GC/MS Library of Various Over the

Counter Drugs
Grace Dauer
Introduction

Chemical Theory

As mentioned by the Organic II Laboratory

instructor and Chemistry Coordinator,
Daphne Olendorf, at Our Lady of the Lake
College (OLOLC), OLOLC is primarily a
medical-based college that offers classes
such as pharmacology, toxicology, and
biochemistry; yet, the college has no Gas
Chromatography/Mass Spectroscopy
(GC/MS) drug-specific library for those premed and pre-graduate school students
wanting to conduct research in
pharmacology or drug analysis (D.
Olendorf, personal communication, February
23, 2015). The proposed project aims to
complete a GC/MS library to contribute to
the education of students at this college.
Students enrolled in the Fall 2014 Organic I
laboratory course, used the GC/MS to
identify the active ingredients in various over
the counter drugs such as Advil and Tylenol.
The class had difficultly reading the mass
spectrums because students had no
information for comparison. This project will
provide comparison spectrums for future
chemistry labs at OLOLC. GC/MS is used in
forensic toxicology laboratories to identify
drugs in human tissue or separately.
Identifying the mass spectrums of various
drugs is a good way to learn about practical
applications of forensic toxicology. Research
has been done to create the most efficient
GC/MS libraries for drugs in toxicology
laboratories. Some studies have been
conducted to create procedures that yield
more precise mass spectrums for better
results as opposed to just inserting the
extracted drug into the instrument. I believe
that the colleges chemistry laboratory has a
gap in materials needed to teach students
about these disciplines specific to toxicology,
and propose that this issue be resolved via a
GC/MS drug library.

Based on the difference in polarities

and molecular weights of the various
drugs tested, each drug should have
different mass spectrums. GC/MS is
one instrument used for qualitative
testing, or testing to identify the
species or compound present. GC, or
gas chromatography, separates
compounds based on retention time
and polarity. The mobile phase that will
be used for the duration of this project
is helium gas, and the stationary
phase is a column packed with silica
gel. The gas chromatograph shows
different sized peaks, where each
peak represents a different molecule.
MS, or mass spectroscopy, will
remove an electron from the molecule,
causing it to fragment fragment the
molecule in a predictable way. The
mass spectrum shows lines of different
heights based on molecular weight. An
FTIR (Fourier Transform Infrared
Spectroscoper) will be used to help
confirm the identification of any
compounds present. In infrared
spectroscopy, IR radiation is passed
through a sample and some is
absorbed by the sample andsome of it
is transmitted. The resulting spectrum
represents the molecular absorption
and transmission, creating a molecular
fingerprint of the sample.

Procedure
Part A
Crush one tablet of ibuprofen using a
clean mortar and pestle and transfer the
powder to a labeled centrifuge tube. Add
2 mL of diethyl either and to the tube,
cap, and shake vigorously. Allow
undissolved fractions to settle at the
bottom of the tube.
After the powder settles after 2 minutes,
transfer the supernatant liquid to a new
centrifuge tube. Centrifuge the mixture for
about 2 minutes. Repeat process of
adding diethyl either until the supernatant
is clear.
Evaporate the solvent by placing the
beaker in a hot water bath. When all of
the solvent has evaporated, cool the
beaker to room temperature.
Repeat steps 1-3 using dichloromethane
(DCM ) in place of diethyl either.
Run both samples (from diethyl either
and from DCM) on the GC/MS and the
FTIR. Whichever solvent yields the best
GC peaks will be used for the other drugs
tested.
Part B
Repeat steps 1-3 in part A for each drug
listed using the solvent that yielded the
best GC peaks.
Acetaminophen
Naproxen
Ranitidine
Pseudoephedrine
Cetirizine

Hypothesis
Each drug will produce a different
mass spectrum and gas
chromatograph based on the
different functional groups and
molecular weights contained in the
active ingredients. The active
ingredients will be extracted using a
solid-liquid extraction procedure.
Each sample will be run on the
GC/MS, and finally on the FTIR for a
comparison. The differences on the
mass spectrum will show in different
line lengths, and the differences in
the mass spectrum will show in
different sized peaks.

References
Nair, H., Woo, F., Hoofnagle, A. N., & Baird, G. S. (2013). Clinical
Validation of a Highly Sensitive GC-MS Platform for Routine Urine Drug
Screening and Real-Time Reporting of up to 212 Drugs. Journal Of
Toxicology, 1-7. doi:10.1155/2013/329407.
http://web.a.ebscohost.com.ezproxy.ololcollege.edu:2048/ehost/d
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libraries. Journal Of Cheminformatics, 2(1), 1-12. doi:10.1186/1758-29462-9.
http://web.a.ebscohost.com.ezproxy.ololcollege.edu:2048/ehost/detail/det
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%40sessionmgr4001&hid=4104&bdata=JnNpdGU9ZWhvc3QtbGl2ZQ
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Yilmaz, B.; Erdem, A. Determination of Ibuprofen in Human Plasma and
Urine by Gas Chromatography/Mass Spectrometry. AOAC. Inter. [Online]
2014, 97, 415-420.
http://web.a.ebscohost.com.ezproxy.ololcollege.edu:2048/ehost/detail/det
ail?vid=15&sid=972fa100-efe6-4502-a64028128c046e68%40sessionmgr4001&hid=4114&bdata=JnNpdGU9ZWhvc
3QtbGl2ZQ%3d%3d#db=a9h&AN=95633969 (Accessed Feb 5, 2015).
Chemdata. Mass Spectral Library and Other Tools: Libraries.
http://chemdata.nist.gov/dokuwiki/doku.php?id=chemdata:start
(Accessed March 4, 2015).
Daphne Olendorf. Our Lady of the Lake College, Baton Rouge, LA.
Personal communication, 2015.