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ALKALOIDS

Chapter Outline
 Introduction
 Properties
 Functions of alkaloids in plants
 Methods of extraction and identification tests
 Classification
 Detailed study of;
• Pyridine - Piperidine alkaloids: Areca nut, Lobelia, Tobacco
• Tropane alkaloids: Belladonna, Hyoscyamus, Stramonium
• Quinoline alkaloids: Cinchona
• Isoquinoline alkaloids: Ipecacuanha, Opium
• Indole alkaloids: Rauwolfia, Catharanthus, Nux-vomica, Physostigma, Ergot
• Imidazole alkaloids: Pilocarpus
• Steroidal alkaloids: Veratrum
• Alkaloidal amines: Ephedra, Colchicum
• Purine Bases: Tea, Coffee

Introduction

• Alkaloids are basic nitrogenous organic compounds, usually of plant origin, that are physiologically active
• Alkaloids are derived from amino acids
• Many families of angiosperms have alkaloid yielding plants
• Gymnosperms only rarely contain alkaloids

Properties of Alkaloids

• Most alkaloids are crystalline solids, although a few are amorphous


• A few alkaloids lack oxygen in their molecules and are liquid e.g. coniine, nicotine, sparteine
• Normally alkaloids are white or colorless
• Few are colored e.g. berberine (yellow), salt of sanguinarine (copper red)
• Alkaloids usually contain 1 nitrogen atom (N), although some, like ergotamine, may contain upto 5
• The N may exist as primary amine (RNH2), as a secondary amine (R2NH) or as a tertiary amine (R3N)
• Because N bears an unshared pair of electrons, such compounds are basic and resemble ammonia’s
chemical properties
• Like ammonia, alkaloids are converted into their salts by aqueous mineral acids

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• When the salt of an alkaloid is treated with hydroxide ion, nitrogen gives up a hydrogen ion and the free
amine is liberated
• Quaternary ammonium compounds (R4N+X˗), such as tubocurarine chloride, has 4 organic groups
covalently bonded to N
• The quaternary ammonium ion, having no proton to give up, is not affected by hydroxide ion
• Free form of alkaloids;
o Insoluble or sparingly soluble in water
o Soluble in ether, chloroform and other relatively nonpolar solvents
• Salt form of alkaloids;
o Freely soluble in water

H H

H N + HCl H N H Cl
H H

Ammonia Ammonium chloride

OH NH CH3 OH NH CH3
CH C CH3 HCl CH C CH3 Cl
H +
H

Ephedrine

Ephedrine hydrochloride
(Ephedrinium chloride)

Functions of Alkaloids in Plants

• As poisonous agents, protect the plants against herbivorous animals and insects
• As by-products of various detoxification reactions, representing a metabolic locking up of compounds,
otherwise harmful or detrimental to the plant
• Alkaloids may be regulatory growth factors in plants
• Act as reserve substances in plants, capable of supplying nitrogen or other necessary elements

Methods of Extraction and Identification Tests

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Classification of Alkaloids

• There are 2 broad divisions of alkaloids;


1. Nonheterocyclic alkaloids 2. Heterocyclic alkaloids
1. Nonheterocyclic alkaloids
H3CO O
• Also called atypical alkaloids, protalkaloids, alkaloidal amines or
NH C CH3
biological amines
H3CO
• Don’t contain nitrogen in a heterocyclic OH NH CH3
OCH3
CH C CH3
ring H O
Colchicine
• Examples: Ephedrine, Colchicine Ephedrine
OCH3
2. Heterocyclic alkaloids
• Also called typical alkaloids or true alkaloids
• Contain nitrogen in a heterocyclic ring, derived from amino acids
• Heterocyclic alkaloids can be further classified, on the basis of the presence of the basic heterocyclic
nucleus, into following classes;
i. Pyridine - piperidine alkaloids
• The alkaloids which contain pyridine-piperidine nucleus in their chemical structure are called pyridine-
piperidine alkaloids.
• Crude drugs containing pyridine-piperidine alkaloids;
N
o Areca nut (arecoline)
N H
o Lobelia (lobeline) Pyridine Piperidine

ii. Tropane alkaloids


• The alkaloids which contain tropane nucleus in their chemical structure are called tropane alkaloids
• Crude drugs containing tropane alkaloids;
N CH3
o Belladonna ((–)-hyoscyamine)
Tropane
o Hyoscyamus ((–)-hyoscyamine)
o Stramonium ((–)-hyoscyamine, scopolamine)
iii. Quinoline alkaloids
• The alkaloids which contain quinoline nucleus in their chemical structure are called 3

quinoline alkaloids
2 N
• Crude drugs containing quinoline alkaloids; 1

o Cinchona (quinine, quinine, cinchonine, cinchonidine) Quinoline

iv. Isoquinoline alkaloids


• The alkaloids which contain isoquinoline nucleus in their chemical structure are called 4

isoquinoline alkaloids N1
3
• Crude drugs containing isoquinoline alkaloids; 2
Isoquinoline

