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ALKALOIDS

OBJECTIVES

To know what are the characteristics of


alkaloids

To know the different sources of alkaloids

To determine the importance of alkaloids and


to identify their applications in pharmacy

To know the different test in determining the


presence of alkaloids

WHAT ARE ALKALOIDS?

These are commonly applied to basic


nitrogenous compounds of plant origin
that are physiologically active.

Organic nitrogenous compounds with a


limited distribution in native nature.

STRUCTURE OF ALKALOIDS

CHARACTERISTICS:

They are bitter in taste.

Derived from amino acids

Alkaloids

form

double

salts

with

compounds of mercury, gold, platinum


and other heavy metals. These salts are
obtained

as

precipitate

microcrystallographic.

which

are

Most but not all alkaloids possess


basic

properties

owing

to

the

presence of amino nitrogen.

Structurally complex end products of


energy- requiring reaction
sequences.

Alkaloids usually contain one nitrogen


atom but some may contain 5 nitrogen
atoms

such

as

ergotamine.

The

nitrogen may exist as a primary amine


(RNH2),

secondary

amine

(R2NH),

tertiary amine (RN), or as quaternary.

PROPERTIES OF ALKALOIDS

Insoluble or sparingly soluble in water,


but the salts formed on reaction with
acids are usually freely soluble.

Most are crystalline solids although a


few are amorphous.

Free alkaloids are usually soluble in


ether, chloroform, or other relatively
non-polar immiscible solvents.

Some alkaloids are liquid because of


lacking of oxygen in their molecules.
(e.g coniine, nicotine, spartenine)

The degree of basicity varies greatly,


depending on the structure of the
molecule

and

the

presence

and

location of other functional groups.

Have high melting points

SOURCES AND OCCURRENCE OF ALKALOIDS

Alkaloids can occur in plant kingdoms;


among

the

angiosperms,

the

Leguminosae, Papaveraceae, Ranunculaceae,


Rubiaceae,

are
plants.

Solanaceae,

outstanding

and

Berberidaceae

alkaloid-yielding

The Labiatae and Rosaceae are almost


free of alkaloids; the gymnosperms only
rarely contain them (Taxaceae).

Specific alkaloids are confined to specific


plant families such as hyoscyamine in
Solanaceae, colchicine in Liliaceae

Although it has been claimed that the


monocotyledons

do

not

generally

produce alkaloids, investigations indicate


that the Amaryllidaceae and Liliaceae are
two of the most promising families (of a
list 11) in which to search for alkaloidyielding plants.

Occur in fungi (e.g ergot from Claviceps


purpurea)

Occur in various parts of the plant; in


seeds

(physostigma,

areca),

underground stems (sanguinaria), roots


(belladonna root), rhizomes and roots
(ipecac, hydrastis), barks (cinchona).

USES OF ALKALOIDS IN PLANTS:

Poisonous agents which protect plants


against insects and herbivores

End products of detoxification reactions


representing a metabolic locking-up of
compounds otherwise harmful to the
plants.

For regulatory growth factors

Reserve

substance

capable

of

supplying nitrogen or other elements


necessary to the plants economy

PHARMACOLOGIC ACTION OF ALKALOIDS:

Analgesic (morphine, codeine)


Narcotics (strychnine, brucine which
are central stimulant)
Mydriatics (atropine)
Miotics (physostigmine, pilocarpine)
Ephedrine (rises in blood pressure)
Reserpine (produce fall in excessive
hypertension)

BIOSYNTHESIS OF ALKALOIDS

The

biosynthesis

of

many

alkaloidal

structures can be rationalized through


simple chemical reactions that involve
amino acids.

The amino acids that are most often


serve

as

alkaloidal

precursors

are:

phenylalanine, tyrosine, tryptophan, histidine,


anthranilic acid, lysine and ornithine.

Some of the general reactions that are of


particular importance include:

decarboxylation

(removal of carboxyl group or carbon dioxide)


and transamination (transfer of an amino group
from one molecule to another without

the

formation of ammonia) of the amino acids to


yield a corresponding amine or aldehyde.

