1052
0.3 m / z: 209.1052 (100.0%), 210.1085 (11.9%)
... . . . . . .
7�
0.2
20�
N, 6.69; 0, 22.94
1!11 ,I.,. 1 · · · "' ""- .. ...111

Q,1 /120 151"
0�0
40
__ ,,,11 1 . _ .• 1.1 .
60
. lllli.. . .. . ..
100 120
. .. . . . ... 1 1. .
1 40
.
. .. . . . ! .. . . . I. 180 200
m/z
BO 160
o< JCCfCH3NH2
....... 166
4.0
MMDA-2 ( #98)
OCH3
3.8
3.6
3.4
3.2
3.0
0 I 0
2.B
2.6 1-(6-methoxybenzo[d] [1,3]dioxol-5-yl)
2.4 propan-2-amine
2.2
2.0
1.8
>- 1.6
1.4 m / z: 209. 1052 (100.0%), 210. 1085 (11.9%)
1.2 Elemental Analysis: C, 63. 14; H, 7.23;
1.0 N, 6.69; 0, 22.94
0.8
/209
0.6
�:� "''
50
..t�. .m .. ,1J(�:75 100
. b1
. .. . .. LJ,
125 1 50
.. L.. ..•
175 200
J
225 250 275 300 325
m/z
Appendix C 501
MMDA-3a ( # 99)
2.8
2.6
2.4
2.2
2.0
1.8
1 .6
1-(4-methoxybenzo[d] [1,3] dioxol-5-yl)
t.4 propan-2-amine
>-
1.2 Chemical Formula: CnH1sN03
1.0
/14
O.B
m / z: 209.1052 (100.0%), 210.1085 (11.9%)
20�
:��l Jl ,I. . . .
0.4 N, 6.69; 0, 22.94
/77
::: ,.1 .. . 1L .. Jl1 •...
40
Jt.J, . . ....�1, . .• . .. . ... . ....... ..L
m/z
60 BO 100 120 140 160 1 BO 200 220 240 260 2BO
1.0 /44 166-'I MMDA-3b (see # 97)
0.9
O.B
0.7
0,6 1-(7-methoxybenzo[ d] [1,3 ]dioxol-4-yl)

propan-2-amine
o.5 Chemical Formula: C11H1sN03
>-
0.3 m / z: 209.1052 (100.0%), 210.1085 (11.9%)
0. 2 N, 6.69; 0, 22.94
50 75
m/z
100 1 25 1 50 1 75 200 225 250 275 300 325
4.8 -...7
. 2 4-MNNA (n.o.c.)
4.5
4.2 CH3
I
4.0
3.8
N , CH3
3.5
3.2
H3CO H3
3,0
2.8 1-(4-methoxyphenyl)-N,N-dimethylpropan-2-amine
2.5 Chemical Formula: C12H19NO
2.2 Exact Mass: 193.1467
>-
1.8 m/ z: 193. 1467 (100.0%), 194.1500 (13.0%)
1 .5
1.2
121" CAS #126002-36-6
17�
1 .0
0.8
J
0.5
11..!1
2
/4
\ �4·�-
0.11 /192
0 . 0 .1.. .1 . • i.1•.. I
• . . ..�u ... •. 1 .. . . ..... . . .. .11 . . , ..11L..
200 240
111/ Z
40 60 80 100 120 140 160 180 220

6.0
H3C O � NH2
21(Y'; MP (see # 91)
5.6
H3co y
5.2
4.6
4.4
4.0
O �CH3
15�
3.6
23�
<
ID 3 , 2 2-(3,4-dimethoxy-5-propoxyphenyl)ethanamine
x
s: 2 . 6 Chemical Formula: C13H21N03
>-
2.4
2.0
m/ z: 239.1521 (100.0%), 240.1555 (14.1%)
1.2 N, 5.85; 0, 20.06
0.6
0.4
o.o
200
m/z
75 1 00 125 150 175 225 250 275 300 325
12000001
mTFMPP ( # 116)
r NH
I
1 1 00000 !
Qr"_J
10000001l·
900000 ,
: ..... ; CF3
700000 1-(3-(trifluoromethyl)phenyl)piperazine
Chemical Formula: C11H13F3N2
m / z: 230.1031 (100.0%), 231 .1064 (11 .9%)
F, 24.76; N, 12.17
1 00000
42 21 1
83 75 83 .95. 105j1 119 1 27 1 34
mtz-> 40 �o eo 10 eo ill 100 1 o 1 20 1� 1 •0 21 0 220 230
1
1 50 1 2-NH -MDMA-TFAA (n.o.c.)
JX):
2
2200000 CH3 I
]
'f"
2000000
'
0 N o
<0 I CH3 CF3
1
1800000
,0
NH2
1400000 1
1600000
N-( 1-( 6-aminobenzo[ d] [ 1,3] dioxol-5-yl)propan-2-y1)
1200000 1 -2,2,2-trifluoro-N-methylacetamide
Chemical Formula: C13H1sF3Nz03
1000000
800000 m/ z: 304.1035 (100.0%), 305.1068 (14.1%)
Elemental Analysis: C, 51 .32; H, 4.97; F, 18.73;
600000
N, 9.21; 0, 15.78
I
400000 Previously unpublished; no CAS #
J
304.1
. ... . . . .... . , (, , I
200000 177·1
42.0 69.0 1 1 0.0
92. 1
.J. '· 1�,t� ,J11 l 1 .lhl.. . 1l1!. 1 . I. , �-�t:.��F 1 1 1 1 !. �.��--� L,..._1�q.� ·- p21?.� . 1 �'!§� -;- rV1·� - � I. .,..,. --rrr
mfz--> 40 50 60 70 80 90 100 1 1 0 120 1 30 140 1 50 160 170 180 1 90 200 210 220 230 240 250 260 270 2_80 290 300 310 320
Appendix C 503
�
p ( # 104)
1.1
1 sri-- 1 68
1.0
y
H3CO NH2
0.9
H3C �
0.8 o
0.7 OCH3
2-(3,5-dimethoxy-4-propoxyphenyl}ethanamine
'f 0 . 6 Chemical Formula: C13H21N03
210
x 0.5
� "" Exact Mass: 239.1521
0.4 m / z: 239.1521 (100.0%), 240.1555 (14.1%)
23�
0.3
N, 5.85; 0, 20.06
:: : �:�k �.- �:J . � JJL.,

0.2
.�. . ... ...L _ ..
50
mlz
75 1 00 1 25 1 50 175 200 225 250 275 300 325
PE (see # 91)
2.2
2.0
1.8
1.6
1.4
1.2
/301 2-(3,5-dimethoxy-4-phenethoxyphenyl)
ethanamine
0,8
0.6 m / z: 301. 1678 (100.0%), 302.1711 (19.5%),
303.1745 (1.8%}
N, 4.65; 0, 15.93
/181
. """-..
- ""
".,... l. W'l'-"=
""' """"T"" ""' ·r····=···=·""f'"""""-r=--"""'r
0.2
24 1"'
.. ..L . "'-'
' Ji..
,,,,,., J ... �
=
125 150 175 200
o . o�'
-'=-l"
Jl= """"-..c. - -=--4--'-+"---"-"
mlz
50 75 1 00 225 250 275 300 325
7 1.....-C Phenmetrazine (n.o.c.)

3.2
3.0
2.8
2.6
2.4
2.2
2.0
1.8 3-methyl-2-phenylmorpholine
l
1 .6 Chemical Formula: C11H1sNO
�
1.4 Exact Mass: 177.1154
>- 1.2 Molecular Weight: 177.24
/ 1 77
1 .0 10 m / z: 177.1154 (100.0%), 178.1187 (11 .9%}
N, 7.90; 0, 9.03
�: �--=· T"l=J1=..l IT".11.=.J=t =-·=ILT'.{=��'T-'�

0,6
CAS # 134-49-6
..'F'
'" ="-"-r
" - ·=
· ---·· . ·· ='T-=-'-'"-.---"'P�"r-"--""r_...-+="-
... -"-'
50 100 125 150 175 200 225 250 275 300 325
mlz
75

PMA ( # 75)
1,7
1'-44
1 .6
� NH2
� CH3
1 .5
1 .4
1.3
1.2
H3CO
/ 122 1-(4-methoxyphenyl)propan-2-amine
1.1
Chemical Formula: C10H1sNO
1 .0
<
Iii Exact Mass: 165.1154
0
....
0.9
0.8
�
>-
m / z: 165.1 154 (100.0%), 166.1187 (10.8%)
0.7
0,6
0,5
/'1
0.4
.JuL.JL.
0.3
J
0.2 /165
0.1
o.o .i.1 ,11..�.LL. ·-.I . . .....

1 75 225
m/z
50 75 100 125 1 50 200 250 275 300 325
2.4 5!.Y"i PMMA ( # l12)

2.2
2.0
1 .8
1 .6
1 .4 1-(4-methoxyphenyl)-N-methylpropan-2-amine
< 1.2
iii
x
�
Exact Mass: 179.13
y
121"
>-
1 .0
0.8 m / z: 1 79.1310 (100.0%), 180.1344 (11 .9%)
0,6
14� /164
.
0.4
ili .J I . . . . ...ilL ...11L . ......

0.2
o.o .1.ili... ...... 11 .
m/z
40 60 80 100 1 20 140 1 60 1Ej0 200 220 240
�
Propynyl ( # 104)
1.9
1 6Yi
1.6
1.7
1.6
H3CO � NH2
./"'....
HC"=�C,..- 'O
1.5
1.4
0
1 .3
1.2 OCH3
�
1.1 2-(3,5-dimethoxy-4-(prop-2-yn-l-yloxy)
1 .0 phenyl)ethanamine
0.9
o.a
>- Exact Mass: 235.12
0.7
0.6
23 �
168
o.5
ml z: 235.1208 (100.0%), 236.1242 (14.1%)
0.4
/91
..i�lJ L .
0.3 N, 5.95; 0, 20.40
,liL.
0.2
7�
o . o .1.. . .. _.. i... • 1.... I . ....
0.1
I
. - _...llk..llit...
I I I I - I I
__
I
-- I
75 100 125 300 3b
m/z
50 150 1 75 200 225 250 275
Appendix C 505
5.6
H3C '-.../ O � NH2

21o---; SB (see # 91)
5.2
H3co y
4.8
4.4
4,0
3.6 O '-.../ CH3
3.2
�
2-(3,5-diethoxy-4-methoxyphenyl)
2.8
ethanamine
/153
23
>-
13�
2.0 Exact Mass: 239.1521
1.6
m / z : 239.1521 (100.0%), 240.1555 (14.1 % )
1.2
Elemental Analysis: C , 65.25; H , 8.84;
, J .J
0.8 N, 5.85; 0, 20.06
::: ,4o., ., . .c.:. J11C.n:1

..... .. . 1il !llL..,,11 Lj
. .. ,_ _ .. .. . , L . . . . 1 . . .... ... !.. ..
I I
60 60 100 2 i4o 160 180 200 220 240 260 280
m/z
1 0
H3C '-.../ S � NH2

197"'1 3-TASB (see # 91)
5.6
H3C /'... O �
5,2
4.8
4.4
4.0
3,6
OCH3
§ /255
U> 3,2 2-(4-ethoxy-3-(ethylthio)-5-methoxyphenyl)
ethanamine
2.8
2.4
� Chemical Formula: C13H21N02S
>- Exact Mass: 255.1293
1.6 m/ z: 255.1293 (100.0%), 256.1327 (14.1 % ),
/137
1.2
257.1251 (4.5%)
7� /37
0.6
J .l
N, 5.48; 0, 12.53; S, 12.56
0.4
l. 275
75 125
JLI
o.o
J.. .. " __ _ · -
50 200
,./z
100 150 175 225 250 300 325
3.6 '-197
3.4
3.2
3.0
2.8
2.6
2.4
2.2
2-(3-ethoxy-4-(ethylthio)-5-methoxyphenyl)
2,0
�
1 .8
ethanamine
1 .6
25
,., 1 .4 Exact Mass: 255.1293
/169
1 .0 m/ z: 255.1293 (100.0%), 256.1327 (14.1%),
I
0.8
257.1251 (4.5%)
0.6
/28�
o.4
1
N , 5.48; 0, 12.53; S, 12.56
��'--'��•-·,.•-· ••��--"L"dJ _,,'[_�

0 2
.. L . ...L
•
. ---• . . ..
O . O·-�""'"''""'i�"""l""" ='i==""'f'-"""=T=""'"'f�""'T�=--T=='-"i'"-'"-"T'-'-'=,-"'---T'-----.
---'
220 240 260 260
m/z
40 60 60 100 1 20 140 160 160 200 300

3,6 '-197
3,4
3,2
3.0
2.8
2.6
2.4
2.2
2.0 2-(3,4-diethoxy-5-(methyithio)
25�
1 .8 phenyl)ethanamine
1 .6 Chemical Formula: C13H21N02S
,... 1.4 Exact Mass: 255.1293
1.2
/169
1 .0 m I z : 255.1293 (100.0%), 256.1327 (14.1%),
I
0.8 257.1251 (4.5% )
/28�
�:�
0.6
l
N, 5.48; 0, 12.53; S, 12.56
. . .. ��'--'��·-··•····'(�:�_,,wL-"'� 1, __ .._ _)L_ �- . _ _ _
� � � � � �
rn/z
00 1 00 1� 1� 1M � � �
H3CO � NH2
6.4 :-.-.183 TB (see #91)
6.0
H3C�S �
5.6
5.2
4.8
24 °"
4.4
4 .0 OCH3
3.6
;;;
( 3,2 2-(4-(butylthio)-3,5-dimethoxyphenyl)
x
s ethanamine
2.B
>-
2.4 Exact Mass: 269.1449
1.6 m/ z: 269.1449 (100.0%), 270.1483 (15.1%),
7� 121" �
1 .2
271 .1407 (4.5%), 271 .1517 (1.1%)
O.B
JLJ � ...1101. .lf- .\..,L....,Ji.J.__, "

16 N, 5.20; 0, 1 1 .88; S, 1 1 .90
..l J.l_ l J_ . .
0. 4
o.o . . •. •• . ..J.. ..
. - ---� ... . _
50 75 100 125 150 175 200 225 250 275 300 325
rn/z
H3CO � NH2
:--.. 183 TE (see # 91)
6.0
H3C/""'-.. S �
5.6
5,2
/2 1 2
4,8
3,6
4.4
4.0 OCH3
< 3,2
;;; 2-(4-(ethylthio)-3,5-dimethoxyphenyl)
0 ethanamine
...
�
2.B Chemical Formula: C12H19N02S
,... 2.4 Exact Mass: 241 .1136
m/ z: 241 .1 136 (100.0%), 242.1170 (13.0%),
2.0
1 .6
7� 151"'
1.2
243.1094 (4.5%)
.i,
0, B 121"' N, 5.80; 0, 13.26; S, 13.29
: :: ,��.-..uh-�1..._..._L .\ I
50 75 100 125 1 50 175 200 225 250 275 300 325
mlz
Appendix C 507
Mass Spectra 202- 204
H3CS � NH2
5.2 '1e3
3-TE (see # 91)
5.0
4.6
4.5
H3C .......--. O �
4,2
4.0
3.6
3, 5
3.2
/2 1 2 OCH3
2.
- 3.0 2-(4-ethoxy-3-methoxy-5-(methylthio)phenyl)
'fl ethanamine
� 2.5
! 2.2
>- 2.0
1 .6 Molecular Weight: 241 .35
1.5 m / z: 241 . 1 136 (100.0%), 242.1170 (13.0%),
243. 1094 (4.5% )
1 .0
1 .2
o. 6
/1 37 N, 5.80; 0, 13.26; S, 13.29
0.5
0.2
o. o . .1. ...... ......... .... .1.u-.ll - ..aili.llll ..... .J•L ..
75 175 325
m/z
50 100 125 150 200 225 250 275 300
'192
1.6
THC-A (n.o.c.)
1 .5
H3C NH2
1.4
H 3C H3
1.3
1 .2
OCH3
1.1 1-(5-methoxy-2,2-dimethyl-2,3
�0
1 ,0 -dihydrobenzofuran-6-yl)propan-2-amine
Chemical Formula: C14"21N02
0.9
...
0 8 Molecular Weight: 235.32
177".
�
>-
0,7
0.6
m/ z: 235.1572 (100.0%), 236.1606 (15.1%),
237.1639 (1.1%)
0.5 Elemental Analysis: C, 71 .46; H, 8.99;
l
0.4 N, 5.95; 0, 13.60
CAS # 952016-51-2
0,3 /4"
o.l1"-··
0,2
/235
�: � .. . ... .. ....... .. . 101��"--·· ·(.�::L , ,1,C.:�.::l

.,.,, ..... ........ -·•• J.. �
m/z
40 60 80 100 1 20 1 40 160 1 80 200 220 240
rtt N H2
19IYI
4.2 3-TIM (see # 72)
4.0
H3CO � OCH3
3.8
3.6
3,4
3.2
3,0
2,8 SCH3
h
2.6
- 2.4 2-(2,4-dimethoxy-3-(methylthio)
2.2 phenyl)ethanamine
...
1 ,8
�
>- 1.6
1.4
1.2 m / z: 227.0980 (100.0%), 228.1014 (11 .9%),
1 .0 229.0938 (4.5%)
14� Elemental Analysis: C, 58.12; H, 7.54;
o.e
0 ,6 N, 6.16; 0, 14.08; S, 14. 1 1
0,4
121"
0.2
.
o . o.�,..�=-=:o="""'""'-'"""
...
50 75
�=="""'=-"""''--"""""""'....""""""'"""'""""'...._
1 50 175 200
..,
225 250 275 300 325
,._.�_...�_,_,
m/z

�
:--... 1 93
5.6 TM (see #91)
5.2
4.8 H3CO ":: NH2

4.4
4.0
H3C, s
o
3.6 OCH3
3.2
2-(3,5-dimethoxy-4-(methyithio)
0 2.0
'f /227
....
phenyl)ethanamine
2.4
� Chemical Formula: C11H17N02S
>- Exact Mass: 227.0980
1 .6 ml z: 227.0980 (100.0%), 228.1014 (11 .9%),
1.2
229.0938 (4.5%)
Elemental Analysis: C, 58. 12; H, 7.54;
0.8 N, 6.16; 0, 14.08; S, 14.11
0.4
1 5 1 5
o.o
5o i5 1 00 2 150 7 200 2z5 25o 275
rn/z
H3CS � NH2
3-TM (see # 91)
3.0
2.0
H3CO �
2. 6
2.4
2.2
2.0 OCH3
1.8 2-(3,4-dimethoxy-5-(methylthio)
< 1.6
;;; phenyl)ethanamine
/227
� 1 .4
�
>-
1.2
1.0
m / z: 227.0980 (100.0%), 228.1014 (11 .9%),
0.0 229.0938 (4.5%)
0.4
N, 6.16; 0, 14.08; S, 14.11
77"" 121""
1ML.
0.2
o. o ..................,....J. ...;L,
• w..... ..
m/z
50 75 100 125 150 175 200 225 250 275 300 325
�CH3NH2
....... 182 TMA ( # 117)
1.2
1.1
H3CO
I
1 .0
0.9 0
0.0
H3CO
0,7
OCH3
'
;<; 1-(3,4,5-trimethoxyphenyl)
propan-2-amine
x
� o.6
0,5
>- Exact Mass: 225.1365
0,3 /4 4 m / z: 225.1365 (100.0%), 226.1398 (13.0%)
13�
.l
0.2 N, 6.22; 0, 21 .31
JLl _Jt.
0.1 10� /225
.. .iw.�·� ...1 .. "_.,_J1h.- •. -11h1.. . .. d1L� .. .. . .. •1u1. . • . .,, ...I.
60 80 100 140 60 1 80 200 220 240 280
o . o ..•.
40 1
m/z
1 20 26 0
Appendix C 509
Mass Spectra 208 - 2 1 0
2.8 :--.-1a2 TMA-2 ( # 118)

2.6
H3CO NH2
�H3
H3CO � nr
2.4
OCH3�
2.2
an
2,0
1. 8 1-(2,4,5-trimethoxyphenyl)
i.6 prop -2-amine
(
1.4
�
x
3 Exact Mass: 225. 1365
1 .2
>-
1 .0 16 ml z: 225.1365 (100.0%), 226.1398 (13.0%)
0.8
N, 6.22; 0, 21 .31
�
0.6
/44
l . .L . . l.
0.4
9°"'
13
/225
Jl.
0.2
0,0 ·'·" ....... __ ,,,,.L .llL. . .. ,,ML ,...11.\,, ..
. J11 .. . .
.•• �··"' .. J_
mlz
40 60 80 100 1 20 1 40 160 180 200 220 240 260 280
1 208.2
H3CO� N O
TMA-2-AA (n.o.c.)
Y
H3CO � OCH3
450000
H3
nrS CH3
181.1
400000
I
1
!
I
350000
I N-(1-(2,4,5-trimethoxyphenyl)propan-2-yl)
1
300000 : 44.0 acetamide
250000
200000 ml z: 267.1471 (100.0%), 268.1504 (15. 1%),
269.1538 (1.1%)
1 50000
N, 5.24; 0, 23.94
CAS # 146724-70-1
I
1 00000
1
] _[,. , 1 I
1 93.0 267.1
oL40. 1I 1 50i111.; . . .60, ,1 1l11 70L ., 111BO. .. l. 90,1 l 1 1L1 00. , ,11110
1 36.1 1
50000
77 .o s1 . 1 121.1
53 o ss.o 1 01 . 1
· " ' , .L .
I
1 11 ,, 1 1, 1 , . . , . , 1 . l 1 1 , , , , 1 . � ''� �35 1, �5 1 0�.� , �
m/z->
• •
,.
1 20 1 30 140 1 50 1 60 170 1 80 1 90 200 210 220 230 240 250 260 270
�182
TMA-3 ( # 119)
6.0
5.6
5.2
4.8
4.4
4.0
3.6
<
;;; 1-(2,3,4-trimethoxyphenyl)propan-2-amine
0 3 . 2 /44
x 2.8
,_
2.0 ml z: 225.1365 (100.0%), 226.1398 (13.0%)
1.6 167"'
/1
1 .2 N, 6.22; 0, 21 .31
•
0.8
.., 1.it... . .111..... JL uhLJt _jL;,1 i J_ ,

0,4 /225
o.o .. .
50 75 100 125 150 175 200 225 250 2 75 300 325
MIZ

1 .6 ...._4 4 TMA-4 ( # 120)
W
1.5
1 .4 H3CO NH2
I
/182
1 .3
� CH3
1.2
1.1
OCH3
OCH3
�
1.0
0.9 16 1-(2,3,5-trimethoxyphenyl)propan-2-amine
0 8
.
0.7 Exact Mass: 225.1365
>-
0.6
m / z: 225.1365 (100.0%), 226.1398 (13.0%)
o.5
0.4 N, 6.22; 0, 21.31
.l
0.3 /224
0.2
/95
...1 1... .�1.J.JL.l�.,_.Jilt .JL
281
·-"
0.1
o . o .l _,.:, "'
50 75 100 125 150 1 75 20 0 225 250 275 300 325
111/z
:--..1 92 TMA-6 ( # 122

6.0
5.6
� NH2
A)l ""OCH3� H3
5.2
4.8
4.4
4 0
.
H3CO
1-(2,4,6-trimethoxyphenyl)propan-2-amine
3.6
3.2 Exact Mass: 225.1365
>- 2.4 m/ z: 225.1365 (100.0%), 226.1398 (13.0%)
1.6
13� /151
N, 6.22; 0, 21.31
c.: J:�Jd JL JIL k

1 .2
I
0.8
0 4
..L
/224
1.1.. t ....L
,
o .o ll •. . _ _ .. ___ ,,,
40 140 160 260

.... .... .. . . ..... ...
100 180 220 240

01/z
60 80 120 200 280
6.0
5.6
5.2 24 1"'
4.8
4.4
4.0
3.6
< 3.2
;;;
0
2-(3-(ethylthio)-4,5-dimethoxyphenyl)
2.8
...
ethanamine
�
>-
2.4 Exact Mass: 241 . 1 136
1.6 m / z: 241 . 1 136 (100.0%), 242.1170 (13.0%),
243.1094 (4.5%)
�
1.2
7
0.8 N, 5.80; 0, 13.26; S, 13.29
0.4
o . o J.J .;,1,. ••.J.1

50 75
. .. .J�L .li
.
100 1 50
L225 250 275 300 325
01/z
125 175 200
Appendix C 511
Mass Spectra 2 1 4 - 2 1 6
�
2,8 19rl 4-TMA ( # 120)
2.6
2,4 H,CO NH ,
2.2
2.0
/212 H3CS ::::,....
1 .8
1.6
O � CH3
2-(3-ethoxy-5-methoxy-4-(methylthio)phenyl)
<
UJ 241"
0
....
1.4 ethanamine
.?:; Chemical Formula: C12H19N02S
>-
1,2
1 ,0
0,8
16�
m/ z: 241 .1 136 (100.0%), 242.1170 (13.0%),
0.6
243.1094 (4.5%)
121"
�
J
0,4 N, 5.80; 0, 13.26; S, 13.29
7
0.2
........ ...J.. I
0 . 0 -'--..... " L..6.J<... L•
1 25 275 325
m/z
�
50 75 100 1 50 175 200 225 250 3 00
1.3 2 1 ?""" 5-TME (see # 91)

1.2
1.1
H,CS NH,
1.0
0,9
H3CO ::::,....
0.8
O � CH3
0.7
2-(3-ethoxy-4-methoxy-5-(methylthio)
(
iD
0
phenyl)ethanamine
.... 241"
16�
.?:;
>- 0 . 5
0,4 m / z: 241 .1 136 (100.0%), 242.1170 (13.0 %),
0,3
J
243.1094 (4.5%)
1 2�
0,2 N, 5.80; 0, 13.26; S, 13.29
J.. IL.JL.Li
0. 1 77"
o . o .J.-L•.i.... ...i.... Jm.• . • . .
125 150 175 225 275 325
rn/z
50 75 100 200 250 300
197....-'. 2,4,5-TMIPA (n.o.c.)
H3CO � NH2
5.0
4.8
OH
Ajl �"OCH3�H3
4.5
4.2
4.0
3.8
3.5
3,2 H3CO
2-amino-1-(2,4,5-trimethoxyphenyI)
2,B
3.0
propan-1-ol
2,5 Chemical Formula: C12H19N04
2,2 Exact Mass: 241 .1314
>-
2,0
1.B
m/ z: 241 .1314 (100.0%), 242.1348 (13.0%)
1.5
1 2
•.
1.0
�
16� N, 5.81; 0, 26.52
0,8 CAS # 1042605-59-3
0,5
t ._ .
/44 241"
...l5
12
....... ...i.J••.• .i...••

.
0.2
75 125
o.o
m/z
0 100 1 50 1 75 200 225 250 275 300 325

Mass Spectra 2 1 7 - 2 1 9
.. 02
:--.1 2T-MMDA-3a (see # 101)
2.4
W�
2.2
"'
.
2 0
O
'-o
1 .8
1 .6
1-(4-{methylthio )benzo[d] [l,3] dioxol-5-yl)
1 .4
0
'f propan-2-amine
1.2 Chemical Formula: CnH1sN02S
x
>- 1.0
0.8 m / z: 225.0823 (100.0%), 226.0857 (11 .9%),
0.6
227.0781 (4.5%)
0.4 N, 6.22; 0, 14.20; S, 14.23
0.2 /225
o.o .L
m/z
40 60 BO 1 00 1 20 140 1 60 180 200 220 240 260 280
4.2 1 eY. TMPEA-2 ( # 124)

4.0
3.8
3.6
3.4
3.2
3.0
2.8
2.6 2-(2,4,5-trimethoxyphenyl)ethanamine
,
2.2
2 4
2.0
"'
>-
1.8 151
1 .6 m / z: 211.1208 {100.0%), 212.1242 { 1 1 .9%)
1 .2 N, 6.63; 0, 22.72
1 .0
o.e
0.6
0.4
0.2
.. •. l.1.
60
o.o ····· · ··
m/z
40 80 100 1 20 14 0 160 1 80 200 220 240
3.8
2-TOET (see # 56)
H3CO � NH2
3.6
H3CH2C � SCH3
3.4
3.2
cr- � H3
3,0
2.8
2.6
2,4 1-(4-ethyl-5-methoxy-2-{methylthio)
2.2
phenyl)propan-2-amine
2.0
1,8
1 .6
,.. 1 .4 Molecular Weight: 239.38
/44
1.2 m / z: 239.1344 (100.0%), 240.1377 (14.1%),
1 .0 241 . 1302 (4.5% )
Q.B
�:� . ,. . . . . . . . . . ... .J:.1J . G�.�.:d1 (�:� . J .l.i 1. . -. . .��J.

0,6 N, 5.85; 0, 6.68; S, 13.40
.. ......Ji1 .... . .......• . . .... ____ ... .. .

BO
m/z
40 60 1 00 120 140 160 1 80 200 220 240 260 280
Appendix C 513
::ca:CH3NH2
:---.1 95 5-TOET (see # 91)
c
5, 6
5.2
H3C
I
4 .8 �
4,4 H3 �
OCH3
4.0
�
3.6 1-(4-ethyl-2-methoxy-5-(methylthio)
3.2
2.8
x
,..
2.0 m / z: 239.1344 (100.0%), 240.1377 (14.1%),
1.6
241 .1302 (4.5%)
C: .1 l
1.2 N, 5.85; 0, 6.68; S, 13.40
-··-�-i'.�).L_C:i.
0,8
0.4
•• . ..
281�
_ __
o.o
:--..102
ml;z
40 60 80 100 1 20 140 160 180 200 220 240 260 280
2-TOM (see # 3)
5.2
H3CO � NH2
H3C M SCH3
4.8
4.4
4,0 Cf' � H3
3,6
1-(5-methoxy-4-methyl-2-(methylthio)
3.2
2,8 Chemical Formula: C12H19NOS
2,4 Exact Mass: 225.1 187
>-
2,0
1.6
m/ z: 225.1 187 (100.0%), 226. 1221 (13.0%),
227.1145 (4.5%)
1.2 /44 . 16� Elemental Analysis: C, 63.96; H, 8.50;
N, 6.22; 0, 7.10; S, 14.23
0.8 91"' 13�
::: ...L 1J••••. J1 .....

•• •• •••.• J ,...1J.1. Ji1, JL 11L
.. ...... ... ..... .... i111 . J
mlz
40 60 80 100 120 140 160 180 200 220 240 260 280
p,4 5-TOM (see #3)

6,0
5.6
H3CS � NH2
H3C M Onr-CH3
5.2
4.8 �H3
4,4
4.0
/44
1-(2-methoxy-4-methyi-5-(methylthio )phenyl)
3.6 propan-2-amine
3.2 Chemical Formula: C12H19NOS
2.8 Exact Mass: 225.1187
>- 2 . 4
m/ z: 225.1187 (100.0%), 226.1221 (13.0%),
2.0
227.1 145 (4.5%)
i:jJ�.i.1�•!!.=-d·J""l,.� l!(i,! J.!;L,!·' ��/d1�35L-�,l,�l.,.Ji.b,,,_ "",_""'_'"-"�"':"".�!=-·=-=·-,,-=, -=·

N, 6.22; 0, 7.10; S, 14.23
�l�...
.. '�i..!oJ
. .. -=
- -.=�---r--
- -r
225
ro/z
50 75 1 00 1 25 150 175 200 250 275 300 325

6.0
H3CO � NH2
:-.. 1 93 TP (see # 107)
5.6
H3C � s y
5.2
4.8
4.4
4.0
3.6
OCH3
<
;;:; 3,2 2-(3,5-dimethoxy-4-(propylthio)
55 phenyl)ethanamine
8
x
2,8 /226 /2 Chemical Formula: C13H21N02S
>- 2 . 4 Exact Mass: 255.1293
1 .6
m/ z: 255.1293 (100.0%), 256.1327 (14.1 % ),
1.2
7� 121"' 16�
257.1251 (4.5%)
�- J
1................L
0.8 N, 5.48; 0, 12.53; S, 12.56
0,4
... __. .1.••. -�..... I

0.0 ..........._ I
75 100 125 175 200 300 325
m/z
50 150 225 250 275
�
6.0 Trichocereine ( # 125)
5.6
CH3
I
I
5.2
4.8
H3CO N , CH3
4.4
4.0 H3CO 0
3,6
3.2
OCH3
N,N-dimethyl-2-(3,4,5-trimethoxyphenyl)
2.8 /226 /2 55 ethanamine
,.. 2.4
2,0
1. 6 m / z: 239.1521 (100.0%), 240.1555 (14.1%)
J ... ..
N, 5.85; 0, 20.06
-
50 75 100 125 150 250 325
13�
m/z
1 75 200 225 275 300
H3C '-.../ O � NH2

22.Y-
6.0
TRIS (see # 91)
5.6
H3C /'... o y
5.2
4,8
4.4
/1 6 7
4.0
3.6
O '-.../ CH3
3,2 2-(3,4,5-triethoxyphenyl)ethanamine
2.8
>-
2.4
2.0
1.2
m / z: 253.1678 (100.0%), 254.1711 (15. 1%),
1,6 255.1745 (1.1%)
Elemental Analysis: C, 66.37; H, 9. 15;
1 1 °"'
. . l.
0,8
N, 5.53; 0, 18.95
/53
o .. 4
o o .U... J J I1.,.,
.t ... J . J_ .. , � L •. d ' ...l . . . J ,___ ... . .. . . .. . . .
40 60
.•
80 1 00 1 20 140 160
m/z
1 80 200 220
\..
240 260 280 300
Appendix C 515
�
:--.2
. 26
3.2
3-TSB (see # 91)
3.0
2.8
H3C � S NH2
2.6
� I
211"
2.4 H3CO
2.0
�
2.2
O � CH3
/255
1.8
2-(3-ethoxy-5-(ethylthio)-4-methoxyphenyl)
1.6
ethanamine
16�
1.4
>-
1 .0 m / z: 255.1293 (100.0%), 256.1327 (14.1 % ),
0,8 257.1251 (4.5%)
0.6
�
0.4
N, 5.48; 0, 12.53; S, 12.56
0.2
o.o ···-·-
40
6
60 BO 100 12 0 140 1 60
m/z
1 80
L. L J
200 220 240 260 280 300
··-
H3C � O � NH2
6,0
4-TSB (see # 91)
5.6
5.2
H3CS �
226
/
4.8
/255
4.4
3, 2
4.0
3.6
O � CH3
<
;;; 2-(3,5-diethoxy-4-(methy!thio)phenyl)
ethanamine
x
� 2.8
2,4
>- Exact Mass: 255.1293
1.6 ml z: 255.1293 (100.0%), 256.1327 (14.1 % ),
257.1251 (4.5%)
l.2
0.0 N, 5.48; 0, 12.53; S, 12.56
0.4 341"
0.0
50 75 100 125 150 1 75 200 225 250 275 325
m/z
300
H3C � S � NH2
6.0 3-T-TRIS (see # 91)
5.6
H3C /'... o y
5.2
4.B
3,6
4.4
4,0
26
�
O � CH3
15�
2-(3,4-diethoxy-5-(ethylthio)phenyl)
<
:0 3.2
18�
ethanamine
)(
;i 2,8
�
>-
1 .6
2.4 Exact Mass: 269 .1449
J_.,� L....
2.0
m / z: 269.1449 (100.0%), 270.1483 (15.1%),
1.2
271 .1407 (4.5%), 271 .1517 (1.1%)
��...�
..C:-4-
o.a N, 5.20; 0, 11 .88; S, 1 1 .90
300 32�
0,4
....
225
o.o
50 75 100 125 150 175 200 :!So 275
m/z

Mass Spectra 229
�
6.0 :--.2
. 11 4-T-TRIS (see # 91)
5.6
5.2 H3C � O NH2

4 ,6 � I
4.4
4.0
H3C ,...... S �
O � CH3
26�
3.6
3.2 2-(3,5-diethoxy-4-(ethylthio)phenyl)
ethanamine
2.B
1.6
,.. 2,4
1.2 15�
m/ z: 269.1449 (100.0%), 270.1483 (15.1%),
271 .1407 (4.5%), 271 .1517 (1.1%}
� : : -·��--�·--��C: u��-J1�:jL�--
N, 5.20; 0, 1 1 .88; S, 1 1 .90
.. _ l ·-
5o is 100 125 150 175 200 225 250 2l5

m/z
Appendix C 517
uuse them with care, and use them with respect
as to the transformations they can achieve, and
you have an extraordinary research tool. . .. Know
what you're using, decide just why you're using
it, and you can have a rich experience. They're
not addictive, and they're certainly not escapist,
either, but they're exceptionally valuable tools for
understanding the human mind, and how it works. "
-Alexander Shulgin
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AL PH ABETICAL INDEX
AA to Aleph-1 9
Compound Names and Compound Names and Locations Page Number
AA 2-Amino-1-phenylethanone 72
see table under DMAP ( #40)
AAM 1-(3,4,5-Trimethoxyphenyl)heptan-2-amine 287

see table under TMA ( # 117)
ABM 1-(3,4,5-Trimethoxyphenyl)hexan-2-amine 287

AEM ( # 1 ) 1-(3,4,5-Trimethoxyphenyl)butan-2-amine 1
a-Ethyl-1-(3,4,5-trimethoxyphenyl)ethylamine
2-Amino-1-(3,4,5-trimethoxyphenyl)butane
1-(3,4,5-Trimethoxybenzyl)propylamine
a-Ethylmescaline
AEPEA 2-Methy1-3-phenylbutan-2-amine 261

see table under PEA ( # 1 07)
Adam MDMA ( #82) 1 86
AHM 1 -(3,4,5-Trimethoxyphenyl)octan-2-amine 287

AL ( #2) 2-(4-(Allyloxy)-3,5-dimethoxyphenyl)ethanamine 1
4-Allyloxy-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-(2-propenyloxy)phenethylamine
ljJ-ALEPH 1 -(2,6-Dimethoxy-4-(methylthio )phenyl)propan-2-amine 3

see table under ALEPH ( #3)
ljJ-ALEPH-2 1-(4-(Ethy lthio )-2,6-dimethoxyphenyl)propan-2-amine 3

ALEPH ( #3) 1-(2,5-Dimethoxy-4-(methylthio )phenyl)propan-2-amine 2

2,5-Dimethoxy-4-methylthioamphetamine
3C-T
DMMTA
DOT
p-DOT
PARA-DOT
ALEPH-2 ( #4) 1-( 4-(E thylthio )-2,5-dimethoxyphenyl)propan-2-amine 5

2,5-Dimethoxy-4-ethylthioamphetamine
ALEPH-4 ( #5) 1-( 4-(Isopropylthio )-2,5-dimethoxyphenyl)propan-2-amine 6

2,5-Dimethoxy-4-(i)-propylthioamphetamine
ALEPH-6 1-(2,5-Dimethoxy-4-(phenylthio )phenyl)propan-2-amine 3

ALEPH-7 ( # 6) 1-(2,5-Dimethoxy-4-(propylthio )phenyl)propan-2-amine 6

2,5-Dimethoxy-4-propylthioamphetamine
ALEPH-19 1-(4-(Butylthio)-2,5-dimethoxyphenyl)propan-2-amine 3
Alphabetical Index 665

ALEPH-S-amyl
ALEPH-S-amyl 1-(2,5-Dimethoxy-4-(pentylthio )phenyl)propan-2-amine 3

ALEPH sulfone 1 -(2,5-Dimethoxy-4-(methylsulfonyl)phenyl)propan-2-amine 3

ALEPH-S-PhEt 1-(4-(Benzylthio )-2,5-dimethoxyphenyl)propan-2-amine 3

AL-463 (d-isomer) METHCATH ( #92) 225
AL-464 (I-isomer) METHCATH ( #92) 225
2-(Ally!amino )-1-(benzo[ d] [ l,3 ] dioxol-5-y l) ALONE 229

propan-1-one see table under Methylone ( # 93)
N-Allyl-N-(1-(4-(methy lthio )phenyl)propan-2-yl) MTDALA 250

prop-2-en-1 -amine see table under MTA ( # 1 03)
N-AL-M N-(3,4,5-Trimethoxyphenethyl)prop-2-en-1 -amine 216

see table under Mescaline ( #91)
ALONE 2-(Allylamino )-1-(benzo[d] [l,3]dioxol-5-yl)propan-1 -one 229

see table under Methylone ( #93)
2-(4-(Allyloxy )-3,5-dichlorophenyl)ethanamine 3,5-Cl-4-ALPEA 24
2-(4-(Allyloxy)-3,5-dimethoxyphenyl)ethanamine AL ( #2) 1
4-Allyloxy-3,5-dimethoxyphenethylamine AL ( #2) 1
1-(4-(Allyloxy)-3,5-dimethoxyphenyl)propan-2-amine 3C-AL 288

see table under TMA ( #117)
2-(4-(Allyloxy)-3-methoxyphenyl)ethanamine MAPEA 89
see table under MEPEA ( #90)
2-(4-(Ally loxy )-3-methoxyphenyl)ethanamine MAPEA 211

see table under DMPEA ( #49)
2-(3-(Allyloxy)phenyl)-2-methoxyethanamine B03A 244

see table under 3-MPEA ( # 1 0 1 )
2-(4-(Allylthio)-2,5-dimethoxyphenyl)ethanamine 2C-T-16 37
see table under 2C-T ( #25)
AL-422 (racemate) METHCATH ( #92) 255
Amiflamine 4-(2-Aminopropyl)-N,N,3-trimethylaniline
see table under DMeA ( #42) 76
2-Amino-5-(2-aminoethyl)benzene-1,4-diol 2,5-H0-4-APEA
see table under TMPEA-2 ( # 1 24) 308
4-Amino-5-(2-aminoethyl)benzene-1,2-diol 4,5-H0-2-APEA
see table under TMPEA-2 ( # 1 24) 308
4-Amino-6-(2-aminoethyl)benzene-1,3-diol 2,4-H0-5-APEA 308

see table under TMPEA-2 ( # 1 24)

2-Amino-1-(2,5-diethoxyphenyl)ethanol
2-Amino-1 -(2-aminopheny!)ethanol fl-H0-2-APEA 242

see table under 2-MPEA ( # 100)
2-Amino-1 -(2-aminophenyl)ethanone 2-APEA-flk 242

see table under 2-MPEA ( # 1 00)
2-Amino-5-(2-aminopropyl)benzene-1,4-diol 2,5-HO-PAA 294

see table under TMA-2 ( # 118)
4-Amino-5-(2-aminopropyl)benzene-1,2-diol 4,5-H0-2-AA 294

4-Amino-6-(2-aminopropyl)benzene-1,3-diol 2,4-H0-5-AA 294

see table under TMA-2 ( # 11 8)
2-Amino-1-(1,3-benzodioxo-5-yl)butane BDB ( # 9) 10
2-Amino-1-(benzo[d] [1,3] dioxol-5-yl)propan-1-ol 1:\-HO-MDA 168

see table under MDA ( # 77)
2-Amino-1-(benzo[ d] [ 1,3] dioxol-5-yl)propan-1-one ONE 229

2-Amino-1-(4-bromo-2,5-dimethoxyphenyl) fl-HO-DOB 16
propan-1-ol see table under BOB ( # 13)
2-Amino-1-(4-bromo-2,5-dimethoxyphenyl) DOB-flk 99
propan-1-one see table under DOB ( #52)
4-(2-Aminobutyl)benzene-1,2-diol DH-a-Et-PEA 49
see table under DHA ( #33)
4-(3-Aminobutyl)benzene-1,2-diol homo-OMA 68
see table under DMA ( #38)
4-(2-Aminobutyl)-2,5-dimethoxyaniline 4C-NH 130

see table under DON ( #61)
4-(2-Aminobutyl)-2,5-dimethoxyphenol 4C-HO 292

1-( 4-(2-Aminobutyl)-2,5-dimethoxypheny!)ethanol 4C-HE 292

(4-(2-Aminobutyl)-2,5-dimethoxyphenyl)methanol 4C-HM 292

4-(2-Aminobutyl)-2-methoxyphenol HM-a-Et-PEA 49
5-(2-Aminobutyl)-2-methylphenol HM-a-EPEA 234

see table under 3,4-MMA ( # 96)
4-(2-Aminobutyl)phenol a-Et-4-HPEA 270

see table under PMA ( #110)
2-Amino-1-(2,5-diethoxyphenyl)ethanol fl-H0-2,5-DEPEA 30
see table under 2C-H ( #22)