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o Ipecacuanha (emetine, cephaeline, psychotrine)
o Opium (morphine, codeine, papaverine, noscapine)
v. Indole alkaloids
• The alkaloids which contain indole nucleus in their chemical structure are called indole alkaloids
• Crude drugs containing indole alkaloids;
o Rauwolfia (reserpine)
o Catharanthus (vinblastine, vincristine) N
Indole H
o Nux vomica (strychnine, brucine)
o Physostigma (physostigmine)
o Ergot (ergotamine, ergonovine)
vi. Imidazole alkaloids
N
• The alkaloids which contain imidazole nucleus in their chemical structure are called imidazole
alkaloids N

• Crude drugs containing imidazole alkaloids; H


Imidazole
o Pilocarpus (pilocarpine)
vii. Purine alkaloids
O
• The alkaloids which contain purine nucleus/base in their 7 H
H 1 1 H
chemical structure are called purine alkaloids N N
N N7
3
• Crude drugs containing purine alkaloids; O N N N N
3
Tea (caffeine, theophylline, theobromine) H Xanthine Purine
Coffee (caffeine)

Pyridine - Piperidine Alkaloids: Areca Nut, Lobelia, Tobacco N


N
H
Pyridine
Piperidine

Areca nut ‫ پان س پاری‬/ ‫چ ھالیہ‬

• Areca, areca nut or betel nut is the dried, ripe seed of Areca catechu (Fam. Palmae)

• Areca is mixed with lime, the leaves of Piper betel (‫ )پان کا پتا‬and occasionally gambir (Uncaria gambir)

• In India, this mixture is known as ‘pun-supari’ (‫)پان‬

• Betel chewing has been practiced since early times O


C OCH3
Constituents
• Alkaloids (0.45%) [these are reduced pyridine derivatives]
N
o Arecoline (0.2%) [most abundant and physiologically most active] Arecoline
CH3
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o Arecaidine
o Guvacoline
• Tannin (15%)
• Lipids
• Volatile oils
• Gum
Uses
• Anthelmintic in veterinary practice
• Employed as vermicide and taenifuge

Lobelia
• Lobelia or Indian tobacco consists of the dried leaves and tops of Lobelia inflata (Fam. Lobeliaceae)
• Lobelia was employed by the Indians, when necessity require, as a substitute for tobacco
Constituents
• 14 alkaloids
o Lobeline (major and most important alkaloid) O OH

• A pungent volatile oil N


• Resin CH3
Lobeline
• Lipids
• Gum
Uses
• Expectorant (Galenic preparations were formerly used as expectorant)
• Respiratory stimulant
• Lobeline sulfate is incorporated in tablets or lozenges that are intended to aid in breaking the tobacco
habit(smoking deterrent)

Tobacco ‫تم پاکو‬

• Tobacco consists of the cured and dried leaves of the Nicotiana tabacum (Solanaceae)
Constituents
• Nicotine (alkaloid)
N
• Carbohydrates
CH3
• Organic acids
Nicotine
Uses
• Sedative
• Narcotic
• Emetic

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• Antiseptic
• As insecticide

