ALKALOIDS

PREPARED BY: NIMRA MAZHAR

INTRODUCTION

 One of the largest groups of chemicals produced by plants is the alkaloids.

 Many of these metabolic by-products are derived from amino acids and
include an enormous number of bitter, nitrogenous compounds.
 Alkaloids often contain one or more rings of carbon atoms, usually with a
nitrogen atom in the ring.
 The position of the nitrogen atom in the carbon ring varies with different
alkaloids and with different plant families.
 Position of the nitrogen atom that affects the properties of these alkaloids.
 They are important as analgesics, antimalarial, antispasmodics, for pupil
dilation, treatment of hypertension, mental disorders and tumors.
INTRODUCTION

 Although they undoubtedly existed long before humans, some alkaloids

have remarkable structural similarities with neurotransmitters in the central
nervous system (CNS) of humans, including dopamine, serotonin and
acetylcholine.
 The amazing effect of these alkaloids on humans has led to the
development of powerful painkiller medications, spiritual drugs, and serious
addictions by people who are ignorant of the properties of these powerful
chemicals.
EXAMPLES OF ALKALOIDS
DEFINITION

 An alkaloid is a nitrogenous organic molecule that has a pharmacological

effect on humans and animals.
 They are a class of compounds which typically contain nitrogen and have
complex ring structures.
OCCURENCE

 Alkaloids are found as secondary metabolites in plants (e.g. in Vinca and

Datura), animals (e.g. in shellfish) and fungi, and can be extracted from
their sources by treatment with acids (usually hydrochloric acid or sulphuric
acid, though organic acids, such as maleic acid and citric acid are
sometimes use.
 Usually alkaloids are derivatives from amino acids. Even though many
alkaloids are poisonous (e.g. strychnine or coniine), some are used in
medicine as analgesics (pain relievers) or anaesthetics, particularly
morphine and codeine.
 Most alkaloids have a very bitter taste.
 CHEMICAL CLASSIFICATION

 There are three main types of alkaloids

 (1) true alkaloids
 (2) protoalkaloids
 (3) pseudoalkaloids.
 True alkaloids and protoalkaloids are derived from amino acids, whereas
pseudoalkaloids are not derived from these compounds.
True Alkaloids

 True alkaloids derive from amino acid and they share a heterocyclic ring
with nitrogen.
 These alkaloids are highly reactive substances with biological activity even
in low doses.
 All true alkaloids have a bitter taste and appear as a white solid, with the
exception of nicotine which has a brown liquid.
 True alkaloids may occur in plants
 (1) in the free state
 (2) as salts
 (3) as N-oxides
 Examples are cocaine, quinine, dopamine and morphine.
TRUE ALKALOIDS

Dopamine
Qunine
Protoalkaloids

 Protoalkaloids are compounds, in which the N atom derived from an amino acid is
not a part of the heterocyclic.
 They form a minority of all alkaloids, Hordenine, mescaline and yohimbine.
 New alkaloids, stachydrine and 4-hydroxystachydrine, derived from Boscia
angustifolia.
 Boscia angustifolia is used for the treatment of mental illness, and occasionally to
combat pain and neuralgia.
Protoalkaloids

Hordenine

Yohimbine
Pseudoalkaloids

 Pseudoalkaloids are compounds, the basic carbon skeletons of which are

not derived from amino acids.
 In reality, pseudoalkaloids are connected with amino acid pathways.
 They are derived from the precursors or post-cursors (derivatives the
indegradation process) of amino acids.
 These alkaloids can also be derived from non aminoacid precursors.
 Examples of pseudoalkaloids include such compounds as coniine,
capsaicin, ephedrine, solanidine, caffeine and theobromine.
Pseudoalkaloids

Capsaicin
Atypical alkaloids & Typical alkaloids

 These are also known as nonheterocyclic alkaloids and contain nitrogen in

aliphatic chain.
 Typical alkaloids are also known as heterocyclic alkaloids and contain
nitrogen in heterocyclic ring system.
CLASSIFICATION ACCORDING TO TYPE
OF RING STRUCTURE

 DERIVATIVES OF TROPENE
 (atropine, hyosciamine, cocaine)