2-Amino-1 -(3,4-diethoxyphenyl)ethanol
2-Amino-1-(3,4-diethoxyphenyl)ethanol DEE 89
2-Amino-1-(2,5-dimethoxy-4-methylphenyl)butane ARIADNE ( #7) 7
2-Amino-1-(2,5-dimethoxyphenyl)ethanol f3-H0-2,5-DMPEA 30
2-Amino-1-(3,4-dimethoxyphenyl)ethanol DME 88
2-Amino-1-(2,5-dimethoxyphenyl)ethanone 2,5-DMPEA-f3k 30
3-(2-Aminoethyl)benzene-1,2-diol 2,3-DHPEA 53
see table under 2,3-DMA ( #34)
5-(2-Aminoethyl)benzene-1,2,4-triol 2,4,5-HO-PEA 308

see table under TMPEA-2 ( # 124)
5-(2-Aminoethyl)-l,3-benzodioxole MDPEA ( # 85) 205
4-(2-Aminoethyl)-2,6-dimethoxyphenol DES METHYL ( #29) 42
5-(2-Aminoethy1)-2,3-dimethoxyphenol 3-DESMETHYL ( #30) 45
2-Amino-1-(2,5-diethoxyphenyl)propan-1-ol f3-H0-2,5-DEA 60
2-Amino-1-(2,5-diethoxyphenyl)propan-1-one 2,5-DEA-f3k 60
2-Amino-1-(3,4-dihydroxyphenyl)ethanone DHPEA-f3k 88
see table under 2,6-DMPEA ( #48)
2-Amino-1-(3,4-dimethoxyphenyl)propane DMA ( #38) 59
1-Amino-2-(2,5-dimethoxypheny l)propan-2-ol f3-HO,Me-2,5-DMPEA 30

2-Amino-1-(2,5-dimethoxyphenyl)propan-1-ol f3-H0-2,5-DMA 60
2-Amino-1-(3,4-dimethoxyphenyl)propan-1-ol f3-HO-DMA 67
2-Amino-1-(2,4-dimethoxyphenyl)propan-1-one 2,4-DMA-f3k 55
2-Amino-1-(2,5-dimethoxyphenyl)propan-1-one 2,5-DMA-f3k 60

2-(2-Aminoethyl)-5-methoxybenzene-1,4-diol
N-(l-(4-Amino-2,5-dimethoxyphenyl) DONHAc 130

propan-2-yl)acetamide see table under DON ( #61)
2-Amino-1 -(3,4-dimethylpheny l)ethanol �-H0-3,4-MePEA 78

see table under DMePEA ( #43)
2-Amino-1-(5-ethoxy-2-hydroxyphenyl)ethanone 2-H0-5-EPEA-�k 30
2-Amino-1-(4-ethoxy-3-methoxyphenyl)ethanol� 88
HO-EMPEA see table under DMPEA ( #49)
4-(2-Aminoethyl)aniline PAPEA 247

5-(2-Aminoethyl)benzene-1,2,3-triol 3,4,5-DESMETHYL 43
see table under DESMETHYL ( #29)
2-(2-Aminoethyl)benzene-1,3-diol 2,6-HPEA 84
4-(2-Aminoethyl)benzene-1,3-diol 2,4-DHPEA 83
5-(2-Aminoethyl)benzene-l,3-diol 3,5-HPEA 94
4-(2-Aminoethyl)-2-bromo-6-methoxyphenol 5-Br-DESMETHYL 43
4-(2-Aminoethyl)-2-chlorophenol 3-Cl-4-HPEA 87
4-(2-Aminoethyl)-2,6-dibromophenol 3,5-Br-DESMETHYL 43
4-(2-Aminoethyl)-2,5-dimethoxyaniline 2C-NH 308

see table under TMPEA-2 ( #124)
5-(2-Aminoethyl)-2,4-dimethoxyaniline 5-NH -2,4-DMPEA 308

2
4-(2-Aminoethy 1)-2,5-dimethoxybenzoic acid 2C-CA 1 05

see table under DOCN ( # 55)
4-(2-Aminoethyl)-2,5-dimethoxybenzonitrile 2C-CN 1 05
(4-(2-Aminoethyl)-2,5-dimethoxyphenyl)methanol 2C-HM 27
see table under 2C-D ( #20)
4-(2-Aminoethyl)-N,N-dimethylaniline 4-N,N-MePEA 247

4-(2-Aminoethyl)guaiacol GEA ( #69) 143
2-(2-Aminoethyl)-5-methoxybenzene-1,4-diol 2,5-HO-MPEA 308


5-(2-Aminoethyl)-2-methoxybenzene-1,3-diol
5-(2-Aminoethyl)-2-methoxybenzene-1,3-diol 3,5-DESMETHYL 45
see table under 3-DESMETHYL ( #30)
5-(2-Aminoethyl)-3-methoxybenzene-1,2-diol 3,4-DESMETHYL 45
2-(2-Aminoethyl)-3-methoxyphenol 2,6-HMPEA 84
see table under 3,5-DMPEA ( # 50)
4-(2-Aminoethyl)-2-methoxyphenol GEA ( #69) 143
4-(2-Aminoethyl)-3-methoxyphenol 2,4-MHPEA 83
5-(2-Aminoethyl)-2-methoxyphenol HMPEA 88
see table under DMPEA (#49)
2-(2-Aminoethyl)-6-methylphenol 2,3-HMePEA 52
4-(2-Aminoethyl)-2-nitrophenol 3-N0 -HPEA 87

2
4-(2-Aminoethyl)-3-nitrophenol 2-N0 -HPEA 83

2
2-(2-Aminoethy!)phenol 2-HPEA 150

see table under Hordenine ( #71)
3-(2-Aminoethyl)phenol 3-HPEA 150

4-(2-Aminoethyl)phenol Tyramine ( # 126) 310
4-(2-Amino-1-hydroxybutyl)benzene-1,2-diol f3,3,4-HO-a-Et-PEA 49
4-(2-Amino-1-hydroxyethyl)-2,6-dimethoxyphenol f3-HO-DESMETHYL 43
5-(2-Amino-1-hydroxyethyl)-2,3-dimethoxyphenol f3,5-HO-DMPEA 45
2-(2-Amino-1-hydroxyethyl)-4-ethoxyphenol f3,2-H0-5-EPEA 30
2-(2-Amino-1-hydroxyethyl)-4-methoxyphenol f3,2-H0-5-MPEA 30

2-Amino-1-(2-methoxy-5-methylphenyl)propan-1 -one
5-(2-Amino-1-hydroxyethyl)-2-methoxyphenol HME 88
2-(2-Amino-1-hydroxyethyl)-4-methylphenol f3,2-H0-5-MePEA 29
2-(2-Amino-1-hydroxyethyl)phenol f3-H0-2-HPEA 150
3-(2-Amino-1-hydroxyethyl)phenol f3-H0-3-HPEA 150

4-(2-Amino-1-hydroxyethyl)phenol f3-HO-HPEA 150

2-Amino-1-(2-hydroxy-5-methoxyphenyl)ethanone 2-H0-5-MPEA-f3k 29
2-Amino-1-(3-hydroxy-4-methoxyphenyl)ethanone HMPEA-f3k 88
2-Amino-1-(4-hydroxy-3-methoxyphenyl)ethanone GEA-f3k 88
2-Amino-1-(4-hydroxy-3-methoxyphenyl) HMMC 227

propan-1-one see table under METHCATH ( #92)
2-Amino-1-(2-hydroxy-5-methylphenyl)ethanone 2-H0-5-MePEA-f3k 29
4-(2-Amino-1-hydroxypropyl)benzene-1,2-diol f3-HO-DHA 49
2-(2-Amino-1-hydroxypropyl)-4-ethoxyphenol f3,2-H0-5-EA 59
2-(2-Amino-1-hydroxypropyl)-4-methoxyphenol f3,2-H0-5-MA 59
2-(2-Amino-1 -hydroxypropy 1)-4-methy1 phenol f3,2-H0-5-MeA 59

3-(2-Amino-1-hydroxypropyl)phenol f3-H0-3-HA 159

see table under 3-MA ( #75)
4-(2-Amino-1-hydroxypropyl)phenol f3-HO-PHA 265

see table under PHA ( # 1 09)
5-(2-Amino-1-methoxyethyl)-3-methoxybenzene f3-M-3,4-DESMETHYL 43
l,2-diol see table under DESMETHYL ( #29)
2-Amino-1-(2-methoxy-5-methylphenyl)ethanol f3-H0-2-M-5-MePEA 30
2-Amino-1-(2-methoxy-5-methylphenyl)propan-1-ol f3-H0-2-M-5-MeA 60
2-Amino-1-(2-methoxy-5-methylphenyl)propan-1-one 2-M-5-MePEA-f3k 30

2-Amino-1-(4-methoxyphenyl)ethanol
2-Amino-1-(4-methoxyphenyl)ethanol f3-H0-4-MPEA 247

2-Amino-1-(4-methoxypheny!)propane PMA ( # llO) 267
2-Amino-1-(4-methoxyphenyl)propan-1-ol f3-HO-PMA 270

see table under PMA ( # 110)
2-Amino-1-(4-methoxyphenyl)propan-1-one PMA-f3k 270

see table under PMMA ( # 110)
4-(Aminomethyl)benzene-1,2-diol DHBA 87
2-Amino-1 -(3,4-methylenedioxyphenyl)butane BDB ( #9) 10
3-Amino-1-(3,4-methylenedioxyphenyl)butane homo-MDA ( # 78) 1 78
2-Amino-1-(4-(methylthio )phenyl)propan-1-ol MTC 250

see table under MTA ( # 1 03)
2-Amino-1-phenylethanol f3-HO-PEA 261

2-Amino-1-phenylethanone AA 72
4-(1-Aminopropan-2-yl)benzene-1,2-diol f3-Me-DHPEA 88
4-( 1-Aminopropan-2-y 1)-2-methoxyphenol f3-Me-GEA 88

4-(1-Aminopropan-2-y 1)-3-methoxyphenol f3,2-MHPEA-3 83

4-(1-Aminopropan-2-yl)phenol f3-Me-HPEA 150

4-(2-Aminopropyl)aniline PAA 256

see table under PCA ( # 1 06)
4-(2-Aminopropyl)benzene-1,2-diol DHA ( #33) 49
4-(3-Aminopropyl)benzene-1,2-diol homo-Dopamine 68
5-(2-Aminopropy l)benzene-1,2,3-triol THA 287

5-(2-Aminopropyl)benzene-1,2,4-triol THA-2 292

5-(2-Aminopropyl)-1,3-benzodioxole MDA ( #77) 165
6-(2-Aminopropyl)benzo[d] [l,3] dioxol-5-ol 6-MDOH 191

see table under MDMA ( # 82)

4-(2-Aminopropyl)-N,N-dimethylaniline
4-(2-Aminopropyl)-2-bromophenol 3-Br-PHA 66
4-(2-Aminopropyl)-2-chlorophenol 3-Cl-PHA 66
2-(2-Aminopropyl)-4,5-dimethoxyaniline 2-NH -4,5-DMA 294

2
see table under TMA-2 ( #118)
4-(2-Aminopropyl)-2,5-dimethoxyaniline DONH 130

5-(2-Aminopropyl)-2,4-dimethoxyaniline 5-NH -2,4-DMA 294

2
4-(2-Aminopropyl)-2,5-dimethoxybenzoic acid DOCA 1 05

4-(2-Aminopropyl)-2,5-dimethoxybenzonitrile DOCN ( #55) 1 05
4-(2-Aminopropy 1)-2,5-dimethoxy-N,N DONMM 130

dimethylaniline see table under DON ( #61)
4-(2-Aminopropyl)-2,5-dimethoxyphenol DOOH 292

see table under TMA-2 ( # 1 1 8)
4-(2-Aminopropyl)-2,6-dimethoxyphenol a-Me-DESMETHYL 287

5-(2-Aminopropyl)-2,3-dimethoxyphenol a-Me-3-DESMETHYL 287

see table under TMA ( # 11 7)
1-(4-(2-Aminopropyl)-2,5-dimethoxyphenoxy ) M(20P)M 292

propan-2-ol see table under TMA-2 ( # 118)
3-( 4-(2-Aminopropy 1)-2,5-dimethoxyphenoxy ) M(30P)M 292

propan-1-ol see table under TMA-2 ( # 11 8)
2-(4-(2-Aminopropyl)-2,5-dimethoxyphenyl)ethanol DOEH 123

see table under DOM ( #60)
1-( 4-(2-Aminopropyl)-2,5-dimethoxyphenyl)ethanone DOAC 1 06

(4-(2-Aminopropyl)-2,5-dimethoxyphenyl)methanol DOHM 123

N-(4-(2-Aminopropyl)-2,5-dimethoxyphenyl) DOAA 130

N-methylacetamide see table under DON ( #61)
1 -(4-(2-Aminopropyl)-2,5-dimethoxyphenyl) DOCOE 1 06
propan-1-one see table under DOCN ( # 55)
4-(2-Aminopropyl)-2,5-dimethoxy-N-propylbenzamide DOCONHP 106

see table under DOCN ( #55)
4-(2-Aminopropyl)-N,N-dimethylaniline DMePAA 256

see table under PCA ( # 106)

4-(2-Aminopropyl)-2,6-dimethylphenol
4-(2-Aminopropyl)-2,6-dimethylphenol 3,5-Me-PHA 287

2-(2-Aminopropyl)hydroquinonedimethylether 2,5-DMA ( #36) 57
2-(2-Aminopropyl)-4-methoxy-5-methylphenol 2-DES-Me-DOM 121

5-(2-Aminopropyl)-4-methoxy-2-methylphenol 5-DES-Me-DOM 121

2-(2-Aminopropyl)-3-methoxyphenol 6-Br-2-MA 64
2-(2-Aminopropyl)-4-methoxyphenol 2,5-HMA 59
2-(2-Aminopropyl)-5-methoxyphenol 2,4-HMA 55
see table under 2,4-DMA ( #35
4-(2-Aminopropyl)-2-methoxyphenol MHA ( #94) 230
5-(2-Aminopropyl)-2-methoxyphenol HMA ( #33) 50

also see table under DHA ( #33)
2-(2-Aminopropyl)-5-methylbenzene-1,4-diol 2,5-DES-Me-DOM 121

2-(2-Aminopropyl)-6-methylphenol 2,3-HMeA 52
5-(2-Aminopropyl)-2-methylphenol 3,4-HMeA 235

see table under 3,4-MMA ( # 96)
2-(2-Aminopropy!)phenol 2-HA 156

see table under 2-MA ( # 74)
3-(2-Aminopropyl)phenol 3-HA 159

4-(2-Aminopropy !)phenol PHA ( # 109) 264
4-(2-Aminopropyl)-pyrocatechol DHA ( #33) 49
4-(2-Aminopropyl)-N,N,3-trimethylaniline Amiflamine 76
see table under DMeA ( #42)
7-Amino-5,6,7,8-tetrahydronaphthalen-1-ol HHAT 254

see table under PAT ( # 1 05)
2-Amino-1-(3,4,5-trimethoxyphenyl)butane AEM ( # 1 ) 1
2-Amino-1-(3,4,5-trimethoxyphenyl)ethanol 13-HOM 216

2-Amino-1-(3,4,5-trimethoxyphenyl)ethanone M-l}k 216


Asymbescaline
2-Amino-1-(3,4,5-trimethoxyphenyl)propane TMA ( # l17) 285
2-Amino-1-(3,4,5-trimethoxyphenyl)propan-1-ol f3-HO-TMA 287

see table under TMA ( # 1 1 7)
2-Amino-3-(3,4,5-trimethoxyphenyl)propan-1-ol a-HMe-M 287

Amphedoxamine MDA ( # 77) 165
1-(p-Anisyl)piperazine MeOPP ( # 88) 209
AcO-MePEA 4-(2-(Methylamino)ethyl)phenyl acetate 150

2-APEA-f3k 2-Amino-1-(2-aminopheny l)ethanone 242

2-MPEA ( # 100)
4-APEA 2-(4-(Pentyloxy )phenyl)ethanamine 247

AMPH-OH N-(l-Phenylpropan-2-yl)hydroxylamine 261

4-Amyl-2,5-dimethoxyamphetamine DOAM ( #51) 95
Anhalin Hordenine ( #71) 147
Anhaline Hordenine ( #71) 147
ANM 1-(3,4,5-Trimethoxyphenyl)undecan-2-amine 287

AOM 1-(3,4,5-Trimethoxyphenyl)decan-2-amine 287

APM 1-(3,4,5-Trimethoxyphenyl)pentan-2-amine 287

Aptrol PMeA ( # 111) 275
ARIADNE ( #7) 1-(2,5-Dimethoxy-4-methylphenyl)butan-2-amine 7

4C-DOM
2,5-Dimethoxy-4-methyl-a-ethylphenethylamine
2-Amino-1-(2,5-dimethoxy-4-methy lpheny 1)-butane
Dimoxamine (R-isomer freebase)
BL-3912 (racemate HCl salt)
BL-3912A (R-isomer HCl salt)
NSC-292248 (R-isomer HCl salt)
ASB ( #8) 2-(3,4-Diethoxy-5-methoxyphenyl)ethanamine 9

3,4-Diethoxy-5-methoxyphenethylamine
Asymbescaline
ASM 1-(3,4,5-Trimethoxyphenyl)nonan-2-amine 287

Asymbescaline ASB ( #8) 9

B
B 2-(4-Butoxy-3,5-dimethoxyphenyl)ethanamine 216
2-BA 1-(2-Bromophenyl)propan-2-amine 156

BAP 2-(Butylamino)-1 -phenylpropan-1-one 72

t-BAP 2-(tert-Butylamino )-1-phenylpropan-1-one 72

BBAT 7-(Dibutylamino)-5,6,7,8-tetrahydronaphthalen-1-ol 254

IP-BBB 1-(2,4,6-Tributoxypheny l)propan-2-amine 304

BCPA 2-(4-Bromophenyl)cyclopropanamine 74
see table under DMCPA ( #41)
BDA DOB ( #52) 96
BDB ( # 9) 1-(Benzo[d] [ 1,3]dioxol-5-yl)butan-2-amine 10

1-(3,4-Methylenedioxypheny1)-2-butanamine
2-Amino-1-(1,3-benzodioxo-5-yl)butane
a-Ethyl-3,4-methylenedioxyphenethylamine
a-E thy 1-1,3-benzodioxole-5-ethanamine
MDP-2-B
J
NSC 1 721 88
2,3-BDB 1-(Benzo[d] [l,3]dioxol-4-yl)butan-2-amine 1 71

B-DFLY ( # 1 0) 1-( 8-Bromobenzo[l,2-b:4,5-b'] difuran-4-yl)propan-2-amine 12

1-( 8-Bromobenzo[ l,2-b;4,5-b'] difuran-4-y1)-2-aminopropane
Bromodragonfly
DOB-Dragonfly
BDMPEA 2C-B ( # 1 8) 20
BEATRICE ( # 1 1 ) 1-(2,5-Dimethoxy-4-methylphenyl)-N-methylpropan-2-amine 13
2,5-Dimethoxy-N,4-dimethylamphetamine
N-Methyl-DOM
N-Me-DOM
R-N-Me-DOM
BEDA 1-(8-bromo-2,3-dihydrobenzo[ b] [ l,4 ]dioxin-6-y l)propan-2-amine 237

see table under MMDA ( #97)
Bees 2C-B ( # 1 8) 20
1-(Benzo[ l,2-b:4,5-b'] difuran-4-yl)-2-aminopropane DFLY ( #32) 47
2-(Benzo[l,2-b:4,5-b ']difuran-4-yl)ethanamine 2C-DFLY 48

see table under DFLY ( #32)

1 -(Benzo[d] [1,3 ]dioxol-5-yl)-N,N-diethylpropan-2-amine
1-(Benzo[ l,2-b:4,5-b'] difuran-4-y l)propan-2-amine DFLY ( #32) 47
1-(Benzo[d] [ 1,3 ] dioxol-5-yl)-N-benzyI propan-2-amine MDBZ 169

1-(Benzo[d] [ 1,3 ]dioxol-4-yl)butan-2-amine 2,3-BDB 1 71

1-(Benzo[d] [l,3]dioxol-5-yl)butan-2-amine BOB ( #9) 10
4-(Benzo[d] [l,3]dioxol-5-yl)butan-2-amine homo-MDA ( # 78) 1 77
N-(1 -(Benzo[d] [ l,3 ] dioxol-5-yl)butan-2-y !) HOBDB 169

hydroxy !amine see table under MDA ( # 77)
N-(4-(Benzo[d] [ 1,3 ] dioxol-5-yl)butan-2-yl) homo-MDOH 1 78

hydroxy lamine see table under homo-MDA ( # 78)
1-(Benzo[ d] [l,3] dioxol-5-yl)-2-(butylamino ) MDBVP 229

pentan-1-one see table under Methylone ( #93)
1 -(Benzo[ d] [ 1,3] dioxol-5-y1)-2-(sec-butylamino ) MDSBVP 229

pentan-1 -one see table under Methylone ( #93)
1-(Benzo[d] [1,3] dioxol-5-yl)-2-(butylamino ) BuONE 229

propan-1-one see table under Methylone ( #93)
1-(Benzo[d] [ l,3 ]dioxol-5-yl)-2-(sec-buty !amino) sBuONE 229

1-(Benzo[d] [ 1,3] dioxol-5-yl)-2-(tert-buty!amino) tBuONE 229

1 -(Benzo[ d] [ 1,3 ]dioxol-5-yl)-N-(tert-butyl) MDTB 169

propan-2-amine see table under MDA ( # 77)
2-(Benzo[d] [ l,3 ] dioxol-5-y l)cyclopropanamine MDCPA 74

l-(Benzo[d] [l,3]dioxol-5-yl)-2-(cyclopropylamino) cPrONE 229

1-(Benzo[d] [ 1,3]dioxol-5-y1)-N-( cyclopropy!methyl) MDCPM 169

1-(Benzo[ d] [l,3]dioxol-5-yl)-2-( diethylamino ) MDDEBP 229

butan-1-one see table under Methylone ( #93)
1-(Benzo[d] [ 1,3] dioxol-5-y 1)-2-( diethylamino ) MDDEHP 229

hexan-1-one see table under Methylone ( #93)
1-(Benzo[d] [1,3]dioxol-5-yl)-2-(diethylamino) MDDEVP 229

1-(Benzo[ d] [ l,3 ]dioxol-5-yl)-N,N-diethylpropan MDDEA 169

-2-amine see table under MDA ( #77)

1 -(Benzo[d] [1,3 ]dioxol-5-yl)-2-(dimethylamino)butan-1 -one
1 -(Benzo[d] [l,3]dioxol-5-yl)-2-(dimethylamino)- MDDMBP 229

1 -(Benzo[ d] [ l,3]dioxol-5-y1)-2-( dimethy !amino)- MDDMHP 229

hexan-1-one see table under Methylone ( #93)
1 -(Benzo[ d] [ 1,3]dioxol-5-y1)-2-( dimethy !amino)- MDDMVP 229

1-(Benzo[d] [l,3] dioxol-5-yl)-2-(dimethylamino)- DMONE 229

1-(Benzo[ d] [ 1,3] dioxol-4-y 1)-N,N-dimethy I- 2,3-MMBDB 1 71

butan-2-amine see table under MDA ( #77)
1-(Benzo[ d] [ 1,3]dioxol-5-y1)-N,N-dimethy I- MMBDB 169

4-(Benzo[d] [l,3]dioxol-5-yl)-N,N-dimethyl- homo-MDDMA 1 78

butan-2-amine see table under homo-MDA ( # 78)
1-(Benzo[ d] [ 1,3]dioxol-5-y1)-N,N-dimethy I- N,N-DMMDBA 80

methanamine see table under a,N-DMMDBA ( #45)
1 -(Benzo[ d] [ 1,3 ]dioxol-5-yl)-N,N-dimethy I- a,N,N-TMMDBA 80

ethanamine see table under a,N-DMMDBA ( #45)
2-(Benzo[d] [l,3]dioxol-4-yl)-N,N-dimethyl- N,N-Me-2,3-MDPEA 1 71

ethanamine see table under MDA ( # 77)
2-(Benzo[d] [l,3]dioxol-5-yl)-N,N-dimethyl- N,N-Me-MDPEA 205

ethanamine see table under MD PEA ( # 85)
1-(Benzo[d] [ l,3]dioxol-4-y1)-N,N-dimethy I- 2,3-MDDMA 171

1-(Benzo[ d] [1,3]dioxol-5-y1)-N,N-dimethy I- MDDMA ( # 80) 1 80

propan-2-amine
1-(Benzo[ d] [ 1,3]dioxol-5-yl)-N,2-dimethyl- MDMP 168

2-(Benzo[d] [l,3]dioxol-5-yl)-N,N-dimethyl- a,a,N,N-TMMDBA 80

propan-2-amine see table under a,N-DMMDBA ( #45)
1-(Benzo[ d] [1,3]dioxol-5-yl)ethanamine a-Me-MDBA 80

see table under a,N-DMMDBA ( #45)
2-(Benzo[d] [l,3]dioxol-4-yl)ethanamine 2,3-MDPEA 1 70

see table under MDA ( #77)
2-(Benzo[d] [l,3]dioxol-5-yl)ethanamine MDPEA ( # 85) 204
2-(Benzodioxol-5-yl)ethylamine MDPEA ( # 85) 204
1-(Benzo[ d] [1,3]dioxol-5-yl)-2-( ethylamino )- MDEBP 229

butan-1 -one see table under Methylone ( #93)

1-(Benzo[d][l,3Jdioxol-5-yl)-2-(isobutylamino)propan-1 -one
1-(Benzo[ d] [l,3]dioxol-5-yl)-2-(ethylamino ) MDEVP 229

1-(Benzo[d] [l,3]dioxol-5-yl)-2-( ethylamino ) EtONE 229

1-(Benzo[ d] [ l,3]dioxol-4-y1)-N-ethy lbutan-2-amine 2,3-EBDB 171

1-(Benzo[d] [ l,3]dioxol-5-y1)-N-ethy lbutan-2-amine EBDB (ETHYL-J) 1 69

4-(Benzo[d] [l,3]dioxol-5-yl)-N-ethylbutan-2-amine homo-MDE 1 78

see table under homo-MDA ( #78)
1-(Benzo[ d] [ l,3]dioxol-5-y1)-N-ethy lethanamine a-Me-N-Et-MDBA 80

2-(Benzo[d] [l,3]dioxol-4-yl)-N-ethylethanamine N-Et-2,3-MDPEA 171

2-(Benzo[d] [l,3]dioxol-5-yl)-N-ethylethanamine N-Et-MDPEA 205

see table under MD PEA ( #85)
2-(Benzo[d] [l,3]dioxol-5-yl)-N-ethyl-N N-Me-N-Et-MDPEA 205

methylethanamine see table under MD PEA ( #85)
1-(Benzo[ d] [l,3]dioxol-5-yl)-N-ethyl-N MDMEA 168

methy lpropan-2-amine see table under MDA ( #77)
1-(Benzo[ d] [ l,3]dioxol-5-y1)-N-ethy lpentan-2-amine ETHYL-K 169

1-(Benzo[d] [l,3 ]dioxol-4-yl)-N-ethy lpropan-2-amine 2,3-MDE 1 71

N-(1-(Benzo[d] [l,3]dioxol-5-yl)ethyl)propan-1-amine a-Me-N-Pr-MDBA 80

N-(1-(Benzo[ d] [ 1,3 ] dioxol-5-y l)ethy l)propan-2-amine a-Me-N-iPr-MDBA 80

N-(2-(Benzo[d] [ 1,3]dioxol-5-yl)ethyl)propan-1-amine N-Pr-MDPEA 205

see table under MDPEA ( # 85)
N-(1-(Benzo[d] [ 1,3 ] dioxol-5-yl)ethyl)propan-2-amine a-Me-N-iPr-MDBA 80

1-(Benzo[d] [ 1,3]dioxol-5-y1)-N-ethy I propan-2-amine MDE (#81) 181
N-(2-(Benzo[d] [l,3]dioxol-5-yl)ethyl)propan-2-amine N-iPr-MDPEA 205

1-(Benzo[ d] [ 1,3]dioxol-5-yl)hexan-2-amine L 1 69
1-(Benzo[d] [ l,3]dioxol-5-y1)-2-(isobuty !amino) iBuONE 229


1 -(Benzo[d][l,3 Jdioxol-5-yl)-2-(isopropylamino)butan-1 -one
1 -(Benzo[ d] [ 1,3] dioxol-5-y1)-2-(isopropy !amino) MDIPBP 229

1 -(Benzo[d] [l,3]dioxol-5-yl)-2-(isopropylamino) MDIPVP 229

pentan-1-one see table under Methylone ( # 93)
1-(Benzo[d] [l,3] dioxol-5-yl)-2-(isopropylamino) iPrONE 229

propan-1 -one see table under Methylone ( # 93)
1-(Benzo[d] [ 1,3]dioxol-5-y1)-N-isopropy l IPBDB 169

bu tan-2-amine see table under MDA ( #77)
4-(Benzo[d] [l,3]dioxol-5-yl)-N-isopropyl homo-MDIP 1 78

butan-2-amine see table under homo-MDA ( # 78)
1 -(Benzo[ d] [ 1,3]dioxol-5-y1)-N-isopropy l-N MDMIPA 169

methy l propan-2-amine see table under MDA ( #77)
1-(Benzo[ d] [1,3]dioxol-5-y1)-N-isopropy lpropan- MDIP 169

2-amine see table under MDA ( #77)
2-(Benzo[d] [l,3]dioxol-5-yl)-2-methoxyethanamine BOH ( # 1 5) 17
1-(Benzo[ d] [ l,3 ]dioxol-5-y l)-N-(2-methoxyethy l) MD MEOET 169

1-(Benzo[d] [l,3] dioxol-5-yl)-2-(methylamino ) MDMBP 229

1-(1,3-Benzodioxol-5-yl)-2-(methylamino )-1- Methylone ( #93) 228

propanone
1-(Benzo[d] [l,3]dioxol-5-yl)-2-(methylamino) MDMVP 229

1-(Benzo[d] [ 1,3]dioxol-5-y1)-2-(methy !amino) Methylone ( #93) 228

propan-1 -one
1 -(Benzo[d] [ l,3]dioxol-4-y1)-N-methy lbutan-2-amine 2,3-MBDB 1 71

1-(Benzo[ d] [ 1,3]dioxol-5-y1)-N-methy lbutan-2-amine MBDB ( # 76) 162
1 -(Benzo[d] [l,3]dioxol-5-yl)-2-methylbutan-2-amine a-Et-MDA 169

1-(Benzo[d] [ l,3 ]dioxol-5-yl)-3-methy lbutan-2-amine a-iPr-MDPEA 169
4-(Benzo[d] [l,3]dioxol-5-yl)-N-methylbutan-2-amine homo-MDMA ( #83) 201
1 -(Benzo[d] [ l,3]dioxol-5-y1)-N-methylmethanamine N-MMDBA 80

1-(Benzo[d] [l,3]dioxol-5-yl)-N-methylethanamine a,N-DMMDBA ( #45) 80
2-(Benzo[d] [l,3]dioxol-4-yl)-N-methylethanamine 2,3-MDMPEA 1 70


2-( (1 -(Benzo[d] [1,3 ]dioxol-5-yl)propan-2-yl)amino)acetonitrile
2-(Benzo[d] [l,3]dioxol-5-yl)-N-methylethanamine N-Me-MDPEA 205

1-(Benzo[ d] [ 1,3]dioxol-5-y1)-N-methy lhexan-2-amine METHYL-L 169

N-(Benzo[d] [l,3]dioxol-4-ylmethyl)-2- INBMDO 112

( 4-iodo-2,5-dimethoxyphenyl)ethanamine see table under DOI ( #58)
1 -(Benzo[ d] [ 1,3]dioxol-5-y1)-N-methy lpentan-2-amine METHYL-K 169

1-(Benzo[ l,3] dioxol-5-y1-methy I )piperazine MDBP ( # 79) 1 79
1 -(Benzo[d] [ 1,3 ]dioxol-5-ylmethyl)piperazine MDBP ( # 79) 1 79
1 -(Benzodioxy 1-5-yl-methy l)piperazine MDBP ( # 79) 1 79
1-(1,3-Benzodioxy 1-5-y1-methy I)piperazine MDBP ( # 79) 1 79
2-(Benzo[d] [ 1,3]dioxol-5-y1)-N-methy lpropan-1-amine f),N-Me-MDPEA 205

1-(Benzo[d] [l,3]dioxol-4-y1)-N-methy lpropan-2-amine 2,3-MDMA 1 71

1 -(Benzo[d] [l,3]dioxol-4-yl)-2-methylpropan-2-amine a,a-Me-2,3-MDPEA 1 70

1-(Benzo[d] [ l,3 ] dioxol-5-y l)-N-methylpropan-2-amine MDMA ( # 82) 1 86
1-(Benzo[d] [ 1,3 ] dioxol-5-yl)-2-methylpropan-2-amine MDPH 169

2-(Benzo[d] [l,3]dioxol-5-yl)-N-methylpropan-2-amine a,a,N-TMMDBA 80

see table under a,N-DMMDBA (#45)
1-(Benzo[ d] [1,3]dioxol-5-yl)pentan-2-amine K 169

2-(Benzo[d] [l,3]dioxol-5-yl)propan-1-amine f)-Me-MDPEA 205

see table under MD PEA ( # 85)
3-(Benzo[d] [l,3]dioxol-5-yl)propan-1-amine homo-MD PEA 1 78

see table under homo-MDA ( # 78)
1-(Benzo[ d] [ l,3 ] dioxol-4-y l)propan-2-amine 2,3-MDA 1 70

1-(Benzo[d] [ l,3 ]dioxol-5-y l)propan-2-amine MDA ( #77) 165
2-(Benzo[d] [l,3]dioxol-5-yl)propan-2-amine a,a-DMMDBA 80

2-( (1-(Benzo[d] [1,3 ]dioxol-5-yl)propan-2-y !) MDCM 169

amino)acetonitrile see table under MDA ( # 77)

2-( (1 -(Benzo[d] [1,3 ]dioxol-5-yl)propan-2-yl)amino)ethanol
2-( (1-(Benzo[ d] [1,3]dioxol-5-yl)propan-2-yl) MDHOET 169

amino )ethanol see table under MDA ( #77)
N-(1-(Benzo[d] [l,3]dioxol-5-yl)propan-2-yl) MDBU 169

N-(1-(Benzo[d] [1,3] dioxol-5-yl)propan-2-yl) MDSB 1 69

butan-2-amine see table under MDA ( # 77)
1-(1-(Benzo[d] [1,3]dioxol-5-yl)propan-2-yl)-2- MDBA 169

(tert-buty !)hydrazine see table under MDA ( # 77)
N-( 1-(Benzo[d] [ 1,3 ]dioxol-5-yl)propan-2-y l) MDHE 169

hexan-1-amine see table under MDA ( # 77)
N-(1-(Benzo[d] [l,3]dioxol-S-yl)propan-2-yl) MDOH ( # 84) 202

hydroxylamine
N-(1-(Benzo[d] [1,3] dioxol-5-yl)propan-2-yl) FLEA 203

N-methylhydroxylamine see table under MDOH ( # 84)
N-(1-(Benzo[ d] [1,3 ]dioxol-5-y l)propan-2-yl)- MDMEO 169

0-methy lhydroxy lamine see table under MDA ( # 77)
N-(1-(Benzo[d] [l,3] dioxol-5-yl)propan-2-yl) MDMPA 168

N-methylpropan-1-amine see table under MDA ( # 77)
N-(1-(Benzo[d] [l,3]dioxol-5-yl)propan-2-yl)- MDIB 169

2-methylpropan-1-amine see table under MDA ( #77)
N-(1-(Benzo[d] [l,3]dioxol-5-yl)propan-2-yl) MDOC 1 69

octan-1-amine see table under MDA ( # 77)
N-(1-(Benzo[d] [l,3]dioxol-5-yl)propan-2-yl) MDAM 169

pentan-1-amine see table under MDA ( # 77)
N-(1-(Benzo[d] [ 1,3 ]dioxol-5-y l)propan-2-y l) MDPR ( # 86) 206

propan-1-amine
N-(1-(Benzo[ d] [l,3]dioxol-5-yl)propan-2-yl) MDAL 1 69

prop-2-en-1-amine see table under MDA ( #77)
N-(1-(Benzo[d] [l,3] dioxol-5-yl)propan-2-yl) MDPL 169

prop-2-yn-1-amine see table under MDA ( #77)
1-(Benzo[d] [l,3]dioxol-5-y1)-2-(propy !amino) MDPBP 229

1 -(Benzo[ d] [ 1,3]dioxol-5-y1)-2-(propy !amino) MDPVP 229

pentan-1-one see table under Methylone ( # 93)
1-(Benzo[d] [ 1,3]dioxol-5-y1)-2-(propylamino ) PrONE 229

1-(Benzo[d] [ 1,3] dioxol-5-y1)-N-propylbutan- PBDB 169

2-amine see table under MDA ( # 77)

BIS-TOM
4-(Benzo[d] [l,3]dioxol-5-yl)-N homo-MD PR 1 78

propy lbutan-2-amine see table under homo-MDA ( #78)
1-(Benzo[d] [ 1,3]dioxol-5-yl)-2- PrONE 229

(prop-2-yn-1-ylamino )propan-1-one see table under Methylone ( #93)
1-(Benzo[d] [ 1,3]dioxol-5-yl)-2- MD PPP 229

(pyrrolidin-1-yl)propan-1-one see table under Methylone ( #93)
Benzylamine Phenylmethanamine 261

N-Benzyl-1-(3,4-dimethoxyphenyl) DMBZ 67
propan-2-amine see table under OMA ( #38)
1 -(4-Benzyl-2,5-dimethoxyphenyl) DOBZ 123

propan-2-amine see table under DOM ( #60)
2-(4-(Benzy loxy )-3,5-dimethoxypheny 1) BZ 217

ethanamine see table under Mescaline ( #91)
1-( 4-(Benzyloxy )-2,5-dimethoxyphenyl) MBZM 294

propan-2-amine see table under TMA-2 ( # 118)
1-(4-(Benzyloxy )phenyl)propan-2-amine 4-BzA 270

1-(4-(Benzy lthio )-2,5-dimethoxypheny l) ALEPH-S-PhEt 3

propan-2-amine see table under ALEPH ( #3)
BF5AP 1-(2,3-Dihydrobenzofuran-5-y l)propan-2-amine 1 72

BF6AP 1-(2,3-Dihydrobenzofuran-6-y l)propan-2-amine 1 72

B-FLY ( #12) 1-(8-Bromo-2,3,6,7-tetrahydrobenzo[ 1,2-b:4,5-b'] difuran-4-y l) 14

propan-2-amine
1-(8-Bromo-2,3,6,7-tetrahydrobenzo[l,2-b:4,5-b' ]difuran-4-y1 )-2-
aminopropane
8-Bromo-2,3,6,7-tetrahydro-a-methylbenzo[l,2-b:4,5-b'] difuran-4-
ethanamine
3C-B-FLY
Bromo-fly
DOB-FLY
BHB 1-(2,5-Dibutoxy-4-hexy lphenyl)propan-2-amine 121

6-B-IBF5AP 1-( 6-Bromo-1,3-dihydroisobenzofuran-5-y l)propan-2-amine 1 72

BIS-TOET 1-(4-Ethy 1-2,5-bis(methy 1 thio )pheny l)propan-2-amine 108

see table under DOET ( #56)
BIS-TOM 1-( 4-Methy 1-2,5-bis(methy lthio )pheny l)propan-2-amine 3


BL-3912A
BL-3912A ARIADNE ( #7) 7
B-PLY 1-(1O-Bromo-2,3,4,7,8,9-hexahydropyrano[2,3-g ]- 142

chromen-5-yl)propan-2-amine
see table under FLY ( #68)
BL-3912 ARIADNE ( # 7) 7
Blue Mystic 2C-T-7 ( #27) 39
2-BM 2-(2-Bromo-3,4,5-trimethoxyphenyl)ethanamine 280

see table under TeMPEA ( # 114)
2,6-BM 2-(2,6-Dibromo-3,4,5-trimethoxyphenyl)ethanamine 263

see table under PeMPEA ( # 1 08)
3-BMAP 1-(3-Bromophenyl)-2-(methylamino)propan-1-one 226

see table under METHCATH ( #92)
4-BMAP 1-(4-Bromophenyl)-2-(methylamino )propan-1-one 226

2,3,4-BMM 2-(2-Bromo-3,4-dimethoxyphenyl)ethanamine 21
see table under 2C-B ( # 1 8)
2,3,5,6-BMMB 2-(2,6-Dibromo-3,5-dimethoxyphenyl)ethanamine 282

see table under TeMPEA-3 ( # 115)
2,3,5,6-BMMBA 1-(2,6-Dibromo-3,5-dimethoxyphenyl)propan-2-amine 282

see table under TeMPEA-3 ( #115)
B03A 2-(3-(Allyloxy)phenyl)-2-methoxyethanamine 244

BOB ( # 13) 2-(4-Bromo-2,5-dimethoxypheny 1)-2-methoxyethanamine 16

4-Bromo-�,2,5-trimethoxyphenethylamine
�,2,5-Trimethoxy-4-bromophenethylamine
BOBE 2-(4-Bromo-2,5-dimethoxyphenyl)-2-ethoxyethanamine 17
see table under BOD ( # 14)

BON
BOD ( # 14) 2-(2,5-Dimethoxy-4-methylphenyl)-2-methoxyethanamine 16

4-Methyl-2,5,�-trimethoxyphenethylamine
�,2,5-Trimethoxy-4-methylbenzeneethanamine
�-Methoxy-2C-D
BOOM 2-(2,5-Dimethoxyphenyl)-2-methoxyethanamine 17
BOE 2-(4-E thy 1-2,5-dimethoxypheny1 )-2-methoxyethanamine 17

B03E 2-(3-Ethoxyphenyl)-2-methoxyethanamine 244

B03EE 2-Ethoxy-2-(3-ethoxyphenyl)ethanamine 244

BOH ( # 15) 2-(Benzo[d] [l,3]dioxol-5-yl)-2-methoxyethanamine 17

�-Methoxy-3,4-methylenedioxyphenethylamine
�-Methoxy-1,3-benzodioxole-5-ethanamine
BOI 2-(4-Iodo-2,5-dimethoxypheny 1)-2-methoxyethanamine 17

BOM ( # 16) 2-Methoxy-2-(3,4,5-trimethoxyphenyl)ethanamine 18

�,3,4,5-Tetramethoxyphenethy!amine
�-Methoxymescaline
B03M 2-Methoxy-2-(3-methoxyphenyl)ethanamine 244

B03MA l-Methoxy-1-(3-methoxyphenyl)propan-2-amine 244

B03MB N-(2-Methoxy-2-(3-methoxypheny l)ethyl)butan-1 -amine 244

B03M2C 2-(2-Chloro-3-methoxyphenyl)-2-methoxyethanamine 81
B03MDM 2-Methoxy-2-(3-methoxyphenyl)-N,N-dimethylethanamine 244

see table under 3-MPEA ( #101)
B03ME 2-Ethoxy-2-(3-methoxyphenyl)ethanamine 244

B03MEA 1 -Ethoxy-1-(3-methoxyphenyl)propan-2-amine 244

B03MIP N-(2-Methoxy-2-(3-methoxyphenyl)ethyl)propan-2-amine 244

B03MM 2-Methoxy-2-(3-methoxyphenyl)-N-methylethanamine 244

BON 2-(2,5-Dimethoxy-4-nitrophenyl)-2-methoxyethanamine 17
see table under BOD ( #14)

B03P
B03P 2-Methoxy-2-(3-propoxyphenyl)ethanamine 244

BOPS 2-(2,5-Dimethoxy-4-(propylthio)phenyl)-2-methoxyethanamine 17
BOT 2-Methoxy-2-(2,4,5-trimethoxyphenyl)ethanamine 17
2-BPEA 2-(2-Bromophenyl)ethanamine 242

4-BPEA 1 -(4-Butoxyphenyl)propan-2-amine 247

3,5-Br-DESMETHYL 4-(2-Aminoethyl)-2,6-dibromophenol 43
5-Br-DESMETHYL 4-(2-Aminoethyl)-2-bromo-6-methoxyphenol 43
4-Br-DPIA DOB ( #52) 96
2-Br-5-MA 1-(2-Bromo-5-methoxyphenyl)-N-methylpropan-2-amine 59
4-Br-2-MA 1-(4-Bromo-2-methoxypheny l)propan-2-amine 55

4-Br-3-MA 1 -(4-Bromo-3-methoxyphenyl)-N-methylpropan-2-amine 67
6-Br-2-MA 2-(2-Aminopropyl)-3-methoxyphenol 64
2-Br-4,5-MDA 1-( 6-Bromobenzo[d] [ 1,3]dioxol-5-yl)propan-2-amine 238
see table under MMDA-2 ( #98)
4-Br-a-Me-ThEA 1-(4-Bromothiophen-2-yl)propan-2-amine 139

see table under FEA ( #67)
5-Br-a-Me-ThEA 1-(5-Bromothiophen-2-y l)propan-2-amine 139

5-Br-a-Me-FEA 1-( 5-Bromofuran-2-y l)propan-2-amine 139

3,5-Br-4-MPEA 2-(3,5-Dibromo-4-methoxyphenyl)ethanamine 216

4-Br-2-MPEA 2-(4-Bromo-2-methoxyphenyl)ethanamine 83
4-Br-PEA 2-(4-Bromophenyl)ethanamine 247

Brolamfetamine DOB ( #52) 96

2-(2-Bromo-3 ,5-dimethoxyphenyl)ethanami ne
Bromo 2C-B ( # 1 8) 20
1-( 8-Bromobenzo[l,2-b;4,5-b' ]difuran-4-y 1)- B-DFLY ( # 10) 12