These can react to form a Schiff base which, in


turn can react with carbanion in a Mannichtype condensation.

TEST FOR ALKALOIDS


Wagners Test

(+) Reddish brown precipitate


Reagent
used:
Wagners
Reagent
[Solution of iodine in potassium iodide]
Mayers Test

(+) Cream color precipitates


Reagent used: Mayers Reagent
[Potassium mercuric iodide solution]

Dragendorffs test

(+) Orange precipitate


Reagent

used:

Dragendorffs

reagent

[Potassium bismuth iodide solution]


Hager's test

(+) Yellow color precipitate


Reagent

used:

Hager's

reagent

[saturated solution of Picric acid]

Tannic acid test

(+)buff color precipitate


Reagent used: 10% Tannic acid solution
Valsers Test

(+) white precipitate


Reagent used: Valsers reagent
(Mercuric Iodide TS

NAMING FOR ALKALOIDS

From the

generic name

or the

genus

of the plant

yielding them (e.g hydrastine, atropine)

The

specific name

or

species

of the plant yielding

alkaloids ( e.g cocaine, belladonnine)

Common name

ergotamine)

of the drug yielding them (e.g

From

their

physiologic

activity

(e.g

emetine, morphine)

From the discoverer (e.g pelletierine)

~ All names of alkaloids should end in -ine.


~ A prefix or suffix is added to the name of a
principal alkaloid from the same source.
(quinine, quinidine, hydroquinine)

CLASSIFICATION OF ALKALOIDS

Pyridine- Piperidine Combined


Tropane
Quinoline
Isoquinoline
Indole
Imidazole
Steroid
Alkaloidal amine
Purine

PYRIDINE- PIPERIDINE COMBINED

Also referred to as Pyrrolizidine


alkaloids

Upon

reduction,

pyridine,

is

the

tertiary

converted

secondary base, piperidine.

into

base,
the

3 Subgroups
Derivatives

of piperidine

Derivatives

of nicotinic acid

Derivatives

of both pyridine and

pyrrolidine

Important alkaloidal drugs and alkaloids


that are classified in this group are:

Areca
Arecoline
Hydrobromide
Lobelia
Lobeline
Nicotine

NICOTINE

A primarily product of
root metabolism, but
the formation of small
amounts, as well as
subsequent reactions
such as demethylation
of nicotine, can occur
in leaves of plants.

It is a pyridine alkaloid obtained from


the dried leaves of the tobacco plant
Nicotiana

tabacum

Linn

(Fam.

Solanaceae)

Nicotiana was named after Jean

Nicot
Europe

who

introduced

tobacco

in

Tabacum refers to the Indian name


for the pipe or tube used in smoking it

It is colorless to pale yellow, very


hygroscopic, oily, volatile liquid with
unpleasant, pungent odor and a sharp,
burning, persistent taste.

USES:

It is bound to an ion exchange resin in a


chewing gum base as a temporary aid to
the cigarette smoker seeking to give up
smoking.

Chronic use of nicotine may result in


psychological and physical dependence.

ARECA

Areca nut or Betel


Nut

A dried, ripe seed of


Areca catechu
(Fam. Palmae)

Areca- a Spanish
and Portuguese
term for betel nut

Catechu-

East

Indian

name

for

an

astringent extract or juice

Areca mixed with lime, the leaves of Piper


bette Linn and occasionally gambir is
known as PUNSUPARI. This mixture is
used as a stimulant masticatory.

Consists of 0.45% alkaloids, 15% tannins,


lipids, volatile oils and gum.

Uses:

Pharmaceutic purposes

Anthelmintic or vermicide in veterinary


practice

Taenifuge

Constituents:

These are reduced

pyridine derivatives.