N CH3
Tropane Alkaloids: Belladonna, Hyoscyamus, Stramonium
Tropane

Belladonna
• Belladonna leaf, belladonna herb or deadly nightshade leaf consists of the dried leaf and flowering or
fruiting top of Atropa belladonna or of its variety acuminata (Fam. Solanaceae)
• ‘Atropa’ is from ‘Atropos’, meaning inflexible. Atropos is the name of Greek Fate who cuts the thread of
life, and probably refers to the poisonous character of the drug
• ‘Belladonna’ is from two Italian words ‘bella’ meaning beautiful, ‘donna’ meaning lady. This probably
refers to the fact that, juice of the berry of plant when placed in the eyes, causes dilation of the pupils,
giving an outstanding appearance
Collection
• The stems are cut about half way down when the fruits begin to form and the alkaloids are most abundant
(in June and July)
• After rains or irrigation, the plant produces a second crop of leaves and flowers, which are gathered in the
fall
• Herb crop is dried or partially dried and extracted with acidified water to obtain alkaloids
• A fine grade of leaf is obtained by hand picking the leaves and drying them rapidly at rather low
temperatures and in the shade
Constituents
• Alkaloids (ranging upto more than 1%)
o (–)-hyoscyamine (3/4th of the isolated alkaloid mixture)
o Atropine (1/4th of the isolated alkaloid mixture)
• Atropine is the racemic mixture of (–)-hyoscyamine and (+)-hyoscyamine. Atropine exists only in traces
in fresh plant. It is formed during extraction process
• Yield of alkaloids;
Roots: 0.6% O CH2OH

Stems: 0.05% N CH3 O C C


H
Leaves: 0.4% Hyoscyamine

Unripe berries: 0.19% O CH2OH


Ripe berries: 0.21% O N CH3 O C C
H
Seeds: 0.33% Scopolamine (Hyoscine)
Uses

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• Spasmolytic agent (due to parasympathetic depressant action)
• To control excess motor activity of GIT and spasm of urinary tract (due to its anticholinergic properties)

Hyoscyamus ‫اجوائن‬

• Hyoscyamus or henbane is the dried leaf, with or without the stem and flowering or fruiting top, of
Hyoscyamus niger (Fam. Solanaceae)
Constituents
• Alkaloids (0.05-0.15%)
o (–)-hyoscyamine (3/4th of the isolated alkaloid mixture)
o Scopolamine/hyoscine (in minor quantity)
Uses
• Hyoscyamus is parasympatholytic, but the crude drug is rarely employed in medicine today
Egyptian henbane
• Egyptian henbane is the dried leaves and flowering tops of Hyoscyamus muticus (Fam. Solanaceae)
• It yields about 1.5% of total alkaloids
• Major portion of alkaloids mixture is hyoscyamine

Stramonium
• Stramonium, jimson weed or Jamestown weed consists of the dried leaf and flowering or fruiting tops
with branches of Datura stramonium (Fam. Solanaceae)
Constituents
• Alkaloids (not less than 0.25%)
o (–)-hyoscyamine (most abundant)
o Scopolamine/hyoscine
Uses
• Powdered stramonium is an ingredient in preparations that are intended to burn. The resultant vapor is
inhaled for the relief of asthma

Stramonium seed
• Stramonium seed is the ripe seed of Datura stramonium (Fam. Solanaceae)
• It contains alkaloids (0.4%), principally hyoscyamine with a small portion of scopolamine and traces of
atropine
 Solanaceous alkaloids: (–)-hyoscyamine, atropine and scopolamine/hyoscine are called solanaceous
alkaloids

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3

Quinoline Alkaloids: Cinchona 2 N


1
Quinoline

Cinchona
• Cinchona, cinchona bark or Peruvian bark is the dried bark of the root of Cinchona succirubra, or its
hybrids, known in commerce as red cinchona; or of C. ledgeriana, C. calisaya, or hybrids of these with
other species of Cinchona, known in commerce as calisaya bark or yellow cinchona (Fam. Rubiaceae)
Constituents CH CH2
H
• Cinchona contains some 25 closely related alkaloids
HO N
• Most abundant alkaloids are;
R
o Quinine Quinine: R = OCH3
o Quinidine Cinchonidine: R = H
N
o Cinchonine CH CH2

o Cinchonidine HO
H N
• In yellow cinchona: Quinine exists in greater proportion
R
• In red cinchona: Cinchonidine exists in greater proportion
Quinidine: R = OCH3
• Cinchotannic acid (2-4%) N
Cinchonine: R = H

• Red color of cinchona bark is caused by an oxidase, similar to the oxidase that causes fruits to darken
when cut
Uses
• In the treatment of malaria fever
• In US, quinine is utilized primarily in the preparation of effervescent tonic water
• Quinidine is now the principal cinchona alkaloid employed therapeutically
• Cinchonism: Toxicity caused by overdoses of cinchona products. Symptoms are; temporary loss of
hearing, impaired sight, ringing in the ears