2-aminopropane
2-(8-Bromobenzo[ l,2-b:4,5-b ']difuran-4-y 1) 2C-B-DFLY 48

ethanamine see table under DFLY ( # 32)
1-(8-Bromobenzo[ 1,2-b:4,5-b'] difuran-4-y 1 ) B-DFLY ( # 1 0) 12

propan-2-amine
1-( 6-Bromobenzo[d] [ 1,3 ] dioxol-5-yl)propan- 2-Br-4,5-MDA 238

2-amine see table under MMDA-2 ( #98)
2-(4-Bromo-2,5-diethoxyphenyl)ethanamine 2C-B-2,5-DIEtO 22
1-(8-Bromo-2,3-dihydrobenzo[b] [ l,4] dioxin-6-yl) BEDA 237

propan-2-amine see table under MMDA ( #97)
5-Bromo-2,3-dihydro-lH-inden-2-amine PBAI 257

1-(6-Bromo-1,3-dihydroisobenzofuran-5-yl) 6-B-IBF5AP 1 72
propan-2-amine see table under MDA ( #77)
7-Bromo-2,3-dihydro-5-methoxy-a-methy 1- B-SF ( # 1 7) 19
4-benzofuranethanamine
4-Bromo-2,5-dimethoxyamphetamine DOB ( #52) 96
1-(4-Bromo-2,5-dimethoxybenzy l)piperazine 2C-B-BZP 1 79

see table under MDBP ( #79)
4-Bromo-2,5-dimethoxyphenethylamine 2C-B ( # 1 8) 20
1-(4-Bromo-2,5-dimethoxyphenethy l)piperidine pip-2C-B 22

1-(4-Bromo-2,5-dimethoxypheny 1)-2-aminopropane DOB ( #52) 96
1-( 4-Bromo-2,5-dimethoxypheny l)butan-2-amine 4C-DOB 99

see table under DOB ( #52)
2-(4-Bromo-2,5-dimethoxyphenyl)-N,N 2C-B-MM 22
dimethylethanamine see table under 2C-B ( # 1 8)
1-(3-Bromo-2,6-dimethoxyphenyl)-N,N N,N-Me-3,2,6-DOB 98
dimethylpropan-2-amine see table under DOB ( #52)
1-(4-Bromo-2,5-dimethoxypheny l)-N,N N,N-Me-DOB 99

dimethy lpropan-2-amine see table under DOB ( #52)
2-(2-Bromo-3,4-dimethoxyphenyl)ethanamine 2,3,4-BMM 21
see table under 2C-B ( # 18)

2-(2-Bromo-3 ,6-dimethoxyphenyl)ethanam ine
see table under 2C-B ( #18)
see table under 2C-B ( #1 8)
2-(3-Bromo-2,4-dimethoxyphenyl)ethanamine 2,3,4-MBM 22
2-(4-Bromo-2,3-dimethoxyphenyl)ethanamine 2,3,4-MMB 22
see table under 2C-B ( #1 8)
2-(4-Bromo-2,5-dimethoxypheny l)ethanamine 2C-B ( # 1 8) 20
2-(5-Bromo-2,3-dimethoxypheny l)ethanamine 2,3,5-MMB 22

2-(5-Bromo-2,4-dimethoxyphenyl)ethanamine 2,4,5-MMB 22
2-( 6-Bromo-2,3-dimethoxyphenyl)ethanamine 2,3,6-MMB 22

2-(4-Bromo-2,5-dimethoxyphenyl)-2- BOBE 17
ethoxyethanamine see table under BOD ( #14)
2-(4-Bromo-2,5-dimethoxyphenyl)-N 2C-B-E 22
ethylethanamine see table under 2C-B ( #18)
4-Bromo-2,5-dimethoxyphenylisopropylamine DOB ( #52) 96
2-(4-Bromo-2,5-dimethoxyphenyl)- BOB ( # 1 3) 16
2-methoxyethanamine
1-(4-Bromo-2,5-dimethoxyphenyl)-1-methoxy [3-MeO-DOB 16
propan-2-amine see table under BOB ( # 13)
2-(4-Bromo-2,5-dimethoxyphenyl)-N 2C-B-M 22
methylethanamine see table under 2C-B ( # 1 8)

4-Bromo-DMA
N-(l-(4-Bromo-2,5-dimethoxyphenyl) DOB-Ac 99
propan-2-yl)acetamide see table under DOB ( #52)
1-(4-Bromo-2,5-dimethoxyphenyl) N-Me-DOB 99
N-methylpropan-2-amine see table under DOB ( #52)
1-(2-Bromo-3,4-dimethoxyphenyl)propan-2-amine 2,3,4-DOB 98
1 -(2-Bromo-3,5-dimethoxypheny l)propan-2-amine 2,3,5-DOB 98

see table under DOB ( # 52)
1 -(2-Bromo-4,5-dimethoxyphenyl)propan-2-amine o-DOB 98
1-(3-Bromo-2,5-dimethoxyphenyl)propan-2-amine 3-DOB 98
1 -(3-Bromo-2,6-dimethoxypheny l)propan-2-amine 3,2,6-DOB 98

1-(4-Bromo-2,5-dimethoxyphenyl)propan-2-amine DOB ( #52) 96
1-(4-Bromo-3,5-dimethoxypheny l)propan-2-amine 4,3,5-DOB 98

1-(5-Bromo-2,4-dimethoxypheny l)propan-2-amine m-DOB 98

1-( 6-Bromo-2,3-dimethoxyphenyl)propan-2-amine 6,2,3-DOB 98

see table under DOB ( #52)s
N-(1-(4-Bromo-2,5-dimethoxyphenyl) N-Pr-DOB 99
propan-2-yl)propan-1-amine see table under DOB ( #52)
4-Bromo-DMA DOB ( #52) 96

Bromodragonfly
Bromodragonfly B-DFLY ( # 10) 12
2-(4-Bromo-2-ethoxy-5-methoxyphenyl)ethanamine 2C-B-2-Et0 22
2-(4-Bromo-5-ethoxy-2-methoxyphenyl)ethanamine 2C-B-5-Et0 22
Bromo-fly B-FLY ( # 12) 14
2-(10-Bromo-2,3,4,7,8,9-hexahydropyrano[2,3-g] 2C-B-PLY 142

chromen-5-yl)ethanamine see table under FLY ( #68)
1-(1O-Bromo-2,3,4,7,8,9-hexahydropyrano[2,3-g ] B-PLY 142

chromen-5-y1 )propan-2-amine see table under FLY ( # 68)
1-(7-Bromo-5-methoxy-2,3-dihydrobenzofuran-4-y1)- B-SF ( # 1 7) 19
2-aminopropane
1-(7-Bromo-5-methoxy-2,3-dihydrobenzofuran-4-yl) B-SF ( # 1 7) 19
propan-2-amine
2-(4-Bromo-2-methoxyphenyl)ethanamine 4-Br-2-MPEA 83
1-(2-Bromo-5-methoxyphenyi)-N 2-Br-5-MA 59
methylpropan-2-amine see table under 2,5-DMA ( #36)
1-(4-Bromo-3-methoxyphenyi)-N 4-Br-3-MA 67
methylpropan-2-amine see table under DMA ( #38)
1-(4-Bromo-2-methoxyphenyi)propan-2-amine 4-Br-2-MA 55
1 -(3-Bromo-4-methoxyphenyl)propan-2-amine 3-Br-PMA 66
2-(4-Bromophenyl)cyclopropanamine BCPA 74
2-(2-Bromophenyl)ethanamine 2-BPEA 242

2-(4-Bromophenyl)ethanamine 4-Br-PEA 247

1-(3-Bromophenyl)-N-ethylpropan-2-amine N-Et-3-BA 159

1-(3-Bromophenyl)-2-(methylamino)propan-1-one 3-BMAP 226

1-(4-Bromophenyl)-2-(methylamino)propan-1-one 4-BMAP 226

1 -(2-Bromophenyl)propan-2-amine 2-BA 156


sBuONE
1-(4-Bromophenyl)propan-2-amine PBA 256

Bromo-semi-fly B-SF ( # 1 7) 19
l-(8-Bromo-2,3,6,7-tetrahydrobenzo[ 1,2-b:4,5-b'] B-FLY ( # 12) 14

difuran-4-yl)-2-aminopropane
2-(8-Bromo-2,3,6, 7-tetrahydrobenzo[ l,2-b:4,5-b '] 2C-B-FLY 141

difuran-4-yl)ethanamine see table under FLY ( #68)
l -(8-Bromo-2,3,6, 7-tetrahydrobenzo[ 1,2-b:4,5-b' ] B-FLY ( # 12) 14

difuran-4-y l)propan-2-amine
8-Bromo-2,3,6,7-tetrahydro-a-methylbenzo B-FLY ( # 12) 14

[1,2-b:4,5-b'] difuran-4-ethanamine
2-(2-Bromo-3,4,5-trimethoxyphenyl)ethanamine 2-BM 280

4-Bromo-[3,2,5-trimethoxyphenethylamine BOB ( # 13) 16
3-Br-PMA 1 -(3-Bromo-4-methoxyphenyl)propan-2-amine 66
B-Semi-fly B-SF ( # 1 7) 19
B-SF ( # 1 7) 1-(7-Bromo-5-methoxy-2,3-dihydrobenzofuran-4-yl)propan-2-amine 19
1-(7-Bromo-5-methoxy-2,3-dihydrobenzofuran-4-yl)-2-aminopropane
7-Bromo-2,3-dihydro-5-methoxy-a-methyl-4-benzofuranethanamine
Bromo-semi-fly
B-Semi-fly
F-4A5,7B
N-Bu-DHPEA 4-(2-(Buty !amino )ethyl)benzene-1,2-diol 87

N-iBu-DHPEA 4-(2-(Isobu tylamino )ethy l)benzene-1,2-diol 87

N-Bu-2-MA N-(1-(2-Methoxyphenyl)propan-2-yl)butan-1-amine 1 56
N-iBu-2-MA N-(1-(2-Methoxyphenyl)propan-2-yl)-2-methylpropan-1-amine 156

N-Bu-3-MA N-(1-(3-Methoxyphenyl)propan-2-yl)butan-1-amine 160

BuONE 1 -(Benzo[ d] [1,3]dioxol-5-yl)-2-(butylamino)propan-1 -one 229

iBuONE 1-(Benzo[d] [1,3]dioxol-5-yl)-2-(isobutylamino )propan-1-one 229

sBuONE 1 -(Benzo[ d] [1,3] dioxol-5-yl)-2-(sec-butylamino)propan-1-one 229


tBuONE
tBuONE 1 -(Benzo[d] [1,3]dioxol-5-yl)-2-(tert-butylamino )propan-1-one 229

4-BuPEA 2-(4-Butylphenyl)ethanamine 247

4-tBuPEA 2-(4-(tert-Butyl)phenyl)ethanamine 247

N-Bu-PHA 4-(2-(Butylamino)propyl)phenol 270

see table under PMA ( # 11 0)
Bupropion 2-(tert-Butylamino)-1-(3-chlorophenyl)propan-1-one 226

a,N-Butenyl-M 2-(3,4,5-Trimethoxybenzy 1)-1,2,3,6-tetrahydropyridine 287

N,N-Butenyl-M 1-(3,4,5-Trimethoxyphenethyl)-2,5-dihydro-lH-pyrrole 216

2-(4-Butoxy-3,5-dichlorophenyl) 3,5-Cl-4-BPEA 24
ethanamine see table under 2C-C ( # 19)
2-(4-Butoxy-2,5-dimethoxyphenyl) 2C-0-19 308

ethanamine see table under TMPEA-2 ( # 1 24)
2-(4-Butoxy-3,5-dimethoxyphenyl) B 216
1-(4-Butoxy-2,5-dimethoxyphenyl) MBM 292

propan-2-amine see table under TMA-2 ( # 11 8)
1-(4-Butoxyphenyl)propan-2-amine 4-BPEA 247

2-(tert-Butylamino )-1-(3-chlorophenyl) Bupropion 226

4-(2-(Butylamino)ethyl)benzene-1,2-diol N-Bu-DHPEA 87
2-(Butylamino)-1-phenylpropan-1-one BAP 72
2-(tert-Butylamino)-1-phenylpropan-1-one t-BAP 72
Butyl-4-(2-aminopropyl)-2,5- DOCEB 1 05
dimethoxybenzoate see table under DOCN ( #55)
4-(2-(Bu tylamino )propyl)phenol N-Bu-PHA 270

7-(Buty lamino )-5,6,7,8-tetrahydro BHAT 254

naphthalen-1 -ol see table under PAT ( # 1 05)
4-Butyl-2,5-dimethoxyamphetamine DOBU ( #53) 1 02

4C-3a
4-Butyl-2,5-dimethoxy-a-methylphenethylamine DOBU ( #53) 1 02
1-(4-Butyl-2,5-dimethoxyphenyl)butan-2-amine 4C-BU 8
see table under ARIADNE ( #7)
2-(4-(tert-Butyl)phenyl)ethanamine 4-tBuPEA 247

2-(4-(Buty lthio )-2,5-dimethoxyphenyl)ethanamine 2C-T-19 37

2-(4-(Butylthio)-3,5-dimethoxyphenyl)ethanamine TB 217
2-(4-(sec-Butylthio)-2,5-dimethoxyphenyl)ethanamine 2C-T-17 37
2-(4-(tert-Butylthio)-2,5-dimethoxyphenyl)ethanamine 2C-T-9 37
1-(4-Butyl-2,5-dimethoxyphenyl)propan-2-amine DOBU ( #53) 1 02
1-(4-(sec-Buty1)-2,5-dimethoxyphenyl)propan-2-amine DOSB 121

1-(4-(tert-Buty1)-2,5-dimethoxyphenyl)propan-2-amine DOTB 121

2-(4-Butylphenyl)ethanamine 4-BuPEA 247

1-( 4-(Bu ty 1 thio )-2,5-dimethoxyphenyl)propan-2-amine ALEPH-19 3

N-(1-(4-(sec-Buty lthio )-2,5-dimethoxyphenyl) HOT-17 37

propan-2-yl)hydroxylamine see table under 2C-T ( #25)
BZ 2-(4-(Benzyloxy)-3,5-dimethoxyphenyl)ethanamine 217
4-BzA 1-( 4-(Benzyloxy )phenyl)propan-2-amin 270

2C-2 2-(6-Methoxybenzo[d] [l,3]dioxol-5-yl)ethanamine 238

2C-3a 2-(4-Methoxybenzo[d] [l,3]dioxol-5-yl)ethanamine 240

see table under MMDA-3a ( #99)
2C-3b 2-(7-Methoxybenzo[d] [l,3] dioxol-4-yl)ethanamine 240

4C-2 1-(6-Methoxybenzo[d] [l,3] dioxol-5-yl)butan-2-amine 239

4C-3a 1-(4-Methoxybenzo[d] [ l,3 ]dioxol-5-yl)butan-2-amine 240


2-CA
2-CA 1-(2-Chlorophenyl)propan-2-amine 156

3-CA 1-(3-Chlorophenyl)propan-2-amine 1 59
4-CA PCA ( # 1 06) 255
CAB 1-(4-Chlorophenyl)butan-2-amine 256

Cactine Hordenine ( #71) 147
3C-AL 1-(4-(Ally loxy )-3,5-dimethoxyphenyl)propan-2-amine 288

Candicine 2-(4-Hydroxyphenyl)-N,N,N-trimethylethanaminium 150

CAT METHCATH ( #92) 225
2C-B ( # 1 8) 2-(4-Bromo-2,5-dimethoxyphenyl)ethanamine 20
4-Bromo-2,5-dimethoxyphenethy !amine
a-DESMETHYL-DOB
BDMPEA
Bees
Bromo
Erox
Nexus
See-bietjies (sea biscuits)
Ubulawu Nomathotholo
Venus
2C-B-BZP 1-(4-Bromo-2,5-dimethoxybenzyl)piperazine 1 79
see table under MDBP ( #79)
2C-B-DFLY 2-(8-Bromobenzo[ l,2-b:4,5-b ']difuran-4-yl)ethanamine 48

2C-B-2,5-DIEtO 2-(4-Bromo-2,5-diethoxyphenyl)ethanamine 22
2C-B-E 2-(4-Bromo-2,5-dimethoxyphenyl)-N-ethylethanamine 22
2C-B-2-Et0 2-(4-Bromo-2-ethoxy-5-methoxyphenyl)ethanamine 22
2C-B-5-Et0 2-(4-Bromo-5-ethoxy-2-methoxyphenyl)ethanamine 22
2C-B-FLY 2-( 8-Bromo-2,3,6,7-tetrahydrobenzo[ l,2-b:4,5-b '] difuran-4-y1)- 141

ethanamine
3C-B-FLY B-FLY ( # 1 2) 14

2C-DMMDA-2
2C-B-M 2-(4-Bromo-2,5-dimethoxyphenyl)-N-methylethanamine 22
2C-B-MM 2-(4-Bromo-2,5-dimethoxyphenyl)-N,N-dimethylethanamine 22
2C-B-PLY 2-(10-Bromo-2,3,4,7,8,9-hexahydropyrano[2,3-g]chromen-5-yl)- 142

ethanamine
4C-BU 1-(4-Bu tyl-2,5-dimethoxyphenyl)butan-2-amine 8

3C-BZ 1-(4-(Benzyloxy )-3,5-dimethoxypheny l)propan-2-amine 288

2C-C ( # 19) 2-(4-Chloro-2,5-dimethoxyphenyl)ethanamine 24

4-Chloro-2,5-dimethoxyphenethylamine
2C-DOC
2C-CA 4-(2-Aminoethyl)-2,5-dimethoxybenzoic acid 1 05

N-CCCl-M 2-Chloro-N-(3,4,5-trimethoxyphenethyl)ethanamine 216

4C-Cl 1-(4-Chloro-2,5-dimethoxyphenyl)butan-2-amine 1 04
see table under DOC ( #54)
2C-CN 4-(2-Aminoethyl)-2,5-dimethoxybenzonitrile 1 05
CCPA 2-(4-Chlorophenyl)cyclopropanamine 74
2C-D ( #20) 2-(2,5-Dimethoxy-4-methylphenyl)ethanamine 25

DMM-PEA
LE-25
2C-D-2,5-DIEtO 2-(2,5-Diethoxy-4-methylphenyl)ethanamine 26
2C-D-2-Et0 1-(2-Ethoxy-5-methoxy-4-methylphenyl)propan-2-amine 26
2C-D-5-Et0 2-(5-Ethoxy-2-methoxy-4-methylphenyl)ethanamine 26
see table under 2C-D ( # 20)
2C-DFLY 2-(Benzo[ 1,2-b:4,5-b '] difuran-4-yl)ethanamine 48

2C-DMMDA 2-(4,7-Dimethoxybenzo[d] [l,3]dioxol-5-yl)ethanamine 79

see table under DMMDA ( #44)
2C-DMMDA-2 2-(6,7-Dimethoxybenzo[d] [l,3]dioxol-5-yl)ethanamine 79


2C-DMMDA-3




4C-DMPEA 1-(3,4-DimethoxyphenyI)butan-2-amine 67
see table under OMA ( #38)
4C-2,3-DMPEA 1 -(2,3-Dimethoxyphenyl)butan-2-amine 53
4C-2,4-DMPEA 1-(2,4-Dimethoxyphenyl)butan-2-amine 55
4C-3,5-DMPEA 1-(3,5-Dimethoxyphenyl)butan-2-amine 71
4C-DOB 1-(4-Bromo-2,5-dimethoxyphenyl)butan�2-amine 99
2C-DOC 2C-C ( # 19) 24
4C-DOM ARIADNE ( # 7) 7
2C-E ( #21) 2-(4-Ethyl-2,5-dimethoxyphenyl)ethanamine 28

2,5-Dimethoxy-4-ethylphenethylamine
3C-E 1-(4-Ethoxy-3,5-dimethoxyphenyl)propan-2-amine 288

4C-E 1-(4-Ethy 1-2,5-dimethoxyphenyl)butan-2-amine 8

2C-EF 2-(4-(2-Fluoroethyl)-2,5-dimethoxyphenyl)ethanamine 26
4C-Et0 1-(4-Ethoxy-2,5-dimethoxypheny l)butan-2-amine 292

3C-FEM 1-(4-( (3-Fl uoropropyl)thio )-3,5-dimethoxyphenyl)propan-2-amine 288

3C-F EM 1-(4-( (2,2-Difluoroethyl)thio )-3,5-dimethoxyphenyl)propan-2-amine 288

2
1-(3,5-Dimethoxy-4-( (2,2,2-trifluoroethyl)thio )phenyl) 288

propan-2-amine
2C-F 2-(4-Fluoro-2,5-dimethoxyphenyl)ethanamine 26

1-(6-Chlorobenzo[d][1,3 ]dioxol-5-yl)-N-methylpropan-2-amine
2C-FLY 2-(2,3,6,7-Tetrahydrobenzo[ 1,2-b:4,5-b ']difuran-4-yl)ethanamine 141

2C-G 2-(2,5-Dimethoxy-3,4-dimethylphenyl)ethanamine 281

2C-G-N 2-(1,4-Dimethoxynaphthalen-2-yl)ethanamine 281

2C-G-1 2-(2,5-Dimethoxybicyclo[4.1.0 ]hepta-1,3,5-trien-3-y l)ethanamine 281

2C-G-2 2-(2,5-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-3-yl)ethanamine 281

2C-G-3 2-(4,7-Dimethoxy-2,3-dihydro-lH-inden-5-y l)ethanamine 281

2C-G-4 2-(1,4-Dimethoxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethanamine 281

2C-G-5 2-(5,8-Dimethoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-6-y1) 281

ethanamine
see table under TeMPEA ( #114)
2C-G-6 2-(5,8-Dimethoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl) 281

ethanamine
2C-G-12 2-(4-Ethyl-2,5-dimethoxy-3-methylphenyl)ethanamine 281

2C-G-21 2-(3-Ethyl-2,5-dimethoxy-4-methylphenyl)ethanamine 281

2C-H ( #22) 2-(2,5-Dimethoxyphenyl)ethanamine 29

2,5-DMPEA
DMPEA-4
NCS 168525
4C-H 1-(2,5-Dimethoxyphenyl)butan-2-amine 292

4C-HE 1-(4-(2-Aminobuty1)-2,5-dimethoxypheny l)ethanol 292

Chicken Power PMA ( # ll O) 267
Chicken Yellow PMA ( # ll O) 267
4-Chloroamphetamine PCA ( # 1 06) 255
2-(7-Chlorobenzo[d] [l,3]dioxol-5-yl)ethanamine 3-Cl-4,5-MDPEA 1 54

see table under Lophophine ( # 73)
1-( 6-Chlorobenzo[d] [ l,3]dioxol-5-yl)-N 2-Cl-4,5-MDMA 238

methylpropan-2-amine see table under MMDA-2 ( #98)

1 -(6-Chlorobenzo[d] [1,3 Jdioxol-5-yl)propan-2-amine
1-( 6-Chlorobenzo[ d] [ l,3 ] dioxol-5-yl)propan-2-amine 2-Cl-4,5-MDA 238

5-Chloro-2,3-dihydro-lH-inden-2-amine PCAI 257

1-( 6-Chloro-1,3-dihydroisobenzofuran-5-yl) 6-C-IBF5AP 1 72

4-Chloro-2,5-dimethoxyphenethylamine 2C-C ( # 19) 24
1-( 4-Chloro-2,5-dimethoxyphenyl)bu tan-2-amine 4C-Cl 1 04

2-(4-Chloro-2,5-dimethoxypheny l)ethanamine 2C-C ( # 1 9) 24
2-(2-Chloro-3,4-dimethoxyphenyl)ethanamine 2-Cl-3,4-DMPEA 24
see table under 2C-C ( # 19)
2-(2-Chloro-4,5-dimethoxypheny l)ethanamine 2-Cl-4,5-DMPEA 24

2-(5-Chloro-2,4-dimethoxypheny l)ethanamine 5-Cl-2,4-DMPEA 24

l-(3-Chloro-4,5-dimethoxyphenyl)propan-2-amine 3-Cl-4,5-DMA 216

1-(4-Chloro-2,5-dimethoxyphenyl)propan-2-amine DOC ( #54) 104
N-(1-( 4-Chloro-2,5-dimethoxyphenyl) DOC-Ac 104

propan-2-yl)acetamide see table under DOC ( # 54)
5-Chloro-N,N-dimethy1-2,3-dihydro-lH N,N-Me-PCAI 257

inden-2-amine see table under PCA ( # 1 06)
2-(2-Chloro-3-methoxyphenyl)-2- B03M2C 81
methoxyethanamine see table under 2,3-DMPEA ( #46)
1-(3-Chloro-4-methoxyphenyl)-N N-Me-3-Cl-MPEA 87
methy 1 propan-2-amine see table under DMPEA ( #49)
1-(4-Chloro-2-methoxypheny l)propan-2-amine 4-Cl-2-MA 55

1-(4-Chloro-3-methoxyphenyl)propan-2-amine 4-Cl-3-MA 67
4-Chloro-a-methylphenethylamine PCA ( # 106) 255
N-( 4-Chlorophenethyl)propan-2-amine N-iPr-4-Cl-PEA 247

1-(4-Chlorophenyl)butan-2-amine CAB 256

4-(4-Chlorophenyl)butan-2-amine homo-PCA 257

see table under PCA ( #106)

2-(4-Chlorophenyl)propan-1 -amine
2-(4-Chlorophenyl)cyclopropanamine CCPA 74
see table under DMCPA ( #41 )
1-(4-Chlorophenyl)-1,1-difluoropropan-2-amine �,IH-PCA 256

2-(2-Chlorophenyl)ethanamine 2-Cl-PEA 242



1-(3-Chlorophenyl)-N-ethylpropan-2-amine N-Et-3-CA 159

1-( 4-Chloropheny1)-N-ethylpropan-2-amine N-Et-PCA 256

1-(4-Chlorophenyl)-N-isopropylpropan-2-amine N-iPr-PCA 256

( 4-Chlorophenyl)methanamine PCBA 257

1-(2-Chlorophenyl)-N-methylpropan-2-amine 2-CMA 156

1-(4-Chlorophenyl)-N-methylpropan-2-amine PCMA 256

1 -(2-Chloropheny1)-2-methylpropan-2-amine 2-Cl-a,a-MePEA 1 56
1-(4-Chloropheny1)-2-methylpropan-2-amine 4-Cl-a,a-MePEA 256

1-(2-Chlorophenyl)piperazine oCPP 33
see table under mCPP ( #24)
1-(3-Chlorophenyl)piperazine mCPP ( # 24) 33
1-(4-Chlorophenyl)piperazine pCPP 33
1 -(2-Chlorophenyl)propan-2-amine 2-CA 156

1 -(3-Chlorophenyl)propan-2-amine 3-CA 159

1-(4-Chlorophenyl)propan-2-amine PCA ( # 106) 255
2-( 4-Chlorophenyl)propan-1-amine �-Me-4-Cl-PEA 247


2-Chloro-4-(piperazin-1 -yl)phenol
2-Chloro-4-(piperazin-1-yl)phenol HO-mCPP 34
6-Chloro-1,2,3,4-tetrahydronaphthalen- PCAT 257

2-amine see table under PCA ( # 1 06)
1 -(3-Chlorothiophen-2-yl)propan-2-amine 3-Cl-a-Me-ThEA 140

1 -(4-Chlorophenyl)-2-methylpropan-2-amine 4-Cl-a-Me-ThEA 140

1-( 5-Chlorothiophen-2-yl)propan-2-amine 5-Cl-a-Me-ThEA 140

2-Chloro-N-(3,4,5-trimethoxyphenethyl) N-CCCl-M 216

2-(2-Chloro-3,4,5-trimethoxyphenyl) 2-CM 280

ethanamine see table under TeMPEA ( # 114)
1 -Chloro-3-(3,4,5-trimethoxyphenyl) a-CMe-M 287

propan-2-amine see table under TMA ( # 117)
2C-HM (4-(2-Aminoethyl)-2,5-dimethoxyphenyl)methanol 27
4C-HM (4-(2-Aminobutyl)-2,5-dimethoxyphenyl)methanol 292

4C-HO 4-(2-Aminobutyl)-2,5-dimethoxyphenol 292

2C-I ( #23) 2-( 4-Iodo-2,5-dimethoxyphenyl)ethanamine 31

2,5-Dimethoxy-4-iodophenethylamine
SPICE
4C-I 1-( 4-Iodo-2,5-dimethoxyphenyl)bu tan-2-amine 113

see table under DOI ( #58)
2C-IB 2-(4-Isobutyl-2,5-dimethoxyphenyl)ethanamine 121

3C-IB 1-( 4-Isobutoxy-3,5-dimethoxyphenyl)propan-2-amine 288

6-C-IBF5AP 1-( 6-Chloro-1,3-dihydroisobenzofuran-5-yl)propan-2-amine 1 72

2C-I-DFLY 2-(8-Iodobenzo[l,2-b:4,5-b ']difuran-4-yl)ethanamine 48

2,5-11CIDNA 1-(4-Iodo-2,5-dimethoxyphenyl)-N-methylpropan-2-amine, 112

N-Me [11C] labeled
2,5-11CIDNNA 1-(4-Iodo-2,5-dimethoxypheny 1)-N,N-dimethy1 propan-2-amine, 112

N-Me [11C] labeled
2

4-Cl-a,a-MePEA
3C-IP 1-(4-Isopropoxy-3,5-dimethoxyphenyl)propan-2-amine 288

4C-iP 1-(4-Isopropy1-2,5-dimethoxyphenyl)butan-2-amine 292

4C-iPrO 1-(4-Isopropoxy-2,5-dimethoxyphenyl)butan-2-amine 292

3,5-Cl-4-ALPEA 2-( 4-(Allyloxy )-3,5-dichlorophenyl)ethanamine 24

3,5-Cl-4-BPEA 2-(4-Butoxy-3,5-dichlorophenyl)ethanamine 24
3-Cl-4,5-DMA 1 -(3-Chloro-4,5-dimethoxyphenyl)propan-2-amine 216

2-Cl-3,4-DMPEA 2-(2-Chloro-3,4-dimethoxyphenyl)ethanamine 24
5-Cl-2,4-DMPEA 2-(5-Chloro-2,4-dimethoxypheny l)ethanamine 24

3,5-Cl-4-EPEA 2-(3,5-Dichloro-4-ethoxyphenyl)ethanamine 24
3-Cl-4-HPEA 4-(2-Aminoethyl)-2-chlorophenol 87
4-Cl-2-MA 1-( 4-Chloro-2-methoxyphenyl)propan-2-amine 55

4-Cl-3-MA 1-( 4-Chloro-3-methoxyphenyl)propan-2-amine 67

3,5-Cl-4-MA 1 -(3,5-Dichloro-4-methoxyphenyl)propan-2-amine 24
2-Cl-4,5-MDA 1-( 6-Chlorobenzo[d] [ l,3 ]dioxol-5-yl)propan-2-amine 238

2-Cl-4,5-MDMA 1-( 6-Chlorobenzo[d] [ l,3 ]dioxol-5-yl)-N-methylpropan-2-amine 238

3-Cl-4,5-MDPEA 2-(7-Chlorobenzo[d] [ 1,3 ]dioxol-5-yl)ethanamine 1 54

see table under Lophophine ( # 73)
2-Cl-a,a-MePEA 1 -(2-Chlorophenyl)-2-methylpropan-2-amine 156

4-Cl-a,a-MePEA 1-( 4-Chloropheny1)-2-methylpropan-2-amine 256


3-Cl-a-Me-ThEA
3-Cl-a-Me-ThEA 1-(3-Chlorothiophen-2-yl)propan-2-amine 140

4-Cl-a-Me-ThEA 1-( 4-Chlorothiophen-2-yl)propan-2-amine 140

5-Cl-a-Me-ThEA 1-(5-Chlorothiophen-2-yl)propan-2-amine 140

3,4-Cl-a-Me-ThEA 1 -(3,4-Dichlorothiophen-2-yl)propan-2-amine 140

3,5-Cl-a-Me-ThEA 1 -(3,5-Dichlorothiophen-2-yl)propan-2-amine 140

4,5-Cl-a-Me-ThEA 1-( 4,5-Dichlorothiophen-2-yl)propan-2-amine 140

3,5-Cl-4-MPEA 2-(3,5-Dichloro-4-methoxyphenyl)ethanamine 24
2-Cl-PEA 2-(2-Chlorophenyl)ethanamine 242


3-MPEA ( #101)

3-Cl-PHA 4-(2-Aminopropyl)-2-chlorophenol 66
3,5-Cl-4-PPEA 2-(3,5-Dichloro-4-propoxyphenyl)ethanamine 24
2-CM 2-(2-Chloro-3,4,5-trimethoxyphenyl)ethanamine 280

2,6-CM 2-(2,6-Dichloro-3,4,5-trimethoxyphenyl)ethanamine 263

2-CMA 1 -(2-Chlorophenyl)-N-methylpropan-2-amine 156

a-CMe-M 1-Chloro-3-(3,4,5-trimethoxyphenyl)propan-2-amine 287

4C-Me0 1-(2,4,5-Trimethoxyphenyl)butan-2-amine 292

4C-2-MPEA 1-(2-Methoxyphenyl)butan-2-amine 156

4C-3-MPEA 1 -(3-Methoxyphenyl)butan-2-amine 244

2C-N 2-(2,5-Dimethoxy-4-nitrophenyl)ethanamine 26

cPr-PEA
2C-NH 4-(2-Aminoethy1)-2,5-dimethoxyaniline 308

4C-NH 4-(2-Aminobuty1)-2,5-dimethoxyaniline 130

see table under DON ( #61) .
4C-NO 1-(2,5-Dimethoxy-4-nitrophenyl)butan-2-amine 130

2C-O TMPEA-2 ( # 124) 307
2C-0-2 2-(4-Ethoxy-2,5-dimethoxyphenyl)ethanamine 308

2C-0-4 2-(4-lsopropoxy-2,5-dimethoxyphenyl)ethanamine 308

2C-0-7 2-(2,5-Dimethoxy-4-propoxyphenyl)ethanamine 308

2C-0-19 2-(4-Butoxy-2,5-dimethoxyphenyl)ethanamine 308

Coryneine 2-(3,4-Dihydroxyphenyl)-N,N,N-trimethylethanaminium 87
2C-P 2-(2,5-Dimethoxy-4-propylphenyl)ethanamine 26
3C-P 1-(3,5-Dimethoxy-4-propoxyphenyl)propan-2-amine 288

4C-P 1 -(2,5-Dimethoxy-4-propylphenyl)butan-2-amine 8
a-CP-2C-D 1 -(2,5-Dimethoxy-4-methylbenzyl)cyclopropanamine 123

2C-PLY 2-(2,3,4,7,8,9-Hexahydropyrano[2,3-g]chromen-5-yl)ethanamine 142

CPM 2-(4-(Cyclopropylmethoxy)-3,5-dimethoxyphenyl)ethanamine 216

N-CPM-M N-(Cyclopropylmethyl)-2-(3,4,5-trimethoxyphenyl)ethanamine 216

m-CPP mCPP ( #24) 33
3-CPP mCPP ( #24) 33
cPrONE 1-(Benzo[d] [l,3]dioxol-5-yl)-2-(cyclopropylamino)propan-1-one 229

4C-Pr0 1 -(2,5-Dimethoxy-4-propoxyphenyl)bu tan-2-amine 292

cPr-PEA 2-Phenylcyclopropanamine 261

see table under PEA ( #107)

2C-SE
2C-SE 2-(2,5-Dimethoxy-4-(methylselanyl)phenyl)ethanamine 308

2C-T ( #25) 2-(2,5-Dimethoxy-4-(methylthio)phenyl)ethanamine 36

2,5-Dimethoxy-4-methylthiophenethylamine
2C-T-2 ( #26) 2-(4-(Ethylthio)-2,5-dimethoxyphenyl)ethanamine 38

2,5-Dimethoxy-4-ethylthiophenethylamine
2C-T-3 2-(2,5-Dimethoxy-4-((2-methylallyl)thio)phenyl)ethanamine 37
2C-T-4 2-(4-(Isopropy lthio )-2,5-dimethoxypheny l)ethanamine 37

2C-T-7 ( #27) 2-(2,5-Dimethoxy-4-(propylthio)phenyl)ethanamine 39

2,5-Dimethoxy-4-(n)-propylthiophenethylamine
Blue Mystic
T7
Tripstasy
Tweety-bird mescaline
2C-T-8 2-( 4-( ( Cyclopropylmethyl)thio)-2,5-dimethoxypheny l)ethanamine 37

see table under 2C-T( #25)
2C-T-9 2-(4-(tert-Butylthio)-2,5-dimethoxyphenyl)ethanamine 37
2C-T-13 2-(2,5-Dimethoxy-4-((2-methoxyethyl)thio)phenyl)ethanamine 37
2C-T-15 2-(4-(Butylthio)-2,5-dimethoxyphenyl)ethanamine 37
2C-T-16 2-(4-(Allylthio)-2,5-dimethoxyphenyl)ethanamine 37
2C-T-17 2-( 4-(sec-Butylthio )-2,5-dimethoxyphenyl)ethanamine 37

2C-T-19 2-(4-(Butylthio)-2,5-dimethoxyphenyl)ethanamine 37
2C-T-21 2-( 4-( (2-Fl uoroethy l)thio )-2,5-dimethoxyphenyl)ethanamine 37

2C-T-21 .5 2-(4-((2,2-Difluoroethyl)thio)-2,5-dimethoxyphenyl)ethanamine 37
2C-T-22 2-(2,5-Dimethoxy-4-((2,2,2-trifluoroethyl)thio)phenyl)ethanamine 37
2C-T-25 1-(4-(Isobutylthio)-2,5-dimethoxyphenyl)propan-2-amine 37
2C-T-28 2-(4-((3-Fluoropropyl)thio)-2,5-dimethoxyphenyl)ethanamine 37

4C-T-7
2C-T-30 2-( 4-( ( 5-Fluoropentyl)thio)-2,5-dimethoxyphenyl)ethanamine 37

'lj!-2C-T 2-(2,6-Dimethoxy-4-(methylthio)phenyl)ethanamine 37
see table under 2C-T( #25)
'lj!-2C-T-4 2-(4-(Isopropylthio)-2,6-dimethoxyphenyl)ethanamine 37
'lj!-2C-T-7 2-(2,6-Dimethoxy-4-(propylthio)phenyl)ethanamine 40
see table under 2C-T-7 ( #27)
2,3,4-2C-T-7 2-(2,3-Dimethoxy-4-(propylthio)phenyl)ethanamine 40
2,4,3-2C-T-7 1 -(2,4-Dimethoxy-3-(propy1thio)phenyl)propan-2-amine 40
4,5,2-2C-T-7 2-( 4,5-Dimethoxy-2-(propylthio)phenyl)ethanamine 40

3C-T ALEPH ( #3) 2
4C-T 1-(2,5-Dimethoxy-4-(methylthio )phenyl)butan-2-amine 3

4C-T-2 1 -(4-(Ethylthio)-2,5-dimethoxyphenyl)butan-2-amine 3
4C-T-7 1-(2,5-Dimethoxy-4-(propyI thio )phenyl)butan-2-amine 3


2C-TFM
2C-TFM ( #28) 2-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)ethanamine 41

2,5-Dimethoxy-4-trifluoromethylphenethy!amine
2C-TMA Mescaline ( #91) 212
2C-TMA-2 TMPEA-2 ( # 1 24) 307
2C-TMA-3 IM ( # 72) 152
4C-TMPEA-3 1 -(2,3,4-Trimethoxyphenyl)butan-2-amine 297

4C-TMPEA-6 1-(2,4,6-Trimethoxyphenyl)butan-2-amine 304

2C-2-TOET 2-(4-Ethyl-5-methoxy-2-(methylthio)phenyl)ethanamine 108

2C-5-TOET 2-(4-Ethyl-2-methoxy-5-(methylthio)phenyl)ethanamine 108

2C-2-TOM 2-(5-Methoxy-4-methyl-2-(methylthio)phenyl)ethanamine 108

2C-5-TOM 1 -(2-Methoxy-4-methyl-5-(methylthio)phenyl)propan-2-amine 108

2C-VI 2-(2,5-Dimethoxy-4-vinylphenyl)ethanamine 27
4-Cyano-2,5-dimethoxyamphetamine DOCN ( #55) 1 05
2-( 4-( Cyclopropylmethoxy )-3,5-dimethoxypheny I) CPM 216

N-( Cyclopropylmethy1)-1-(4-iodo-2,5-dimethoxypheny l) 2,5-131INCPMA 113

propan-2-amine, [1311] labeled see table under DOI ( #58)
2-( 4-( ( Cyclopropylmethyl)thio)-2,5-dimethoxyphenyl) 2C-T-8 37

ethanamine see table under 2C-T( #25)
N-(Cyclopropylmethyl)-2-(3,4,5-trimethoxyphenyl) N-CPM-M 216

2-(4-(Cyclopropylthio)-2,5-dimethoxyphenyl) 2C-T-15 37
ethanamine see table under 2C-T( #25)
2C-YN 2-(4-Ethynyl-2,5-dimethoxyphenyl)ethanamine 27
2C-1 Lophophine ( #73) 1 54
2,5-DEA-f:lk 2-Amino-1-(2,5-diethoxyphenyl)propan-1-one 60
DCA 1-(3,4-Dichlorophenyl)propan-2-amine 66

a-DESMETHYL-DOB
2,4-DCA 1-(2,4-Dichlorophenyl)propan-2-amine 55
2,6-DCA 1-(2,6-Dichlorophenyl)propan-2-amine 64
DCPEA 2-(3,4-Dichlorophenyl)ethanamine 87
DEA 1 -(3,4-Diethoxyphenyl)propan-2-amine 67
2,5-DEA-f:lk 2-Amino-1-(2,5-diethoxyphenyl)propan-1 -one 60

DEAP 2-(Diethylamino )-1-phenylpropan-1-one 72

Death PMA ( # 11 0) 267
DEE 2-Amino-1-(3,4-diethoxyphenyl)ethanol 89
DEONE 1-(Benzo[ d] [l,3]dioxol-5-yl)-2-(diethylamino )propan-1-one 229

DEPEA 2-(3,4-Diethoxyphenyl)ethanamine 89
2,4-DEPEA 2-(2,4-Diethoxyphenyl)ethanamine 83
2-DES-Me-DOM 5-(2-Aminopropyl)-4-methoxy-2-methylphenol 121

5-DES-Me-DOM 5-(2-Aminopropyl)-4-methoxy-2-methylphenol 121

2,5-DES-Me-DOM 2-(2-Aminopropy1)-5-methylbenzene-1,4-diol 121

DESMETHYL ( #29) 4-(2-Aminoethyl)-2,6-dimethoxyphenol 42

3,5-Dimethoxytyramine
4-0-Desmethylmescaline
NSC 167759
DESMETHYL-iPr 4-(2-(Isopropylamino )ethy 1)-2,6-dimethoxyphenol 43

DESMETHYL-M 2,6-Dimethoxy-4-(2-(methylamino)ethyl)phenol 43
DESMETHYL-MM 4-(2-(Dimethylamino)ethyl)-2,6-dimethoxyphenol 43
a-DESMETHYL-DOB 2C-B ( # 1 8) 20

3-DESMETHYL
3-DESMETHYL ( #30) 5-(2-Aminoethyl)-2,3-dimethoxyphenol 45

3-Desmethy!mescaline
3-Hydroxy-4,5-dimethoxyphenethyI amine
3,4-DESMETHYL 5-(2-Aminoethy1)-3-methoxybenzene-1,2-diol 43
3,5-DESMETHYL 5-(2-Aminoethy1)-2-methoxybenzene-l,3-diol 45
3,4,5-DESMETHYL 5-(2-AminoethyI)benzene-1,2,3-triol 43
3-Desmethylmescaline 3-DESMETHYL ( #30) 45
4-Desmethy !mescaline DESMETHYL ( #29) 42
4-0-Desmethy!mescaline DESMETHYL ( #29) 42
DESOXY ( #31) 2-(3,5-Dimethoxy-4-methylphenyl)ethanamine 46

4-Desoxymescaline
4-Desoxymescaline DESOXY (#31) 46
DES-TMPEA-6 4-(2-Aminoethyl)-3,5-dimethoxyphenol 304

DFA 1 -(3,4-DifluorophenyI)propan-2-amine 66
2,4-DFA 1 -(2,4-Difl uoropheny l)propan-2-amine 55

2,5-DFA 1 -(2,5-Difluorophenyl)propan-2-amine 59
DFLY ( #32) 1-(Benzo[ l,2-b:4,5-b']difuran-4-y l)propan-2-amine 47

1-(Benzo[ 1,2-b:4,5-b']difuran-4-y 1)-2-aminopropane
a-Methyl-benzo[l,2-b:4,5-b'] difuran-4-ethanamine
DHA ( #33) 4-(2-Aminopropyl)benzene-l,2-diol 49

3,4-Dihydroxyamphetamine
4-(2-Aminopropyl)-pyrocatechol
a-Methyl dopamine
HHA
a-MeDA
DHAOH 4-(2-(Hydroxyamino)propy I)benzene-1,2-diol 49

DHBA 4-(Aminomethyl)benzene-1,2-diol 87
DHEA 4-(2-(Ethy !amino )propy l)benzene-1,2-diol 49