Arecoline (arecaidine methyl ester) <most


abundant and physiologically active>

Arecaidine (N-methyl guvacine)

Guvacine (Tetrahydronicotinic acid)

Guvacoline (Guvacine methyl ester)

LOBELIA

Indian tobacco

Consists of dried leaves


and tops of Lobelia
inflata Linn (Fam.
Lobeliaceae)

Lobelia named in
honour of a Flemish
botanist Matthias de L
Obel

Inflata refers to a hollow and distended


fruit

Substitute for tobacco

Uses:

Similar but weaker pharmacological effects


in nicotine on the peripheral circulation,
neuromuscular junctions, and CNS.

Anti-smoking preparations

Lobeline

sulfate

incorporated in tablets or

lozenges are smoking deterrents.

Lobeline

had placebo effect on decreasing the

physical craving for cigarettes.

Traditionally used by the Native Americans for

asthma
Chronic bronchitis

Injection of lobeline hydrochloride is used in


the resuscitation of newborn infants

Constituents:

Contains 14 alkaloids which

LOBELINE is the major and most important.


It has a pungent, volatile oil, resin, lipids,
and gum.

Lobeline, (-) lobeline or alpha lobeline


This occurs as colorless crystals which are
slightly soluble in water but readily soluble in
hot alcohol.

TROPANE ALKALOIDS

A dicyclic compound formed by the condensation


of a pyrrolidine precursor (ornithine) with three
acetate-derived carbon atoms. Both pyrrolidine
and piperidine ring system can be discerned in
the molecule.

The 3-hydroxy derivative of tropane is known as


tropine. Its esterification with (-)- tropic acid
yields hyoscamine (tropine, tropate), which may
be racemized to form atropine.

Important alkaloidal drugs and alkaloids


that are classified in this group are:

Belladonna leaf
Hyoscyamus
Stramonium
Atropine
Hyoscyamine
Scopolamine
Coca
Cocaine

BELLADONNA

Belladonna leaf,
Belladonna herb or deadly
nightshade leaf

Consists of dried leaf and


flowering or fruiting top of
Atropa belladonna

Linn or

of its variety acuminata


Royle ex Lindley (Fam.
Solanaceae)

Atropa is from Atropos meaning


inflexible

Belladonna

from

Italian

word

bella meaning beautiful and donna


meaning lady
Uses:

It acts as an antimuscarinic agent


which

accounts

for

its

use

as

Used as a adjunctive therapy in the treatment


of peptic ulcer; functional digestive disorders

It possesses anticholinergic properties and is


used to control excess motor activity of the GI
tract and spasm of the urinary tract.

It is commonly administered in the tincture


(3mg alkaloids/ 100ml) or the extract (1.25 g
alkaloids/100g)

Constituents:

(-)- hyoscyamine
remainder atropine
Apoatropine
Belladonnine
Cuscohygrine
Scopolamine

SOLANACEOUS ALKALOIDS

The principal alkaloids of this group are:

(-) hyoscyamine

atropine [() hyoscyamine]

scopolamine (also known as hyoscine)

These are tropine derivatives and esters and may


be

prepared

synthetically

but

are

usually

obtained by extraction from plants of the


Solanaceae such as:

Atropa belladonna

Datura stramonium

Hyoscyamus niger

Hyoscyamus muticus (also known as Henbane)

Dubosia plants

Atropine

An antidote in case of poisoning


caused by cholinesterase inhibitors.

It is a CNS stimulant.

Scopolamine

It has a depressant activity on the CNS.

It is used to treat motion sickness.

It

is

employed

for

preanesthetic

sedation and for obstetric amnesia in


conjunction with analgesics and to
calm delirium.

Toxicity symptoms occur in using


atropine, scopolamine and belladonna
tincture include:
Skin rash
Skin flushing
Mouth dryness
Difficulty in urination
Eye pain
Blurred vision
Light sensitivity

Hyoscyamine

a tropine ester of (-)-tropic acid

Hyoscyamine sulfate

extremely poisonous

It occurs as white, odourless crystals or as


crystalline powder.

It is a deliquescent and is affected of light.

It is an anticholinergic and used as an


aid in the control of gastric secretion,
visual spasm, hypermotility in spastic
colitis, pylorospasm and abdominal
cramps.