Isoquinoline Alkaloids: Ipecacuanha, Opium N1


3
2
Isoquinoline

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Ipecacuanha

• Ipecac consists of the dried rhizome and roots of the Cephaelis ipecacuanha, known in commerce as Rio
ipecac or Brazilian ipecac, or of C. acuminata known in commerce as Cartagena ipecac or Panama ipecac
(Fam. Rubiaceae). H3CO

Constituents
N
H3CO
• 5 alkaloids (2-2.5%)
• 3 principal alkaloids are; CH2CH3
o Emetine CH2

o Cephaeline H3CO
N
o Psychotrine
HO
• Starch (40%)
Psychotrine
• In Rio (Brazilian) ipecac:
H3CO
2/3rd of total alkaloids is emetine
N
1/3rd of total alkaloids is cephaeline H3CO
• In Cartagena (Panama) ipecac:
CH2CH3
2/3rd of total alkaloids is cephaeline CH2
rd
1/3 of total alkaloids is emetine H3CO H
N
Uses
• Emetic (in the form of a syrup) R

Usual dose is 15 ml, may be repeated once in 20 minutes Emetine: R = OCH3


Cephaeline: R = OH
• Ipecac syrup is included in poison antidote kit
• ‘Ipecac fluid extract’ is 14 times stronger than ‘Ipecac syrup’
• Ipecac mixed with opium, acts as a diaphoretic

Opium ‫افیم‬

• Opium or gum opium is the air dried milky exudate obtained by incising the unripe capsules of opium
poppy Papaver somniferum (Fam. Papaveraceae)
Cultivation, collection and commerce
• The cultivation of the opium poppy is controlled internationally by the International Narcotics Control
Board of the United Nations
• At the present time, licit (legal/lawful) production takes place primarily in India, Turkey, the Soviet Union
and China
• Poppy seeds are sown in October
• The seeds germinate in the fall
• Seedlings may be 2 to 3 cm high when snow falls, this protects them from freezing

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• In the spring, when the plants are about 15 cm (6 inches) in height, they are transplanted about 60 cm apart
• It blossoms in April to May
• Capsules mature in June or July
• Each plant bears 5 to 8 capsules
• Ripening capsules, about 4 cm in diameter, change in color from bluish green to yellowish
• This time is critical for latex collection
• The capsules are incised with a knife, which is usually 3 bladed, and the incision is made along the
circumference of the capsule
• Great skill is required so that endocarp is not cut. When endocarp is broken, the latex flows into the interior
of the capsule and is lost
• The latex, white at first, rapidly coagulates and turns brown
• Usually incision is done in the evening and the latex is removed (scraped off with a knife) in the early
following/next morning and is transferred to a poppy leaf
• Each capsule is incised several times at intervals of 2 or 3 days
• When sufficient latex is collected, it is kneaded (squeezed/pressed) into balls that are wrapped in poppy
leaves and dried in the shade
• The latex (opium) is the inspected
• After inspection, the opium is usually packed with the brown-winged fruits of a Rumex, which prevents
cohering (sticking/adhering)
Properties of opium
• Opium occurs as more or less rounded, somewhat flattened masses that are usually about 8 to 15 cm in
diameter and weigh from 300 g to 2 kg each
• Externally, opium is pale olive-brown or olive-gray
• It is covered with fragments of poppy leaves and, at times, with fruits of a species of Rumex that adheres
from the packing
• It is more or less plastic when fresh
• Becomes hard and brittle or tough when kept
• Internally, it is coarsely granular or nearly smooth, reddish brown, frequently interspersed with lighter
areas and somewhat lustrous
• Odor is characteristic
• Taste is bitter and characteristic
Constituents of opium
• Alkaloids (more than 30 alkaloids have been obtained from opium and its extracts)
• Most important of these alkaloids are;
o Morphine (4-21%)
o Codeine (0.8-2.5%)
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o Noscapine (4-8%)
o Papaverine (0.5-2.5%)
o Thebaine (0.5-2%)
• Other alkaloids are: Narceine, protopine, laudanine, codamine, cryptopine, lanthopine, meconidine
• Meconic acid (3-5%) [exists free or in combination with alkaloids]
 Meconic acid gives red color with ferric chloride solution. Because Meconic acid is found only in opium,
this test may be used for the detection of opium.
Commercial varieties of opium
• Turkish opium, Indian opium, Chinese opium
Uses
• Opium is a pharmaceutic necessity for powdered opium
• It acts chiefly on CNS
O
• First stimulates and then depresses nerve responses
OH
• Narcotic analgesic
• Hypnotic HOOC O COOH
• Checks excessive peristalsis Meconic acid
• Contracts the pupil of the eye