1 -(3 ,4-Dichlorophenyl)propan-2-amine
DH-a-Et-PEA 4-(2-Aminobutyl)benzene-1,2-diol 49
DHMA 4-(2-(Methy !amino )propyl)benzene-1,2-diol 49

DHMAOH 4-(2-(Hydroxy(methy!)amino )propy l)benzene-1,2-diol 49

DHPEA-f:\k 2-Amino-1-(3,4-dihydroxyphenyl)ethanone 88
2,3-DHPEA 3-(2-Aminoethyl)benzene-1,2-diol 53
2,4-DHPEA 4-(2-Aminoethyl)benzene-1,3-diol 83
2-(2,6-Dibromo-3,5-dimethoxyphenyl) 2,3,5,6-BMMB 282

ethanamine see table under TeMPEA-3 ( # 115)
1 -(2,6-Dibromo-3,5-dimethoxyphenyl) 2,3,5,6-BMMBA 282

propan-2-amine see table under TeMPEA-3 ( # 115)
2-(3,5-Dibromo-4-methoxyphenyl) 3,5-Br-4-MPEA 216

ethanamine see table under Mescaline (#91)
2-(2,6-Dibromo-3,4,5-trimethoxyphenyl) 2,6-BM 263

ethanamine see table under PeMPEA ( # 1 08)
1 -(2,5-Dibutoxy-4-hexylphenyl) BHB 121

7-(Dibuty !amino )-5,6,7,8-tetrahydro BBAT 254

naphthalen-1-ol see table under PAT ( # 1 05)
2-(3,5-Dichloro-4-ethoxyphenyl)ethanamine 3,5-Cl-4-EPEA 24
2-(3,5-Dichloro-4-methoxyphenyl) 3,5-Cl-4-MPEA 24
ethanamine see table under 2C-C ( # 1 9)
1-(3,5-Dichloro-4-methoxyphenyl) 3,5-Cl-4-MA 24
propan-2-amine see table under 2C-C ( # 19)
2-(3,4-Dichlorophenyl)ethanamine DCPEA 87
1 -(3,4-Dichlorophenyl)-N-methyl N-Me-DCA 66
propan-2-amine see table under DMA ( #38)
1 -(2,4-Dichlorophenyl)propan-2-amine 2,4-DCA 55
1 -(2,6-Dichlorophenyl)propan-2-amine 2,6-DCA 64
1 -(3,4-Dichlorophenyl)propan-2-amine DCA 66
see table under DMA ( # 38)

2-(3,5-Dichloro-4-propoxyphenyl)ethanamine
2-(3,5-Dichloro-4-propoxyphenyl)ethanamine 3,5-Cl-4-PPEA 24
1 -(3,4-Dichlorothiophen-2-yl)propan-2-amine 3,4-Cl-a-Me-ThEA 140

1 -(3,5-Dichlorothiophen-2-yl)propan-2-amine 3,5-Cl-a-Me-ThEA 140

1-(4,5-Dichlorothiophen-2-y l)propan-2-amine 4,5-Cl-a-Me-ThEA 140

2-(2,6-Dichloro-3,4,5-trimethoxyphenyl)ethanamine 2,6-CM 263

1 -(3,4-Diethoxy-5-(ethy lthio )pheny l)propan-2-amine 3-T-TRIS 217

2-(3,5-Diethoxy-4-(ethylthio)phenyl)ethanamine 4-T-TRIS 217

3,4-Diethoxy-5-methoxyphenethylamine ASB ( #8) 9
2-(3,4-Diethoxy-5-methoxyphenyl)ethanamine ASB ( #8) 9
2-(3,5-Diethoxy-4-methoxyphenyl)ethanamine SB 217
1-(2,4-Diethoxy-5-methoxyphenyl)propan-2-amine EEM 293

1-(2,5-Diethoxy-4-methoxyphenyl)propan-2-amine EME 293

1-( 4,5-Diethoxy-2-methoxyphenyl)propan-2-amine MEE 292

2-(2,4-Diethoxy-6-methylphenyl)ethanamine 6-Me-2,4-DEPEA 303

2-(2,5-Diethoxy-4-methylphenyl)ethanamine 2C-D-2,5-DIEtO 26
1 -(2,5-Diethoxy-4-methylphenyl)propan-2-amine DOM-2,5-DIEtO 121

2-(3,4-Diethoxy-5-(methylthio)phenyl)ethanamine 5-TASB 217

2-(3,5-Diethoxy-4-(methylthio)phenyl)ethanamine 4-TSB 217

2-(2,4-Diethoxyphenyl)ethanamine 2,4-DEPEA 83
2-(3,4-Diethoxypheny l)ethanamine DEPEA 89


1 -(2 ,2-Difluorobenzo[d] [ 1 ,3]dioxol-5-yl)-N-methy lpropan-2-amine
2-(3,4-Diethoxyphenyl)-N,N-dimethylethanamine N,N-Me-DEPEA 89
1 -(2,5-Diethoxypheny1)-2-(methy !amino )ethanol f:\-HO-N-Me-2,5-DEPEA 30

1 -(2,5-Diethoxypheny 1)-2-(methy !amino )ethanone N-Me-2,5-DEPEA-f:\k 30

1 -(2,5-Diethoxyphenyl)-2-(methylamino )propan-1-ol f:\-HO-N-Me-2,5-DEA 60

2-(3,4-Diethoxyphenyl)-N-methylethanamine N-Me-DEPEA 89
1-(3,4-Diethoxyphenyl)propan-2-amine DEA 67
2-(Diethylamino )-1-phenylpropan-1-one DEAP 72

7-(Diethylamino )-5,6,7,8-tetrahydronaphthalen-1-ol EEAT 254

1 -(3,4-Diethyl-2,5-dimethoxyphenyl)propan-2-amine G-22 279

see table under TeMA ( # 113)
N,N-Diethyl-1-(4-iodo-2,5-dimethoxyphenyl)- 2,5-131INNEA 113

propan-2-amine see table under DOI ( # 58)
N,N-Diethyl-2-(3-methoxyphenyl)ethanamine N,N-Et-3-MPEA 244

N,N-Diethyl-1-(2-methoxyphenyl)propan-2-amine N,N-Et-2-MA 156

N,N-Diethyl-1-(3-methoxyphenyl)propan-2-amine N,N-Et-3-MA 1 59
N,N-Diethyl-1-(4-(methy!thio)phenyl)propan-2-amine MTDEA 250

1 -(2,2-Difl uorobenzo[d] [ 1,3] dioxol-5-y I) butan-2-amine F -BDB 11

2
see table under BDB ( #9)
2-(2,2-Difl uorobenzo[d] [ 1,3]dioxol-5-yl)ethanamine F -MDPEA 205

2
1-(2,2-Difluorobenzo[d] [l,3]dioxol-5-yl)- F -MDE 1 84

2
N-ethylpropan-2-amine see table under MDE ( #81)
1-(2,2-Difluorobenzo[d] [ l,3]dioxol-5-y1)- F -MBDB 163

2
N-methylbutan-2-amine see table under MBDB ( # 76)
1 -(2,2-Difluorobenzo[d] [l,3]dioxol-5-yl)- F -MDMA 191

2
N-methylpropan-2-amine see table under MDMA ( #82)

1 -(2,2-Difluorobenzo[d][1,3 ]dioxol-5-yl)propan-2-amine
1 -(2,2-Difluorobenzo[d] [1,3] dioxol-5-yl)propan-2-amine F -MDA 168

2
2-( 4-( (2,2-Difluoroethy l)thio )-2,5-dimethoxypheny1) 2C-T-21 .5 37

ethanamine see table under 2C-T ( #25)
2-(4-( (2,2-Difluoroethyl)thio)-3,5-dimethoxypheny 1) F EM 44

2
ethanamine see table under DESMETHYL ( #29)
1-(4-( (2,2-Difluoroethyl)thio)-3,5-dimethoxyphenyl) 3C-F EM 288

2
propan-2-amine see table under TMA ( # 11 7)
1 -(2,4-Difluorophenyl)propan-2-amine 2,4-DFA 55
1 -(2,5-Difluorophenyl)propan-2-amine 2,5-DFA 59
see table under 2,5-DMA ( # 36)
1 -(3,4-Difluorophenyl)propan-2-amine DFA 66
2-(2,3-Dihydrobenzo[b] [l,4]dioxin-6-yl)-N,N ED-N-DMPEA 136

dimethylethanamine see table under EDA ( #65)
1-(2,3-Dihydrobenzo[ b] [ 1,4 ]dioxin-6-yl)-N,N ED-NDMA 137

dimethylpropan-2-amine see table under EDA ( #65)
2-(2,3-Dihydrobenzo[ b J [1,4 ]dioxin-6-yl)ethanamine ED PEA 1 36

see table under EDA ( #65)
4-(2-(2,3-Dihydrobenzo[b] [l,4]dioxin-6-yl)ethyl) ED-mor-PEA 137

morpholine see table under EDA ( #65)
1-(2,3-Dihydrobenzo[bJ [1,4]dioxin-6-yl)-N EDEA 137

ethylpropan-2-amine see table under EDA ( #65)
1 -(2-(2,3-Dihydrobenzo[ b] [ 1,4 ] dioxin-6-yl)ethy 1) ED-pyr-PEA 136

pyrrolidine see table under EDA ( #65)
1 -(2,3-Dihydrobenzo[ b] [ 1,4 ] dioxin-6-yl)-N EDMA 137

methy lpropan-2-amine see table under MDMA ( #82)
1-(2,3-Dihydrobenzo[ b] [ 1,4 ]dioxin-6-yl)propan-2-amine EDA ( #65) 136
4-(1 -(2,3-Dihydrobenzo[ bJ [1,4 ] dioxin-6-yl) ED-mor-A 137

propan-2-yl)morpholine see table under EDA ( #65)
1-(1-(2,3-Dihydrobenzo[b] [1,4]dioxin-6-yl) ED-pyr-A 137

propan-2-y l)pyrrolidine see table under EDA ( #65)
1-(2,3-Dihydrobenzofuran-5-y l)propan-2-amine BF5AP 1 72

1 -(2,3-Dihydrobenzofuran-6-yl)propan-2-amine BF6AP 1 72
6,7-Dihydro-5H-indeno[5,6-d] [l,3]dioxol-6-amine 5,6-MDAI 1 71


2-(5,7-Dimethoxybenzo[d] [1,3 ]dioxol-4-yl)ethanamine
7,8-Dihydro-6H-indeno[4,5-d] [l,3]dioxol-7-amine 4,5-MDAI 1 71

1 -(2,3-Dihydro-lH-inden-5-yl)-N-methylpropan-2-amine IMA 76
1 -(2,3-Dihydro-lH-inden-5-yl)propan-2-amine IAP 76
1-(1,3-Dihydroisobenzofuran-5-y l)-N IBF5MAP 1 72

methy lpropan-2-amine see table under MDA ( #77)
1-(1,3-Dihydroisobenzofuran-5-y l)propan-2-amine IBF5AP 1 72

2,3-Dihydro-5-methoxy-a-methyl-6- F ( #66) 137

benzofuranethanamine
3,4-Dihydroxyamphetamine DHA ( #33) 49
1-(3,4-Dihydroxypheny 1)-2-(isopropy !amino )ethanone N-iPr-DHPEA-f)k 88

1 -(3,4-Dihydroxyphenyl)-2-(isopropy!amino) N-iPr-DHA-f)k 49
propan-1-one see table under DHA ( #33)
1 -(3,4-Dihydroxypheny1)-2-(methy !amino )ethanone N-Me-DHPEA-f)k 88

2-(3,4-Dihydroxyphenyl)-N,N,N-trimethylethanaminium Coryneine 87
DIME TH N,N-Dimethyl-1-phenylpropan-2-amine 261

see table under PEA ( #1 07)
2,3-Dimethoxyamphetamine 2,3-DMA ( #34) 51
3,4-Dimethoxyamphetamine DMA ( #38) 65
2-(4,6-Dimethoxybenzo[d] [l,3]dioxol-5-yl)ethanamine 2C-DMMDA-4 79

2-(4,7-Dimethoxybenzo[d] [l,3]dioxol-5-yl)ethanamine 2C-DMMDA 79




2-(6,7-Dimethoxybenzo[d][l ,3]dioxol-4-yl)ethanamine
2-(6,7-Dimethoxybenzo[d] [l,3]dioxol-4-yl) 2C-DMMDA-3 79

ethanamine see table under DMMDA ( #44)
2-(6,7-Dimethoxybenzo[d] [l,3]dioxol-5-yl) 2C-DMMDA-2 79

ethanamine see table under DMMDA ( #44)
2-(4,7-Dimethoxybenzo[d] [l,3]dioxol-5-yl)-N N-Me-2C-DMMDA 79

methy lethanamine see table under DMMDA ( #44)
2-(6,7-Dimethoxybenzo[d] [l,3]dioxol-4-yl)-N N-Me-2C-DMMDA-3 79

methylethanamine see table under DMMDA ( #44)
2-(6,7-Dimethoxybenzo[d] [l,3]dioxol-5-yl)-N N-Me-2C-DMMDA-2 79

methylethanamine see table under DMMDA ( #44)
1 -(4,7-Dimethoxybenzo[d] [1,3]dioxol-5-yl)-N Methyl-DMMDA 79

methylpropan-2-amine see table under DMMDA ( #44)
1-( 4,6-Dimethoxybenzo[d] [1,3]dioxol-5-yl) DMMDA-4 79

propan-2-amine see table under DMMDA ( #44)
1-( 4,7-Dimethoxybenzo[d] [1,3]dioxol-5-yl) DMMDA ( #44) 79

propan-2-amine
1-( 5,6-Dimethoxybenzo[d] [ l,3 ]dioxol-4-yl) DMMDA-6 79

1-(6,7-Dimethoxybenzo[d] [1,3]dioxol-4-yl) DMMDA-3 79

2-(2,5-Dimethoxybicyclo[4.1 .0 ]hepta- 2C-G-1 281

1,3,5-trien-3-yl)ethanamine see table under TeMPEA ( #114)
1-(2,5-Dimethoxybicyclo[ 4.1 .0]hepta- G-1 279

1,3,5-trien-3-yl)propan-2-amine see table under TeMA ( #113)
2-(2,5-Dimethoxybicyclo[4.2.0]octa- 2C-G-2 281

1,3,5-trien-3-yl)ethanamine see table under TeMPEA ( #114)
1 -(2,5-Dimethoxybicyclo[ 4.2.0]octa- G-2 279

1,3,5-trien-3-yl)propan-2-amine see table under TeMA ( # 113)
2,5-Dimethoxy-4-bromoamphetamine DOB ( #52) 96
1-(2,5-Dimethoxy-4-n-buty lpheny 1)-2-aminopropane DOBU ( #53) 102
2,5-Dimethoxy-4-chloroamphetamine DOC ( # 54) 104
2-(6,7-Dimethoxy-2,3-dihydrobenzofuran-4-yl) Me0-2C-ISF 20
ethanamine see table under B-SF ( # 1 7)
1-(5,7-Dimethoxy-2,3-dihydrobenzofuran-4-y I) DMMDA-5 79

2-(4,7-Dimethoxy-2,3-dihydro-lH-inden-5-yl) 2C-G-3 281

1-(4,7-Dimethoxy-2,3-dihydro-lH-inden-5-yl) G-3 279

propan-2-amine see table under TeMA ( #113)

2,6-Dimethoxy-4-(2-(methylamino)ethyl)phenol
2,5-Dimethoxy-N,4-dimethylamphetamine BEATRICE ( # 1 1 ) 13
2-(2,5-Dimethoxy-3,4-dimethylphenyl)ethanamine 2C-G 281

1 -(2,5-Dimethoxy-3,4-dimethy lphenyl)propan-2-amine G 279

2,5-Dimethoxy-4-ethoxyamphetamine MEM ( # 87) 207
3,5-Dimethoxy-4-ethoxyphenethylamine Escaline ( #64) 134
1-(2,5-Dimethoxy-4-ethoxypheny1)-2-aminopropane MEM ( # 87) 279
2,5-Dimethoxy-4-ethy!amphetamine DOET ( #56) 1 06
2,5-Dimethoxy-4-ethylphenethylamine 2C-E ( #21) 28
1-(2,5-Dimethoxy-4-ethylpheny1)-2-aminopropane DOET ( #56) 1 06
2,5-Dimethoxy-4-ethylthioamphetamine ALEPH-2 ( #4) 5
2,5-Dimethoxy-4-ethylthiophenethy !amine 2C-T-2 ( #26) 38
3,5-Dimethoxy-4-ethoxyphenethylamine Escaline ( #64) 1 34
2,5-Dimethoxy-4-fluoroamphetamine DOF ( #57) 110
1-(2,5-Dimethoxy-4-fluorophenyl)-2-aminopropane DOF ( #57) 110
3,4-Dimethoxy-5-hydroxyphenethylamine 3-DESMETHYL ( #30) 45
3,5-Dimethoxy-4-hydroxyphenethylamine DESMETHYL ( #29) 42
2,5-Dimethoxy-4-iodoamphetamine DOI ( #58) 111
2,5-Dimethoxy-4-iodophenethylamine 2C-I ( #23) 31
1 -(2,5-Dimethoxy-4-iodopheny1)-2-aminopropane DOI ( #58) 111
2,5-Dimethoxy-4-isopropylamphetamine DOIP ( #59) 117
1 -(2,5-Dimethoxy-4-isopropyIpheny1)-2-aminopropane DOIP ( #59) 117
2-(3,5-Dimethoxy-4-( (2-methy !ally l)oxy )pheny1) MAL 217

2-(2,5-Dimethoxy-4-((2-methylallyl)thio)phenyl) 2C-T-3 37
1 -(3,4-Dimethoxyphenyl)-2-(methy !amino )ethanol N-Me-DME 88

2,3-Dimethoxy-5-(2-(methylamino)ethyl)phenol N-Me-3-DESMETHYL 45
see table under 3-DESMETHYL ( # 30)
2,6-Dimethoxy-4-(2-(methylamino)ethyl)phenol DESMETHYL-M 43

2,5-Dimethoxy-4-methylamphetamine DOM ( #60) 118
2,6-Dimethoxy-a-methylbenzeneethanamine 2,6-DMA ( #37) 63
3,4-Dimethoxy-a-methylbenzeneethanamine DMA ( #38) 65
3,5-Dimethoxy-a-methylbenzeneethanamine 3,5-DMA ( #39) 70
4,7-Dimethoxy-a-methyl-1,3-benzodioxole-5-ethanamine DMMDA ( #44) 78
1 -(2,5-Dimethoxy-4-methylbenzy l)cyclopropanamine a-CP-2C-D 123

4,7-Dimethoxy-5-methy 1-2,3-dihydro-lH-inden-2-amine DOMAI 123

2,5-Dimethoxy-3,4-methylenedioxyamphetamine DMMDA ( #44) 78
2,5-Dimethoxy-4-methyl-a-ethylphenethylamine ARIADNE ( # 7) 7
4,7-Dimethoxy-5-methyl-lH-inden-2-amine DOMAD 123

2,3-Dimethoxy-a-methylphenethylamine 2,3-DMA ( # 34) 51
2,4-Dimethoxy-a-methylphenethylamine 2,4-DMA ( #35) 54
2,5-Dimethoxy-a-methyl-phenethy!amine 2,5-DMA ( #36) 57
3,4-Dimethoxy-a-methylphenethylamine OMA ( #38) 65
3,5-Dimethoxy-a-methylphenethylamine 3,5-DMA ( #39) 70
2,5-Dimethoxy-4-methylphenethylamine 2C-D ( #20) 25
3,5-Dimethoxy-4-methylphenethylamine DESOXY ( #31) 46
1 -(2,5-Dimethoxy-4-methy1 phenyl)butan-2-amine ARIADNE ( #7) 7
3-(2,5-Dimethoxy-4-methylphenyl)butan-2-amine [)-Me-DOM 121

4-(2,5-Dimethoxy-4-methylphenyl)butan-2-amine homo-DOM 121

2-(2,5-Dimethoxy-4-methylphenyl)cyclopropanamine DMCPA ( #41) 73
trans-2-(2,5-Dimethoxy-4-methylphenyl)cyclopropylamine DMCPA ( #41) 73
3-(2,5-Dimethoxy-4-methylphenyl)-2,3- a,f),f)-Me-DOM 121

dimethylbutan-2-amine see table under DOM ( #60)
2-(2,5-Dimethoxy-4-methylphenyl)-N,N N,N-Me-2C-D 26
dimethylethanamine see table under 2C-D ( #20)
1-(2,5-Dimethoxy-4-methy lphenyl)-N,N N,N-Me-DOM 14

dimethylpropan-2-amine see table under BEATRICE ( # 11 )
1-(2,5-Dimethoxy-4-methylphenyl)-N,2- a-Me-DOM 121

dimethy lpropan-2-amine see table under DOM ( #60)

1-(2 ,5-Dimethoxy-3-methylphenyl)propan-2-amine
2-(2,4-Dimethoxy-6-methylphenyl)ethanamine 6-Me-2,4-DMPEA 303

2-(2,5-Dimethoxy-4-methylphenyl)ethanamine 2C-D ( #20) 25
2-(2,6-Dimethoxy-4-methylphenyl)ethanamine 4-Me-2,6-DMPEA 303

1-(2,5-Dimethoxy-4-methy1pheny1)-N N-Et-DOM 14
ethy lpropan-2-amine see table under BEATRICE ( # 1 1 )
N-(2,5-Dimethoxy-4-methylphenethyl) N-H0-2C-D 26
hydroxylamine see table under 2C-D ( #20)
2-(2,5-Dimethoxy-4-methylphenyl)-2- BOD ( # 14) 16

methoxyethanamine
3-(2,5-Dimethoxy-4-methylphenyl)-2- a,f3-Me-DOM 121

methylbutan-2-amine see table under DOM ( #60)
3-(2,5-Dimethoxy-4-methylphenyl)-3- f3,f3-Me-DOM 121

methylbutan-2-amine see table under DOM ( #60)
2-(2,5-Dimethoxy-4-methylphenyl)-3- DMMCPA 74
methylcyclopropanamine see table under DMCPA ( #41)
2-(2,5-Dimethoxy-4-methylphenyl)-N N-Me-2C-D 26
methylethanamine see table under 2C-D ( #20)
1 -(2,5-Dimethoxy-4-methy lphenyl)-N BEATRICE ( # 11 ) 13

methy l propan-2-amine
1-(2,5-Dimethoxy-4-methylpheny1)-2- a-Me-DOM 121

methy 1 propan-2-amine see table under DOM ( #60)
2-(2,5-Dimethoxy-4-methylphenyl)-2- f3,f3-Me-2C-D 26
methy1 propan-1-amine see table under 2C-D ( #20)
1-(2,3-Dimethoxy-4-methy lpheny l)propan-2-amine 4-Me-2,3-DOM 120

1 -(2,3-Dimethoxy-5-methy lpheny l)propan-2-amine 5-Me-2,3-DOM 120

1 -(2,3-Dimethoxy-6-methylphenyl)propan-2-amine 6-Me-2,3-DOM 120

1-(2,4-Dimethoxy-3-methylphenyl)propan-2-amine 3-Me-2,4-DOM 120

1-(2,4-Dimethoxy-5-methylphenyl)propan-2-amine m-DOM 120

1-(2,4-Dimethoxy-6-methylphenyl)propan-2-amine 6-Me-2,4-DOM 120

see table under DOM ( # 60)
1-(2,5-Dimethoxy-3-methylphenyl)propan-2-amine 3-DOM 120


2-(2,5-Dimethoxy-4-methylphenyl)propan-1 -amine
2-(2,5-Dimethoxy-4-methylphenyl)propan-1-amine �-Me-2C-D 26
1-(2,6-Dimethoxy-3-methylphenyl)propan-2-amine 3-Me-2,6-DOM 1 20
1 -(2,6-Dimethoxy-4-methylphenyl)propan-2-amine ljl-DOM 1 20
1 -(2,5-Dimethoxy-4-methy1 phenyl)propan-2-amine DOM ( #60) 118
1 -(3,4-Dimethoxy-5-methylphenyl)propan-2-amine 5-Me-3,4-DOM 1 20
1 -(3,5-Dimethoxy-2-methylpheny l)propan-2-amine 2-Me-3,5-DOM 1 20

1-(3,5-Dimethoxy-4-methy1 pheny l)propan-2-amine 4-Me-3,5-DOM 1 20

1-(4,5-Dimethoxy-2-methy1phenyl)propan-2-amine o-DOM 1 20
N-(1-(2,5-Dimethoxy-4-methylphenyl)propan- N-HO-DOM 1 23
2-y l)hydroxy lamine see table under DOM ( #60)
2-(2,5-Dimethoxy-4-(methylselanyl)phenyl) 2C-SE 308

ethanamine see table under TMPEA-2 ( #124)
1-(2,5-Dimethoxy-4-(methylsulfonyl)phenyl) ALEPH sulfone 3

5,8-Dimethoxy-6-methy1-1,2,3,4-tetrahydro DOMAT 1 23
naphthalen-2-amine see table under DOM ( #60)
2,5-Dimethoxy-4-methylthioamphetamine ALEPH ( #3) 2
2,5-Dimethoxy-4-methylthiophenethylamine 2C-T ( #25) 36
1-(2,5-Dimethoxy-4-(methylthio )phenyl)butan-2-amine 4C-T 3

sdd under ALEPH ( # 3)
2-(2,3-Dimethoxy-4-(methylthio )phenyl)ethanamine 4-TIM 152

see table under IM ( #72)
2-(2,4-Dimethoxy-3-(methylthio)phenyl)ethanamine 3-TIM 153

2-(2,5-Dimethoxy-4-(methylthio)phenyl)ethanamine 2C-T ( #25) 36
2-(2,6-Dimethoxy-4-(methylthio )phenyl)ethanamine ljl-2C-T 37


1 -(2,5-Dimethoxy-4-nony lpheny l)propan-2-amine
2-(3,4-Dimethoxy-2-(methylthio)phenyl)ethanamine 2-TIM 153

see table under IM ( # 72)
2-(3,4-Dimethoxy-5-(methylthio )phenyl)ethanamine 3-TM 217

2-(3,5-Dimethoxy-4-(methylthio)phenyl)ethanamine TM 217
1 -(2,5-Dimethoxy-4-(methylthio )phenyl)-N N-Me-4C-T 3

methy lbutan-2-amine see table under ALEPH ( #3)
1 -(2,5-Dimethoxy-4-(methylthio )phenyl)-N N-Me-ALEPH 3

methylpropan-2-amine see table under ALEPH ( #3)
1 -(2,4-Dimethoxy-5-(methylthio )phenyl) m-DOT 3

1-(2,5-Dimethoxy-4-(methylthio)phenyl) ALEPH ( #3) 2

propan-2-amine
1 -(2,6-Dimethoxy-4-(methylthio )phenyl) 'lj!-ALEPH 3

1-(4,5-Dimethoxy-2-(methylthio )phenyl o-DOT 3

)propan-2-amine see table under ALEPH ( #3)
2-(1,4-Dimethoxynaphthalen-2-yl)ethanamine 2C-G-N 281

1 -(1,4-Dimethoxynaphthalen-2-yl)propan-2-amine G-N 279

2,5-Dimethoxy-4-nitroamphetamine DON (#61) 1 29
1 -(2,5-Dimethoxy-4-nitrophenyl)-2-aminopropane DON ( #61) 1 29
1-(2,5-Dimethoxy-4-nitrophenyl)butan-2-amine 4C-NO 130

2-(2,5-Dimethoxy-4-nitrophenyl)ethanamine 2C-N 26
2-(2,5-Dimethoxy-4-nitrophenyl)-2- BON 17
methoxyethanamine see table under BOC ( # 14)
1 -(2,3-Dimethoxy-5-nitrophenyl)propan-2-amine 3-DON 1 30
1-(2,5-Dimethoxy-4-nitrophenyl)propan-2-amine DON ( #61) 129
1-(4,5-Dimethoxy-2-nitrophenyl)propan-2-amine o-DON 1 30
N-(1-(2,5-Dimethoxy-4-nitrophenyl)propan- DON-Ac 1 30
2-yl)acetamide see table under DON ( #61)
1-(2,5-Dimethoxy-4-nonylphenyl)propan-2-amine DONO 121


1-(2 ,5-Dimethoxy-4-octy lphenyl)propan-2-amine
1 -(2,5-Dimethoxy-4-octylphenyl)propan-2-amine DOOC 121

2,5-Dimethoxy-4-penty !amphetamine DOAM ( #51) 95
1-(2,5-Dimethoxy-4-(penty loxy )phenyl)propan- MAM 292

2-amine see table under TMA-2 ( # 118)
1-(2,5-Dimethoxy-4-penty1 pheny l)propan-2-amine DOAM (#51) 95
1 -(2,5-Dimethoxy-4-(pentylthio )phenyl)propan- ALEPH-S-amyl 3

2-amine see table under ALEPH ( #3)
2-(3,5-Dimethoxy-4-phenethoxyphenyl)ethanamine PE 217
2,3-Dimethoxyphenethylamine 2,3-DMPEA ( #46) 81
2,5-Dimethoxyphenethylamine 2C-H ( #22) 29
3,4-Dimethoxyphenethylamine DMPEA ( #49) 85
1 -(2,5-Dimethoxyphenyl)-2-aminopropane 2,5-DMA ( #36) 57
1 -(3,4-Dimethoxypheny1)-2-aminopropane DMA ( #38) 65
1-(2,4-Dimethoxyphenyl)butan-2-amine 4C-2,4-DMPEA 55
1 -(2,5-Dimethoxyphenyl)butan-2-amine 4C-H 8
1-(3,4-Dimethoxyphenyl)butan-2-amine 4C-DMPEA 67
1-(3,5-Dimethoxyphenyl)butan-2-amine 4C-3,5-DMPEA 71
2-(3,4-Dimethoxyphenyl)cyclopropanamine 3,4-DMCPA 74
1 -(2,5-Dimethoxypheny1)-2-( dimethylamino)ethanol 13-HO-N,N-Me-2,5-DMPEA 30

1 -(3,4-Dimethoxypheny1)-2-( dimethylamino )ethanol N,N-Me-DME 88

1-(3,5-Dimethoxyphenyl)-2-( dimethylamino )ethanol 13-HO-N,N-Me-3,5-DMPEA 94

1 -(2,5-Dimethoxyphenyl)-2-( dimethylamino)ethanone N,N-Me-2,5-DMPEA-13k 30


N-(2-(3,4-Dimethoxyphenyl)-2-hydroxyethyl)-N-methylformamide
1 -(2,5-Dimethoxyphenyl)-2-( dimethylamino ) B-HO-N,N-Me-2,5-DMA 60

propan-1 -ol see table under 2,5-DMA ( # 36)
2-(2,3-Dimethoxyphenyl)-N,N-dimethylethanamine N,N-Me-DMPEA-2 82
2-(2,5-Dimethoxyphenyl)-N,N-dimethylethanamine N,N-Me-2,5-DMPEA 30
2-(3,4-Dimethoxyphenyl)-N,N-dimethylethanamine N,N-Me-DMPEA 82
2-(2,5-Dimethoxyphenyl)-N,N-dimethylpropan-1-amine B,N,N-Me-2,5-DMPEA 30
1 -(2,4-Dimethoxyphenyl)-N,N-dimethylpropan-2-amine 2,4-DNNA 55
1 -(3,4-Dimethoxyphenyl) -N,N-dimethylpropan-2-amine N,N-Me-DMA 67

3-(2,5-Dimethoxyphenyl)-N,N-dimethylpropan-1-amine homo-N,N-Me-2,5-DMPEA 31
2-(2,3-Dimethoxyphenyl)ethanamine 2,3-DMPEA ( #46) 81
2-(2,5-Dimethoxyphenyl)ethanamine 2C-H ( #22) 29
2-(3,4-Dimethoxyphenyl)ethanamine DMPEA ( #49) 85
2-(3,4-Dimethoxyphenyl)-N-ethylethanamine N-Et-DMPEA 88
1 -(3,4-Dimethoxypheny1)-N-ethy lpropan-2-amine DMEA 67

N-(2-(3,4-Dimethoxyphenyl)-2-hydroxyethyl) N-Me,CHO-DME 88
N-methylformamide see table under DMPEA ( #49)

2 ,3-Dimethoxyphenylisopropy [amine
2,3-Dimethoxyphenylisopropylamine 2,3-DMA ( #34) 51
1 -(2,5-Dimethoxyphenyl)isopropy!amine 2,5-DMA ( #36) 57
3,4-Dimethoxyphenylisopropylamine DMA ( #38) 65
1-(2,5-Dimethoxyphenyl)-2-(isopropylamino ) f:\-H0-2,5-DMIPA 60
propan-1-ol see table under 2,5-DMA ( #36)
2-(3,4-Dimethoxyphenyl)-2-methoxy-N,N N,N-Me-f:\,3,4-TMPEA 88
dimethylethanamine see table under DMPEA ( #49)
2-(2,5-Dimethoxyphenyl)-2-methoxyethanamine BODM 17
2-(3,4-Dimethoxyphenyl)-2-methoxyethanamine f:\,3,4-TMPEA 88
2-(3,4-Dimethoxyphenyl)-2-methoxy-N N-Me-f:\,3,4-TMPEA 88
methylethanamine see table under DMPEA ( #49)
1-(2,5-Dimethoxypheny1)-2-(methy !amino )ethanol f:\-HO-N-Me-2,5-DMPEA 30

1-(2,6-Dimethoxyphenyl)-2-(methylamino )ethanol f:\-HO-N-Me-2,6-DMPEA 84

1-(3,4-Dimethylphenyl)-2-(methylamino )ethanol f:\-H0-3,4,N-MePEA 78

1-(3,5-Dimethoxypheny1)-2-(methy!amino )ethanol f:\-HO-N-Me-3,5-DMPEA 94

1-(2,5-Dimethoxyphenyl)-2-(methylamino )propan-1 -ol f:\-HO-N-Me-2,5-DMA 60

2-(2,5-Dimethoxyphenyl)-1 -(methylamino )propan-2-ol f:\-HO-f:\,N-Me-2,5-DMPEA 30

1-(2,5-Dimethoxypheny1)-2-(methylamino ) 2,5-DMMA-f:\k 60
propan-1 -one see table under 2,5-DMA ( # 36)
1-(2,3-Dimethoxypheny1)-N-methylbutan-2-amine 4C-2,3-DMPEA 53
2-(2,3-Dimethoxyphenyl)-N-methylethanamine N-Me-DMPEA-2 82
2-(2,4-Dimethoxyphenyl)-N-methylethanamine N-Me-DMPEA-3 83
2-(2,5-Dimethoxyphenyl)-N-methylethanamine N-Me-2,5-DMPEA 30
2-(3,4-Dimethoxyphenyl)-N-methylethanamine N-Me-DMPEA 82

N-(1 -(3,4-Dimethoxyphenyl)propan-2-yl)propan-1 -amine
2-(2,6-Dimethoxypheny1)-1-methy lethy!amine 2,6-DMA ( #37) 59
1-(2,3-Dimethoxyphenyl)-N-methylpropan-2-amine N-Me-2,3-DMA 53
1 -(2,4-Dimethoxypheny1)-N-methyI propan-2-amine 2,4-DMMA 55

1 -(2,5-Dimethoxypheny1)-N-methylpropan-2-amine 2,5-DMMA 60
1-(3,4-Dimethoxypheny1)-N-methy lpropan-2-amine DMMA 67

2-(2,5-Dimethoxyphenyl)-N-methylpropan-1 -amine f:\,N-Me-2,5-DMPEA 30

3-(2,5-Dimethoxypheny1)-N-methylpropan-1 -amine homo-N-Me-2,5-DMPEA 31

l-(3,4-Dimethoxyphenyl)-2-methyl-3-(3,4,5- a-MV-M 287

trimethoxyphenyl)propan-2-amine see table under TMA ( # 1 1 7)
1 -(2,3-Dimethoxyphenyl)propan-2-amine 2,3-DMA ( #34) 51
1 -(3,4-Dimethoxyphenyl)propan-2-amine DMA ( #38) 65
2-(2,5-Dimethoxyphenyl)propan-1-amine f:\-Me-2,5-DMPEA 30
2-(3,4-Dimethoxyphenyl)propan-1-amine f:\-Me-DMPEA 88
ee under DMPEA ( #49)
N-(1 -(2,5-Dimethoxyphenyl)propan-2-yl)acetamide 2,5-DMA-Ac 60

N-(1-(3,4-Dimethoxyphenyl)propan-2-yl)hydroxylamine DMAOH 67
N- (1-(3,4-Dimethoxyphenyl)propan-2-y1)-N DMMAOH 67
methylhydroxylamine see table under DMA ( #38)
N-( 1-(3,4-Dimethoxyphenyl)propan-2-yl)propan- DMPA 67

1 -amine see table under DMA ( #38)

1-(3 ,4-Dimethoxyphenyl)-2-propylamine
1-(3,4-Dimethoxypheny1)-2-propy!amine DMA ( #38) 65
1 -(2,5-Dimethoxy-4-(3-phenylpropyl)phenyl)propan- DOPh3 123

2-amine see table under DOM ( #60)
1 -(2,5-Dimethoxy-4-(phenylthio )phenyl)propan- ALEPH-6 3

3,5-Dimethoxy-4-(2-propenyloxy)phenethy!amine AL ( #2) 1
3,5-Dimethoxy-4-propoxyphenethylamine Proscaline ( # 1 04) 252
2-(3,4-Dimethoxy-5-propoxyphenyl)ethanamine MP 217
1 -(2,5-Dimethoxy-4-propoxyphenyl)butan-2-amine 4C-Pr0 292

2-(2,5-Dimethoxy-4-propoxyphenyl)ethanamine 2C-0-7 308

2-(3,5-Dimethoxy-4-propoxyphenyl)ethanamine Proscaline ( # 1 04) 252
1 -(2,5-Dimethoxy-4-propoxyphenyl)propan-2-amine MPM 292

1-(3,5-Dimethoxy-4-propoxyphenyl)propan-2-amine 3C-P 288

2,5-Dimethoxy-4-propylamphetamine DOPR ( #62) 131
1-(2,5-Dimethoxy-4-propylpheny1)-2-aminopropane DOPR ( # 62) 131
1 -(2,5-Dimethoxy-4-propylphenyl)butan-2-amine 4C-P 8
2-(2,5-Dimethoxy-4-propylphenyl)ethanamine 2C-P 26
1-(2,5-Dimethoxy-4-propylphenyl)propan-2-amine DOPR ( # 62) 131
2,5-Dimethoxy-4-propylthioamphetamine ALEPH-7 ( #6) 6
2,5-Dimethoxy-4-(i)-propylthioamphetamine ALEPH-4 ( #5) 6
2,5-Dimethoxy-4-(n)-propylthiophenethylamine 2C-T-7 ( #27) 39
N-(2,5-Dimethoxy-4-(propylthio)phenethyl) HOT-7 37
hydroxylamine see table under 2C-T ( #25)
1 -(2,5-Dimethoxy-4-(propylthio )pheny l)butan-2-amine 4C-T-7 3

2-(2,3-Dimethoxy-5-(propylthio)phenyl)ethanamine 2,3,5-2C-T-7 40

1-(5,8-Dimethoxy-1,2,3 ,4-tetrahydro-1,4-ethanonaphthalen-6-yl)propan-2-amine
1 -(2,4-Dimethoxy-3-(propy1 thio )phenyl)ethanamine 2,4,3-2C-T-7 40

2-(2,5-Dimethoxy-4-(propylthio )phenyl)ethanamine 2C-T-7 ( #27) 39
2-(2,6-Dimethoxy-3-(propylthio )phenyl)ethanamine 2,6,3-2C-T-7 40

2-(2,6-Dimethoxy-4-(propylthio)phenyl)ethanamine t!J-2C-T-7 40
2-(3,5-Dimethoxy-4-(propylthio)phenyl)ethanamine TP 40
2-(2,5-Dimethoxy-4-(propylthio )phenyl)-2- BOPS 17

methoxyethanamine see table under BOD ( #14)
1-(2,5-Dimethoxy-4-(propy lthio )phenyl)-N N-Me-4C-T-7 3

methylbutan-2-amine see table under ALEPH ( #3)
1-(2,5-Dimethoxy-4-(propylthio)phenyl)-N N-Me-ALEPH-7 3
methy 1 propan-2-amine see table under ALEPH ( #3)
1-(2,5-Dimethoxy-4-(propylthio )phenyl)propan-2-amine ALEPH-7 ( #6) 6
2-(3,5-Dimethoxy-4-(prop-2-yn-1-yloxy )phenyl) PROPYNYL 216

2-(5,8-Dimethoxy-1,2,3,4-tetrahydro-1,4- 2C-G-6 281

ethanonaphthalen-6-yl)ethanamine see table under TeMPEA ( # 114)
1 -(5,8-Dimethoxy-1,2,3,4-tetrahydro-l,4- G-6 279

ethanonaphthalen-6-yl)propan-2-amine see table under TeMA ( # 113)

2-(5,8-Dimethoxy-1 ,2,3, 4-tetrahydro-1,4-methanonaph thalen-6-yl )ethanamine
2-(5,8-Dimethoxy-1,2,3,4-tetrahydro-1,4- 2C-G-5 281

methanonaphthalen-6-yl)ethanamine see table under TeMPEA ( #114)
1-(5,8-Dimethoxy-1,2,3,4-tetrahydro-1,4- G-5 279

methanonaphthalen-6-yl)propan-2-amine see table under TeMA ( # 113)
2-(1,4-Dimethoxy-5,6,7,8-tetrahydronaphthalen- 2C-G-4 281

2-yl)ethanamine see table under TeMPEA ( # 114)
1-(1,4-Dimethoxy-5,6,7,8-tetrahydronaphthalen- G-4 279

2-yl)propan-2-amine see table under TeMA ( #113)
2-(2,5-Dimethoxy-4-( (2,2,2-trifluoroethyl)thio ) 2C-T-22 37

pheny l)ethanamine see table under 2C-T ( #25)
2-(3,5-Dimethoxy-4-( (2,2,2-trifluoroethyl)thio ) F EM 44
3
pheny l)ethanamine see table under DESMETHYL ( #29)
1 -(3,5-Dimethoxy-4-( (2,2,2-trifluoroethyl)thio)phenyl) 3C-F EM 288

3
2,5-Dimethoxy-4-trifluoromethylamphetamine DOTFM ( #63) 133
2,5-Dimethoxy-4-trifluoromethylphenethylamine 2C-TFM ( #28) 41
1-(2,5-Dimethoxy-4-( trifluoromethyl)pheny1)-2- DOTFM ( #63) 133

aminopropane
1-(2,6-Dimethoxy-4-( trifluoromethyl)phenyl) DOTFM-6 133

propan-2-amine see table under DOTFM ( #63)
2-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl) 2C-TFM ( #28) 31

ethanamine
1-(2,5-Dimethoxy-4-( trifluoromethyl)phenyl) DOTFM ( #63) 133

propan-2-amine
4,7-Dimethoxy-N,N,5-trimethyl-2,3-dihydro N,N-Me-DOMAI 123

lH-inden-2-amine see table under DOM ( #60)
2-(2,5-Dimethoxy-3,4,6-trimethylphenyl)ethanamine 3,4,6-Me-2,5-DMPEA 264

3,5-Dimethoxytyramine DESMETHYL ( #29) 42
2-(2,5-Dimethoxy-4-vinylphenyl)ethanamine 2C-VI 27
1 -(2,5-Dimethoxy-4-vinylphenyl)propan-2-amine DOVI 123

3-(2-(Dimethylamino )ethyl)benzene-1,2-diol N,N-Me-2,3-DHPEA 53

4-(2-(Dimethylamino)ethyl)benzene-1,2-diol N,N-Me-DHPEA 87
5-(2-(Dimethylamino)ethyl)-2,3-dimethoxyphenol N,N-Me-3-DESMETHYL 45

7-(Dimethylamino)-5,6,7,8-tetrahydronaphthalen-1 -ol
2-(2-(Dimethy!amino )ethy 1)-4-methoxyphenol N,N-Me-2,5-HMPEA 30

4-(2-(Dimethylamino)ethyl)-2-methoxyphenol MM-GEA 88
2-(2-(Dimethylamino)ethyl)-6-methylphenol 2,3-HMeMMPEA 52
2-(2-(Dimethy !amino )ethyl)phenol N,N-Me-2-HPEA 1 50

3-(2-(Dimethy!amino )ethyl)phenol N,N-Me-3-HPEA 150

4-(2-(Dimethy!amino )ethy!)phenol Hordenine ( # 71 ) 147
4-(2-(Dimethy!amino )ethyl)pheny I acetate Hordenine acetate 150

4-(2-(Dimethylamino )ethyl)-1,2-phenylene diacetate N,N-Me-DHPEA-AA 89

4-(2-(Dimethylamino )-1-hydroxyethyl)benzene- f:\,3,4-HO-N,N-MePEA 88

1,2-diol see table under DMPEA ( #49)
5-(2-(Dimethylamino )-1 -hydroxyethyl)-2- N,N-Me-HME 88

methoxyphenol see table under DMPEA ( #49)
4-(2-(Dimethylamino )-1 -hydroxyethyl)phenol f:\-HO-Hordenine 150

see table under Hordenine ( # 71)
4-(2-(Dimethylamino)-1-hydroxypropyl)phenol PHMMA 270