In Parkinsonism, it is used to reduce


rigidity and tremors and to control
associated

sialorrhea

and

Atropine sulfate

It occurs as colorless crystals or as a


white, crystalline powder.

It is extremely poisonous.

It effloresces in dry air and is slowly


affected by light.

It is an anticholinergic, used in surgery as


an antisialogogue.

Scopolamine or hyoscine

An alkaloid abundant in Datura fastuosa var.


alba and in D. Metel.

It is an ester that, upon hydrolysis, yields


tropic acid and scopoline.

It occurs as an almost colorless, syrupy


liquid from its chloroformic solution and
colorless crystals from its ether solution.

LEVOROTATORY

Scopolamine hydrobromide or hyoscine


hydrobromide

It occurs as colorless or white crystals or as a white,


granular powder that is odourless and slightly
efflorescent in dry air. It is extremely poisonous.

It is classified as anticholinergic.

It is employed for preanesthetic sedation and for


obstetric amnesia in conjunction with analgesics
and to calm delirium. It is administered SC or IM in a
single dose.

Hyoscyamus

Also known as Henbane

dried leaf with or without the stem


and

flowering

Hyoscyamus

or

fruiting

niger

crop

of

Linn

(Fam.

than

0.04%

Solanaceae)

It

contains

not

less

alkaloids of hyoscyamus.

Hyoscyamus

(a Greek and Latin

name formed from two Greek words,


meaning hog and bean.

The plant is poisonous to swine.

The

alkaloids,

scopolamine,

hyoscyamine

0.05%

to

0.15%

and
of

which three fourths is hyoscyamine


are the active ingredients.

HYOSCYAMUS

STRAMONIUM

Also known as Jimson


weed, Jamestown
weed

dried leaf with or


without the stem and
flowering or fruiting
crop of Datura
stramonium Linn
(Fam. Solanaceae)

It yields not less than 0.25% of alkaloids.

Datura (from Sanskrit dhatura, and from


Arabic tatura or tatula, the native name)

Stramonium

(from the French word

stramoine meaning stinkweed)

It was used as a pot herb

It can serves as atropine

STRAMONIUM SEED

from D. stramonium

The seed contains


0.4% of alkaloids,
principally
hyoscyamine with a
small portion of
scopolamine and
traces of atropine.

It is generally regarded as a noxious weed


and has frequently caused poisoning in

children when seeds were ingested.


The chief toxic symptoms are those of
atropine:
Dilated pupils
Impaired visions
Dryness of the skin
Secretions
Extreme thirst
Hallucination
Loss of consciousness

COCAINE

Coca leaves or Coca

Dried leaves of
Erythroxylum coca
Lamarck which is
commercially known as
Huanuco coca or of E.
truxillense Rusby
Truxillo coca (Fam.
Erythroxylaceae)

Erythroxylum (is from the two Greek


words meaning red and wood)

Coca ( is the Spanish name for the tree)

Truxillense (from Truxillo a coastal city

in Peru)
Contains three basic types of alkaloids:
Derivatives of ecgonine
Derivatives of tropine
Derivatives of hygrine

Huanuco coca

Contains 0.5 to 1% of ester


alkaloids, derivatives of tropine and
ecgonine

Cuscohygrine is the principal


nonester alkaloid in the leaf.

Truxillo coca

Has lower content of ester alkaloids


but higher percentage of cocaine
(75%)

The shrub was known as The Divine


Plant of the Incas

Cocaine hydrochloride

Colorless

crystals

or

as

white,

crystalline powder.

Ingredient in Bromptons cocktail

Use to control severe pain

CNS stimulant

Administered IV or SC while cocaine freebased is smoked

Crack

extremely addictive smokable forms


of cocaine processed from cocaine
hydrochloride

Its name refers to the sound made


when rocks of cocaine are smoked.