R
O HO

N
O CH3 O
N CH3
H3CO
O Morphine: R = OH
HO Codeine: R = OCH3
H3CO O
4
Noscapine O 2 N CH3 H3CO
3 1
H3CO
Morphine
N O
H3CO HO N CH3
OCH3
Bold lines indicate isoquinoline nucleus Thebaine
Papaverine H3CO

OCH3

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Indole Alkaloids: Rauwolfia, Catharanthus, Nux vomica
Physostigma, Ergot N
Indole H

Rauwolfia
• Rauwolfia is the dried root of Rauwolfia serpentina (Fam. Apocynaceae)
• Sometimes, fragments of rhizome and aerial stem bases are attached
Constituents
• From the 25 or more species of Rauwolfia investigated, at least 50 alkaloids have been reported
• The principal alkaloids are;
o Reserpine
o Rescinnamine
o Deserpidine H3CO N Reserpine
N
• Other minor alkaloids are; H OCH3
o Ajmaline O O
o Isoajmaline H3CO C O C OCH3

o Rauwolfinine OCH3
OCH3
o Serpentine
o Serpentinine
o Alstonine
Uses
• Hypotensive agent (due to reserpine)
• Has sedative activity (due to reserpine)

Catharanthus ‫سدا بہار‬

• Catharanthus or vinca is the dried whole plant of Catharanthus roseus (Fam. Apocynaceae), formerly
designated Vinca rosea
Constituents
• More than 55 different alkaloids have been isolated from catharanthus
• These alkaloids are generally indole and dihydroindole derivatives
• These alkaloids are present in two forms [1. Monomeric; 2. Dimeric]
• Monomeric alkaloid forms;
o Ajmalicine
o Serpentine
o Tetrahydroalstonine
o Lochnerine

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• Dimeric alkaloid forms;
OH
o Vinblastine C2H5
N
o Vincristine Vinblastine: R = CH3
Vincristine: R = CHO
o Vinleurosine
o Vinrosidine N COOCH3
N
• Anticancer property is found only in Dimeric alkaloids Indole H

• 500 kg catharanthus gives 1 g of vincristine C2H5


Uses H3CO N COOCH3
HO COOCH3
• Vinblastine Dihydroindole R

o Used to treat a wide variety of neoplasms


o Generalized Hodgkin’s disease and choriocarcinoma resistant to other therapy
• Vincristine
o To treat acute leukemia
o In combination therapy in Hodgkin’s disease

Nux vomica ‫کچلہ‬

• Nux vomica is the dried ripe seed of Strychnos nux-vomics (Fam. Loganiaceae)
Constituents
N
• Alkaloids (1.5-5%) R
o Strychnine (major alkaloid)
R
o Brucine N

Uses O O
• Circulatory stimulant Strychnine: R = H
• Brucine is less toxic than strychnine Brucine: R = OCH3

• Brucine is used commercially as alcohol denaturant

Physostigma
• Physostigma, Calabar bean or ordeal bean is the dried, ripe seed of Physostigma venenosum (Fam.
Leguminosae)
Constituents
• Physostigmine (eserine) [major alkaloid] O
CH3
H3C HN C O
• Eseramine
• Geneserine
N N
Physostigmine
• Physovenine CH3 CH3
Uses
• Physostigmne is reversible inhibitor of ACE

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• It decreases intraocular pressure
• It is used to treat glaucoma