2-(Dimethylamino )-1 -phenylethanol f:\-HO-N,N-Me-PEA 261

2-(Dimethy !amino )-1-pheny lethanone DMAA 72

2-(Dimethylamino )-1-phenylpropan-1-one DMAP ( #40) 71
2-Dimethylaminopropiophenone DMAP ( #40) 71
4-(2-(Dimethy!amino )propyl)benzene-1,2-diol N,N-Me-DHA 49

4-(2-(Dimethy!amino )propyl)benzene-1,2-diol N,N-Me-DHA (diacetate) 50

3-(2-(Dimethylamino)propyl)-4-methoxyphenol N,N-Me-2,5-HMA 59
2-(2-(Dimethylamino)propyl)-6-methylphenol 2,3-HMeMMA 53
7-(Dimethylamino)-5,6,7,8-tetrahydronaphthalen-1-ol MMAT 254


2-(Dimethylamino)-1 -(3-( trifluoromethyl)phenyl)propan-1 -one
2-(Dimethylamino)-1-(3-(trifluoromethyl)phenyl)- 3-TFMDMAP 226

3,4-Dimethylamphetamine DMeA ( #42) 75
a,N-Dimethyl-1,3-benzodioxole-5-ethanamine MDMA ( # 82) 1 86
a,N-Dimethyl-1,3-benzodioxole-5-methanamine a,N-DMMDBA ( #45) 80
a,N-Dimethyl-1,3-benzodioxole-5-propy!amine homo-MDMA ( #83) 201
1-(2,2-Dimethylbenzo[d] [l,3]dioxol-5-yl)propan- IDA 1 72

Di-0-methyldopamine DMPEA ( #49) 85
N,N-Dimethyl-4-hydroxyphenethylamine Hordenine ( # 71 ) 147
N,N-Dimethyl-MDA MDDMA ( # 80) 180
N,N-Dimethylmescaline Trichocereine ( # 125) 309
N,N-Dimethyl-3,4-methylenedioxyamphetamine MDDMA ( # 80) 180
a,N-Dimethyl-3,4-methylenedioxybenzylamine a,N-DMMDBA ( #45) 45
a,N-Dimethyl-3,4-methylenedioxy)phenethylamine MDMA ( # 82) 1 86
a,N-Dimethyl-3-(3,4-methylenedioxyphenyl)- homo-MDMA ( # 83) 201

propylamine
N, 1-Dimethy 1-3-(3,4-methylenedioxyphenyl)- homo-MDMA ( #83) 201

propylamine
N,N-Dimethyl-1-(4-(methy!thio)phenyl)- MTDMA 250

propan-2-amine see table under MTA ( # 1 03)
3,4-Dimethylphenethylamine DMePEA ( #43) 77
1-(2,5-DimethyIp henyl)-N,N-dimethyI prop an- N,N-Me-2,5-DMeA 76

2-amine see table under DMeA ( #42)
N,N-Dimethyl-2-phenylethanamine N,N-MePEA 260

see table under PEA ( # 107)
2-(2,3-Dimethylphenyl)ethanamine 2,3-DMePEA 77
2-(3,4-Dimethylphenyl)ethanamine DMePEA ( #43) 77

1-(3,4-Dimethylphenyl)-2-(methy !amino )ethanol [l-H0-3,4,N-MePEA 78

1-(2,5-Dimethylphenyl)-N-methyI propan-2-amine N-Me-2,5-DMeA 76

1-(3,4-Dimethylpheny1)-N-methy lpropan-2-amine N-Me-DMeA 76

N,N-Dimethyl-1-phenylpropan-2-amine DIME TH 261

N,2-Dimethyl-3-phenylpropan-1-amine homo-[l,N-MePEA 261

1-(2,3-Dimethylphenyl)propan-2-amine 2,3-DMeA 75
1-(2,4-DimethyI phenyl)propan-2-amine 2,4-DMeA 75

1-(3,4-DimethylphenyI )propan-2-amine DMeA ( #42) 75
1-(3,5-DimethylphenyI )propan-2-amine 3,5-DMeA 76

a,N-Dimethylpiperonylamine a,N-DMMDBA ( #45) 80
Dimethylpropion DMAP ( #40) 71
N,N-Dimethyl-3,4,5-trimethoxyphenethylamine Trichocereine ( # 125) 309
N,N-Dimethyl-2-(3,4,5-trimethoxyphenyl)ethanamine Trichocereine ( # 125) 309
N,N-dimethyl-1-(2,4,5-trimethoxyphenyl) N,N-Me-TMA-2 292

propan-2-amine see table under TMA-2 ( #118)
N,N-Dimethyltyramine Hordenine ( #71) 147
Dimoxamine (R-isomer freebase) ARIADNE ( #7) 7
6-(2-(Dipropy !amino )ethyl)-5,6,7,8- 6-HO-PPAT 55

tetrahydronaphthalen-2-ol see table under 2,4-DMA ( #35)
7-(2-(Di propy!amino )ethy 1)-5,6,7,8- 7-HO-PPAT 59

tetrahydronaphthalen-2-ol see table under 2,5-DMA ( #36)
2-(N,N-Dipropyl)amino-8-hydroxytetralin PAT ( # 105) 253

6-(Dipropylamino)-5,6,7,8-tetrahydronaphthalen-1 -ol
6-(Dipropylamino )-5,6,7,8-tetrahydronaphthalen-1-ol 5-HO-PPAT 52

7-(Dipropylamino)-5,6,7,8-tetrahydro-1-naphthalenol PAT ( # 105) 253
7-(Dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-ol PAT ( # 1 05) 253
DIMPEA DMPEA ( #49) 85
DMA 2,5-DMA ( #36) 57
DMA ( #38) 1-(3,4-Dimethoxyphenyl)propan-2-amine 65

a-Methyl-3,4-dimethoxyphenethylamine
1-(3,4-Dimethoxyphenyl)-2-propy!amine
2-Amino-1-(3',4' -dimethoxyphenyl)propane
a-Methylhomoveratrylamine
3,4-DMA
EA-1316
NSC 14471 7
DMA-2 2,3-DMA ( #34) 51
DMA-3 2,4-DMA ( #35) 54
DMA-4 2,5-DMA ( #36) 57
DMA-5 2,6-DMA ( #37) 63
DMA-6 3,5-DMA ( #39) 70
2,3-DMA ( #34) 1-(2,3-Dimethoxyphenyl)propan-2-amine 51

DMA-2
NSC 1 72189

DMA-3

2,5-Dimethoxy-a-methyl-phenethylamine
1-(2,5-Dimethoxyphenyl)isopropy!amine
2-(2-Aminopropyl)hydroquinonedimethylether
DMA
DMA-4
NSC 367445

DMeA

2-(2,6-Dimethoxyphenyl)-1-methylethylamine
DMA-5
3,4-DMA DMA ( #38) 65

DMA-6
NSC 660980
3,5-DMA ( #39) see table under 2,5-DMA ( #36) 59
2,4-DMA-f:lk 2-Amino-1-(2,4-dimethoxyphenyl)propan-1-one 55
2,5-DMA-f:lk 2-Amino-1-(2,5-dimethoxyphenyl)propan-1-one 60
2,5-DMA-Ac N-( 1-(2,5-Dimethoxyphenyl)propan-2-yl)acetamide 60

DMAA 2-(Dimethylamino)-1-phenylethanone 72
DMAOH N-( 1-(3,4-Dimethoxyphenyl )propan-2-yl)hydroxy!amine 67

DMAP ( #40) 2-(Dimethylamino)-1 -phenylpropan-1-one 71

2-Dimethylaminopropiophenone
N-Methylephedrone
Dimethy I propion
Metamfepramone
Metamfepyramone
DMPI
MG 559
NSC 234706
UR 1430
DMBZ N-Benzy1-1-(3,4-dimethoxyphenyl)propan-2-amine 67
DMCPA (#41) 2-(2,5-Dimethoxy-4-methylphenyl)cyclopropanamine 73

trans-2-(2,5-Dimethoxy-4-methylphenyl)cyclopropylamine
4-Methyl-2,5-methoxycyclopropylamine
3,4-DMCPA 2-(3,4-Dimethoxyphenyl)cyclopropanamine 74
see table under DMCPA (#41)
DME 2-Amino-1 -(3,4-dimethoxyphenyl)ethanol 88

DMeA ( #42) 1-(3,4-Dimethylphenyl)propan-2-amine 75

3,4-Dimethy!amphetamine

DMeA
(DMeA con't) a,3,4-Trimethylphenethylamine 75

Xylopropamine
3,4-DMeA
2,3-DMeA 1 -(2,3-DimethyI phenyl)propan-2-amine 75

2,4-DMeA 1-(2,4-Dimethylpheny l)propan-2-amine 75

2,5-DMeA 1 -(2,5-Dimethylphenyl)propan-2-amine 76
2,6-DMeA 1-(2,6-Dimethylphenyl)propan-2-amine 76
3,4-DMeA DMeA ( #42) 75
3,5-DMeA 1-(3,5-Dimethylphenyl)propan-2-amine 76
DMEA DOET ( #56) 106
DMEA MEM ( # 87) 207
DMEA 1-(3,4-Dimethoxyphenyl)-N-ethylpropan-2-amine 67
DMePAA 4-(2-Aminopropyl)-N,N-dimethylaniline 256

DMePEA ( #43) 2-(3,4-Dimethylphenyl)ethanamine 77

3,4-Dimethylphenethylamine
2,3-DMePEA 2-(2,3-Dimethylphenyl)ethanamine 77
DMMA 1-(3,4-Dimethoxypheny1)-N-methylpropan-2-amine 67
2,4-DMMA 1-(2,4-Dimethoxypheny1)-N-methylpropan-2-amine 55
2,5-DMMA 1-(2,5-Dimethoxyphenyl )-N-methy1 propan-2-amine 60


DMPEA
2,5-DMMA-j3k 1-(2,5-Dimethoxyphenyl)-2-(methylamino )propan-1-one 60

DMMAOH N-(1-(3,4-Dimethoxyphenyl)propan-2-y1)-N-methy lhydroxylamine 67

DMMCPA 2-(2,5-Dimethoxy-4-methylphenyl)-3-methylcyclopropanamine 74
DMMDA ( #44) 1-(4, 7-Dimethoxybenzo[d] [ 1,3]dioxol-5-yl)propan-2-amine 78

2,5-Dimethoxy-3,4-methylenedioxyamphetamine
4, 7-Dimethoxy-a-methyl-1,3-benzodioxole-5-ethanamine
DMMDA-3 1-( 6, 7-Dimethoxybenzo[d] [ l,3 ] dioxol-4-yl)propan-2-amine 79

DMMDA-4 1-( 4,6-Dimethoxybenzo[ d] [ 1,3 ]dioxol-5-yl)propan-2-amine 79

DMMDA-5 1-(5, 7-Dimethoxy-2,3-dihydrobenzofuran-4-yl)propan-2-amine 79

DMMDA-6 1-( 5,6-Dimethoxybenzo[d] [ 1,3 ]dioxol-4-yl)propan-2-amine 79

a,a-DMMDBA 2-(Benzo[ d] [ 1,3] dioxol-5-yl)propan-2-amine 80

a,N-DMMDBA ( #45) 1-(Benzo[d] [ 1,3]dioxol-5-y1)-N-methylethanamine 80

a,N-Dimethylpiperonylamine
a,N-Dimethyl-3,4-methylenedioxybenzylamine
a,N-Dimethyl-1,3-benzodioxole-5-methanamine
MDMIEA
N,N-DMMDBA 1-(Benzo[d] [l,3]dioxol-5-yl)-N,N-dimethylethanamine 80

DMM-PEA 2C-D ( #20) 25
DMMTA ALEPH ( #3) 2
DMMTA DOM ( #60) 118
DMONE 1-(Benzo[ d] [ l,3]dioxol-5-yl)-2-( dimethylamino )propan-1 -one 229

DMPA N-(1-(3,4-Dimethoxyphenyl)propan-2-yl)propan-1-amine 67
DMPE DMPEA ( #49) 85
DMPEA ( #49) 2-(3,4-Dimethoxyphenyl)ethanamine 85

Di-0-methyldopamine
Dopamine dimethyl ether
Homoveratrylamine
DIMPEA
3,4-DMPEA

DMPEA
(DMPEA can't) DMPE 85

NSC 6328
NSC 16948
NSC 26152
NSC 113958
NSC 14471 7
DMPEA-2 2,3-DMPEA ( #46) 81
DMPEA-3 2,4-DMPEA ( #47) 82
DMPEA-4 2C-H ( #22) 29
DMPEA-5 2,6-DMPEA ( #48) 84
DMPEA-6 3,5-DMPEA ( #50) 94
j3,4-DMPEA 2-Methoxy-2-(4-methoxyphenyl)ethanamine 247

2,3-DMPEA ( #46) 2-(2,3-Dimethoxyphenyl)ethanamine 81

DMPEA-2

DMPEA-3
2,5-DMPEA 2C-H ( #22) 29

DMPEA-5
3,4-DMPEA DMPEA ( #49) 85

DMPEA-6
2,5-DMPEA-�k 2-Amino-1-(2,5-dimethoxyphenyl)ethanone 30
DMPI DMAP ( #40) 72
2,4-DNNA 1-(2,4-Dimethoxyphenyl)-N,N-dimethylpropan-2-amine 55
2,6-DNNA 1-(2,6-Dimethoxyphenyl)-N,N-dimethy1 propan-2-amine 64

DOAA N-(4-(2-Aminopropyl)-2,5-dimethoxyphenyl)-N-methylacetamide 130

see table under DON (#61)

5,2,3-DOB
DOAC 1-( 4-(2-Aminopropyl )-2,5-dimethoxyphenyl)ethanone 1 06

DOAM ( #51) 1-(2,5-Dimethoxy-4-pentyl phenyl)propan-2-amine 95

4-Amyl-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-pentylamphetamine
DOB ( #52) 1-( 4-Bromo-2,5-dimethoxyphenyl)propan-2-amine 96

1-( 4-Bromo-2,5-dimethoxypheny1)-2-aminopropane
4-Bromo-2,5-dimethoxyphenylisopropylamine
4-Bromo-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-bromoamphetamine
Brolamfetamine
BDA
4-Bromo-DMA
4-Br-DPIA
m-DOB 1-( 5-Bromo-2,4-dimethoxyphenyl)propan-2-amine 98

a-DOB 1 -(2-Bromo-4,5-dimethoxyphenyl)propan-2-amine 98
3-DOB 1-(3-Bromo-2,5-dimethoxyphenyl)propan-2-amine 98
2,3,4-DOB 1-(2-Bromo-3,4-dimethoxyphenyl)propan-2-amine 98
3,4,5-DOB 1-(3-Bromo-4,5-dimethoxypheny l)propan-2-amine 98

4,2,3-DOB 1-( 4-Bromo-2,3-dimethoxyphenyl)propan-2-amine 98




6,2,3-DOB

DOB-Ac N-(1-( 4-Bromo-2,5-dimethoxyphenyl)propan-2-yl)acetamide 99

DOB-j3k 2-Amino-1-( 4-bromo-2,5-dimethoxyphenyl)propan-1-one 99

DOB-Dragonfly B-DFLY ( # 10) 12
DOB-FLY B-FLY ( # 12) 14
DOBU ( #53) 1-( 4-Buty1-2,5-dimethoxyphenyl)propan-2-amine 102

4-Butyl-2,5-dimethoxyamphetamine
4-Butyl-2,5-dimethoxy-a-methylphenethylamine
1-(2,5-Dimethoxy-4-n-butylpheny1)-2-aminopropane
DOBZ 1-( 4-Benzyl-2,5-dimethoxyphenyl)propan-2-amine 123

DOC ( #54) 1-( 4-Chloro-2,5-dimethoxyphenyl)propan-2-amine 104

2,5-Dimethoxy-4-chloroamphetamine
DOCA 4-(2-Aminopropyl)-2,5-dimethoxybenzoic acid 1 05

DOC-Ac N-( 1-(4-Chloro-2,5-dimethoxyphenyl)propan-2-yl)acetamide 1 04

DOC EB Butyl 4-(2-aminopropyl)-2,5-dimethoxybenzoate 105

DOCEP Propyl 4-(2-aminopropyl)-2,5-dimethoxybenzoate 1 05

DOCN ( #55) 4-(2-Aminopropy1)-2,5-dimethoxybenzonitrile 1 05

4-Cyano-2,5-dimethoxyamphetamine
DOCOE 1-( 4-(2-Aminopropyl)-2,5-dimethoxyphenyl)propan-1-one 106

see table under DOCN (#55)
DOCONHP 4-(2-Aminopropyl)-2,5-dimethoxy-N-propylbenzamide 106

DOEF 1-( 4-(2-Fluoroethy 1)-2,5-dimethoxyphenyl)propan-2-amine 123

DOEH 2-(4-(2-Aminopropyl)-2,5-dimethoxyphenyl)ethanol 123

DOET ( # 56) 1-(4-Ethyl-2,5-dimethoxyphenyl)propan-2-amine 106

2,5-Dimethoxy-4-ethylamphetamine
1-(2,5-Dimethoxy-4-ethylpheny1)-2-aminopropane
DMEA
2,3,4-DOET 1-(2-E thyl-3,4-dimethoxyphenyl)propan-2-amine 108


DOHP
2,3,5-DOET 1-(2-Ethyl-3,5-dimethoxyphenyl)propan-2-amine 1 08
2,3,6-DOET 1-(2-Ethy 1-3,6-dimethoxyphenyl)propan-2-amine 1 08

2,4,5-DOET 1-(2-E thyl-4,5-dimethoxyphenyl)propan-2-amine 1 08

see table under DOET ( # 56)
2,4,6-DOET 1-(2-E thyl-4,6-dimethoxyphenyl)propan-2-amine 108

3,2,4-DOET 1-(3-E thy1-2,4-dimethoxyphenyl)propan-2-amine 1 08

3,2,5-DOET 1-(3-Ethy1-2,5-dimethoxyphenyl)propan-2-amine 1 08
3,2,6-DOET 1-(3-Ethyl-2,6-dimethoxyphenyl)propan-2-amine 108

3,4,5-DOET 1-(3-E thy1-4,5-dimethoxyphenyl)propan-2-amine 108

4,2,3-DOET 1-( 4-E thyl-2,3-dimethoxyphenyl)propan-2-amine 1 08

4,2,6-DOET 1-(4-Ethyl-2,6-dimethoxyphenyl)propan-2-amine 1 08
4,3,5-DOET 1-(4-Ethy 1-3,5-dimethoxyphenyl)propan-2-amine 1 08

5,2,3-DOET 1-(5-E thyl-2,3-dimethoxyphenyl )propan-2-amine 108

5,2,4-DOET 1-(5-Ethy 1-2,4-dimethoxyphenyl)propan-2-amine 108

6,2,3-DOET 1-( 6-E thyl-2,3-dimethoxyphenyl)propan-2-amine 108

DOF ( #57) 1-( 4-Fluoro-2,5-dimethoxyphenyl)propan-2-amine 110

2,5-Dimethoxy-4-fluoroamphetamine
1-(2,5-Dimethoxy-4-fluorophenyl)-2-aminopropane
DOFM 1-( 4-(Fluoromethy1)-2,5-dimethoxypheny1)- 123

propan-2-amine
DOHE 1-( 4-Hexy 1-2,5-dimethoxyphenyl)propan-2-amine 121

DOHM (4-(2-Aminopropyl)-2,5-dimethoxyphenyl)methanol 123

DOHP 1-( 4-Hepty1-2,5-dimethoxyphenyl)propan-2-amine 121


DOI
DOI ( #58) 1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-amine 111

2,5-Dimethoxy-4-iodoamphetamine
1-(2,5-Dimethoxy-4-iodopheny1)-2-aminopropane
DOI-Ac N-(1-( 4-Iodo-2,5-dimethoxyphenyl)propan-2-yl)acetamide 112

see table under DOI ( # 58)
DOIB 1-(4-Isobutyl-2,5-dimethoxyphenyl)propan-2-amine 121

DOIP ( #59) 1-( 4-Isopropyl-2,5-dimethoxyphenyl)propan-2-amine 117

2,5-Dimethoxy-4-isopropylamphetamine
1 -(2,5-Dimethoxy-4-isopropylphenyl)-2-aminopropane
DOM ( # 60) 1-(2,5-Dimethoxy-4-methylphenyl)propan-2-amine 118

DMMTA
a-Me-2C-D
STP
'l!J-DOM 1 -(2,6-Dimethoxy-4-methylphenyl)propan-2-amine 120

m-DOM 1 -(2,4-Dimethoxy-5-methylphenyl)propan-2-amine 120

a-DOM 1-( 4,5-Dimethoxy-2-methylphenyl)propan-2-amine 120

3-DOM 1 -(2,5-Dimethoxy-3-methylphenyl)propan-2-amine 120

DOMAD 4, 7-Dimethoxy-5-methyl-lH-inden-2-amine 123

DOMAI 4,7-Dimethoxy-5-methy1-2,3-dihydro-lH-inden-2-amine 123

DOMAT 5,8-Dimethoxy-6-methyl-1,2,3,4-tetrahydronaphthalen-2-amine 123

DOM-DFLY 1-( 8-Methylbenzo[ l,2-b:4,5-b ']difuran-4-yl)propan-2-amine 48

DOM-2,5-DIETO 1-(2,5-Diethoxy-4-methylphenyl)propan-2-amine 121

DOM-FLY 1-( 8-Methyl-2,3,6,7-tetrahydrobenzo[ l,2-b:4,5-b '] difuran-4-y l) 142

propan-2-amine
DON ( #61) 1-(2,5-Dimethoxy-4-nitrophenyl)propan-2-amine 129

1-(2,5-Dimethoxy-4-nitropheny1)-2-aminopropane
2,5-Dimethoxy-4-nitroamphetamine
o-DON 1-( 4,5-Dimethoxy-2-nitrophenyl)propan-2-amine 130


DOTFM-6
3-DON 1 -(2,3-Dimethoxy-5-nitrophenyl)propan-2-amine 1 30
DON-Ac N-( 1-(2,5-Dimethoxy-4-nitrophenyl)propan-2-yl)acetamid 1 30

DONH 4-(2-Aminopropyl)-2,5-dimethoxyaniline 130

DONH-Ac N-( 1-(4-Amino-2,5-dimethoxyphenyl)propan-2-yl)acetamide 130

DONMM 4-(2-Aminopropyl)-2,5-dimethoxy-N,N-dimethylaniline 130

DONO 1 -(2,5-Dimethoxy-4-nonylphenyl)propan-2-amine 121

DOOC 1-(2,5-Dimethoxy-4-octylphenyl)propan-2-amine 121

DOOH 4-(2-Aminopropyl)-2,5-dimethoxyphenol 292

Doone PMMA ( # 112) 277
Dopamine dimethyl ether DMPEA ( #49) 85
DOPh3 1-(2,5-Dimethoxy-4-(3-phenylpropyl)phenyl)propan-2-amine 123

DOPR ( #62) 1 -(2,5-Dimethoxy-4-propylphenyl)propan-2-amine 131

1-(2,5-Dimethoxy-4-propylpheny1)-2-aminopropane
2,5-Dimethoxy-4-propylamphetamine
DOSB 1-( 4-(sec-Buty1)-2,5-dimethoxyphenyl)propan-2-amine 121

DOT 1-(2,5-Dimethoxy-4-(methylthio )phenyl)propan-2-amine 2

ALEPH ( #3)
m-DOT 1 -(2,4-Dimethoxy-5-(methylthio )phenyl)propan-2-amine 3

o-DOT 1-(4,5-Dimethoxy-2-(methylthio )phenyl)propan-2-amine 3

see table under ALEPH ( # 3)
p-DOT 1-(2,5-Dimethoxy-4-(methylthio)phenyl)propan-2-amine 3
ALEPH ( #3)
DOTB 1-( 4-(tert-Buty1)-2,5-dimethoxyphenyl)propan-2-amine 121

DOTFM ( #63) 1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)propan-2-amine 133

2,5-Dimethoxy-4-trifluoromethy!amphetamine
1 -(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane
DOTFM-6 1 -(2,6-Dimethoxy-4-( trifluoromethyl)phenyl)propan-2-amine 133

See table under DOTFM ( #63)

DOVI
DOVI 1 -(2,5-Dimethoxy-4-vinylphenyl)propan-2-amine 123

DOYN 1-(4-E thyny 1-2,5-dimethoxyphenyl)propan-2-amine 123

E Escaline ( #64) 134
E MDMA ( # 82) 1 86
EA-1298 MDA ( # 77) 165
EA-1 302 3-MPEA ( # 101) 243
EA-1316 DMA ( #38) 65
2-EA 1 -(2-Ethoxyphenyl)propan-2-amine 1 56
3-EA 1 -(3-Ethoxyphenyl)propan-2-amine 1 60
4-EA 1-( 4-Ethoxyphenyl)propan-2-amine 270

EAP 2-(Ethylamino )-1-phenylpropan-1-one 72

EASE Methylone ( #93) 228
EBDB (ETHYL-J) l-(Benzo[d] [l,3] dioxol-5-yl)-N-ethylbutan-2-amine 169

Ecstasy MDMA ( # 82) 1 86
EDA ( #65) 1 -(2,3-Dihydrobenzo[ b] [ 1,4 ] dioxin-6-yl)propan-2-amine 136

a-Methy1-1,4-benzodioxan-6-ethy!amine
3,4-Ethylenedioxyamphetamine
EDA-6
EDA-6 EDA ( #65) 136
ED-N-DMPEA 2-(2,3-Dihydrobenzo[b] [l,4]dioxin-6-yl)-N,N-dimethylethanamine 136

EDEA 1-(2,3-Dihydrobenzo[ b] [ 1,4 ]dioxin-6-yl)-N-ethy lpropan-2-amine 137

EDEN MBDB ( # 76) 1 62
EDMA 1-(2,3-Dihydrobenzo[ b] [ 1,4 ]dioxin-6-yl)-N-methylpropan-2-amine 191

see table under MDMA ( #82)
ED-mor-A 4-(1 -(2,3-Dihydrobenzo[ b] [ 1,4 ] dioxin-6-yl)propan-2-yl)morpholine 137

ED-mor-PEA 4-(2-(2,3-Dihydrobenzo[b] [l,4] dioxin-6-yl)ethyl)morpholine 137

see table under EDA ( # 65)

Erox
ED-ND MA 1-(2,3-Dihydrobenzo[ b] [ 1,4] dioxin-6-yl)-N,N 137

dimethylpropan-2-amine
ED PEA 2-(2,3-Dihydrobenzo[b] [l,4]dioxin-6-yl)ethanamine 136

ED-pyr-A 1-(1-(2,3-Dihydrobenzo[ b] [1,4]dioxin-6-yl)propan-2-yl)pyrrolidine 137

ED-pyr-PEA 1-(2-(2,3-Dihydrobenzo[ b] [ l,4 ]dioxin-6-yl)ethyl)pyrrolidine 136

see table under EDA ( # 65)
EEAT 7-(Diethy !amino )-5,6,7,8-tetrahydronaphthalen-1-ol 254

EEE 1 -(2,4,5-Triethoxyphenyl)propan-2-amine 293

EEM 1-(2,4-Diethoxy-5-methoxyphenyl)propan-2-amine 293

EHAT 7-(Ethylamino )-5,6,7,8-tetrahydronaphthalen-1-ol 254

EMA 1 -(3-Ethoxy-4-methoxyphenyI)propan-2-amine 67
EMDA MDE ( #81) 181
EME 1-(2,5-Diethoxy-4-methoxyphenyl)propan-2-amine 293

EMM Methylone ( #93) 228
EMM 1-(2-E thoxy-4,5-dimethoxyphenyI)propan-2-amine 293

EMPEA 2-(3-Ethoxy-4-methoxyphenyl)ethanamine 89
2,3-EMPEA 2-(2-Ethoxy-3-methoxyphenyl)ethanamine 82
2,4-EMPEA 2-(2-Ethoxy-4-methoxyphenyl)ethanamine 55
a-EMTPEA 1-(4-(Methylthio )phenyl)butan-2-amine 250

see table under MTA ( # 103)
4-EPEA 2-(4-Ethoxyphenyl)ethanamine 247

Ephedrone METHCATH ( #92) 255
Eremursine Hordenine ( #71) 147
Erox 2C-B ( # 1 8) 20

Escaline
Escaline ( #64) 2-(4-E thoxy-3,5-dimethoxyphenyl)ethanamine 134

3,5-Dimethoxy-4-ethoxyphenethylamine
E
ETA 1-(4-(E thylthio)pheny l)propan-2-amine 251

N-Et-3-BA 1-(3-Bromophenyl)-N-ethylpropan-2-amine 159

N-Et-3-CA 1-(3-Chloropheny1)-N-ethyI propan-2-amine 159

N-Et-DHPEA 4-(2-(Ethylamino)ethyl)benzene-1,2-diol 87
N-Et-DMPEA 2-(3,4-Dimethoxyphenyl)-N-ethylethanamine 88
N-Et-DOM 1-(2,5-Dimethoxy-4-methylpheny 1)-N-ethylpropan-2-amine 14

see table under BEATRICE ( # 11 )
N-Et-3-FA N-Ethyl-1-(3-fluorophenyl)propan-2-amine 159

N-Et-3-HA 3-(2-(E thylamino )propy!)phenol 159

Ethanamine PEA ( # 107) 259
1-(4-Ethoxy-2,5-dimethoxyphenyl)butan-2-amine 4C-Et0 292

2-(3-Ethoxy-4,5-dimethoxyphenyl)ethanamine ME 217
2-(4-Ethoxy-2,5-dimethoxyphenyl)ethanamine 2C-0-2 308

2-(4-Ethoxy-3,5-dimethoxyphenyl)ethanamine Escaline ( #64) 134
1-(2-E thoxy-4,5-dimethoxyphenyl)propan-2-amine EMM 228

1-(4-E thoxy-2,5-dimethoxyphenyl)propan-2-amine MEM ( # 87) 207
1-(4-E thoxy-3,5-dimethoxyphenyl)propan-2-amine 3C-E 288

1-(5-Ethoxy-2,4-dimethoxyphenyl)propan-2-amine MME 292

2-(2-Ethoxy-4,6-dimethylphenyl)ethanamine 4,6-Me-2-EPEA 303

2-(4-Ethoxy-2,6-dimethylphenyl)ethanamine 2,6-Me-4-EPEA 247


2-(3-Ethoxy-4-methoxyphenyl)-N,N-dimethylethanamine
2-Ethoxy-2-(3-ethoxyphenyl)ethanamine B03EE 244

2-(3-Ethoxy-4-(ethylthio)-5-methoxyphenyl) 4-TASB 217

2-(3-Ethoxy-5-(ethylthio)-4-methoxyphenyl) 3-TSB 217

2-( 4-E thoxy-3-( ethylthio )-5-methoxyphenyl) 3-TASB 217

4-E thoxy-2-(1 -hydroxy-2-(methylamino )ethyl)phenol j),2-HO-N-Me-5-EPEA 30

4-Ethoxy-2-(1-hydroxy-2-(methylamino)propyl) j),2-HO-N-Me-5-EA 59
phenol see table under 2,5-DMA ( #36)
1 -(5-E thoxy-2-hydroxyphenyl)-2-(methylamino ) 2-HO-N-Me-5-EPEA-j)k 30

ethanone see table under 2C-H ( #22)
1-(5-Ethoxy-2-hydroxyphenyl)-2-(methylamino ) 2-HO-N-Me-5-EA-j)k 59
propan-1 -one see table under 2,5-DMA ( #36)
2-(2-Ethoxy-4-methoxy-6-methylphenyl)ethanamine 6-Me-2,4-EMPEA 303

2-(2-Ethoxy-5-methoxy-4-methylphenyl)ethanamine 2C-D-2-Et0 26
2-(5-Ethoxy-2-methoxy-4-methylphenyl)ethanamine 2C-D-5-Et0 26
1-(2-E thoxy-5-methoxy-4-methylphenyl) FLORENCE 121

1-(2-E thoxy-6-methoxy-4-methylphenyl) 4-Me-2,6-MEA 304

propan-2-amine see table under TMA-6 ( # 1 22)
1-(5-Ethoxy-2-methoxy-4-methylphenyl) IRIS 121

2-(3-Ethoxy-4-methoxy-5-(methylthio)phenyl) 5-TME 217

2-(3-Ethoxy-5-methoxy-4-(methylthio)phenyl) 4-TME 217

2-( 4-E thoxy-3-methoxy-5-(methylthio)pheny1) 3-TE 216

4-Ethoxy-3-methoxyphenethylamine MEPEA ( #90) 89
2-(2-Ethoxy-3-methoxyphenyl)-N,N N,N-Me-2,3-EMPEA 82
dimethylethanamine see table under 2,3-DMPEA ( #46)

2-(4-E thoxy-3-methoxyphenyl)-N,N-dimethy lethanamine
2-Ethoxy-2-(3-methoxyphenyl)ethanamine B03ME 244

2-(2-Ethoxy-3-methoxyphenyl)ethanamine 2,3-EMPEA 82
2-(2-Ethoxy-4-methoxyphenyl)ethanamine 2,4-EMPEA 55
2-(3-Ethoxy-4-methoxyphenyl)ethanamine EMPEA 89
2-( 4-E thoxy-3-methoxyphenyl)ethanamine MEPEA ( #90) 211
2-(2-Ethoxy-3-methoxyphenyl)-N N-Me-2,3-EMPEA 82
methylethanamine see table under 2,3-DMPEA ( #46)
2-(3-Ethoxy-4-methoxyphenyl)-N-methylethanamine N-Me-EMPEA 89
1 -Ethoxy-1-(3-methoxyphenyl)propan-2-amine B03MEA 244

1-(3-Ethoxy-4-methoxypheny1 )propan-2-amine EMA 67

1-( 4-E thoxy-3-methoxyphenyl)propan-2-amine MEA 67

1-( 4-Ethoxyphenyl)butan-2-amine 4-EtO-a-EtPEA 270

2-(2-Ethoxyphenyl)-N,N-dimethylethanamine N,N-Me-2-EPEA 242

2-(4-Ethoxyphenyl)-N,N-dimethylethanamine N,N-Me-4-EPEA 247

1-(3-Ethoxyphenyl)-N,N-dimethylpropan-2-amine N,N-Me-3-EPEA 244

2-(4-E thoxyphenyl)ethanamine 4-EPEA 247

2-(3-Ethoxyphenyl)-2-methoxyethanamine B03E 244

2-(2-Ethoxyphenyl)-N-methylethanamine N-Me-2-EPEA 242




1 -(3-Ethyl-2,5-dimethoxy-4-methylphenyl)propan-2-amine
1-(3-E thoxypheny1)-N-methylpropan-2-amine N-Me-3-EA 160

1-( 4-E thoxyphenyl)-N-methy lpropan-2-amine 4-EtO-METH 270

1 -(2-Ethoxyphenyl)propan-2-amine 2-EA 1 56
1-(3-E thoxyphenyl)propan-2-amine 3-EA 160

1-( 4-Ethoxyphenyl)propan-2-amine 4-EA 270

a-Et-4-HPEA 4-(2-Aminobutyl)phenol 270

4-(2-(Ethylamino)ethyl)benzene-1,2-diol N-Et-DHPEA 87
4-(2-(Ethylamino)-1 -hydroxyethyl)benzene-1,2-diol j),3,4-HO-N-Et-PEA 88

2-(Ethylamino)-1-phenylpropan-1-one EAP 72
4-(2-(E thylamino)propyl)benzene-1,2-diol DHEA 49

4-(2-(E thy lamina )propy1)-2-methoxyphenol MHEA 231

see table under MHA ( #94)
5-(2-(E thylamino)propyl)-2-methoxyphenol HMEA 50

3-(2-(Ethylamino)propyl)phenol N-Et-3-HA 159

4-(2-(Ethylamino)propyl)phenol PHEA 270

7-(Ethylamino )-5,6,7,8-tetrahydronaphthalen-1 -ol EHAT 254

a-E thy1-1,3-benzodioxole-5-ethanamine BDB ( #9) 10
1-( 4-Ethyl-2,5-bis(methylthio )phenyl) BIS-TOET 108

propan-2-amine see table under DOET ( #56)
2-(3-Ethyl-2,5-dimethoxy-4-methylphenyl) 2C-G-21 281

2-(4-Ethyl-2,5-dimethoxy-3-methylphenyl) 2C-G-12 281

1 -(3-E thy 1-2,5-dimethoxy-4-methylphenyl) G-21 279

propan-2-amine see table under TeMA ( # 113)

1-(4-E thyl-2,5-dimethoxy-3-methylphenyl)propan-2-amine
1-(4-Ethy1-2,5-dimethoxy-3-methylphenyl) G-12 279

propan-2-amine see table under TeMA ( # 113)
1-(4-Ethyl-2,5-dimethoxyphenyl)butan-2-amine 4C-E 8
2-(4-E thy1-2,5-dimethoxyphenyl)ethanamine 2C-E ( #21) 28
2-(4-Ethyl-2,5-dimethoxyphenyl)-2- BOE 17
methoxyethanamine see table under BOD ( # 14)
1-(2-Ethyl-3,4-dimethoxyphenyl)propan-2-amine 2,3,4-DOET 108

1-(2-Ethy1-3,5-dimethoxyphenyl)propan-2-amine 2,3,5-DOET 108

1-(2-E thy1-3,6-dimethoxyphenyl)propan-2-amine 2,3,6-DOET 108

1-(2-E thyl-4,6-dimethoxyphenyl)propan-2-amine 2,4,6-DOET 108


1-(3-Ethy 1-2,5-dimethoxyphenyl)propan-2-amine 3,2,5-DOET 108

1-(3-E thy 1-2,6-dimethoxyphenyl)propan-2-amine 3,2,6-DOET 108


1-(4-E thyl-2,3-dimethoxyphenyl)propan-2-amine 4,2,3-DOET 108

1-( 4-E thyl-2,5-dimethoxypheny l)propan-2-amine DOET ( #56) 106


1-(5-Ethy1-2,3-dimethoxyphenyl)propan-2-amine 5,2,3-DOET 108

1-( 5-E thy 1-2,4-dimethoxyphenyl)propan-2-amine 5,2,4-DOET 108

1-( 6-E thyl-2,3-dimethoxyphenyl)propan-2-amine 6,2,3-DOET 108


2-(4-Ethylphenyl)ethanamine
3,4-Ethylenedioxyamphetamine EDA ( # 65) 136
N-Ethyl-1-(3-fluorophenyl)propan-2-amine N-Et-3-FA 159

N-Ethyl-1-(3-iodophenyl)propan-2-amine N-Et-3-IA 159

ETHYL-K 1-(Benzo[d] [ l,3]dioxol-5-yl)-N 169

ethylpentan-2-amine
a-Ethylmescaline AEM ( # 1 ) 1
2-(4-Ethyl-2-methoxy-5-(methylthio)phenyl) 2C-5-TOET 108

ethanamine see table under DOET ( #56)
2-(4-Ethyl-5-methoxy-2-(methylthio)phenyl) 2C-2-TOET 108

1-(4-Ethyl-2-methoxy-5-(methylthio)phenyl) 5-TOET 108

1-(4-Ethy 1-5-methoxy-2-(methy1 thio)phenyl) 2-TOET 108

N-Ethyl-2-(3-methoxyphenyl)ethanamine N-Et-3-MPEA 244

N-Ethyl-1-(2-methoxyphenyl)propan-2-amine N-Et-2-MA 156

N-Ethyl-1-(3-methoxyphenyl)propan-2-amine N-Et-3-MA 159

N-Ethyl-1-(4-methoxyphenyl)propan-2-amine N-Et-PMA 270

N-Ethyl-2-( 4-methoxyphenyl)propan-1-amine j)-Me-N-Et-4-MPEA 247

a-E thy 1-N-methy1-1,3-benzodioxole-5-ethanamine MBDB ( # 76) 162
N-Ethyl-3,4-methylenedioxyamphetamine MDE ( #81) 181
a-Ethyl-3,4-methylenedioxyphenethylamine BDB ( #9) 10
N-Ethyl-1-(4-(methylthio )phenyl)propan-2-amine MTEA 250

N-Ethyl-1-(3-nitrophenyl)propan-2-amine N-Et-3-N0 -A 159

2
N-Ethyl-2-phenylethanamine N-EtPE 261

2-(4-Ethylphenyl)ethanamine 4-EtPEA 247


N-Ethyl-2-phenylpropan-1 -amine
N-Ethyl-2-phenylpropan-1-amine j3-Me-N-Et-PEA 261

7-(E thyl(propy!)amino)-5,6, 7,8- PEAT 254

tetrahydronaphthalen-1-ol see table under PAT ( # 1 05)
N-(4-(E thylthio)-2,5-dimethoxyphenethy!) HOT-2 37

hydroxy !amine see table under 2C-T ( #25)
1-(4-(E thy I thio)-2,5-dimethoxyphenyl) 4C-T-2 3

butan-2-amine see table under ALEPH ( #3)
2-(3-(E thyIthio)-4,5-dimethoxypheny1) 3-TME 217

2-(4-(E thy lthio )-2,5-dimethoxypheny1) 2C-T-2 ( #26) 38

ethanamine
2-(4-(E thylthio )-3,5-dimethoxypheny1) TE 217

ethanamine see table under Mescaline (#91)
1-( 4-(Ethylthio)-2,5-dimethoxyphenyl)-N N-Me-4C-T-2 3

methy !bu tan-2-amine see table under ALEPH ( #3)
1-( 4-(E thylthio )-2,5-dimethoxyphenyl)-N N-Me-ALEPH-2 3

methy lpropan-2-amine see table under ALEPH ( #3)
1-(4-(E thy I thio)-2,5-dimethoxyphenyl) ALEPH-2 ( #4) 5

propan-2-amine
1-(4-(Ethylthio)-2,6-dimethoxyphenyl) t)J-ALEPH-2 3
1-( 4-(E thylthio)phenyl)propan-2-amine ETA 251

N-Ethyl-2-(3-(trifluoromethyl)phenyl)- N-Et-3-TFMPEA 133

ethanamine see table under DOTFM ( #63)
a-Ethyl-1-(3,4,5-trimethoxyphenyl)- AEM ( # 1 ) 1
ethylamine
2-(4-E thyny 1-2,5-dimethoxypheny1)- 2C-YN 27

ethanamine see table under 2C-D ( #20)
1 -(4-Ethynyl-2,5-dimethoxyphenyl)- DOYN 1 23
propan-2-amine see table under DOM ( # 60)
N-Et-3-IA N-Ethyl-1-(3-iodophenyl)propan-2-amine 159

a-E t-Lophophine 1 -(7-Methoxybenzo[ d] [ 1,3 ] dioxol-5-y!)bu tan-2-amine 154

see table under Lophophine ( #73)
N-Et-2-MA N-Ethyl-1-(2-methoxyphenyl)propan-2-amine 156

N-Et-3-MA N-Ethyl-1-(3-methoxyphenyl)propan-2-amine 159


Explosion
N,N-Et-2-MA N,N-Diethyl-1-(2-methoxyphenyl)propan-2-amine 156

N,N-Et-3-MA N,N-Diethyl-1-(3-methoxyphenyl)propan-2-amine 159

a-Et-MDA 1-(Benzo[d] [ l,3]dioxol-5-y1)-2-methy lbutan-2-amine 169

N-Et-MDPEA 2-(Benzo[d) [l,3]dioxol-5-yl)-N-ethylethanamine 205

N-Et-2,3-MDPEA 2-(Benzo[d] [ 1,3]dioxol-4-y1)-N-ethylethanamine 171

a-Et-MPEA 1-( 4-Methoxyphenyl)butan-2-amine 270

N-Et-3-MPEA N-Ethyl-2-(3-methoxyphenyl)ethanamine 244

see table under 3-MPEA ( # 1 01 )
N,N-Et-3-MPEA N,N-Diethyl-2-(3-methoxyphenyl)ethanamine 244

see table under 3-MPEA ( # 1 01 )
N-Et-3-N0 -A N-Ethyl-1-(3-nitrophenyl)propan-2-amine 1 59
2
4-EtO-a-EtPEA 1 -(4-Ethoxyphenyl)butan-2-amine 270

4-EtO-METH 1-(4-Ethoxyphenyl)-N-methylpropan-2-amine 270

EtONE 1-(Benzo[d] [ 1,3]dioxol-5-y1)-2-(ethy lamino)propan-1 -one 229

N-Et-PCA 1-(4-Chloropheny1)-N-ethy lpropan-2-amine 256

N-EtPEA N-Ethyl-2-phenylethanamine 261

4-EtPEA 2-(4-Ethylphenyl)ethanamine 247

N-Et-PMA N-E thy1-1-(4-methoxyphenyl)propan-2-amine 270

N-Et-3-TFMPEA N-Ethyl-2-(3-(trifluoromethyl)phenyl)ethanamine 1 33
see table under DOTFM ( #63)
a-Et-ThEA 1 -(Thiophen-2-yl)butan-2-amine 139