QUINOLINE ALKALOIDS

These are alkaloids which contain quinoline as their


nucleus

including

those

obtained

from

cinchona

(quinine, quinidine, cinchonine, and cinchonidine)

Cinchona and its alkaloids are the only members of


this

group

that

are

therapeutically

important

at

present. Cinchonine, is isomeric with cinchonidine


which is the parent alkaloid of the quinine series.
Quinine

and

its

methoxycinchonine.

isomer,

quinidine,

represent

6-

CINCHONA BARK

Cinchona bark or Peruvian bark

dried bark of the stem or of the root of


Cinchona succirubra Pavon et Klotzch or its
hybrids, known in commerce as red cinchona
or of C. ledgeriana (Howard) Moens et
Trimen, C. calisaya Weddell, or hybrids of
these with other species of Cinchona, known
in commerce as calisaya bark or yellow
cinchona (Fam. Rubiaceae)

Cinchona (named in honor of the


Countess of Chinchon, wife of viceroy of
Peru)

Succirubra (Latin word meaning red


juice)

Calisaya (a tree)

Ledgeriana

Charles Ledger)

named

in

honor

of

Cinchona toxicity results in temporary loss


of hearing and in impaired sight. Ringing in
the ears is one of the symptoms of toxicity.

When these symptoms are produced as the


result of continuous use of cinchona or of
quinine. The condition has been called
cinchoism.

Cinchona was formerly given in doses of 1g.

CUPREA BARK

obtained from Remijia purdieana Triana and


R. Pedunculata Fluckiger (Fam.Rubiaceae)

it has a copper red color hard , compact, and


heavy

it

contains

numerous

transversely

elongated stone cells and 2-6 % of alkaloids of


which 1/3 maybe quinine its a commercial
source of quinidine.

CINCHONA ALKALOIDS

Quinidine

Its a stereoisomer of quinine and is


present in cinchona barks to the extent
of 0.25-1.25%.

It depresses myocardial excitability,


conduction velocity and to a lesser
extent, contractility.

Use

to

treat

various

cardiac

arrhythmias such as mature atrial , AV


junctional, and ventricular contractions
: atrial flutter and atrial fibrilations.

When administered orally, the peak


serum levels are slightly lower with the
gluconate and poylgalacturonate salt
than with sulfate salt .

The usual real dose available is 10 to 20


mg/kg/day in 4 to 6 divided doses in order to
obtain the average therapeutic serum levels
of 3 to 6mcg/ml.

toxic

reaction

occurs

at

levels

above

8mcg/ml.

The patient should be instructed to notify the


physician if skin rash,fever,unusual
bleeding/bruising,ringing in the ears,or visual
disturbance occurs.

Quinidine sulfate

sulfate of an alkaloid obtain from cinchona from


Remijia pedunculata or prepared from quinine.

It occurs as fine needle like white crystals that


frequently cohere in masses.

It is odorless , has a bitter taste and darkens


when exposed to light.

It is readily soluble in water, alcohol, methanol


and chloroform.

Quinidine gluconate

It occurs as a white powder odorless


and has a bitter taste available in
sustained release tablet.

Quinidine polygalacturonate

It affords control and more uniforms


absorptions through the intestinal
mucosa than does quinidine sulfate.

In

addition

it

produces

incidence of GI irritation

lower

Quinine

Diastereoisomer of quinidine

It occurs as white, odourless, bulky


crystals or as a crystalline powder.

It darkens when exposed to light and


effloresces in dry air.

It is freely soluble in alcohol, ether and


chloroform but slightly soluble in water.

Quinine Sulfate

a sulfate of an alkaloid obtained from the


bark of Cinchona species.

A white, odourless, bitter, fine, needlelike


crystals that are usually lusterless.

It becomes brownish when exposed to light.

It is not readily soluble in water, alcohol,


chloroform or ether.

Uses

Antimalarial

For treating of chloroquinine resistant falciparum


malaria combination with pyrimethamine and
sulfadoxine or tetracycline or clindamycin.

It has a skeletal muscle relaxant effect.

It

is

widely

used

for

the

prevention

and

treatment of nocturnal recumbency leg cramps.

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