Ergot
• Ergot, rye ergot or secale cornutum is the dried sclerotium of Claviceps purpurea (Fam. Hypocreaceae)
developed on plants of rye Secale cereale (Fam. Gramineae)
Constituents
• Alkaloids (not less than 0.15%)
o Ergonovine
o Ergotamine
o Mixture of ergocristine, ergokryptine and eregocornine
Formerly collectively known as ergotoxine
• Alkaloids of ergot can be divided into two types depending on their water solubility;
o Water soluble alkaloids (non-peptidal alkaloids): Ergonovine
o Water insoluble alkaloids (peptidal alkaloids): Ergotamine, ergotoxine
• Significant semisynthetic alkaloids: Methylergonovine, dihydroergotamine, hydergine, methysergide and
LSD
• All medicinally useful alkaloids (natural or semisynthetic) are derivatives of (+)-lysergic acid
• (+)-lysergic acid is readily converted to its isomer (+)-isolysergic acid. So, derivatives of (+)-isolysergic
acid are also present in the plant material and also produced during extraction process.
o Derivatives of (+)-lysergic acid: Physiologically/therapeutically active
o Derivatives of (+)-isolysergic acid: Physiologically/therapeutically inactive/inert
• Ergot also contains;
o Fixed oil (upto 35%)
o Steroids (ergosterol)
o Histamine
o Tyramine
Uses
• Ergot is a source of ergotamine which is used to treat migraine
• Dihydroergotamine, a semisynthetic analog of ergotamine, prepared by hydrogenation of the ∆9 double
bond in the lysergic acid nucleus. It is more effective and better tolerated than ergotamine.
• Ergot is a source of ergonovine which is used for the prevention and treatment of postpartum (occurring
in or relating to the period immediately after childbirth) hemorrhage caused by uterine atony (lack of
normal muscle tone)
• Methylergonovine, a semisynthetic homolog of ergonovine, is slightly more active and long lasting than
ergonovine

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• Ergotoxine (ergocristine+ergokryptine+eregocornine), a mixture of equal parts of these component
alkaloids is hydrogenated to eliminate the ∆9 double bond of lysergic acid nucleus and to yield an
equivalent mixture of dihydroergocristine, dihydroergokryptine and dihydroeregocornine.
o This mixture is used to treat selected symptoms in elderly patients
o They produce vasorelaxation, increased cerebral blood flow, lowering of systemic blood pressure and
bradycardia

COR COR
H 7 H 7
6 6
9 8 5 N CH3 9 8 5 N CH3

3 4 3 4

1 2 1 2
N N
H H
I II

R I II
OH (+)-Lysergic acid (+)-Lysergic acid
Lysergic acid amide Lysergic acid amide
NH2
(Ergine) (Erginine)
C2H5
Lysergic acid diethylamide
N
C2H5 (LSD)
H
HN C CH3 Ergonovine (Ergometrine) Ergometrinine
CH2OH

CH3 OH
O
HN N
N
O O Ergotamine Ergotaminine
H2C

• Methysergide maleate is a salt of methylergonovine


o It is a serotonin antagonist, used in the prophylaxis of vascular headache
• LSD, doesn’t occur in nature. It is prepared by semi-synthesis
o It has 2-fold action
o Produces a predominant central sympathetic stimulation that parallels a slight depression
o It is the most active psychotomimetic agent known
o LSD is of considerable interest and value in experimental psychiatry
o The drug is available only to qualified scientific investigators
Page 15 of 19
N

Imidazole Alkaloids: Pilocarpus N


H
Imidazole

Pilocarpus
• Pilocarpus or jaborandi consists of the leaflets of Pilocarpus jaborandi, of P. microphyllus, or of P.
pinnatifolius (Fam. Rutaceae)
• The plants are shrubs, indigenous to Brazil
Constituents
H2
• Pilocarpine (0.5-1%) C2H5 C CH3
N
• Isopilocarpine
• Pilocarpidine O O N
Pilocarpine
• Pilosine
• Even under ideal storage conditions, the leaves loose at least half of their Alkaloidal content in 1 year
through deterioration
• Leaves that are 2 years old are partially worthless
Uses
• In the treatment of glaucoma

Steroidal Alkaloids: Veratrum

Veratrum
• Veratrum viride, American or green hellebore consists of the dried rhizome and roots of Veratrum
viride (Fam. Liliaceae)
• The plant grown in wet meadows in the mountainous sections
Constituents
• It contains a large number of alkaloids, classified into 3 groups, on the basis of their chemical constitution
o Group I: Consist of esters of steroidal bases (alkamines) with organic acids
Examples: Cevadine, germidine, germitrine, neogermitrine, neoprotoveratrine, protoveratrine, veratridine
o Group II: Glucosides of the alkamines
Examples: Pseudojervine, veratrosine
o Group III: Alkamines
Examples: Germine, jervine, rubijervine, veratramine
 The ester alkaloids germidine and germitrine, are probably the most important therapeutically

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Uses CH3
• Hypotensive
Protoveratrine A
• Cardiac depressant N
• Sedative OH
• Valuable in the treatment of hypertension CH3
CH3 OH
• Small doses principally effect blood pressure O CH3
O OH
without notably changing respiratory rate or HO C O CH
O C CH2CH3
cardiac rate H3CH2C
CH3 OH OCOCH3 O
 Protoveratrines A and B are the active alkaloids OCOCH3
of V. album, and represent the constituents possessing hypotensive activity