Eve MDE ( #81) 181
Explosion Methylone ( #93) 228

F
F ( #66) l -(5-Methoxy-2,3-dihydrobenzofuran-6-yl)propan-2-amine 137

2,3-Dihydro-5-methoxy-a-methyl-6-benzofuranethanamine
Semi-fly
F-2 1 -(5-Methoxy-2-methy1-2,3-dihydrobenzofuran-6-y l)propan-2-amine 138

see table under F ( #66)
F-22 1-(5-Methoxy-2,2-dimethy1-2,3-dihydrobenzofuran-6-y l)propan-2-amine 138

F-23 1 -(5-Methoxy-2,3-dimethy1-2,3-dihydrobenzofuran-6-yl)propan-2-amine 138

F-233 1 -(5-Methoxy-2,3,3-trimethy1-2,3-dihydrobenzofuran-6-yI )propan-2-amine 138

2-FA 1-(2-Fluorophenyl)propan-2-amine 156

3-FA 1-(3-Fluorophenyl)propan-2-amine 159

F-4A5,7B B-SF ( # 1 7) 19
F -BDB l -(2,2-Difluorobenzo[d] [l,3] dioxol-5-yl)butan-2-amine 11

2
see table under BDB ( #9)
2-F-4,5-DMA 1 -(2-Fluoro-4,5-dimethoxyphenyI )propan-2-amine 294

5-F-2,4-DMA 1-( 5-Fluoro-2,4-dimethoxyphenyl)propan-2-amine 294

18F-2,4-DNNA 1-(5-Fluoro-2,4-dimethoxypheny1)-N,N-dimethylpropan-2-amine, 294

[18F labeled]
2,4-FDNNA 1-(5-Fluoro-2,4-dimethoxypheny1)-N,N-dimethylpropan-2-amine 294

FEA ( #67) 2-(Furan-2-yl)ethanamine 138

2-Fury lethy !amine
2-Furanethanamine
FEM 2-(4-((2-Fluoroethyl)thio)-3,5-dimethoxyphenyl)ethanamine 43
F EM 2-(4-((2,2-Difluoroethyl)thio)-3,5-dimethoxyphenyl)ethanamine 44
2
2-(3,5-Dimethoxy-4-((2,2,2-trifluoroethyl)thio)phenyl)ethanamine 44
Flatliners MTA ( # 103) 250
FLEA N-( 1 -(Benzo[d] [ 1,3]dioxol-5-yl)propan-2-y1)-N-methy!hydroxy !amine 203

see table under MDOH ( #84)

1 -(2-Fluorophenyl)propan-2-amine
FLORENCE 1-(2-E thoxy-5-methoxy-4-methylphenyl)propan-2-amine 121

1-( 6-Fluorobenzo[d] [ 1,3 ]dioxol-5-y l)propan-2-amine, 2-[18F]-4,5-MDA 238

[1"F labeled] see table under MMDA-2 ( #98)
5-Fluoro-2,3-dihydro-lH-inden-2-amine PFAI 257

1-( 5-Fluoro-2,4-dimethoxypheny 1)-N,N 2,4-FDNNA 294

dimethy 1 propan-2-amine see table under TMA-2 ( #118)
1-(5-Fluoro-2,4-dimethoxyphenyl)-N,N 18F-2,4-DNNA 294

dimethylpropan-2-amine, [18F labeled] see table under TMA-2 ( # 11 8)
2-( 4-Fluoro-2,5-dimethoxyphenyl)ethanamine 2C-F 26

1 -(2-Fluoro-4,5-dimethoxypheny l)propan-2-amine 2-F-4,5-DMA 294

1-(4-Fluoro-2,5-dimethoxyphenyl)propan-2-amine DOF ( #57) 110
1-(5-Fluoro-2,4-dimethoxyphenyl)propan-2-amine 5-F-2,4-DMA 294

2-( 4-(2-Fluoroethy 1)-2,5-dimethoxypheny1) 2C-EF 26

ethanamine see table under 2C-D ( #20)
1-(4-(2-Fluoroethy1)-2,5-dimethoxypheny l) DOEF 123

2-(4-((2-Fluoroethyl)thio)-2,5-dimethoxyphenyl) 2C-T-21 37
2-(4-((2-Fluoroethyl)thio)-3,5-dimethoxyphenyl) FEM 43
ethanamine see table under DESMETHYL ( #29)
1-(4-(Fl uoromethy 1)-2,5-dimethoxyphenyl) DOFM 1 23

2-(4-( (5-Fluoropentyl)thio )-2,5-dimethoxypheny1) 2C-T-30 37

2-(4-Fluorophenyl)ethanamine 4-FPEA 247

1-( 4-Fluoropheny1)-2-(methy lamina)propan-1-one 4-F-MCAT 226

1-( 4-Fluoropheny 1)-N-methylpropan-2-amine PFMA 256

1-(4-Fluorophenyl)piperazine 4-FPP 33
1-(2-Fluorophenyl)propan-2-amine 2-FA 156


1-(3-Fluorophenyl)propan-2-amine
1 -(3-Fluorophenyl)propan-2-amine 3-FA 1 59
1-(4-Fluorophenyl)propan-2-amine PFA 256

2-(4-((3-Fluoropropyl)thio)-2,5-dimethoxyphenyl) 2C-T-28 37
1-(4-( (3-Fluoropropyl)thio )-3,5-dimethoxyphenyl) 3C-FEM 288

FLY ( #68) 1-(2,3,6,7-Tetrahydrobenzo[l,2-b:4,5-b')difuran-4-yl)propan-2-amine 141

1-(2,3,6,7-Tetrahydrobenzo[ 1,2-b:4,5-b')difuran-4-y 1)-2-aminopropane
2,3,6,7-Tetrahydro-a-methy1-benzo[ 1,2-b:4,5-b')difuran-4-ethanamine
F -MBDB 1-(2,2-Difluorobenzo[d) [l,3)dioxol-5-yl)-N-methylbutan-2-amine 163

2
see table under MBDB ( # 76)
4-F-MCAT 1-(4-Fluorophenyl)-2-(methylamino)propan-1-one 226

see table under METHCATH ( # 92)
F -MDA 1 -(2,2-Difluorobenzo[d] [l,3]dioxol-5-yl)propan-2-amine 168

2
2-[18F]-4,5-MDA 1 -(6-Fluorobenzo[d] [l,3)dioxol-5-yl)propan-2-amine, ['8F labeled] 238

F -MD E 1 -(2,2-Difluorobenzo[d] [ l,3]dioxol-5-y1)-N-ethy lpropan-2-amine 1 84

2
see table under MDE ( #81)
F -MDMA 1-(2,2-Difluorobenzo[d] [ 1,3]dioxol-5-yl)-N-methylpropan-2-amine 191

2
see table under MDMA ( #82)
F -MDPEA 2-(2,2-Difluorobenzo[d) [l,3]dioxol-5-yl)ethanamine 205

2
see table under MDPEA ( #85)
j3, j3-F-PCA 1-(4-Chloropheny 1)-1, 1-difluoropropan-2-amine 256

4-FPEA 2-(4-Fluorophenyl)ethanamine 247

4-FPP 1 -(4-Fluorophenyl)piperazine 33
2-Furanethanamine FEA ( #67) 138
2-(Furan-2-yl)ethanamine FEA ( #67) 138
N-(Furan-2-ylmethyl)-1-(2-methoxyphenyl) N-fur-2-MA 156

propan-2-amine see table under 2-MA ( # 74)
N-fur-2-MA N-(Furan-2-ylmethy1)-1-(2-methoxyphenyl)propan-2-amine 156

2-Furylethylamine FEA ( #67) 138

2-HA
G 1-(2,5-Dimethoxy-3,4-dimethylpheny I )propan-2-amine 279

see table under TeMA ( #113)
G-1 1 -(2,5-Dimethoxybicyclo[ 4 . 1 .0 ]hepta-1,3,5-trien-3-y l)propan-2-amine 279

G-2 1-(2,5-Dimethoxybicyclo[4.2.0Jocta-1,3,5-trien-3-yl)propan-2-amine 279

G-3 1-(4,7-Dimethoxy-2,3-dihydro-lH-inden-5-yl)propan-2-amine 279

G-4 1-(1,4-Dimethoxy-5,6,7,8-tetrahydronaphthalen-2-yl)propan-2-amine 279

G-5 1 -(5,8-Dimethoxy-1,2,3,4-tetrahydro-l,4-methanonaphthalen-6-yl) 279

propan-2-amine
G-6 1-(5,8-Dimethoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl) 279

propan-2-amine
G-12 1-(4-E thy 1-2,5-dimethoxy-3-methylphenyl)propan-2-amine 279

G-21 1 -(3-Ethy 1-2,5-dimethoxy-4-methy lpheny l)propan-2-amine 279

G-22 1 -(3,4-Diethy1-2,5-dimethoxyphenyl)propan-2-amine 279

GEA ( #69) 4-(2-Aminoethyl)-2-methoxyphenol 143

4-Hydroxy-3-methoxyphenethylamine
4-(2-Aminoethy l)guaiacol
Guaiacylethy!amine
Homovanillylamine
3-0-Methyldopamine
Methoxytyramine
3-Methoxytyramine
Vanillylethylamine
Vanillyl-PEA
4-H0-3-MeO-PEA
MHPEA
3-MT
GEA-j3k 2-Amino-1-(4-hydroxy-3-methoxyphenyl)ethanone 88
G-N 1-(1,4-Dimethoxynaphthalen-2-yl)propan-2-amine 279

Golden Eagles MTA ( # 103) 250
Guaiacylethy!amine GEA ( #69) 143
2-HA 2-(2-Aminopropy!)phenol 156


3-HA
3-HA 3-(2-Aminopropyl)phenol 1 59
4-HA PHA ( # 109) 1 09
N-He-2-MA N-(1-(2-Methoxyphenyl)propan-2-yl)hexan-1-amine 1 56
4-HePEA 2-(4-Hexylphenyl)ethanamine 247

1-(4-Hepty 1-2,5-dimethoxypheny l)propan-2-amine DOHP 121

2-(4-(Hepty loxy )phenyl)ethanamine 4-SPEA 247

2-(2,3,4,7,8,9-Hexahydropyrano[2,3-g]chromen-5-yl) 2C-PLY 142

ethanamine see table under FLY ( #68)
1-(2,3,4, 7,8, 9-Hexahydropyrano[2,3-g ]chromen-5-yl) PLY 142

propan-2-amine see table under FLY ( # 68)
1-(4-Hexy 1-2,5-dimethoxyphenyl)propan-2-amine DOHE 121

2-(4-Hexylphenyl)ethanamine 4-HePEA 247

HHA DHA ( #33) 49
HHAT 7-Amino-5,6,7,8-tetrahydronaphthalen-1 -ol 254

HMA 5-(2-Aminopropyl)-2-methoxyphenol 50
MHA ( #94)
2-HMA 2-(2-(Methy!amino)propy!)phenol 156

2,4-HMA 2-(2-Aminopropyl)-5-methoxyphenol 55
2,5-HMA 2-(2-Aminopropyl)-4-methoxyphenol 59
HMDA homo-MDA ( # 78) 1 77
HMDMA homo-MDMA ( #83) 201
HME 5-(2-Amino-1-hydroxyethyl)-2-methoxyphenol 88
HMEA 5-(2-(E thy !amino )propy 1)-2-methoxyphenol 50

2,3-HMeA 2-(2-Aminopropyl)-6-methylphenol 52

3,5-HMPEA
3,4-HMeA 5-(2-Aminopropyl)-2-methylphenol 235

see table under 3,4-MMA ( #96)
a-HMe-M 2-Amino-3-(3,4,5-trimethoxyphenyl)propan-1-ol 287

2,3-HMeMA 2-Methyl-6-(2-(methylamino)propyl)phenol 53
2,3-HMeMMA 2-(2-(Dimethylamino)propyl)-6-methylphenol 53
2,3-HMeMMPEA 2-(2-(Dimethylamino)ethyl)-6-methylphenol 52
2,3-HMeMPEA 2-Methyl-6-(2-(methylamino)ethyl)phenol 52
HMePEA ( #70) 4-(2-(Methy !amino)ethy !)phenol 145

N-Methyl-2-(4-hydroxyphenyl)ethylamine
4-Hydroxy-N-methylphenethylamine
N-Methyltyramine
NSC 113958
HM-a-EPEA 5-(2-Aminobutyl)-2-methylphenol 235

see table under 3,4-MMA ( #96)
2,3-HMePEA 2-(2-Aminoethyl)-6-methylphenol 52
HM-a-Et-PEA 4-(2-Aminobutyl)-2-methoxyphenol 50
HMMA 2-Methoxy-5-(2-(methylamino)propyl)phenol 50
HMMC 2-Amino-1 -(4-hydroxy-3-methoxyphenyl)propan-1 -one 227

HM PEA 5-(2-Aminoethyl)-2-methoxyphenol 88
HMPEA-f3k 2-Amino-1-(3-hydroxy-4-methoxyphenyl)ethanone 88
3-HMPEA 3-(2-(Methy !amino)ethy !)phenol 1 50

2,3-HMPEA 2-(2-Aminoethyl)-6-methoxyphenol 53

2,4-H0-5-AA
2,4-H0-5-AA 4-Amino-6-(2-aminopropyI) benzene-1,3-diol 294

4,5-H0-2-AA 4-Amino-5-(2-aminopropyl)benzene-1,2-diol 294

f3-H0-2-APEA 2-Amino-1-(2-aminophenyl)ethanol 242

2,4-H0-5-APEA 4-Amino-6-(2-aminoethyl)benzene-1,3-diol 308



HOB DB N-( 1 -(Benzo[ d] [ l,3 ] dioxol-5-yI)butan-2-y !)hydroxy !amine 169

N-H0-2C-D N-(2,5-Dimethoxy-4-methylphenethyl)hydroxylamine 26
f3-H0-2,5-DEA 2-Amino-1-(2,5-diethoxyphenyl)propan-1-ol 60
[3-H0-2,5-DEPEA 2-Amino-1-(2,5-diethoxyphenyl)ethanol 30
f3-HO-DESMETHYL 4-(2-Amino-1-hydroxyethyl)-2,6-dimethoxyphenol 43
f3-HO-DHA 4-(2-Amino-1-hydroxypropyl)benzene-1,2-diol 49
f3-HO-DHMA 4-(1-Hydroxy-2-(methylamino)propyl)benzene-1,2-diol 49
f3-HO-DMA 2-Amino-1-(3,4-dimethoxyphenyl)propan-1 -ol 67

f3-H0-2,5-DMA 2-Amino-1-(2,5-dimethoxyphenyl)propan-1-ol 60
f3,2-H0-5,N-DMeA 2-(1-Hydroxy-2-(methy !amino )propy 1)-4-methy !phenol 59

f3-H0-2,5-DMIPA 1 -(2,5-Dimethoxyphenyl)-2-(isopropylamino)propan-1-ol 60
[3-H0-2,5-DMPEA 2-Amino-1-(2,5-dimethoxyphenyl)ethanol 30
[3-H0-2,6-DMPEA 2-Amino-1 -(2,6-dimethoxyphenyl)ethanol 84

[3-H0-3,5-DMPEA 2-Amino-1 -(3,5-dimethoxyphenyl)ethanol 94


f3,2-H0-5-MA
f3,5-HO-DMPEA 5-(2-Amino-1 -hydroxyethyl)-2,3-dimethoxyphenol 45

f3-HO-DOB 2-Amino-1-(4-bromo-2,5-dimethoxyphenyl)propan-1-ol 16
see table under BOB ( #13)
N-HO-DOM N-( 1-(2,5-Dimethoxy-4-methylpheny l)propan-2-yl)hydroxylamine 123

8-HO-DPAT PAT ( # 105) 253
f3,2-H0-5-EA 2-(2-Amino-1 -hydroxypropyl)-4-ethoxyphenol 59

f3-HO-EMPEA 2-Amino-1-( 4-ethoxy-3-methoxyphenyl)ethanol 88

2-H0-5-EPEA-f3k 2-Amino-1 -(5-ethoxy-2-hydroxyphenyl)ethanone 30

f3,2-H0-5-EPEA 2-(2-Amino-1-hydroxyethyl)-4-ethoxyphenol 30
f3,3,4-HO-a-Et-PEA 4-(2-Amino-1 -hydroxybutyl)benzene-l,2-diol 49

f3,3,4-HO-N-Et-PEA 4-(2-(Ethylamino)-1 -hydroxyethyl)benzene-1,2-diol 88

f3-H0-3-HA 3-(2-Amino-1-hydroxypropyl)phenol 1 59
f3-HO-HMA 4-(1 -Hydroxy-2-(methylamino)propyl)phenol 266

f3-HO-Hordenine 4-(2-(Dimethylamino)-1-hydroxyethyl)phenol 150

f3-HO-HPEA 4-(2-Amino-1-hydroxyethyl)phenol 150

f3-H0-2-HPEA 2-(2-Amino-1-hydroxyethyl)phenol 150

f3-H 0-3-HPEA 3-(2-Amino-1 -hydroxyethyl)phenol 150

f3-HO-N-iPr-DHPEA 4-(1-Hydroxy-2-(isopropylamino )ethyl)benzene-1,2-diol 88

f3-HO-N-iPr-GEA 4-(1 -Hydroxy-2-(isopropylamino)ethyl)-2-methoxyphenol 88

f3-HOM 2-Amino-1-(3,4,5-trimethoxyphenyl)ethanol 216

f3,2-H0-5-MA 2-(2-Amino-1 -hydroxypropyl)-4-methoxyphenol 59


HO-mCPP
HO-mCPP 2-Chloro-4-(piperazin-1-yl)phenol 34
f3-HO,Me-2,5-DMPEA 1 -Amino-2-(2,5-dimethoxyphenyl)propan-2-ol 30
f3-HO-MDA 2-Amino-1-(benzo[d] [l,3]dioxol-5-yl)propan-1 -ol 168

f3,2-H0-5-MeA 2-(2-Amino-1-hydroxypropyl)-4-methylphenol 59
f3-HO-N-Me-2,5-DEA 1-(2,5-Diethoxyphenyl)-2-(methylamino)propan-1 -ol 60

f3-HO-N-Me-2,5-DEPEA 1-(2,5-Diethoxypheny1)-2-(methylamino)ethanol 30
f3-HO-N-Me-2,5-DMA 1-(2,5-Dimethoxyphenyl)-2-(methylamino )propan-1-ol 60

f3-HO-N,N-Me-2,5-DMA 1-(2,5-Dimethoxyphenyl)-2-(dimethylamino)propan-1 -ol 60

f3-HO-N-Me-2,5-DMPEA 1 -(2,5-Dimethoxyphenyl)-2-(methylamino)ethanol 30
f3-HO-N-Me-2,6-DMPEA 1 -(2,6-Dimethoxyphenyl)-2-(methylamino)ethanol 30
f3-HO-N-Me-3,5-DMPEA 1-(3,5-Dimethoxyphenyl)-2-(methylamino)ethanol 94
f3-HO-f3,N-Me-2,5-DMPEA 2-(2,5-Dimethoxyphenyl)-1-(methylamino )propan-2-ol 30

f3-HO-N,N-Me-2,5-DMPEA 1-(2,5-Dimethoxyphenyl)-2-(dimethylamino)ethanol 30
f3-HO-N,N-Me-3,5-DMPEA 1 -(3,5-Dimethoxyphenyl)-2-(dimethylamino)ethanol 94
see table under 3,5-DMPEA ( #SO)
2-HO-N-Me-5-EA-f3k 1-(5-Ethoxy-2-hydroxyphenyl)-2-(methylamino)propan-1 -one 59

f3,2-HO-N-Me-5-EA 4-E thoxy-2-( 1-hydroxy-2-(methylamino )propyl)phenol 59

2-HO-N-Me-5-EPEA-f3k 1-(5-Ethoxy-2-hydroxyphenyl)-2-(methylamino )ethanone 30

f3,2-HO-N-Me-5-EPEA 4-E thoxy-2-(1-hydroxy-2-(methylamino)ethyl)phenol 30

f3-HO-N-Me-HPEA 4-( 1-Hydroxy-2-(methylamino)ethyl)phenol 150

f3-HO-N-Me-3-HPEA 3-( 1-Hydroxy-2-(methylamino )ethyl)phenol 150


homo-DOM
13,2-HO-N-Me-5-MA 2-(1-Hydroxy-2-(methylamino)propyl)-4-methoxyphenol 59
13-HO-N-Me-2-M-5-MePEA 1-(2-Methoxy-5-methylphenyl)-2-(methylamino )ethanol 30

5-HO-N-Me-2-MPEA-13k 1-(5-Hydroxy-2-methoxyphenyl)-2-(methylamino)ethanone 30
13,2-HO-N-Me-5-MPEA 2-(1-Hydroxy-2-(methylamino)ethyl)-4-methoxyphenol 30
13,5-HO-N-Me-2-MPEA 3-(1-Hydroxy-2-(methylamino)ethyl)-4-methoxyphenol 30
4-H0-3-MeO-PEA GEA ( #69) 143
13-HO-N,N-Me-PEA 2-(Dimethylamino)-1-phenylethanol 261

13-H0-3,4-MePEA 2-Amino-1 -(3,4-dimethylphenyl)ethanol 78

13-H0-3,4,N-MePEA 1 -(3,4-Dimethylphenyl)-2-(methylamino )ethanol 78

2-H0-5-MePEA-13k 2-Amino-1-(2-hydroxy-5-methylphenyl)ethanone 29
2-H0-5,N-MePEA-13k 1-(2-Hydroxy-5-methylphenyl)-2-(methylamino)ethanone 30
13,2-H0-5-MePEA 2-(2-Amino-1-hydroxyethyl)-4-methylphenol 29
13,2-H0-5,N-MePEA 2-( 1-Hydroxy-2-(methylamino)ethyl)-4-methylphenol 29

13,3,4-HO-N,N-MePEA 4-(2-(Dimethylamino)-1-hydroxyethyl)benzene-1,2-diol 88
13-HO-M-M 2-(Methylamino)-1-(3,4,5-trimethoxyphenyl)ethanol 216

13-H0-2-M-5-MeA 2-Amino-1-(2-methoxy-5-methylphenyl)propan-1 -ol 60

13-H0-2-M-N-Me-MeA 1-(2-Methoxy-5-methylphenyl)-2-(methylamino )propan-1-ol 60

13-H0-2-M-5-MePEA 2-Amino-1-(2-methoxy-5-methylphenyl)ethanol 30
Homoanisylamine 4-MPEA ( # 1 02) 245
homo-DOM 4-(2,5-Dimethoxy-4-methylphenyl)butan-2-amine 121


homo-Dopamine
homo-Dopamine 4-(3-Aminopropyl)benzene-1,2-diol 68
homo-DMA 4-(3-Aminobutyl)benzene-1,2-diol 68
homo-MDA ( # 78) 4-(Benzo[d] [l,3]dioxol-5-yl)butan-2-amine 1 77

1-(3,4-Methylenedioxy lphenyl)-3-isobuty!amine
a-Methyl-g-(3,4-methylenedioxyphenyl)propylamine
HMDA
homo-MDE 4-(Benzo[d] [l,3]dioxol-5-yl)-N-ethylbutan-2-amine 1 78

see table under homo-MDA ( # 78)
homo-MDMA ( #83) 4-(Benzo[d] [l,3]dioxol-5-yl)-N-methylbutan-2-amine 201

3-Methylamino-1 -(3,4-methylenedioxyphenyl)butane
N-Methyl-1-(3,4-methylenedioxyphenyl)-3-isobutylamine
a,N-Dimethyl-3-(3,4-methylenedioxyphenyl)propylamine
a,N-Dimethyl-1,3-benzodioxole-5-propylanamine
N, 1-Dimethy1-3-(3,4-methylenedioxyphenyl)propylamine
HMDMA
MDP-3-MB
homo-MDOH N-(4-(Benzo[d] [l,3]dioxol-5-yl)butan-2-yl)hydroxylamine 1 78

see table under homo-MDA ( #78)
homo-N-Me-2,5-DMPEA 3-(2,5-Dimethoxyphenyl)-N-methylpropan-1-amine 31
homo-N,N-Me-2,5-DMPEA 3-(2,5-Dimethoxypheny1)-N,N-dimethylpropan-1-amine 31
Homopiperony!amine MDPEA (#85) 204
homo-TMA-2 4-(2,4,5-Trimethoxyphenyl)butan-2-amine 219


see table under Mescaline (#91)

Homovanillylamine GEA ( #69) 143
Homoveratrylamine DMPEA ( #49) 85
(3-H0-4-MPEA 2-Amino-1-(4-methoxyphenyl)ethanol 247

f3,2-H0-5-MPEA 2-(2-Amino-1-hydroxyethyl)-4-methoxyphenol 30
2,5-HO-MPEA 2-(2-Aminoethyl)-5-methoxybenzene-1,4-diol 308

2,5-HO-PAA 2-Amino-5-(2-aminopropyl)benzene-1,4-diol 294


HOT-1 7
�-HO-PEA 2-Amino-1-phenylethanol 261

4-HO-PEA Tyramine ( # 126) 310
2,4,5-HO-PEA 5-(2-Aminoethyl)benzene-1,2,4-triol 308

�-HO-PHA 4-(2-Amino-1-hydroxypropyl)phenol 265

�-HO-PMA 2-Amino-1-(4-methoxyphenyl)propan-1-ol 270

N-HO-PMA N-( 1-(4-Methoxyphenyl)propan-2-yl)hydroxylamine 270

HOPP 4-(Piperazin-1-yl)phenol 209

see table under MeOPP ( #88)
5-HO-PPAT 6-(Dipropylamino)-5,6,7,8-tetrahydronaphthalen-1 -ol 52

6-HO-PPAT 6-(2-(Dipropylamino)ethyl)-5,6,7,8-tetrahydronaphthalen-2-ol 55
7-HO-PPAT 7-(2-(Dipropylamino)ethyl)-5,6,7,8-tetrahydronaphthalen-2-ol 59
�-HO-N-Pr-PMA 1-(4-Methoxyphenyl)-2-(propylamino)propan-1 -ol 270

Hordenin Hordenine (#71) 147
Hordenine ( #71) 4-(2-(Dimethylamino)ethyl)phenol 147

N,N-Dimethyl-4-hydroxyphenethylamine
N,N-Dimethyltyramine
Anhalin
Anhaline
Cactine
Eremursine
Hordenin
Ordenina
Peyocactine
m-Tyramine
Hordenine acetate 4-(2-(Dimethylamino)ethyl)phenyl acetate 150

HOT-2 N-(4-(E thyI thio )-2,5-dimethoxyphenethy !)hydroxy!amine 37

HOT-7 N-(2,5-Dimethoxy-4-(propylthio)phenethyl)hydroxylamine 37
HOT-17 N-(l-(4-(sec-Butylthio)-2,5-dimethoxyphenyl)propan-2-yl) 37
hydroxylamine

[3-HO-TMA
f3-HO-TMA 2-Amino-1 -(3,4,5-trimethoxyphenyl)propan-l-ol 287

N-HO-TMA N-(1-(3,4,5-Trimethoxyphenyl)propan-2-yl)hydroxylamine 287

HPEA Tyramine ( # 126) 310
2-HPEA 2-(2-Aminoethyl)phenol 1 50
3-HPEA 3-(2-Aminoethyl)phenol 150

4-HPEA Tyramine ( # 1 26) 310
2,6-HPEA 2-(2-Aminoethyl)benzene-l,3-diol 84
3,5-HPEA 5-(2-Aminoethyl)benzene-l,3-diol 94
N-Hydroxy MDA MDOH ( #84) 202
4-(2-(Hydroxyamino)propyl)benzene-1,2-diol DHAOH 49
4-(2-(Hydroxyamino)propyl)-2-methoxyphenol MHAOH 50
p-Hydroxyamphetamine PHA ( # l 09) 264
4-Hydroxyamphetamine PHA ( # l09) 264
3-Hydroxy-4,5-dimethoxyphenethylamine 3-DESMETHYL ( #30) 45
8-Hydroxy-2-(dipropylamino)tetralin PAT ( # 1 05) 253
4-(1-Hydroxy-2-(isopropylamino )ethyl) f3-HO-N-iPr-DHPEA 88

benzene-1,2-diol see table under DMPEA ( #49)
4-(1-Hydroxy-2-(isopropy lamino )ethyl)- f3-HO-N-iPr-GEA 88

2-methoxyphenol see table under DMPEA ( #49)
4-Hydroxy-3-methoxyamphetamine MHA ( #94) 230
4-Hydroxy-3-methoxy-a-methylphenethylamine MHA ( #94) 230
4-Hydroxy-3-methoxyphenethylamine GEA ( #69) 143
1 -(3-Hydroxy-4-methoxyphenyl)-2- N-Me-HMPEA-f3k 88
(methylamino )ethanone see table under DMPEA ( #49)
1 -(4-Hydroxy-3-methoxyphenyl)-2- N-Me-GEA-f3k 88
(methylamino )ethanone see table under DMPEA ( #49)
1 -(5-Hydroxy-2-methoxyphenyl)-2- 5-HO-N-Me-2-MPEA-f3k 30
(methylamino)ethanone see table under 2C-H ( #22)

2-(3-Hydroxyphenyl)-N,N,N-trimethylethanaminium
1 -(3-Hydroxy-4-methoxyphenyl)-2- MHMC 227

(methylamino )propan-1-one see table under METHCATH ( #92)
2-(3-Hydroxy-4-methoxyphenyl) Salicifoline 88
N,N,N-trimethylethanaminium see table under DMPEA ( #49)
2-(1-Hydroxy-2-(methylamino)ethyl)- f3,2-HO-N-Me-5-MPEA 30
4-methoxyphenol see table under 2C-H ( #22)
3-(1-Hydroxy-2-(methylamino)ethyl)- f3,5-HO-N-Me-2-MPEA 30
4-methoxyphenol see table under 2C-H ( #22)
5-(1-Hydroxy-2-(methylamino)ethyl)- N-Me-HME 88
2-methoxyphenol see table under DMPEA ( #49)
2-(1-Hydroxy-2-(methylamino)ethyl)- f3,2-H0-5,N-MePEA 29
4-methylphenol see table under 2C-H ( #22)
3-(1-Hydroxy-2-(methylamino)ethy!)phenol f3-HO-N-Me-3-HPEA 1 50
4-( 1-Hydroxy-2-(methylamino)ethy!)phenol f3-HO-N-Me-HPEA 150

4-(1-Hydroxy-2-(methylamino)propyl) f3-HO-DHMA 49
benzene-1,2-diol see table under DHA ( #33)
4-(2-(Hydroxy(methyl)amino )propyl) DHMAOH 49

benzene-1,2-diol see table under DHA ( #33)
2-( 1-Hydroxy-2-(methylamino)propyl)- f3,2-HO-N-Me-5-MA 59

4-methoxyphenol see table under 2,5-DMA ( #36)
4-(2-(H ydroxy(methyl)amino )propyl)- MHMAOH 50

2-methoxyphenol see table under DHA ( #33)
2-(1-Hydroxy-2-(methy!amino)propyl)- f3,2-H0-5,N-DMeA 59
4-methylphenol see table under 2,5-DMA ( #36)
4-(1 -Hydroxy-2-(methy!amino)propyl)phenol f3-HO-HMA 266

see table under PHA ( #109)
N-Hydroxy-a-methyl-1,3-benzodioxole-5-ethanamine MDOH ( # 84) 202
N-Hydroxy-3,4-methylenedioxyamphetamine MDOH ( # 84) 202
N-Hydroxy-1-(3,4-methylenedioxyphenyl)- MDOH ( #84) 202

2-aminopropane
4-Hydroxy-N-methylphenethylamine HMePEA ( #70) 145
1 -(2-Hydroxy-5-methylphenyl)-2- 2-H0-5,N-MePEA-f3k 30
(methylamino)ethanone see table under 2C-H ( #22)
4-Hydroxyphenethylamine Tyramine ( # 126) 310
2-(3-Hydroxyphenyl)-N,N,N Leptodactyline 150

trimethylethanaminium see table under Hordenine ( #71)

2-(4-Hydroxyphenyl)-N,N,N-trimethylethanaminium
2-(4-Hydroxyphenyl)-N,N,N Candicine 150

trimethylethanaminium see table under Hordenine ( #71)
IAP 1-(2,3-Dihydro-lH-inden-5-yl)propan-2-amine 76
IB 2-(4-lsobutoxy-3,5-dimethoxyphenyl)ethanamine 217
IBF5AP 1-( l,3-Dihydroisobenzofuran-5-yl)propan-2-amine 1 72

IBF5MAP 1-( 1,3-Dihydroisobenzofuran-5-yl)-N-methylpropan- 1 72

2-amine
IDA 1 -(2,2-Dimethylbenzo[d] [ l,3 ] dioxol-5-yl)propan-2-amine 1 72

1-DFLY 1-(8-Iodobenzo[ l,2-b:4,5-b '] difuran-4-yl)propan-2-amine 48

2-1-3,5-DMA l -(2-lodo-3,5-dimethoxyphenyl)propan-2-amine 300

3-1-2,6-DMA l -(3-lodo-2,6-dimethoxyphenyl)propan-2-amine 301

5-1-2,4-DMA 1-( 5-lodo-2,4-dimethoxyphenyl)propan-2-amine 294

2,5-131IDMAPA N-( 1-(4-Iodo-2,5-dimethoxypheny l)propan-2-yl)-N,N ll3

dimethylpropane-1,3-diamine, ['311] labeled
2,5-131IDMNiPrNMeA 1-(4-lodo-2,5-dimethoxyphenyl)-N-isopropyl-N ll3

methylpropan-2-amine, [1311] labeled
2,5-IDNA l-(4-lodo-2,5-dimethoxyphenyl)-N 112

methylpropan-2-amine
2,5-131IDNA 1-(4-Iodo-2,5-dimethoxypheny1)-N-methylpropan- ll3

2-amine, [1311] labeled
2,4-IDNNA l -(5-Iodo-2,4-dimethoxyphenyl)-N,N 294

2,4-122IDNNA l -(5-Iodo-2,4-dimethoxyphenyl)-N,N 294

dimethylpropan-2-amine, [1 221 labeled]
2,4-1 25IDNNA l -(5-Iodo-2,4-dimethoxyphenyl)-N,N 294

dimethylpropan-2-amine, [1 251 labeled]
see table under TMA-2 ( # ll8)

IMA
2,5-IDNNA 1-(4-Iodo-2,5-dimethoxyphenyl)-N,N- 112

2,5-1 22IDNNA 1-(4-Iodo-2,5-dimethoxypheny1)-N,N-dimethylpropan- 113

2-amine, [1 22 I] labeled
2,5-131IDNNA 1-(4-Iodo-2,5-dimethoxypheny1)-N,N-dimethylpropan- 113

2-amine, [131I] labeled
2,6-IDNNA 1-(3-Iodo-2,6-dimethoxyphenyl)-N,N-dimethylpropan- 301

2-amine
2,6-1 22IDNNA 1-(3-Iodo-2,6-dimethoxypheny1)-N,N-dimethylpropan- 301

2-amine, [' 22 I labeled]
2,6-125IDNNA 1-(3-Iodo-2,6-dimethoxypheny1)-N,N-dimethylpropan- 301

2-amine, [' 25I labeled]
3,5-IDNNA-2 1-(2-Iodo-3,5-dimethoxypheny1)-N,N-dimethylpropan- 300

2-amine
3,5-1 22IDNNA-2 1-(2-Iodo-3,5-dimethoxypheny1)-N,N-dimethylpropan- 300

2-amine, [1 22I labeled]
3,5-1 25IDNNA-2 1-(2-Iodo-3,5-dimethoxyphenyl)-N,N-dimethylpropan- 300

2-amine, [1 25I labeled]
3,5-1 22IDNNA-4 1-( 4-Iodo-3,5-dimethoxyphenyl)-N,N-dimethylpropan- 287

2-amine, [' 22 I labeled]
I-FLY ( 8-Iodo-2,3,6,7-tetrahydrobenzo[ l,2-b:4,5-b ']difuran-4-yl)- 142

propan-2-amine
IM 2-(2,3,4-Trimethoxyphenyl)ethanamine 216
IM ( # 72) 2-(2,3,4-Trimethoxyphenyl)ethanamine 152

2,3,4-TMPEA
2,3,4-Trimethoxyphenethy!amine
Isomescaline
Reciprocal mescaline
2C-TMA-3
TMPEA-3
IMA 1 -(2,3-Dihydro-lH-inden-5-y1)-N-methylpropan-2-amine 76

2-1-5-MA
2-1-5-MA 1-(2-lodo-5-methoxypheny1)-N-methylpropan-2-amine 59
4-1-2-MA 1-(4-Iodo-2-methoxyphenyl)propan-2-amine 55
5-1-2-MA 1-(5-Iodo-2-methoxyphenyl)propan-2-amine 59
2-1-4,5-MDA 1-(6-Iodobenzo[ d] [ 1,3 ]dioxol-5-yl)propan-2-amine 238

2-1-4,5-MDMA 1-( 6-Iodobenzo[ d] [1,3]dioxol-5-yl)-N-methy1propan-2-amine 238

2-1-4,5-MDPEA 2-(6-Iodobenzo[d] [l,3]dioxol-5-yl)-N,N-dimethylethanamine 238

2,5-131INAA ( 1-( 4-Iodo-2,5-dimethoxyphenyl)propan-2-yl)hydrazine, 113

[1311] labeled
INBMDO N-(Benzo[d] [l,3 ]dioxol-4-ylmethyl)-2-( 4-iodo-2,5-dimethoxyphenyl) 113

ethanamine
INBMeO 2-(4-lodo-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine 113

2,5-131INCNMA 2-( (1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-yl)amino )acetonitrile, 113

[1311] labeled
2,5-131INCPMA N-(Cyclopropylmethyl)-1-(4-iodo-2,5-dimethoxyphenyl) 113

propan-2-amine, [1311] labeled
2,5-131INDoA N-(1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-yl) 113

dodecan-1-amine, [1311] labeled
2,5-'3'1NHA N-(1-( 4-lodo-2,5-dimethoxyphenyl)propan-2-yl) 113

hydroxylamine, [1311] labeled
2,5-131INHeA N-(1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-yl) 113

hexan-1-amine, [1311] labeled
2,5-131INHeNMeA N-(1-(4-lodo-2,5-dimethoxyphenyl)propan-2-yl)-N 113

methylhexan-1-amine, [1311] labeled
2,5-1311NiPrA 1-(4-Iodo-2,5-dimethoxyphenyl)-N-isopropylpropan- 113


1-(4-Iodo-2,5-dimethoxyphenyl)-N,N-dimethylpropan-2-amine
2,5-131INMeOEtA 1-(4-lodo-2,5-dimethoxyphenyl)-N-(2-methoxyethyl)propan- 113

2,5-131INNEA N,N-Diethyl-1-(4-iodo-2,5-dimethoxyphenyl)propan- 113

2-( 8-lodobenzo[ l,2-b:4,5-b ']difuran-4-yl)ethanamine 2C-l-DFLY 48

l-(8-lodobenzo[l,2-b:4,5-b ']difuran-4-yl)propan-2-amine 1-DFLY 48

2-(6-lodobenzo[d] [l,3]dioxol-5-yl)-N,N-dimethylethanamine 2-1-4,5-MDPEA 238

l-(6-lodobenzo[d] [l,3]dioxol-5-yl)-N,N-dimethylpropan-2-amine 2-1-4,5-MDDMA 238

l-(6-lodobenzo[d] [l,3]dioxol-5-yl)-N-methylpropan-2-amine 2-1-4,5-MDMA 238

l-(6-lodobenzo[d] [l,3]dioxol-5-yl)propan-2-amine 2-1-4,5-MDA 238

1-(4-lodo-2,5-dimethoxyphenyl)butan-2-amine 4C-I 114

l -(2-Iodo-3,5-dimethoxyphenyl)-N,N-dimethylpropan-2-amine 3,5-IDNNA-2 300

l -(2-lodo-3,5-dimethoxypherw l)-N,N-dimethylpropan-2-amine, 3,5-1 22IDNNA-2 300

[1 221 labeled] see table under TMA-4 ( # 120)
l-(2-lodo-3,5-dimethoxyphenyl)-N,N-dimethylpropan-2-amine, 3,5-1 25IDNNA-2 300

[1 251 labeled J see table under TMA-4 ( # 120)
l-(3-lodo-2,6-dimethoxyphenyl)-N,N-dimethylpropan-2-amine 2,6-IDNNA 301

l -(3-Iodo-2,6-dimethoxyphenyl)-N,N-dimethylpropan-2-amine, 2,6-1 22 IDNNA 301

[1 221 labeled] see table under TMA-5 ( # 1 2 1 )
l -(3-lodo-2,6-dimethoxyphenyl)-N,N-dimethylpropan-2-amine, 2,6-1 25IDNNA 301

[1251 labeled] see table under TMA-5 ( #121)
1-(4-Iodo-2,5-dimethoxyphenyl)-N,N-dimethylpropan-2-amine 2,5-IDNNA 112

1-(4-lodo-2,5-dimethoxypheny1)-N,N-dimethy1propan-2-amine, 2,5_1 22 IDNNA 113

[1 221] labeled see table under DOI ( #58)
1-(4-Iodo-2,5-dimethoxyphenyl)-N,N-dimethylpropan-2-amine, 2,5-131IDNNA 113

[1311] labeled see table under DOI ( #58)
l-(4-lodo-2,5-dimethoxyphenyl)-N,N-dimethylpropan-2-amine, 2,5-11CIDNNA 112

N-Me [11C] labeled see table under DOI ( #58)
2

1 -(4-Iodo-3 ,5-dimethoxyphenyl)-N,N-dimethylpropan-2-amine
1-(4-Iodo-3,5-dimethoxypheny 1)-N,N- 3,5-1 22IDNNA-4 287

dimethylpropan-2-amine, [1 221 labeled] see table under TMA ( # 11 7)
1 -(5-Iodo-2,4-dimethoxypheny 1)-N,N- 2,4-IDNNA 294

dimethylpropan-2-amine see table under TMA-2 ( # 11 8)
1-( 5-Iodo-2,4-dimethoxypheny 1)-N,N- 2,4-1 22IDNNA 294

dimethylpropan-2-amine, [1 221 labeled] see table under TMA-2 ( #118)
1 -(5-Iodo-2,4-dimethoxyphenyl)-N,N- 2,4-1 2smNNA 294

dimethylpropan-2-amine, [1 251 labeled] see table under TMA-2 ( # 118)
2-(4-Iodo-2,5-dimethoxyphenyl)ethanamine 2C-I ( #23) 31
l-(4-Iodo-2,5-dimethoxyphenyl)-N-isopropyl-N- 2,5-131IDMNiPrNMeA 113

methylpropan-2-amine, [1311] labeled see table under DOI ( # 58)
1-(4-Iodo-2,5-dimethoxypheny1)-N-isopropy1 propan- 2,5-131INiPrA 113

2-amine, [1311] labeled see table under DOI ( # 58)
2-(4-Iodo-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)- INBMeO 113

ethanamine see table under DOI ( # 58)
2-(4-Iodo-2,5-dimethoxypheny 1)-2-methoxyethanamine BOI 17

l-(4-Iodo-2,5-dimethoxyphenyl)-N-(2-methoxyethyl)- 2,5-131INMeOEtA 113

propan-2-amine, [1311] labeled see table under DOI ( # 58)
1-( 4-Iodo-2,5-dimethoxyphenyl)-N- 2,5-IDNA 113

methylpropan-2-amine see table under DOI ( #58)
1-(4-Iodo-2,5-dimethoxyphenyl)-N-methy lpropan- 2,5-131IDNA 113

2-amine, [1311] labeled see table under DOI ( #58)
1-( 4-Iodo-2,5-dimethoxyphenyl)-N-methylpropan- 2,5-11CIDNA 113

2-amine, N-Me [11C] labeled see table under DOI ( # 58)
l -(2-Iodo-3,5-dimethoxyphenyl)propan-2-amine 2-I-3,5-DMA 300

1-(3-Iodo-2,6-dimethoxyphenyl)propan-2-amine 3-I-2,6-DMA 301

1-( 4-Iodo-2,5-dimethoxyphenyl)propan-2-amine DOI ( #58) 112
l -(5-Iodo-2,4-dimethoxypheny l)propan-2-amine 5-I-2,4-DMA 294

N-(l-(4-Iodo-2,5-dimethoxyphenyl)propan-2-yl)- DOI-Ac 112

acetamide see table under DOI ( # 58)
2-((1-(4-lodo-2,5-dimethoxyphenyl)propan-2-yl)amino)- 2,5-131INCNMA 113

acetonitrile, [131 I] labeled see table under DOI ( #58)
N-(1-( 4-Iodo-2,5-dimethoxyphenyl)propan-2-y1)-N,N- 2,5-131IDMAPA 113

dimethylpropane-1,3-diamine, [1311] labeled see table under DOI ( #58)

N-iPr-OHA-�k
N-(1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-y l) 2,5-1311NDoA 113

dodecan-1-amine, [1311] labeled see table under DOI ( #58)
N-( 1-( 4-Iodo-2,5-dimethoxyphenyl)propan-2-y l) 2,5-131INHeA 113

hexan-1-amine, [1311] labeled see table under DOI ( # 58)
( 1-(4-Iodo-2,5-dimethoxypheny l)propan-2-y !) 2,5-131INAA 113

hydrazine, [131I] labeled see table under DOI ( # 58)
N-(1-( 4-Iodo-2,5-dimethoxypheny l)propan-2-yl) 2,5-1311NHA 113

hydroxylamine, [1311] labeled see table under DOI ( # 58)
N-(1-( 4-Iodo-2,5-dimethoxyphenyl)propan-2-yl) 2,5-131INHeNMeA 113

N-methylhexan-1-amine, [1311] labeled see table under DOI ( #58)
1-(7-Iodo-5-methoxy-2,3-dihydrobenzofuran-4-yl) I-SF 20
propan-2-amine see table under B-SF ( # 1 7)
1-(2-Iodo-5-methoxyphenyl)-N-methylpropan- 2-1-5-MA 59
2-amine see table under 2,5-DMA ( #36)
1-( 3-Iodo-4-methoxyphenyl)propan-2-amine 3-1-PMA 66

1-( 4-Iodo-2-methoxypheny l)propan-2-amine 4-1-2-MA 55

1-( 5-Iodo-2-methoxyphenyl)propan-2-amine 5-1-2-MA 59

2-(4-Iodophenyl)ethanamine 4-1-PEA 247

(8-Iodo-2,3,6,7-tetrahydrobenzo[ 1,2-b:4,5-b ']difuran- I-FLY 142

4-yl)propan-2-amine see table under FLY ( #68)
IP 2-(4-Isopropoxy-3,5-dimethoxyphenyl)ethanamine 216
IPBDB 1-(Benzo[d] [l,3] dioxol-5-yl)-N-isopropylbutan-2-amine 169

4-1-PEA 2-(4-Iodophenyl)ethanamine 247

iPHAT 7-(Isopropylamino)-5,6,7,8-tetrahydronaphthalen-1-ol 254

3-1-PMA 1-(3-Iodo-4-methoxyphenyl)propan-2-amine 66
4-iPrA 1-(4-Isopropylphenyl)propan-2-amine 275

see table under PMeA ( #111)
N-iPr-4-Cl-PEA N-( 4-Chlorophenethy l)propan-2-amine 247

N-iPr-DHA-j3k 1-(3,4-Dihydroxyphenyl)-2-(isopropylamino)propan-1-one 49

N-iPr-OHPEA-f'>k
N-iPr-DHPEA-�k 1 -(3,4-Dihydroxyphenyl)-2-(isopropy!amino )ethanone 88

N-iPr-2-MA N-Isopropyl-1 -(2-methoxyphenyl)propan-2-amine 1 56

a-iPr-MDPEA 1-(Benzo[ d] [ l,3 ]dioxol-5-yl)-3-methy lbutan-2-amine 169

N-iPr-MDPEA N-(2-(Benzo[d] [l,3] dioxol-5-yl)ethyl)propan-2-amine 205

iPrONE 1-(Benzo[d] [ 1,3] dioxol-5-yl)-2-(isopropylamino )propan-1 -one 229

N-iPr-PCA 1-( 4-Chloropheny1)-N-isopropy lpropan-2-amine 256

N-iPrPEA N-Phenethylpropan-2-amine 261

4-iPrPEA 2-(4-Isopropy lpheny l)ethanamine 247

N-iPr-PMA N-Isopropyl-1-( 4-methoxyphenyl)propan-2-amine 270

IPTA 1-(4-(Isopropy lthio)pheny l)propan-2-amine 251

IRIS 1-( 5-Ethoxy-2-methoxy-4-methyI phenyl)propan-2-amine 121

I-SF l -(7-Iodo-5-methoxy-2,3-dihydrobenzofuran-4-yl)propan-2-amine 20
see table under B-SF ( # 1 7)
2-(4-Isobutoxy-3,5-dimethoxyphenyl)ethanamine IB 217
see table under Mescaline ( #9 1 )
1-( 4-Isobu toxy-3,5-dimethoxyphenyl)propan- 3C-IB 288

2-amine see table under TMA ( # 1 1 7)
4-(2-(Isobuty!amino )ethyl)benzene-1,2-diol N-iBu-DHPEA 87

2-(4-Isobutyl-2,5-dimethoxyphenyl)ethanamine 2C-IB 121

1-( 4-Isobutyl-2,5-dimethoxyphenyl)propan-2-amine DOIB 121

1-( 4-(Isobu tylthio )-2,5-dimethoxypheny I )propan- 2C-T-25 37

2-amine see table under 2C-T ( #25)
Isomescaline IM ( # 72) 152
1-( 4-Isopropoxy-2,5-dimethoxyphenyl)butan- 4C-iPrO 292

2-amine see table under TMA-2 ( # 11 8)

K
2-(4-Isopropoxy-3,5-dimethoxyphenyl)ethanamine IP 216
1-(4-Isopropoxy-2,5-dimethoxyphenyl)propan- MIPM 292

2-amine see table under TMA-2 ( # 11 8)
1-(4-Isopropoxy-3,5-dimethoxyphenyl)propan- 3C-IP 288

2-amine see table under TMA ( # 1 1 7)
4-(2-(Isopropylamino)ethyl)-2,6-dimethoxyphenol DESMETHYL-iPr 43
2-(Isopropylamino )-1-phenylpropan-l-one i-PAP 72

7-(Isopropy !amino )-5,6,7,8-tetrahydronaphthalen iPHAT 254

l -ol see table under PAT ( # 1 05)
1-(4-Isopropy 1-2,5-dimethoxypheny l)butan-2-amine 4C-iP 8

1-( 4-Isopropyl-2,5-dimethoxyphenyl)propan-2-amine DOIP ( # 59) 117
N-Isopropyl-1-(2-methoxyphenyl)propan-2-amine N-iPr-2-MA 156

N-Isopropy1-1-(4-methoxyphenyl)propan-2-amine N-iPr-PMA 270

4-(2-(Isopropy l(methy!)amino )ethy I) benzene-1,2-diol N-Me,N-iPr-DHPEA 87

2-(4-Isopropylphenyl)ethanamine 4-iPrPEA 247

1-( 4-Isopropylphenyl)propan-2-amine 4-iPrA 275

see table under PMeA ( # 111)
2-(4-(Isopropylthio)-2,5-dimethoxyphenyl) 2C-T-4 37
2-(4-(Isopropylthio)-2,6-dimethoxyphenyl) 1j!-2C-T-4 37
1-(4-(IsopropyI thio )-2,5-dimethoxypheny l)propan- ALEPH-4 ( #5) 6

2-amine
1-( 4-(Isopropylthio )phenyl)propan-2-amine IPTA 251

I-TRIS 2-(2,3,4-Triethoxypheny l)ethanamine 153

BOB ( #9) 10
Jeff METHCATH ( #92) 226
K 1-(Benzo[d] [ l,3]dioxol-5-y l)pentan-2-amine 169


�-Ketomethamphetamine
13-Ketomethamphetamine METHCATH ( #92) 226
13-Keto-N-methyl-3,4-methylenedioxyamphetamine Methylone ( #93) 228
L 1-(Benzo[d] [l,3]dioxol-5-yl)hexan-2-amine 169

LE-25 2C-D ( #20) 25
Leptodacty line 2-(3-Hydroxyphenyl)-N,N,N-trimethylethanaminium 1 50

Lophophine ( #73) 2-(7-Methoxybenzo[d] [l,3]dioxol-5-yl)ethanamine 154

3-Methoxy-4,5-methylenedioxyphenethylamine
7-Methoxy-1,3-benzodioxole-5-ethanamine
5-Methoxy-homopiperonylamine
2C-l
Love Drug MDMA ( # 82) 1 86
M Mescaline (#91) 212
M-13k 2-Amino-1-(3,4,5-trimethoxyphenyl)ethanone 216

2-MA ( # 74) 1 -(2-Methoxypheny l)propan-2-amine 1 55

1-(2-Methoxyphenyl)-2-aminopropane
NSC 1139
3-MA ( # 75) 1-(3-Methoxyphenyl)propan-2-amine 1 58

1-(3-Methoxypheny1)-2-aminopropane
4-MA PMA ( # llO) 267
MAA 2-(Methylamino )-1-phenylethanone 72

MAM 1-(2,5-Dimethoxy-4-(pentyloxy )pheny l)propan-2-amine 292

MAP EA 2-(4-(Allyloxy )-3-methoxyphenyI )ethanamine 211

see table under MEPEA ( #90)
MAPEA 2-(4-(Ally loxy )-3-methoxyphenyl)ethanamine 89

MB MBDB ( # 76) 162
MBDB ( # 76) 1-(Benzo[ d] [ l,3]dioxol-5-y1)-N-methy lbutan-2-amine 162

(±)-N-Methy1-1-(1,3-benzodioxol-5-yl)-2-bu tanamine
a-Ethyl-N-methyl-1,3-benzodioxole-5-ethanamine
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-aminobutane
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-buty!amine
N-Methy 1-1-(3,4-methy lenedioxypheny 1)-2-butanamine
EDEN
MB
MDBD
Methyl-J

MDBD
MBDZP MDBP ( # 79) 1 79
4-M-benzylamine (4-Methoxypheny l)methanamine 261

2,3,4-MBM 2-(3-Bromo-2,4-dimethoxyphenyl)ethanamine 22
MBZM 1-(4-(Benzy loxy )-2,5-dimethoxyphenyl)propan-2-amine 294

MCPA 2-(3,4,5-Trimethoxyphenyl)cyclopropanamine 74
see table under DMCPA (#41)
mCPP (#24) 1 -(3-Chlorophenyl)piperazine 33

m-CPP
3-CPP
NSC 49307
MDA ( #77) 1-(Benzo[ d] [ 1,3 ) dioxol-5-yl)propan-2-amine 165

1 -(3,4-Methylenedioxypheny1)-2-aminopropane
a-Methy 1-1,3-benzodioxole-5-ethanamine
a-Methyl-3,4-(methylenedioxy)phenethylamine
5-(2-Aminopropyl)-l,3-benzodioxole
3,4-Methylenedioxyphenylisopropylamine
3,4-Methylenedioxyamphetamine
Amphedoxamine
Tenamfetamine
EA-1298
NSC 9978
NSC 27106
SKF-5
4,5-MDAI 7,8-Dihydro-6H-indeno[4,5-d] [l,3)dioxol-7-amine 1 71

5,6-MDAI 6,7-Dihydro-5H-indeno[5,6-d) [l,3)dioxol-6-amine 1 71

5,6-MDAT 6,7,8, 9-Tetrahydronaphtho[l,2-d) [ l,3 ]dioxol-7-amine 1 72

6,7-MDAT 5,6,7,8-Tetrahydronaphtho[2,3-d) [ 1,3 ] dioxol-6-amine 1 71

MDBD MBDB ( # 76) 162

MOBP
MDBP ( #79) 1-(Benzo[ d] [ l,3 ]dioxol-5-ylmethy l)piperazine 1 79

1-(3,4-Methylenedioxybenzy l)piperazine
1-(Benzo[ l,3]dioxol-5-y1-methyl)piperazine
1-(1,3-Benzodioxyl-5-y 1-methyl)piperazine
1-(Benzodioxy1-5-y1-methyl)piperazine
1 -(4-Piperonyl)piperazine
N-Piperonylpiperazine
MBDZP
MDCPA 2-(Benzo[d] [l,3]dioxol-5-yl)cyclopropanamine 74

MDDEHP 1 -(Benzo[d] [l,3]dioxol-5-yl)-2-( diethylamino)hexan-1-one 229

MDDMA ( #80) 1-(Benzo[ d] [ l,3 ]dioxol-5-yl)-N,N-dimethylpropan-2-amine 1 80

N,N-Dimethyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxy-N,N-dimethylamphetamine
N,N-Dimethyl-MDA
MDMMA
MDE ( #81) 1-(Benzo[d] [ l,3]dioxol-5-y1)-N-ethylpropan-2-amine 181

N-Ethyl-3,4-methylenedioxyamphetamine
EMDA
Eve
MDEA
MDEA MDE ( #81) 181
[3-M-3,4-DESMETHYL 5-(2-Amino-1-methoxyethyl)-3-methoxybenzene-l,2-diol
f3k-MDMA Methylone ( #93) 228
MDMA ( #82) 1-(Benzo[d] [ 1,3 ]dioxol-5-yl)-N-methylpropan-2-amine 1 86

3,4-Methylenedioxymethamphetamine
a,N-Dimethyl-1,3-benzodioxole-5-ethanamine
a,N-Dimethyl-3,4-methylenedioxy )phenethylamine
N-Methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane
Methylsafrylamin
Adam
E
Ecstasy
Love Drug
XTC
Yaoto-wang Oapan)
NSC-168383
4,5-MDMAI N-Methyl-7,8-dihydro-6H-indeno[4,5-d) [l,3]dioxol-7-amine 1 72

5,6-MDMAI N-Methyl-6,7-dihydro-5H-indeno[5,6-d] [l,3]dioxol-6-amine 171

6,7-MDMAT N-Methyl-5,6,7,8-tetrahydronaphtho[2,3-d) [l,3]dioxol-6-amine 1 71

MDMC Methylone ( #93) 228

a-Me-2C-D
MDMCAT Methylone ( #93) 228
MDMlEA a,N-DMMDBA ( #45) so
MOMMA MDDMA ( # SO) 1 80
MDOH ( # 84) N-(1-(Benzo[d] [ 1,3 ]dioxol-5-yl)propan-2-yl)hydroxy!amine 202

N-Hydroxy-3,4-methylenedioxyamphetamine
N-Hydroxy-a-methyl-1,3-benzodioxole-5-ethanamine
N-H ydroxy-1-(3,4-methylenedioxypheny1)-2-aminopropane
N-Hydroxy MDA
NOHMDA
6-MDOH 6-(2-Aminopropyl)benzo[d] [ l,3 ] dioxol-5-ol 191

see table under MOMA ( # 82)
MDPA MDPR ( # 86) 206
MDP-2-B BOB ( #9) 10
MDPEA ( # S5) 2-(Benzo[ d] [ l,3 ]dioxol-5-yl)ethanamine 204

3,4-Methylenedioxyphenethylamine
2-(Benzodioxol-5-yl)ethylamine
5-(2-Aminoethyl)-1,3-benzodioxole
2-(3,4-Methylenedioxyphenyl)ethylamine
Homopiperonylamine
MDP-3-MB homo-MDMA ( # S3) 201
MDPR ( # 86) N-(1-(Benzo[ d] [l,3]dioxol-5-yl)propan-2-yl)propan-1-amine 206

3,4-Methylenedioxy-N-propylamphetamine
a-Methy l-N-(propyl)-1,3-benzodioxole-5-ethanamine
MDPA
ME 2-(3-Ethoxy-4,5-dimethoxyphenyl)ethanamine 217
MEA 1-(4-E thoxy-3-methoxypheny l)propan-2-amine 67

2-MeA 1-(o-Tolyl)propan-2-amine 275

3-MeA 1 -(m-Tolyl)propan-2-amine 275

4-MeA PMeA ( # 111) 275
N-Me-ALEPH 1-(2,5-Dimethoxy-4-(methylthio )pheny 1)-N-methy I propan-2-amine 3

N-Me-ALEPH-2 1-( 4-(Ethylthio)-2,5-dimethoxypheny 1)-N-methy lpropan-2-amine 3

N-Me-ALEPH-7 1 -(2,5-Dimethoxy-4-(propylthio)pheny1)-N-methyI propan-2-amine 3

a-Me-2C-D DOM ( #60) 118

�-Me-2C-D
j3-Me-2C-D 2-(2,5-Dimethoxy-4-methylphenyl)propan-1 -amine 26

j3, j3-Me-2C-D 2-(2,5-Dimethoxy-4-methylphenyl)-2-methylpropan-1-amine 26

N-Me-2C-D 2-(2,5-Dimethoxy-4-methylphenyl)-N-methylethanamine 26
N,N-Me-2C-D 2-(2,5-Dimethoxy-4-methylphenyl)-N,N-dimethylethanamine 26
N-Me-2C-DMMDA 2-(4,7-Dimethoxybenzo[d) [l,3]dioxol-5-yl)-N-methylethanamine 79

N-Me-2C-DMMDA-2 2-(6,7-Dimethoxybenzo[d) [l,3]dioxol-5-yl)-N-methylethanamine 79

N-Me-2C-DMMDA-3 2-(6,7-Dimethoxybenzo[d) [l,3)dioxol-4-yl)-N-methylethanamine 79

N-Me,CHO-DME N-(2-(3,4-Dimethoxyphenyl)-2-hydroxyethyl)-N- 88
methylformamide
N-Me-3-Cl-MPEA 1-(3-Chloro-4-methoxyphenyl)-N-methylpropan-2-amine 87
N-Me-4C-T 1 -(2,5-Dimethoxy-4-(methylthio )phenyl)-N-methylbutan-2-amine 3

N-Me-4C-T-2 1-(4-(Ethy!thio)-2,5-dimethoxyphenyl)-N-methylbutan-2-amine 3
N-Me-4C-T-7 1-(2,5-Dimethoxy-4-(propylthio )phenyl)-N-methylbutan-2-amine 3

a-MeDA DHA ( #33) 49
N-Me-DCA 1 -(3,4-Dichlorophenyl)-N-methylpropan-2-amine 66
N-Me-DEPEA 2-(3,4-Diethoxyphenyl)-N-methylethanamine 89
N,N-Me-DEPEA 2-(3,4-Diethoxyphenyl)-N,N-dimethylethanamine 89
N-Me-2,5-DEPEA-j3k 1-(2,5-Diethoxypheny 1)-2-(methy!amino )ethanone 30

N,N-Me-DEPEA 2-(3,4-Diethoxyphenyl)-N,N-dimethylethanamine 89
a-Me-DESMETHYL 4-(2-Aminopropyl)-2,6-dimethoxyphenol 287

N-Me-3,4,5-DESMETHYL 5-(2-(Methylamino)ethyl)benzene-1,2,3-triol 43

N-Me-2,5-0MeA
a-Me-3-DESMETHYL 5-(2-Aminopropyl)-2,3-dimethoxyphenol 287

N,N-Me-3-DESMETHYL 5-(2-(Dimethylamino)ethyl)-2,3-dimethoxyphenol 45
N-Me-3-DESMETHYL 2,3-Dimethoxy-5-(2-(methylamino)ethyl)phenol 45
N,N-Me-DHA 4-(2-(Dimethy !amino )propyl)benzene-1,2-diol 49

N,N-Me-DHA (diacetate) 4-(2-(Dimethy !amino )propyl)benzene-1,2-diol 50

j3-Me-DHPEA 4-(1 -Aminopropan-2-yl)benzene-l,2-diol 88

N-Me-DHPEA 4-(2-(Methy !amino )ethyl)benzene-1,2-diol 87

N-Me-DHPEA-j3k 1-(3,4-Dihydroxypheny 1)-2-(methy!amino )ethanone 88

N,N-Me-DHPEA 4-(2-(Dimethy !amino )ethy l)benzene-1,2-diol 87

N,N-Me-2,3-DHPEA 3-(2-(Dimethy !amino )ethyl)benzene-1,2-diol 53

N-Me-DHPEA-AA 4-(2-(Methylamino)ethyl)-1,2-phenylene diacetate 89

N,N-Me-DHPEA-AA 4-(2-(Dimethylamino)ethyl)-l,2-phenylene diacetate 89

N-Me-2,3-DMA 1-(2,3-Dimethoxypheny1)-N-methy lpropan-2-amine 53

N-Me-2,6-DMA 1-(2,6-Dimethoxypheny1)-N-methyl propan-2-amine 64

N,N-Me-DMA 1-(3,4-Dimethoxypheny1)-N,N-dimethylpropan-2-amine 67
N-Me-3,5-DMA 1 -(3,5-Dimethoxyphenyl)-N-methylpropan-2-amine 70
N-Me-DME 1 -(3,4-Dimethoxypheny 1)-2-(methy !amino )ethanol 88

N,N-Me-DME 1-(3,4-Dimethoxyphenyl)-2-(dimethylamino)ethanol 88
N-Me-DMeA 1-(3,4-Dimethy lpheny 1)-N-methy lpropan-2-amine 76

N-Me-2,5-DMeA 1 -(2,5-Dimethylpheny1)-N-methy lpropan-2-amine 76


N,N-Me-2,5-DMeA
N,N-Me-2,5-DMeA 1 -(2,5-DimethylphenyI )-N,N-dimethylpropan-2-amine 76

13-Me-DMPEA 2-(3,4-Dimethoxyphenyl)propan-1-amine 88
13-Me-2,5-DMPEA 2-(2,5-Dimethoxyphenyl)propan-1-amine 30
13,N-Me-2,5-DMPEA 2-(2,5-Dimethoxyphenyl)-N-methylpropan-1-amine 30
13,N,N-Me-2,5-DMPEA 2-(2,5-Dimethoxypheny l)-N,N-dimethylpropan-1-amine 30

N-Me-DMPEA 2-(3,4-Dimethoxyphenyl)-N-methylethanamine 88
N-Me-2,5-DMPEA 2-(2,5-Dimethoxyphenyl)-N-methylethanamine 30
see table under 3,5-DMPEA ( # 50)
N-Me-DMPEA-2 2-(2,3-Dimethoxyphenyl)-N-methylethanamine 82
N-Me-DMPEA-3 2-(2,4-Dimethoxyphenyl)-N-methylethanamine 83
N,N-Me-DMPEA 2-(3,4-Dimethoxyphenyl)-N,N-dimethylethanamine 88
N,N-Me-DMPEA-2 2-(2,3-Dimethoxyphenyl)-N,N-dimethylethanamine 82
N,N-Me-2,5-DMPEA 2-(2,5-Dimethoxyphenyl)-N,N-dimethylethanamine 30
N,N-Me-2,5-DMPEA-13k 1 -(2,5-Dimethoxyphenyl)-2-( dimethy!amino )ethanone 22

N-Me-DOB 1-(4-Bromo-2,5-dimethoxyphenyI )-N-methylpropan-2-amine 99

N,N-Me-DOB 1 -(4-Bromo-2,5-dimethoxyphenyl)-N,N-dimethylpropan-2-amine 99
N,N-Me-3,2,6-DOB 1-(3-Bromo-2,6-dimethoxyphenyl)-N,N-dimethylpropan-2-amine 98

N-Me-3-EA
a-Me-DOM 1-(2,5-Dimethoxy-4-methylphenyl)-2-methy 1 propan-2-amine 121

a,13-Me-DOM 3-(2,5-Dimethoxy-4-methylphenyl)-2-methylbutan-2-amine 121

a,13,13-Me-DOM 3-(2,5-Dimethoxy-4-methylphenyl)-2,3-dimethylbutan-2-amine 121

13-Me-DOM 3-(2,5-Dimethoxy-4-methylphenyl)butan-2-amine 121

13,13-Me-DOM 3-(2,5-Dimethoxy-4-methylphenyl)-3-methylbutan-2-amine 121

N-Me-DOM BEATRICE ( #11) 13
N,N-Me-DOM 1 -(2,5-Dimethoxy-4-methy1pheny1 )-N,N-dimethy lpropan-2-amine 14

see table under BEATRICE ( #11)
R-N-Me-DOM BEATRICE ( # 1 1 ) 13
2-Me-3,4-DOM 1-(3,4-Dimethoxy-2-methylphenyl)propan-2-amine 120

2-Me-3,5-DOM 1-(3,5-dimethoxy-2-methylphenyl)propan-2-amine 120





4-Me-3,5-DOM 1-(3,5-Dimethoxy-4-methy1pheny1 )propan-2-amine 120

5-Me-2,3-DOM 1 -(2,3-Dimethoxy-5-methylphenyl)propan-2-amine 120

5-Me-3,4-DOM 1-(3,4-Dimethoxy-5-methy1phenyl)propan-2-amine 120

6-Me-2,3-DOM 1-(2,3-Dimethoxy-6-methy lphenyl)propan-2-amine 120


N-Me-2,6-DMA 1 -(2,6-Dimethoxyphenyl)-N-methylpropan-2-amine 64
N-Me-3-EA 1-(3-E thoxyphenyl)-N-methy lpropan-2-amine 160


N-Me-EMPEA
N-Me-EMPEA 2-(3-Ethoxy-4-methoxyphenyl)-N-methylethanamine 89
N-Me-2,3-EMPEA 2-(2-Ethoxy-3-methoxyphenyl)-N-methylethanamine 82
N,N-Me-2,3-EMPEA 2-(2-Ethoxy-3-methoxyphenyl)-N,N-dimethylethanamine 82
6-Me-2,4-EMPEA 2-(2-Ethoxy-4-methoxy-6-methylphenyl)ethanamine 303

N-Me-2-EPEA 2-(2-Ethoxyphenyl)-N-methylethanamine 242



N,N-Me-2-EPEA 2-(2-Ethoxyphenyl)-N,N-dimethylethanamine 242

4,6-Me-2-EPEA 2-(2-Ethoxy-4,6-dimethylphenyl)ethanamine 303

N-Me-a-Et-GEA 2-Methoxy-4-(2-(methylamino)butyl)phenol 88
a-Me-N-Et-MDBA 1-(Benzo[ d] [ 1,3] dioxol-5-yl)-N-ethylethanamine 80

3-Me-a-Et-MPEA 1-(4-Methoxy-3-methylpheny1)-N-methy lbutan-2-amine 67

13-Me-GEA 4-( 1-Aminopropan-2-y1)-2-methoxyphenol 88

N-Me-GEA 2-Methoxy-4-(2-(methylamino)ethyl)phenol 88
N-Me-GEA-j:lk 1-(4-Hydroxy-3-methoxyphenyI )-2-(methy!amino )ethanone 88

N,N-Me-2,5-HMA 3-(2-(Dimethylamino)propyl)-4-methoxyphenol 59
N-Me-HME 5-(1-Hydroxy-2-(methylamino)ethyl)-2-methoxyphenol 88
N,N-Me-HME 5-(2-(Dimethylamino )-1-hydroxyethyl)-2-methoxyphenol 88


MeONE
N-Me-HMPEA 2-Methoxy-5-(2-(methylamino )ethy !)phenol 88

N-Me-HMPEA-�k 1-(3-Hydroxy-4-methoxypheny1)-2-(methy !amino )ethanone 88

N,N-Me-2,5-HMPEA 2-(2-(Dimethylamino)ethyl)-4-methoxyphenol 30
�-Me-HPEA 4-(1 -Aminopropan-2-yl)phenol 150

N-Me,N-iPr-DHPEA 4-(2-(Isopropyl(methyI )amino )ethyl)benzene-1,2-diol 87

a-Me-N-iPr-MDBA N-( 1-(Benzo[d] [ 1,3 ] dioxol-5-yl)ethyl)propan-2-amine 80

MEM ( # 87) 1-( 4-E thoxy-2,5-dimethoxyphenyl)propan-2-amine 207

2,5-Dimethoxy-4-ethoxyamphetamine
1-(2,5-Dimethoxy-4-ethoxyphenyl)-2-aminopropane
DMEA
4,N-Me-2-MA 1-(2-Methoxy-4-methylphenyl)-N-methylpropan-2-amine 55
a-Me-MD BA 1-(Benzo[d] (l,3]dioxol-5-yl)ethanamine 80

4-Me-2,6-MEA 1-(2-E thoxy-6-methoxy-4-methylphenyl) 304

propan-2-amine
�,N-Me-2-MPEA 2-(2-Methoxyphenyl)-N-methylpropan-1-amine 242

N,N-Me-2-MPEA 2-(2-Methoxyphenyl)-N,N-dimethylethanamine 242

see table under 2-MPEA ( #1 00)
N,N-Me-3-MPEA 2-(3-Methoxyphenyl)-N,N-dimethylethanamine 244

a,a,3-Me-MPEA 1-(4-Methoxy-3-methy lphenyl)-N,2-dimethylpropan-2-amine 66

�,N,N-Me-3-MPEA 2-(3-Methoxyphenyl)-N,N-dimethylpropan-1 -amine 244

4,6-Me-2-MPEA 2-(2-Methoxy-4,6-dimethylphenyl)ethanamine 303

Me0-2C-ISF 2-(6,7-Dimethoxy-2,3-dihydrobenzofuran-4-yl)ethanamine 20
�-MeO-DOB 1-(4-Bromo-2,5-dimethoxyphenyl)-1-methoxypropan-2-amine 16
see table under BOB ( # 13)
MeONE Methylone ( #93) 228

MeOPP
MeOPP ( #88) 1-(4-Methoxyphenyl)piperazine 209

4-MeOPP
1 -(p-Anisyl)piperazine
Paraperazine
4-MeOPP MeOPP ( # 88) 209
MEPEA ( #90) 2-(4-Ethoxy-3-methoxyphenyl)ethanamine 211

4-Ethoxy-3-methoxyphenethylamine
3-Methoxy-4-ethoxyphenethylamine
N-MePEA ( # 89) N-Methyl-2-phenylethanamine 210

N-Methylphenethylamine
NSC 113957
2-MePEA 2-(o-Tolyl)ethanamine 242

3-MePEA 2-(m-Tolyl)ethanamine 244

4-MePEA 2-(p-Tolyl)ethanamine 247

4-N,N-MePEA 4-(2-Aminoethyl)-N,N-dimethylaniline 247

3,5-Me-PHA 4-(2-Aminopropyl)-2,6-dimethylphenol 287

3-Me-PMMA 1-(4-Methoxy-3-methy lphenyl)-N-methy lpropan-2-amine 66

a-Me-N-Pr-MDBA N-(1-(Benzo[d] [l,3]dioxol-5-yl)ethyl)propan-1-amine 80

Mescalin Mescaline (#91) 212
Mescaline ( #91) 2-(3,4,5-Trimethoxyphenyl)ethanamine 212

3,4,5-Trimethoxy-b-phenethylamine
2-(3,4,5-Trimethoxyphenyl)ethy!amine
Mezcaline
Mescalin
M
2C-TMA
TMPEA
NSC 30419
2-Mesitylethanamine TMePEA-6 306

see table under TMePEA ( # 1 23)
1-Mesitylpropan-2-amine TMeA-6 306

see table under TMePEA ( #123)
Metamfepramone DMAP ( #40) 72
Metamfepyramone DMAP ( #40) 72

2-(2-Methoxy-4,6-dimethylphenyl)ethanamine
METHCATH ( #92) 2-(Methylamino )-1-phenylpropan-1-one 225

Methcathinone
2-Methy laminopropiophenone
13-Ketomethamphetamine
CAT
Ephedrone
Jeff
Rakefet
AL-422 (racemate)
AL-463 (d-isomer)
AL-464 (I-isomer)
UR 1431
Methcathinone METHCATH ( #92) 225
4-Methoxy-a-methyl-1,3-benzodioxole-5-ethanamine MMDA-3a ( #99) 240
6-Methoxy-a-methyl-1,3-benzodioxole-5-ethanamine MMDA-2 ( #98) 238
2-Methoxyamphetamine 2-MA ( # 74) 155
3-Methoxyamphetamine 3-MA ( # 75) 158
4-Methoxyamphetamine PMA ( # 110) 267
4-Methoxybenzeneethanamine 4-MPEA ( # 1 02) 245
13-Methoxy-l,3-benzodioxole-5-ethanamine BOH ( # 15) 17
7-Methoxy-1,3-benzodioxole-5-ethanamine Lophophine ( # 73) 154
2-(7-Methoxybenzo[d] [l,3]dioxol-5-yl)ethanamine Lophophine ( #73) 154
1 -(4-Methoxybenzo[d] [l,3]dioxol-5-yl)propan-2-amine MMDA-3a ( #99) 240
1-(6-Methoxybenzo[d] [l,3]dioxol-5-yl)propan-2-amine MMDA-2 ( #98) 238
1-(7-Methoxybenzo[d] [l,3]dioxol-5-yl)propan-2-amine MMDA ( #97) 235
1-(5-Methoxybenzo[d] [l,3]oxathiol-6-yl)propan-2-amine 4T-MMDA-2 239

13-Methoxy-2C-D BOD ( #14) 16
1-(5-Methoxy-2,3-dihydrobenzofuran-4-yl)propan- SF 20
2-amine see table under B-SF ( # 1 7)
1-( 5-Methoxy-2,3-dihydrobenzofuran-6-y l)propan- F ( #66) 137

2-amine
1-(5-Methoxy-2,2-dimethy1-2,3-dihydrobenzofuran- F-22 138

6-yl)propan-2-amine see table under F ( #66)
1-(5-Methoxy-2,3-dimethyl-2,3-dihydrobenzofuran- F-23 1 38
2-(2-Methoxy-4,6-dimethylphenyl)ethanamine 4,6-Me-2-MPEA 303


3-Methoxy-4-ethoxyphenethylamine
3-Methoxy-4-ethoxyphenethylamine MEPEA ( #90) 211
5-Methoxy-homopiperonylamine Lophophine ( #73) 154
3-Methoxy-4-hydroxyamphetamine MHA ( #94) 230
P-Methoxymescaline BOM ( # 16) 18
p-Methoxymethamphetamine PMMA ( #l12) 277
2-Methoxy-4-(2-(methylamino)butyl)phenol N-Me-a-Et-GEA 88
2-Methoxy-4-(2-(methylamino)ethyl)phenol N-Me-GEA 88
2-Methoxy-5-(2-(methylamino)ethyl)phenol N-Me-HMPEA 88
2-Methoxy-5-(2-(methylamino)propyl)phenol HMMA 50
4-Methoxy-3-(2-(methylamino)propyl)phenol 2,5-MH-MMA 60
3-Methoxy-4-methylamphetamine 3,4-MMA ( #96) 234
4-Methoxy-N-methylamphetamine PMMA ( # ll2) 277
4-Methoxy-a-methylbenzeneethanamine PMA ( # 110) 267
4-Methoxy-a-methy1-1,3-benzodioxole-6-ethanamine MMDA ( #97) 235
1-( 5-Methoxy-2-methy1-2,3-dihydrobenzofuran-6-yl) F-2 1 38

propan-2-amine see table under F ( # 66)
2-Methoxy-3,4-methylenedioxyamphetamine MMDA-3a ( #99) 240
2-Methoxy-4,5-methylenedioxyamphetamine MMDA-2 ( #98) 238
3-Methoxy-4,5-methylenedioxyamphetamine MMDA ( #97) 235
P-Methoxy-3,4-methylenedioxyphenethylamine BOH ( # 1 5) 17
3-Methoxy-4,5-methylenedioxyphenethylamine Lophophine ( #73) 154
2-(5-Methoxy-4-methyl-2-(methylthio)phenyl) 2C-2-TOM 1 08
1-(2-Methoxy-4-methy 1-5-(methyl thio )phenyl)propan- 2C-5-TOM 1 08

2-amine see table under DOET ( #56)
1-(2-Methoxy-4-methy 1-5-(methy lthio )phenyl)propan- 5-TOM 3

1-( 5-Methoxy-4-methy1-2-(methy lthio )phenyl)propan- 2-TOM 3

p-Methoxy-a-methylphenethylamine PMA ( # llO) 267

2-(3-Methoxyphenyl)-N,N-dimethylethanamine
4-Methoxy-a-methylphenethylamine PMA ( # 110) 267
1-(2-Methoxy-3-methylpheny 1)-N,N-dimethy Ipropan- 2,3-MMeMMA 53

1-(4-Methoxy-3-methylphenyI )-N,2-dimethylpropan- a,a,3-Me-MPEA 66

2-amine see table under DMA ( #38)
2-(2-Methoxy-4-methylphenyl)ethanamine 2,4-MMPEA 83
1-(2-Methoxy-5-methylpheny1)-2-(methy !amino) 13-HO-N-Me-2-M-5-MePEA 30

ethanol see table under 2C-H ( #22)
1-(2-Methoxy-5-methylpheny1)-2-(methy !amino) 13-H0-2-M-N-Me-MeA 60

propan-1-ol see table under 2,5-DMA ( #36)
1-(4-Methoxy-3-methylpheny1)-N-methy !bu tan- 3-Me-a-Et-MPEA 67

2-amine see table under DMA ( # 38)
1-(2-Methoxy-3-methylpheny1)-N-methylpropan- 2,3-MMeMA 53
1 -(2-Methoxy-4-methyI phenyl)-N-methylpropan- 4,N-Me-2-MA 55

1-(4-Methoxy-3-methylphenyl)-N-methylpropan- 3-Me-PMMA 66
2-amine see table under DMA ( #38)
1-(2-Methoxy-3-methyI phenyl)propan-2-amine 2,3-MMeA 53

1-(2-Methoxy-4-methylphenyl)propan-2-amine 2,4-MMA 55
1-(3-Methoxy-4-methylpheny l)propan-2-amine 3,4-MMA ( #96) 234
o-Methoxyphenethylamine 2-MPEA ( # 1 00) 241
p-Methoxyphenethylamine 4-MPEA ( # 1 02) 245
2-Methoxyphenethylamine 2-MPEA ( # 1 00) 241
3-Methoxyphenethy !amine 3-MPEA ( #101) 243
4-Methoxyphenethylamine 4-MPEA ( # 1 02) 245
1 -p-Methoxypheny 1-2-aminopropane PMA ( #l10) 267
1-(2-Methoxypheny1)-2-aminopropane 2-MA ( # 74) 155
1-(3-Methoxyphenyl)-2-aminopropane 3-MA ( # 75) 158
2-(2-Methoxyphenyl)-N,N-dimethylethanamine N,N-Me-2-MPEA 242

2-(3-Methoxyphenyl)-N,N-dimethylethanamine N,N-Me-3-MPEA 244


2-(3-Methoxyphenyl)-N,N-dimethylpropan-1 -amine
2-(3-Methoxyphenyl)-N,N-dimethy lpropan-1-amine j3,N,N-Me-3-MPEA 244

see table under 3-MPEA ( # 1 0 1 )
2-(p-Methoxyphenyl)ethylamine 4-MPEA ( # 1 02) 245
2-(3-Methoxyphenyl)ethanamine 3-MPEA ( # 101) 243
2-(2-Methoxypheny l)ethanamine 2-MPEA ( # 100) 241
2-(4-Methoxyphenyl)ethanamine 4-MPEA ( # 102) 245
2-(4-Methoxyphenyl)ethylamine 4-MPEA ( # 102) 245
4-Methoxyphenylethylamine 4-MPEA ( # 1 02) 245
( 4-Methoxypheny l)methanamine 4-M-benzylamine 261

1-(4-Methoxypheny1)-2-(methy !amino )propan- PMMA-j3k 277

1 -one see table under PMMA ( #112)
2-(4-Methoxyphenyl)-1 -methylethylamine PMA ( # 110) 267
1-(4-Methoxyphenyl)-N-methylpropan-2-amine PMMA ( # 112) 277
2-(2-Methoxyphenyl)-N-methylpropan-1 -amine j3,N-Me-2-MPEA 242

1-(4-Methoxyphenyl)piperazine MeOPP ( # 88) 209
1-(2-Methoxyphenyl)propan-2-amine 2-MA ( # 74) 155
1-(3-Methoxyphenyl)propan-2-amine 3-MA ( # 75) 158
1-(4-Methoxyphenyl)propan-2-amine PMA ( # 110) 267
N-(1-(2-Methoxyphenyl)propan-2-yl)hexan-1-amine N-He-2-MA 156

N-( 1-(4-Methoxyphenyl)propan-2-y!)hydroxy!amine N-HO-PMA 270

l -p-Methoxyphenyl-2-propy !amine PMA ( # 110) 267
1-( 4-Methoxyphenyl)-2-(propylamino )propan-1-ol 13-HO-N-Pr-PMA 270

2-Methoxy-2-(2,4,5-trimethoxyphenyl)ethanamine BOT 17
see table under BOD ( #14)
2-Methoxy-2-(3,4,5-trimethoxyphenyl)ethanamine BOM ( # 16) 18
1-(5-Methoxy-2,3,3-trimethy1-2,3-dihydrobenzofuran- F-233 1 38
Methoxytyramine GEA ( #69) 143
3-Methoxytyramine GEA ( # 69) 143

1 -(4-Methyl-2,5-bis(methylthio)phenyl)propan--2-amine
4-(2-(Methylamino )ethyl)benzene-1,2-diol N-Me-DHPEA 87

5-(2-(Methylamino )ethyl)benzene-1,2,3-triol N-Me-3,4,5-DESMETHYL 43

4-(2-(Methylamino)ethyl)phenol HMePEA ( # 70) 145
4-(2-(Methylamino)ethyl)phenyl acetate AcO-MePEA 150

see table under Hordenine (#71)
4-(2-(Methylamino )ethyl)-1,2-phenylene diacetate N-Me-DHPEA-AA 89

2-Methylamino-1-(3,4-methy lenedioxypheny !)butane MBDB ( # 76) 162
3-Methylamino-1-(3,4-methylenedioxyphenyl)butane homo-MOMA ( #83) 201
2-Methylamino-1-(3,4-methylenedioxyphenyl) Methylone ( #93) 228

propan-1-one
2-(Methylamino)-1-phenylethanone MAA 72
2-(Methylamino )-1-phenylpropan-1-one METHCATH ( #92) 225
2-Methy laminopropiophenone METHCATH ( #92) 225
4-(2-(Methy!amino )propy l)benzene-1,2-diol DHMA 49

5-(2-(Methy!amino )propy I )benzene-1,2,4-triol THMA-2 292

2-(2-(Methy!amino)propy !)phenol 2-HMA 156

2-(Methylamino )-1-(3,4,5-trimethoxyphenyl)ethanol �-HO-M-M 216

4-Methylamphetamine PMeA ( # 111) 275
1-(8-Methy lbenzo[ 1,2-b:4,5-b ']difuran-4-yl)propan- DOM-DFLY 48

2-amine see table under DFLY ( #32)
a-Methyl-benzo[l,2-b:4,5-b'] difuran-4-ethanamine DFLY ( #32) 47
a-Methyl-1,4-benzodioxan-6-ethylamine EDA ( #65) 136
a-Methy1-1,3-benzodioxole-5-ethanamine MDA ( # 77) 165
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-aminobutane MBDB ( #76) 162
(±)-N-Methyl-1-(1,3-benzodioxol-5-y1)-2-butanamine MBDB ( # 76) 162
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butylamine MBDB ( # 76) 162
1-(4-Methy 1-2,5-bis(methy lthio )phenyl)propan- BIS-TOM 3


N-Methyl-6,7-dihydro-5H-indeno[5,6-d][l,3]dioxol-6-amine
N-Methyl-6,7-dihydro-5H-indeno[5,6-d] [l,3]dioxol- 5,6-MDMAI 1 71

N-Methyl-7,8-dihydro-6H-indeno[4,5-d] [l,3]dioxol- 4,5-MDMAI 1 72

a-Methyl-3,4-dimethoxyphenethylamine DMA ( #38) 65
N-Methyl-DOM BEATRICE ( #11) 13
a-Methyl dopamine DHA ( #33) 49
3-0-Methy !dopamine GEA ( #69) 143
Methyl-DMMDA 1-(4,7-Dimethoxybenzo[d] [1,3] dioxol-5-yl)-N 79

methy lpropan-2-amine
3,4-Methylenedioxyamphetamine MDA ( #77) 165
1 -(3,4-Methylenedioxybenzyl)piperazine MDBP ( #79) 1 79
3,4-Methylenedioxy-N,N-dimethylamphetamine MDDMA ( #80) 1 80
3,4-Methylenedioxymethamphetamine MDMA ( # 82) 1 86
3,4-Methylenedioxymethcathinone Methylone ( #93) 228
3,4-Methylenedioxyphenethylamine MDPEA ( #85) 204
1-(3,4-Methylenedioxypheny1)-2-aminopropane MDA ( # 77) 165
1 -(3,4-Methylenedioxypheny1)-2-butanamine BDB ( #9) 10
2-(3,4-Methylenedioxypheny l)ethy!amine MDPEA ( #85) 204
1-(3 ,4-Methylenedioxy Ipheny 1)-3-isobu ty!amine homo-MDA ( # 78) 1 77
3,4-Methylenedioxyphenylisopropylamine MDA ( # 77) 165
3,4-Methylenedioxy-N-propylamphetamine MDPR ( # 86) 206
N-Methylephedrone DMAP ( #40) 71
a-Methylhomoveratrylamine DMA ( #38) 65
N-Methyl-2-(4-hydroxyphenyl)ethylamine HMePEA ( #70) 145
Methyl-J MBDB ( #76) 1 62
METHYL-MA PMMA ( # 11 2) 277
dl-a-Methylmescaline TMA ( # 11 7) 285
N-Methylmescaline M-M ( #95) 233
4-Methyl-2,5-methoxycyclopropylamine DMCPA ( #41) 73

N-Methyl-1-(2,3,4,5-tetramethoxyphenyl)propan-2-amine
2-Methyl-6-(2-(methylamino)ethyl)phenol 2,3-HMeMPEA 52
2-Methy 1-6-(2-(methy !amino )propy !)phenol 2,3-HMeMA 53

3-0-Methyl-a-methyldopamine MHA ( #94) 230
a-Methy 1-3,4-( methy lenedi oxy )phenethy!amine MDA ( #77) 165
N-Methy1-1-(3,4-methylenedioxypheny 1)-2-aminopropane MDMA ( #82) 186
N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine MBDB ( # 76) 162
N-Methyl-1 -(3,4-methylenedioxypheny 1)-3-isobuty !amine homo-MD MA ( #83) 201
a-Methyl-g-(3,4-methylenedioxyphenyl)propylamine homo-MDA ( #78) 1 77
a-Methyl-4-methylthiophenethylamine MTA ( # 1 03) 250
Methylone ( #93) 1-(Benzo[d] [1,3]dioxol-5-yl)-2-(methylamino )propan-1 -one 228