Alkaloidal Amines: Ephedra, Colchicum

Ephedra
• Ephedra or ma huang is the entire plant or the overground portion of Ephedra sinica (Fam. Gnetaceae)
• It has been used as a medicine in China for more than 5000 years
• Its use in modern medicine began in 1923 with the discovery of the valuable properties of ephedrine
• At the present time, northwestern India and Pakistan represent the areas from which ephedra is obtained
Constituents
OH NH CH3
• Alkaloids (0.5-2.0%)
CH C CH3
H
o (–)-Ephedrine (major constituent)
Ephedrine
o Pseudoephedrine
Uses
• Potent sympathomimetic (both α and β)
• Causes vasoconstriction (when α receptors are activated)
• Causes bronchodilation and increased heart rate (when β receptors are activated)
• Produces effects similar to those of epinephrine
• Produces rather lasting rise of blood pressure, caused mydriasis and diminishes hyperemia

Colchicum
• Colchicum seed is the dried, ripe seed of Colchicum autumnale (Fam. Liliaceae)
• Colchicum corm is the dried corm of the same species
H3CO O
Constituents
NH C CH3
• Colchicine
H3CO
(upto 0.8% in the seed and 0.6% in the corm) OCH3
Uses O
Colchicine
• Source of colchicine OCH3

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• Colchicine is gout suppressant

O
1 H
H 1 7 H
N N7 N N
Purine Bases: Tea, Coffee 3
N N
3 O N N
Purine
H Xanthine

Tea
• Thea or tea consists of the prepared leaves and leaf buds of Camellia sinensis (Fam. Theaceae)
• It is a shrub or tree with alternate, evergreen leaves
Green tea
• It is prepared in China and Japan
• It is prepared by rapidly drying the freshly picked eaves in copper pans over a mild artificial heat.
• The leaves are often rolled in the palm of the hand as they dry
Black tea
• It is prepared in Siri Lanka and India
• It is prepared b heaping the fresh leaves until fermentation has begun. They are then rapidly dried
artificially with heat.
Properties of tea
• More or less crumpled, bright green or blackish green masses
• Odor is agreeable and aromatic
• Taste is pleasantly astringent and bitter
Constituents
• Alkaloids
o Caffeine (1-4%)
o Adenine (in small amount)
o Theobromine (in small amount)
o Theophylline (in small amount) O
o Xanthine (in small amount) H 1 7 H
N N
o Gallotannic acid (15%) 3
O N N
• Yellow volatile oil (0.75%)
H Xanthine
Solid at ordinary temperature, has a strong aromatic odor and taste
In xanthine nucleus;
1=CH3 3=CH3 7=CH3 1,3,7-trimethylxanthine Caffeine
1=CH3 3=CH3 7=H 1,3-diimethylxanthine Theophylline
1=H 3=CH3 7=CH3 3,7-dimethylxanthine Theobromine
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Uses
• Theophylline is smooth muscle relaxant, used for relief or prevention of bronchial asthma
• Theophylline possesses diuretic properties
• Caffeine is CNS stimulant

Coffee
• Coffee bean or coffee seed is the dried, ripe seed of Coffea arabica or C. liberica (Fam. Rubiaceae),
deprives of most of the seed coat
• Roasted coffee is coffee roasted until it acquires a dark brown color and develops the characteristic aroma
Constituents
• Caffeine (1-2%)
• Trigonelline (0.25%)
• Tannin (3-5%)
• Glucose and dextrin (15%)
• Fatty oil, consisting chiefly of olein and palmitin (10-13%)
• Proteins (10-13%)
• The aroma is caused by an oil, caffeol. It is produced during the roasting process
• Caffeine exist in combination with chlorogenic acid in unroasted seeds. During roasting process, caffeine
is freed from chlorogenic acid.
Decaffeinized coffee (coffee without caffeine)
• It is the coffee, prepared by extracting most of the caffeine from the coffee bean, yet retaining the pleasant
characteristic aroma of coffee
Uses
• Diuretic
• CNS stimulant
• To treat poisoning of certain CNS depressants
• Chlorogenic acid and caffeol are also physiologically active and responsible for unpleasant side effects
Hafiz Abdul Khaliq ֎ hakhaliq@yahoo.com

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