2-Methylamino-1 -(3,4-methylenedioxyphenyl)propan-1 -one
1 -(1,3-Benzodioxol-5-yl)-2-(methylamino )-1-propanone
�-Keto-N-methyl-3,4-methylenedioxyamphetamine
3,4-Methylenedioxymethcathinone
EASE
EMM (street name)
Explosion (street name in the Netherlands)
�k-MDMA
MDMC
MDMCAT
MeONE
N-Methylphenethylamine N-MePEA ( #89) 210
2-Methyl-3-phenylbutan-2-amine AEPEA 261

N-Methyl-2-phenylethanamine N-MePEA ( #89) 210
2-( 4-Methylpiperazin-1 -y 1)-1-phenylpropan-1 -one PZAP 73

a-Methy 1-N-(propy1)-1,3-benzodi oxole-5-ethanamine MDPR ( # 86) 206
2-(1 -MethyI pyrrolidin-2-yl)ethanamine TH-NMEA 140

Me thylsafry lamin MDMA ( #82) 186
1-( 8-Methy1-2,3,6, 7-tetrahydrobenzo[ 1,2-b:4,5-b '] DOM-FLY 142

difuran-4-y l)propan-2-amine see table under FLY ( #68)
N-Methyl-5,6,7,8-tetrahydronaphtho[2,3-d] [l,3] 6,7-MDMAT 1 71

dioxol-6-amine see table under MDA ( # 77)
N-Methy1-1-(2,3,4,5-tetramethoxyphenyl)propan- TeMA ( # 113) 279

2-amine

p-Methylthioamphetamine
p-Methylthioamphetamine MTA ( # 103) 250
4-Methylthioamphetamine MTA ( # 103) 250
1-(4-(Methylthio)benzo[d] [l,3]dioxol-5-yl)propan- 2T-MMDA-3a 240

2-amine see table under MMDA-3a ( #99)
1 -(4-(Methylthio )phenyl)butan-2-amine a-EMTPEA 250

1-(4-(Methylthio )phenyl)propan-2-amine MTA ( # 103) 250
N-Methyl-2-(3-(trifluoromethyl)phenyl)ethanamine 3-TFMMPEA 133

a-Methyl-2,3,5-trimethoxyphenethylamine TMA-4 ( # 1 20) 299
a-Methyl-2,3,6-trimethoxyphenethylamine TMA-5 ( #121) 301
a-Methyl-2,4,6-trimethoxyphenethylamine TMA-6 ( # 1 22) 302
a-Methyl-3,4,5-trimethoxyphenethylamine TMA ( # l 1 7) 285
N-Methyl-3,4,5-trimethoxyphenethylamine M-M ( #95) 233
4-Methyl-2,5,fl-trimethoxyphenethylamine BOD ( # 14) 16
N-Methyl-2-(3,4,5-trimethoxyphenyl)ethanamine M-M ( #95) 233
Methy!tyramine 4-MPEA ( # 1 02) 245
a-Methyltyramine PHA ( # l09) 264
N-Methyltyramine HMePEA ( #70) 145
0-Methyltyramine 4-MPEA ( # 1 02) 245
N-Me-fl,3,4-TMPEA 2-(3,4-Dimethoxyphenyl)-2-methoxy-N-methylethanamine 88
N,N-Me-fl,3,4-TMPEA 2-(3,4-Dimethoxyphenyl)-2-methoxy-N,N-dimethylethanamine 88
Mezcaline Mescaline ( #91) 212
MG 559 DMAP ( #40) 71
MHA ( #94) 4-(2-Aminopropyl)-2-methoxyphenol 230

3-Methoxy-4-hydroxyamphetamine
4-Hydroxy-3-methoxy-a-methylphenethylamine
4-Hydroxy-3-methoxyamphetamine
3-0-Methyl-a-methyldopamine
HMA
NSC-172191
MHAOH 4-(2-(Hydroxyamino)propyl)-2-methoxyphenol 50

N-MMDBA
MHMAOH 4-(2-(Hydroxy(methyl)amino)propyl)-2-methoxyphenol 50
MHMC 1-(3-Hydroxy-4-methoxyphenyl)-2-(methylamino )propan-1 -one 227

see table under METHCATH (#92)
2,5-MH-MMA 4-Methoxy-3-(2-(methy!amino )propy!)phenol 60

MHPEA GEA ( # 69) 143
�,2-MHPEA-3 4-( 1 -Aminopropan-2-y 1)-3-methoxyphenol 83

2,4-MHPEA 4-(2-Aminoethyl)-3-methoxyphenol 83
MIPM 1-( 4-Isopropoxy-2,5-dimethoxypheny I)propan-2-amine 292

M-M ( #95) N-Methyl-2-(3,4,5-trimethoxyphenyl)ethanamine 233

N-Methy!mescaline
N-Methyl-3,4,5-trimethoxyphenethylamine
2,4-MMA 1-(2-Methoxy-4-methy lphenyl)propan-2-amine 55

3,4-MMA ( #96) 1-(3-Methoxy-4-methylpheny l)propan-2-amine 234

3-Methoxy-4-methylamphetamine
4-MMA PMMA ( # l12) 277
2,3,4-MMB 2-(4-Bromo-2,3-dimethoxyphenyl)ethanamine 22
MMDA ( #97) 1-(7-Methoxybenzo[ d] [ 1,3 ]dioxol-5-yl)propan-2-amine 235

MMDA-2 ( #98) 1 -(6-Methoxybenzo[d] [l,3] dioxol-5-yl)propan-2-amine 238

MMDA-3a ( #99) 1-(4-Methoxybenzo[ d] [1,3] dioxol-5-yl)propan-2-amine 240

N-MMDBA 1-(Benzo[d] [ 1,3]dioxol-5-y1)-N-methylethanamine 80


MME
MME 1-(5-E thoxy-2,4-dimethoxypheny I)propan-2-amine 292

2,3-MMeA 1-(2-Methoxy-3-methy1 phenyl)propan-2-amine 53

2,3-MMeMA 1-(2-Methoxy-3-methy lpheny1)-N-methylpropan-2-amine 53

2,3-MMeMMA 1-(2-Methoxy-3-methylphenyl)-N,N-dimethylpropan-2-amine 53
2-M-5-MePEA-f3k 2-Amino-1-(2-methoxy-5-methylphenyl)propan-l-one 30
MM-GEA 4-(2-(Dimethy lamina )ethy 1)-2-methoxyphenol 88
MM-M Trichocereine ( #125) 309
2,4-MMPEA 2-(2-Methoxy-4-methylphenyl)ethanamine 83
Molly mTFMPP ( # ll6) 283
M(20P)M 1-(4-(2-Aminopropy1)-2,5-dimethoxyphenoxy )propan-2-ol 292

see table under TMA-2 ( #ll8)
M(30P)M 3-( 4-(2-Aminopropy 1)-2,5-dimethoxyphenoxy )propan-1 -ol 292

MPEA 4-MPEA ( # 1 02) 245
2-MPEA ( # 1 00) 2-(2-Methoxyphenyl)ethanamine 241

o-Methoxyphenethylamine
3-MPEA ( # 101) 2-(3-Methoxyphenyl)ethanamine 243

3-Methoxyphenethy !amine
EA-1302 (Edgewood Arsenal)
NSC 124706
4-MPEA ( # 1 02) 2-( 4-Methoxyphenyl)ethanamine 245

Paramethoxyphenethylamine
2-(4-Methoxyphenyl)ethy !amine
2-(p-Methoxypheny l)ethy !amine
4-Methoxybenzeneethanamine
4-Methoxyphenylethy !amine
Homoanisylamine
0-Methyltyramine
p-Methoxyphenethylamine
Methyltyramine
Tyramine methyl ether
MPEA
PM PEA
NSC 43687
3-MT GEA ( #69) 250

NSC 1 139
MTA ( #1 03) 1-(4-(Methylthio)phenyl)propan-2-amine 250

4-Methylthioamphetamine
a-Methyl-4-methylthiophenethylamine
p-Methylthioamphetamine
Flatliners
Golden Eagles
4-MTA
PMTA
p 1 882
4-MTA MTA ( # 103) 250
MTC 2-Amino-1 -( 4-(methylthio )phenyl)propan-1-ol

250
MTDALA N-Allyl-N-(1-( 4-(methy 1 thio )phenyl)propan-2-yl)prop- 250
2-en-1-amine
mTFMPP ( # 116) 1-(3-(Trifluoromethy l)phenyl)piperazine 283

3-(Trifluoromethyl)phenylpiperazine
TFMPP
TFTP
Molly
NSC 128882
1 -(N aphthalen-1 -yl)- 1-NP 34

piperazine see table under mCPP ( #24)
NCS 168525 2C-H ( #22) 29
Nexus 2C-B ( # 1 8) 20
2-NH -4,5-DMA 2-(2-Aminopropy 1)-4,5-dimethoxy aniline 294

2
5-NH -2,4-DMA 5-(2-Aminopropyl)-2,4-dimethoxyaniline 294

2
5-NH -2,4-DMPEA 5-(2-Aminoethyl)-2,4-dimethoxyaniline 308

2
NOHMOA MDOH ( # 84) 202
2-N0 -HPEA 4-(2-Aminoethyl)-3-nitrophenol 83

2
3-N0 -HPEA 4-(2-Aminoethyl)-2-nitrophenol 87

2
Norveritol PHA ( # l 09) 264
1 -NP 1-(N aphthalen-1 -yl)piperazine 34

NSC 1139 2-MA ( # 74) 155

NSC 6328
NSC 6328 DMPEA ( #49) 85
NSC 9978 MDA ( #77) 165
NSC 10811 PEA ( # 1 07) 259
NSC 16948 DMPEA ( #49) 85
NSC 26152 DMPEA ( #49) 85
NSC 27106 MDA ( #77) 1 65
NSC 27114 PMeA ( # lll) 275
NSC 30419 Mescaline (#91) 212
NSC 32757 PMA ( # llO) 267
NSC 43687 4-MPEA ( # 1 02) 245
NSC 49307 mCPP ( #24) 33
NSC 61065 PHA ( # 1 09) 264
NSC 113957 N-MePEA ( #89) 210
NSC 113958 HMePEA ( #70) 145
NSC 113958 DMPEA ( #49) 85
NSC 124706 3-MPEA ( # 101) 243
NSC 128882 mTFMPP ( # 116) 283
NSC 144717 DMA ( #38) 65
NSC 144717 DMPEA ( #49) 85
NSC 167759 DESMETHYL ( #29) 42
NSC 167759 TMA ( # 11 7) 285
NSC-168383 MDMA ( # 82) 1 86
NSC 1 70995 PHA ( #109) 264
NSC 1 72188 BDB ( #9) 10
NSC 1 72189 2,3-DMA ( #34) 51
NSC-172191 MHA ( #94) 230
NSC 234706 DMAP ( #40) 71
NSC 249188 Tyramine ( # 1 26) 310
NSC 287208 PCA ( # 1 06) 255
NSC-29224 ARIADNE ( #7) 7

PBAI
NSC 367445 2,5-DMA ( #36) 57
NSC 367445 TMA-6 ( # 122) 302
NSC 660980 3,5-DMA ( #39) 70
oCPP 1 -(2-Chlorophenyl)piperazine 33
see table under mCPP (#24)
ONE 2-Amino-1-(benzo[d] [l,3]dioxol-5-yl)propan-1-one 229

Ordenina Hordenine ( #71) 147
oTFMPP 1 -(2-(Trifluoromethyl)phenyl)piperazine 284

see table under mTFMPP ( # 116)
P Proscaline ( # 1 04) 252
P 1 882 MTA ( # 1 03) 250
PAA 4-(2-Aminopropyl)aniline 256

PAL 313 PMeA ( #111) 275
PARA-DOT ALEPH ( #3) 2
Paramethoxyamphetamine PMA ( #110) 267
Paramethoxyphenethylamine 4-MPEA ( # 1 02) 245
Paramethoxy-a-methylphenethylamine PMA ( # 110) 267
Paraperazine MeOPP ( #88) 209
Paredrine PHA ( # 1 09) 264
Paredrinex PHA ( # 109) 264
PAP 1 -Pheny 1-2-(propy!amino)propan-1-one 72

i-PAP 2-(Isopropylamino )-1-phenylpropan-1-one 72

PAPEA 4-(2-Aminoethyl)aniline 247

PAT ( # 1 05) 7-(Dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-ol 253

7-(Dipropylamino)-5,6,7,8-tetrahydro-1-naphthalenol
8-Hydroxy-2-( dipropylamino)tetralin
PPAT
8-HO-DPAT
PBAI 5-Bromo-2,3-dihydro-lH-inden-2-amine 257


PCA
PCA ( # 106) 1 -(4-Chlorophenyl)propan-2-amine 255

4-Chloroamphetamine
4-Chloro-a-methylphenethylamine
4-CA
NSC 287208
Ro 4-6614 / 001
pCPP 1-( 4-Chloropheny l)piperazine 33

PEA ( # 1 07) 2-Phenylethanamine 259

Phenethylamine
Ethanamine
NSC 10811
Pedrolon PHA ( # 109) 264
PeMPEA ( # 1 08) 2-(2,3,4,5,6-Pentamethoxyphenyl)ethanamine 263

Pentamethoxyphenethylamine
2,3,4,5,6-Pentamethoxyphenethylamine
2,3,4,5,6-Pentamethoxyphenethylamine PeMPEA ( # 1 08) 263
2-(2,3,4,5,6-Pentamethoxyphenyl)ethanamine PeMPEA ( # 1 08) 263
Pentamethoxyphenethylamine PeMPEA ( # 1 08) 263
2-(4-(Pentyloxy)phenyl)ethanamine 4-APEA 247

Peyocactine Hordenine (#71) 147
PHA ( # l 09) 4-(2-Aminopropyl)phenol 264

4-HA
4-Hydroxyamphetamine
p-Hydroxyamphetamine
a-Methyltyramine
Norveritol
Paredrine
Paredrinex
Pedrolon
Pulsoton
NSC 61065
NSC 1 70995
Phenethylamine PEA ( # 1 07) 259
N-Phenethylpropan-2-amine N-iPrPEA 261

2-Phenylcyclopropanamine cPr-PEA 261

2-Phenylethanamine PEA ( # 1 07) 259
1-Phenyl-2-(piperidin-1-yl)propan-1-one PIAP 73
N-(l-Phenylpropan-2-yl)hydroxylamine AMPH-OH 261


PMMA
1-Pheny1-2-(propy !amino)propan-1 -one PAP 72

1-Phenyl-2-(pyrrolidin-1-yl)propan-1-on PPP 72
PIAP 1-Phenyl-2-(piperidin-1-yl)propan-1-one 73
pip-2C-B 1-(4-Bromo-2,5-dimethoxyphenethyl)piperidine 22
2-(Piperazin-1 -yl)pyrimidine 2-PmP 34

2-(Piperazin-1-yl)quinoline Quipazine 34
N-Piperonylpiperazine MDBP ( # 79) 1 79
1-(4-Piperonyl)piperazine MDBP ( # 79) 1 79
PMA ( # l10) 1-( 4-Methoxyphenyl)propan-2-amine 267

Paramethoxyamphetamine
Paramethoxy-a-methylphenethylamine
p-Methoxy-a-methylphenethylamine
1-p-Methoxypheny1-2-aminopropane
1-p-Methoxypheny1-2-propy !amine
2-( 4-Methoxypheny1)-1-methylethy!amine
2-Amino-1-(4-methoxypheny!)propane
4-Methoxy-a-methylbenzeneethanamine
4-Methoxy-a-methyIphenethy !amine
4-MA
Chicken Power
Chicken Yellow
Death
White Mitsubishi
NSC 32757
2-Amino-1 -( 4-methoxyphenyl)propan-1-one 270

PMeA ( # 111) 1-(p-Tolyl)propan-2-amine 275

4-Methylamphetamine
p-Tolylaminopropane
1-(p-Tolyl)-2-aminopropane
Aptrol
4-MeA
p-TAP
PAL 313
NSC 27114
PMMA ( # 11 2) 1-(4-Methoxypheny1)-N-methyI propan-2-amine 277

METHYL-MA
4-Methoxy-N-methylamphetamine
p-Methoxymethamphetamine
4-MMA
Doone

PMMA-f)K
PMMA-Pk 1-(4-Methoxyphenyl)-2-(methylamino )propan-1 -one 277

see table under PMMA ( # 112)
2-PmP 2-(Piperazin-1-yl)pyrimidine 34
see table under mCPP (#24)
PMPEA 4-MPEA ( # 1 02) 245
PMTA MTA ( # l 03) 250
PPAT PAT ( # 1 05) 253
PPP 1-Phenyl-2-(pyrrolidin-1-yl)propan-1-on 72
N-Pr-DOB N-(l-(4-Bromo-2,5-dimethoxyphenyl)propan-2-yl)propan-1 -amine 99

PrONE 1-(Benzo[d] [1,3]dioxol-5-yl)-2-(propylamino )propan-1-one 229

PRONE 1-(Benzo[ d] [l,3]dioxol-5-yl)-2-(prop-2-yn-1-ylamino )propan-1-one 229

Propyl 4-(2-aminopropyl)- DOCEP 1 05

2,5-dimethoxybenzoate see table under DOCN ( #55)
Proscaline ( # 1 04) 2-(3,5-Dimethoxy-4-propoxyphenyl)ethanamine 252

3,5-Dimethoxy-4-propoxyphenethylamine
pTFMPP 1-(4-(Trifluoromethyl)phenyl)piperazine 284

Pulsoton PHA ( # l 09) 264
PZAP 2-(4-Methylpiperazin-1-yl)-1-phenylpropan-1-one 73
Quipazine 2-(Piperazin-1-yl)quinoline 34
Rakefet METHCATH ( #92) 225
Reciprocal mescaline IM ( # 72) 152
Ro 4-6614 / 001 PCA ( # 1 06) 255
Salicifoline 2-(3-Hydroxy-4-methoxyphenyl)-N,N,N-trimethylethanaminium 88
SB 2-(3,5-Diethoxy-4-methoxyphenyl)ethanamine 217
See-bietjies 2C-B ( # 18) 20
Semi-fly F ( #66) 137

TeMeA-2
SF 1 -(5-Methoxy-2,3-dihydrobenzofuran-4-yl)propan-2-amine 20
SKF-5 MDA ( # 77) 165
4-SPEA 2-( 4-(Heptyloxy )phenyl)ethanamine 247

SPICE 2C-I ( #23) 31
STP DOM ( #60) 118
Systogene Tyramine ( # 1 26) 310
T7 2C-T-7 ( #27) 39
TA TeMA ( # l13) 279
TAP 1-( 5,6, 7,8-Tetrahydronaphthalen-2-yl)propan-2-amine 76

p-TAP PMeA ( # 111) 275
3-TASB 2-(4-Ethoxy-3-(ethylthio)-5-methoxyphenyl)ethanamine 217

4-TASB 2-(3-Ethoxy-4-(ethylthio)-5-methoxyphenyl)ethanamine 217

5-TASB 2-(3,4-Diethoxy-5-(methylthio)phenyl)ethanamine 217

TB 2-(4-(Butylthio)-3,5-dimethoxyphenyl)ethanamine 217
4-tBuPEA 2-(4-(tert-Butyl)phenyl)ethanamine 247

TE 2-(4-(Ethylthio)-3,5-dimethoxyphenyl)ethanamine 217
3-TE 2-(4-Ethoxy-3-methoxy-5-(methylthio)phenyl)ethanamine 216

TeMA ( # 113) N-Methyl-1-(2,3,4,5-tetramethoxyphenyl)propan-2-amine 279

2,3,4,5-Tetramethoxyamphetamine
TA
TeMA-2 1 -(2,3,4,6-Tetramethoxyphenyl)propan-2-amine 282

TeMA-3 1-(2,3,5,6-Tetramethoxyphenyl)propan-2-amine 282

TeMeA 1-(2,3,4,5-Tetramethylphenyl)propan-2-amine 306

TeMeA-2 1-(2,3,4,6-Tetramethoxyphenyl)propan-2-amine 306


TeMeA-3
TeMeA-3 1 -(2,3,5,6-Tetramethylphenyl)propan-2-amine 306

see table under TMePEA ( # 123)
TeMePEA 2-(2,3,4,5-Tetramethylphenyl)ethanamine 306

TeMePEA-2 2-(2,3,4,6-Tetramethylphenyl)ethanamine 306

TeMePEA-3 2-(2,3,5,6-Tetramethylphenyl)ethanamine 306

TeMPEA ( # 114) 2-(2,3,4,5-Tetramethoxyphenyl)ethanamine 280

TeMPEA-2 2-(2,3,4,6-Tetramethoxyphenyl)ethanamine 282

TeMPEA-3 ( # 115) 2-(2,3,5,6-Tetramethoxyphenyl)ethanamine 282

Tenamfetamine MDA ( # 77) 165
TEtPEA-6 2-(2,4,6-Triethylphenyl)ethanamine 306

1-(2,3,6,7-Tetrahydrobenzo[ 1,2-b:4,5-b'] difuran- FLY ( #68) 141

4-yl)-2-aminopropane
2-(2,3,6,7-Tetrahydrobenzo[l,2-b:4,5-b ']difuran-4-y 1) 2C-FLY 141

ethanamine see table under FLY ( #68)
1-(2,3,6,7-Tetrahydrobenzo[ l,2-b:4,5-b'] difuran-4-yl) FLY ( #68) 141

propan-2-amine
2,3,6,7-Tetrahydro-a-methyl-benzo[ l,2-b:4,5-b']difuran- FLY ( #68) 141

4-ethanamine
1-(5,6,7,8-Tetrahydronaphthalen-2-yl)propan-2-amine TAP 76
5,6,7,8-Tetrahydronaphtho[2,3-d] [ 1,3 ]dioxol-6-amine 6,7-MDAT 171

6,7,8, 9-Tetrahydronaphtho[ 1,2-d] [ l,3 ] dioxol-7-amine 5,6-MDAT 1 72

2,3,4,5-Tetramethoxyamphetamine TeMA ( # l13) 279
j3,3,4,5-Tetramethoxyphenethylamine BOM ( #16) 18
2,3,4,5-Tetramethoxyphenethy lamine TeMPEA ( # 114) 280
2,3,5,6-Tetramethoxyphenethy lamine TeMPEA-3 ( # 115) 282
2-(2,3,4,5-Tetramethoxyphenyl)ethanamine TeMPEA ( # l14) 280
2-(2,3,4,6-Tetramethoxyphenyl)ethanamine TeMPEA-2 282


THA
2-(2,3,5,6-Tetramethoxyphenyl)ethanamine TeMPEA-3 ( # 115) 282
1 -(2,3,4,6-Tetramethoxyphenyl)propan-2-amine TeMA-2 282

see table under TeMPEA-3 ( #115)
1 -(2,3,4,6-Tetramethoxyphenyl)propan-2-amine TeMeA-2 306

1-(2,3,5,6-Tetramethoxyphenyl)propan-2-amine TeMA-3 282

2-(2,3,4,5-Tetramethylphenyl)ethanamine TeMePEA 306

2-(2,3,4,6-Tetramethylphenyl)ethanamine TeMePEA-2 306

2-(2,3,5,6-Tetramethylphenyl)ethanamine TeMePEA-3 306

1 -(2,3,4,5-Tetramethylphenyl)propan-2-amine TeMeA 306

1-(2,3,5,6-Tetramethylphenyl)propan-2-amine TeMeA-3 306

TFMA 1 -(4-(Trifluoromethyl)phenyl)propan-2-amine 133

2-TFMA 1-(2-(Trifluoromethyl)phenyl)propan-2-amine 133

3-TFMA 1-(3-(Trifluoromethyl)phenyl)propan-2-amine 133

3-TFMDMAP 2-(Dimethylamino)-1 -(3-(trifluoromethyl)phenyl) 226

propan-1-one
TFM-DFLY 1-(8-(Trifluoromethyl)benzo[ l,2-b:4,5-b ']difuran-4-yl) 48

propan-2-amine
TFM-FLY 1-( 8-(Trifluoromethyl)-2,3,6,7-tetrahydrobenzo 142

[ l,2-b:4,5-b ']difuran-4-yl)propan-2-amine
3-TFMMPEA N-Methyl-2-(3-(trifluoromethyl)phenyl)ethanamine 133

3-TFMPEA 2-(3-(Trifluoromethyl)phenyl)ethanamine 133

TFMPP mTFMPP ( # 116) 283
TFTP mTFMPP ( # 116) 283
THA 5-(2-Aminopropyl)benzene-1,2,3-triol 287


THA-2
THA-2 5-(2-Aminopropyl)benzene-1,2,4-triol 292

ThEA 2-(Thiophen-2-yl)ethanamine 139

3-ThEA 2-(Thiophen-3-yl)ethanamine 140

TH-FEA 2-(Tetrahydrofuran-2-yl)ethanamine 1 39
l-(Thiophen-2-yl)butan-2-amine a-Et-ThEA 139

THMA-2 5-(2-(Methylamino )propyl)benzene-1,2,4-triol 292

TH-NMEA 2-( 1-Methy lpyrrolidin-2-y l)ethanamine 140

2-TIM 2-(3,4-Dimethoxy-2-(methylthio)phenyl)ethanamine 153

3-TIM 2-(2,4-Dimethoxy-3-(methylthio)phenyl)ethanamine 153

4-TIM 2-(2,3-Dimethoxy-4-(methylthio )phenyl)ethanamine 1 52

TM 2-(3,5-Dimethoxy-4-(methylthio)phenyl)ethanamine 217
3-TM 2-(3,4-Dimethoxy-5-(methylthio)phenyl)ethanamine 217

TMA ( # ll7) 1-(3,4,5-Trimethoxyphenyl)propan-2-amine 285

1-(3,4,5-Trimethoxypheny1)-2-aminopropane
1-(3,4,5-Trimethoxybenzyl)ethylamine
2-Amino-1-(3,4,5-trimethoxyphenyl)propane
d/-a-Methylmescaline
NSC 167759
TMA-2 1-(2,4,5-Trimethoxyphenyl)propan-2-amine 287

see table under TMA (#11 7)
TMA-2 ( #118) 1-(2,4,5-Trimethoxyphenyl)propan-2-amine 291

2,4,5-TMA
1-(2,4,5-Trimethoxypheny1)-2-aminopropane
2,4,5-Trimethoxylphenylisopropylamine


TMeA-5
TMA-3 ( # 119) 1-(2,3,4-Trimethoxyphenyl)propan-2-amine 297

TMA-4 1 -(2,3,5-Trimethoxyphenyl)propan-2-amine 287

see table under TMA (#1 1 7)
TMA-4 ( # 1 20) 1 -(2,3,5-Trimethoxyphenyl)propan-2-amine 299

2,3,5-Trimethoxypheny lisopropy lamine

see table under TMA (#JJ 7)
TMA-5 ( # 121) 1-(2,3,6-Trimethoxyphenyl)propan-2-amine 301

TMA-6 1 -(2,4,6-Trimethoxyphenyl)propan-2-amine 287

TMA-6 ( # 1 22) 1 -(2,4,6-Trimethoxyphenyl)propan-2-amine 302

NSC 367445
2,4,5-TMA TMA-2 ( # 118) 291
TMAT 5,6, 7-Trimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine 288

TMCPA 2-(2,4,5-Trimethoxyphenyl)cyclopropanamine 74
3-TME 2-(3-(Ethylthio)-4,5-dimethoxyphenyl)ethanamine 217

see table under Mescaline ( #91 )
4-TME 2-(3-Ethoxy-5-methoxy-4-(methylthio)phenyl)ethanamine 217

see table under Mescaline ( #91 )
5-TME 2-(3-Ethoxy-4-methoxy-5-(methylthio)phenyl)ethanamine 217

TMeA 1 -(3,4,5-Trimethylphenyl)propan-2-amine 306

TMeA-2 1 -(2,4,5-Trimethylphenyl)propan-2-amine 306

TMeA-3 1-(2,3,4-Trimethylphenyl)propan-2-amine 306

TMeA-4 1-(2,3,5-Trimethylphenyl)propan-2-amine 306

TMeA-5 1 -(2,3,6-Trimethylphenyl)propan-2-amine 306


TMeA-6
TMeA-6 1-Mesitylpropan-2-amine 306

T-Mel N,N,N-Trimethyl-2-(3,4,5-trimethoxyphenyl)ethanaminium 216

TMePEA ( # 123) 2-(3,4,5-Trimethylphenyl)ethanamine 305

3,4,5-TMePEA
3,4,5-tris-Desoxymescaline
TMePEA-2 2-(2,4,5-Trimethylphenyl)ethanamine 306


TMePEA-4 2-(2,3,5-Trimethylpheny l)ethanamine 306

TMePEA-6 2-Mesitylethanamine 306

3,4,5-TMePEA TMePEA ( # 123) 305
TMMDA 1-(4,6,7-Trimethoxybenzo[d] [l,3] dioxol-5-yl)propan-2-amine 264

2T-MMDA-3a 1-(4-(Methylthio )benzo[d] [ l,3 ]dioxol-5-yl)propan-2-amine 240

4T-MMDA-2 1 -(5-Methoxybenzo[d] [ l,3 ]oxathiol-6-yl)propan-2-amine 239

see table under MMDA-2 ( # 98)
a,N,N-TMMDBA 1 -(Benzo[d] [ 1,3 ]dioxol-5-yl)-N,N-dimethylethanamine 80

a,a,N-TMMDBA 2-(Benzo[d] [l,3] dioxol-5-yl)-N-methylpropan-2-amine 80

a,a,N,N-TMMDBA 2-(Benzo[d] [l,3]dioxol-5-yl)-N,N-dimethylpropan-2-amine 80

TMPEA Mescaline ( #91) 212
TMPEA-2 2-(2,4,5-Trimethoxyphenyl)ethanamine 308

TMPEA-2 ( # 1 24) 2-(2,4,5-Trimethoxyphenyl)ethanamine 307

2,4,5-Trimethoxy-("l-phenethylamine
2C-O
2C-TMA-2
TMPEA-3 IM ( # 72) 152

5-TOM






f:l,3,4-TMPEA 2-(3,4-Dimethoxyphenyl)-2-methoxyethanamine 88
2,3,4-TMPEA IM ( # 72) 152
Tocosine Tyramine ( #126) 310
2-TOET 1-(4-Ethyl-5-methoxy-2-(methylthio )phenyl)propan-2-amine 108

5-TOET 1-( 4-Ethyl-2-methoxy-5-(methylthio )phenyl)propan-2-amine 108

p-Tolylaminopropane PMeA ( #111) 275
1 -(p-Tolyl)-2-aminopropane PMeA ( # 111) 275
2-(m-Tolyl)ethanamine 3-MePEA 244

2-(o-Tolyl)ethanamine 2-MePEA 242

see table under 2-MPEA ( #1 00)
2-(p-Tolyl)ethanamine 4-MePEA 247

1-(m-Tolyl)propan-2-amine 3-MeA 275

see table under PMeA ( #111)
1-(o-Tolyl)propan-2-amine 2-MeA 275

1 -(p-Tolyl)propan-2-amine PMeA ( # 111) 275
2-TOM 1 -(5-Methoxy-4-methyl-2-(methy lthio )phenyl)propan-2-amine 3

5-TOM 1 -(2-Methoxy-4-methy1-5-(methylthio )phenyl)propan-2-amine 3


5-TOMSO
5-TOMSO 1-(2-Methoxy-4-methy1-5-(methylsulfinyl)pheny l)propan-2-amine 123

TP 2-(3,5-Dimethoxy-4-(propylthio)phenyl)ethanamine 40
1 -(2,4,6-Tributoxyphenyl)propan- \If-BBB 304

2-amine see table under TMA-6 ( # 122)
Trichocereine ( # 1 25) N,N-Dimethyl-2-(3,4,5-trimethoxyphenyl)ethanamine 309

N,N-Dimethyl-3,4,5-trimethoxyphenethylamine
N,N-Dimethylmescaline
3,4,5-Trimethoxy-N,N-dimethylbenzeneethanamine
MM-M
2-(2,3,4-Triethoxyphenyl)ethanamine I-TRIS 153

2-(2,4,6-Triethoxyphenyl)ethanamine 2,4,6-TRIS 304

2-(3,4,5-Triethoxyphenyl)ethanamine TRIS 217

1-(2,4,5-Triethoxyphenyl)propan-2-amine EEE 293

2-(2,4,6-Triethylphenyl)ethanamine TEtPEA-6 306

1-(8-(Trifluoromethyl)benzo[l,2-b:4,5-b '] difuran- TFM-DFLY 48

4-yl)propan-2-amine see table under DFLY ( #32)
2-(3-(Trifluoromethyl)phenyl)ethanamine 3-TFMPEA 133

3-(Trifluoromethyl)phenylpiperazine mTFMPP ( # 116) 283
1 -(2-(Trifluoromethyl)phenyl)pi perazine oTFMPP 284

1-(3-(Trifluoromethyl)phenyl)piperazine mTFMPP ( # 116) 283
1-( 4-(Trifluoromethyl)phenyl)piperazine pTFMPP 284

1-(2-(Trifluoromethy l)phenyl)propan-2-amine 2-TFMA

133
1-(3-(Trifluoromethyl)pheny l)propan-2-amine 3-TFMA 133

1-(4-(Trifluoromethy l)pheny l)propan-2-amine TFMA 133

1-(8-(Trifluoromethy1)-2,3,6,7-tetrahydrobenzo TFM-FLY 142

[ 1,2-b:4,5-b ']difuran-4-yl)propan-2-amine see table under FLY ( #68)

1-(2,4,6-Trimethoxyphenyl)butan-2-amine
2,3,4-Trimethoxyamphetamine TMA-3 ( # 119) 297
2,4,6-Trimethoxyamphetamine TMA-6 ( # 1 22) 302
3,4,5-Trimethoxyamphetamine TMA ( #l17) 285
1-( 4,6,7-Trimethoxybenzo[ d] [1,3 ]dioxol-5-yl)propan- TMMDA 264

2-amine see table under PeMPEA ( # 1 08)
1-(3,4,5-Trimethoxybenzyl)ethylamine TMA ( # l17) 285
1 -(3,4,5-Trimethoxybenzyl)propylamine AEM ( # 1 ) 1
2-(3,4,5-Trimethoxybenzy1)-1,2,3,6- a,N-Butenyl-M 287

tetrahydropyridine see table under TMA ( # 11 7)
p,2,5-Trimethoxy-4-bromophenethylamine BOB ( # 13) 16
3,4,5-Trimethoxy-N,N-dimethylbenzeneethanamine Trichocereine ( # 1 25) 309
2,4,5-Trimethoxylphenylisopropylamine TMA-2 ( # 118) 291
p,2,5-Trimethoxy-4-methylbenzeneethanamine BOD ( # 14) 16
2,3,4-Trimethoxy-a-methylphenethylamine TMA-3 ( # 119) 297
2,4,5-Trimethoxy-a-methylphenethylamine TMA-2 ( #118) 291
2,3,4-Trimethoxyphenethylamine IM ( # 72) 152
3,4,5-Trimethoxyphenethylamine Mescaline ( #91) 212
3,4,5-Trimethoxy-p-phenethylamine Mescaline ( #91) 212
1 -(3,4,5-Trimethoxyphenethyl)-2,5-dihydro N,N-Butenyl-M 216

lH-pyrrole see table under Mescaline ( #91)
N-(3,4,5-Trimethoxyphenethyl)prop-2-en N-AL-M 216

l -amine see table under Mescaline ( #91)
1-(2,4,5-Trimethoxypheny1)-2-aminopropane TMA-2 ( # 11 8) 291
1-(3,4,5-Trimethoxypheny 1)-2-aminopropane TMA ( # l1 7) 285
1 -(2,3,4-Trimethoxyphenyl)butan-2-amine 4C-TMPEA-3 297

1-(2,4,5-Trimethoxyphenyl)butan-2-amine 4C-Me0 292

1-(2,4,6-Trimethoxyphenyl)butan-2-amine 4C-TMPEA-6 304


1-(3,4,5-Trimethoxyphenyl)butan-2-amine
1-(3,4,5-Trimethoxyphenyl)butan-2-amine AEM ( # 1 ) 1
4-(2,3,4-Trimethoxyphenyl)butan-2-amine homo-TMA-3 219



2-(2,4,5-Trimethoxyphenyl)cyclopropanamine TM CPA 74
2-(3,4,5-Trimethoxyphenyl)cyclopropanamine MCPA 74
1-(3,4,5-Trimethoxyphenyl)decan-2-amine AOM 287

2-(2,3,4-Trimethoxyphenyl)ethanamine IM ( # 72) 152
2-(2,3,4-Trimethoxyphenyl)ethanamine IM 216
2-(2,3,5-Trimethoxyphenyl)ethanamine TMPEA-4 300




2-(2,4,5-Trimethoxyphenyl)ethanamine TMPEA-2 ( # 1 24) 307


2-(3,4,5-Trimethoxyphenyl)ethanamine Mescaline ( #91) 212
2-(3,4,5-Trimethoxyphenyl)ethylamine Mescaline ( #91) 212
1-(3,4,5-Trimethoxyphenyl)heptan-2-amine AAM 287

1-(3,4,5-Trimethoxyphenyl)hexan-2-amine ABM 287

2,3,4-Trimethoxyphenylisopropylamine TMA-3 ( # 119) 297
2,3,5-Trimethoxyphenylisopropylamine TMA-4 ( # 120) 299

3,4,5-Trimethoxyphenylisopropy!amine TMA ( # 117) 285
1-(3,4,5-Trimethoxyphenyl)nonan-2-amine ASM 287

1-(3,4,5-Trimethoxyphenyl)octan-2-amine AHM 287

1-(3,4,5-Trimethoxyphenyl)pentan-2-amine APM 287

1-(2,3,4-Trimethoxyphenyl)propan-2-amine TMA-3 ( # 119) 297
1-(2,3,4-Trimethoxyphenyl)propan-2-amine TMA-3 287

1-(2,3,5-TrimethoxyphenyI )propan-2-amine TMA-4 ( # 120) 299

1 -(2,3,6-Trimethoxyphenyl )propan-2-amine TMA-5 ( # 121) 301



1-(3,4,5-Trimethoxyphenyl)propan-2-amine TMA ( # l17) 285
3-(3,4,5-Trimethoxyphenyl)propan-1-amine homo-Mescaline 219

N-(3,4,5-Trimethoxyphenethyl)propan-1-amine N-Pr-M 216

1-(3,4,5-Trimethoxyphenyl)propan-2-amine TMA ( # 117) 285
N-(1-(3,4,5-Trimethoxyphenyl)propan-2-yl) N-HO-TMA 287

hydroxylamine see table under TMA ( # 117)
1-(3,4,5-Trimethoxyphenyl)undecan-2-amine ANM 287

5,6,7-Trimethoxy-1,2,3,4-tetrahydronaphthalen- TMAT 288

2-amine see table under TMA ( # 117)
a,3,4-Trimethylphenethylamine DMeA ( #42) 75
3,4,5-Trimethylphenethylamine TMePEA ( # 123) 305

2-(2,3,4-Trimethylphenyl)ethanamine
2-(2,3,4-Trimethylphenyl)ethanamine TMePEA-3 306



2-(3,4,5-Trimethylphenyl)ethanamine TMePEA ( # 123) 305
1-(2,3,4-Trimethylphenyl)propan-2-amine TMeA-3 306


1 -(2,3,6-Trimethylphenyl)propan-2-amine TMeA-5 306


1-(3,4,5-Trimethylphenyl)propan-2-amine TMeA 306

N,N,N-Trimethyl-2-(3,4,5-trimethoxyphenyl) T-Mel 216

ethanaminium see table under Mescaline ( #91)
Tripstasy 2C-T-7 ( #27) 39
TRIS 2-(3,4,5-Triethoxyphenyl)ethanamine 217

3,4,5-tris-Desoxymescaline TMePEA ( # 1 23) 305
2,4,6-TRIS 2-(2,4,6-Triethoxyphenyl)ethanamine 304

3-TSB 2-(3-Ethoxy-5-(ethylthio)-4-methoxyphenyl)ethanamine 217

4-TSB 2-(3,5-Diethoxy-4-(methylthio)phenyl)ethanamine 217

3-T-TRIS 1-(3,4-Diethoxy-5-(ethylthio )phenyl)propan-2-amine 217

4-T-TRIS 2-(3,5-Diethoxy-4-(ethylthio)phenyl)ethanamine 217

Tweety-bird mescaline 2C-T-7 ( #27) 39
Tyramine ( # 126) 4-(2-Aminoethyl)phenol 310

4-Hydroxyphenethylamine
p-Tyramine
Sys to gene
Tocosine

Yaoto-wang (Japan)
(Tyramine con't) Tyrosamine 310

Utera
HPEA
4-HPEA
4-HO-PEA
NSC 249188
m-Tyramine Hordenine ( #71) 147
p-Tyramine Tyramine ( # 1 26) 310
Tyramine methyl ether 4-MPEA ( # 1 02) 245
Tyrosamine Tyramine ( # 126) 310
Ubulawu Nomathotholo 2C-B ( # 18) 20
UR 1430 DMAP ( #40) 72
UR 1431 METHCATH ( #92) 225
Uteramine Tyramine ( # 126) 310
Vanillylethylamine GEA ( #69) 143
Vanillyl-PEA GEA ( #69) 143
Venus 2C-B ( # 1 8) 20
White Mitsubishi PMA ( # llO) 267
XTC MDMA ( #82) 1 86
Xylopropamine DMeA ( #42) 75
Yaoto-wang Oapan) MDMA ( #82) 186

NOTES
NOTES
NOTES
NOTES
NOTES

The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds

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THE SHULGIN INDEX

BERKELEY, CA, USA

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For information contact:

Additional copies of this book may be purchased on our website

Editor, Layout and Project Manager

Cover and Jacket Design

Printed in the United States of America

First Edition, First Printing 2011

' .......�/" /'-';;i

Main Entry Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1

CAS Registry Numbers Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 363

Appendix A - Additional Notes on IUPAC Nomenclature . . . . . . . . . . 423

Appendix B - State Law on the Web . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 429

Appendix C - Mass Spectra . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 434

Alphab etical Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 665

What are the Psychedelics?

Aims and Scope

xii The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

How to use this Book

xiv The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

pharmacological, toxicological, and forensic literature. Code numbers applied by

Despite efforts to the contrary, scientific literature is often bedeviled by inconsistent or

xvi The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

Figure 1 . General structure and nomenclature of

Figure 2. Ring-numbering and compound name examples.

Figure 3. Examples of a furylethylamine and a phenylpiperazine,

The phenethylamines and amphetamines generally contain a six-carbon, unsaturated

Phenethylamines are abbreviated PEA, with substituents noted as prefixes. Thus,

xviii The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

2 2,3- DMA-2 2,3-Dimethoxyamphetamine

3 3,4,5- TMA 3,4,5-Trimethoxyamphetamine

4 2,3,4,5- TeMA 2,3,4,5-Tetramethoxyamphetamine

5 2,3,4,5,6- PeMA Pentamethoxyamphetamine

3- 4,5- MMDA 3-Methoxy-4,5-methylenedioxyamphetamine

The TMA series is of particular historical interest. TMA itself (3,4,5-trimethoxyamphet­

Code Structure Reference

2-CT CT is chlorotryptamine; 2 is the ring position

HOT N-Hydroxyphenethylamine thio ethers (e.g.: HOT-2,

xx The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

"psi") refers to a 2,6-dimethoxy arrangement, instead of the parent 2,5-dimethoxy pattern,

Synthesis and Chemistry

Fragmentation patterns of some fifty-five phenethylamines were determined by a variety

Exact Mass: 239.1521

Elemental Analysis: C, 65.25; H, 8.84; N , 5.85; 0 , 20.06

Main Entry Compounds

Synthesis and Chemistry

From homosyringonitrile (with ally! iodide, base) t o 3,5-dimethoxy-4-allylphenylaceto­

Exact Mass: 237. 1365

Synthesis and Chemistry

2 The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

Exact Mass: 241 . 1136

Homologues and Analogues

Main Entry Compounds 3

4 The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

Synthesis and Chemistry

Exact Mass: 255.1293

The electron withdrawing or donating nature of the 4-position substituent is correlated

Main Entry Compounds 5

Synthesis and Chemistry

Exact Mass: 269.1449

Synthesis and Chemistry

6 The Shulgin Index - Psychedelic Phenethylamines and Related Compounds

Exact Mass: 269.1449

The TMA series is of particular historical interest. TMA itself (3,4,5-trimethoxyamphet

From homosyringonitrile (with ally! iodide, base) t o 3,5-dimethoxy-4-allylphenylaceto

From 5-bromobourbonal (with Etl) t o 3-bromo-4,5-diethoxybenzaldehyde; (with butyl

N-trifluoroacetyl-2,3,6,7-tetrahydro-4-alanylbenzo[l,2-b;4,5-b'] difuran; (with triethylsi

Cross-reactivity of several substituted amphetamines with the Roche Abuscreen® radio