Tropine
CLASSIFICATION ACCORDING TO TYPE
OF RING STRUCTURE

 DERIVATIVES OF QUINOLIZINE AND QUINOLIZIDINE (NOR-LUPINANE)

 E.g sparteine, cytisine

Quinolizine Quinolizidine
CLASSIFICATION ACCORDING TO TYPE
OF RING STRUCTURE

 DERIVATIVES OF QUINOLINE & ISOQUINOLINE

 opium alkaloids

Quinoline Isoquinoline
OPIUM ALKALOIDS
 CLASSIFICATION ACCORDING TO TYPE
OF RING STRUCTURE

 DERIVATIVES OF IMIDAZOLE
 pilocarpine

H N N

Imidazole
CLASSIFICATION ACCORDING TO TYPE
OF RING STRUCTURE
DERIVATIVES OF INDOLE
physostigmine, strychnine, ergot alkaloids

Indole
CLASSIFICATION ACCORDING TO TYPE
OF RING STRUCTURE

 DERIVATIVES OF PURINE
 caffeine, theobromine, theophylline

Purine
IMPORTANCE

 Alkaloids are substances very well known for their biological activity at the
beginning of world civilization.
 They were used in shamanism.
 only alkaloids are molecules of natural origin with highly important benefits
and diagnostic uses.
 They can be characterized as the most useful and also the most
dangerous products of nature.
 Alkaloids are most abundant in higher plants.
 At least 25% of higher plants contain these molecules.
 FUNCTIONS OF ALKALOIDS

 They may act as reserve substances to supply nitrogen.

 They may be end products of detoxification mechanisms otherwise their accumulation in
plants may otherwise cause damage to the plants.
 They may act as a poisonous substance which afford plant safety from herbivores and
insects.
 They may function as plant stimulants or regulators similar to the hormone in the activities
like growth, metabolism and reproduction.
 They may act as reservoirs for protein synthesis.
ALKALOIDS

ALKALOID SOURCE PHYSIOLOGICAL

ACTIVITY
Quinine Cinchona Bark Anti-Malarial
Reserpine Rauwolfia Hypertension and
mental disorders
Morphine Opium poppy plant Powerful analgesic
Codeine Opium poppy plant Pain killer, cough
suppressant
Atropine Belladonna Used for dilation of pupil
Nicotine Tobacco plant Stimulant
Colchicine Meadow saffron Gout
EXTRACTION

 The extraction of alkaloids is based on their basic character and solubility

profiles. Generally alkaloids are extracted mainly using two methods.
METHOD A The powdered material that
contains alkaloidal salts is
moistened with alkaline substances
like sodium bicarbonate, ammonia,
calcium hydroxide, etc., which
combines with acids, tannins and
other phenolic substances and sets
free the alkaloids bases.

Extraction is then carried out with organic solvents

such as ether or petroleum spirit.

The concentrated organic liquid is then shaken with aqueous acid

and allowed to separate. Alkaloid salts will be present in aqueous
liquid, while many impurities remain behind in the organic liquid.
METHOD B

The collected powdered material is extracted with water or

aqueous alcohol containing dilute acid. Chloroform or other
organic solvents are added and shaken to remove the
pigments and other unwanted materials.

The free alkaloids are then precipitated by the addition of excess

alkalis like, sodium bicarbonate or ammonia and separated by
filtration or by extraction with organic solvents.
IDENTIFICATION TESTS

 The chemical tests are performed from neutral or slightly acidic solution of drug.
 DRAGENDORFF’S TEST
 Drug solution + Dragendroff ’s reagent (Potassium Bismuth Iodide), formation of Orangish
red color.
 MAYER’S TEST
 Drug solution + few drops of Mayer’s reagent (potassium mercuric iodide), formation of
creamy-white precipitant.
IDENTIFICATION TESTS

 HAGER’S TEST
 Drug solution + few drops of Hagers reagent (Saturated aq. Solution of Picric
acid), formation of crystalline yellow precipitate.
 WAGNER’S TEST
 Drug solution + few drops of Wagner’s reagent (dilute Iodine solution),
formulation of reddish-brown precipitate.
 TANNIC ACID TEST
 Drug solution + few drops of tannic acid solution, formation of buff colored
precipitate.
PYRIDINE & PIPERIDINE ALKALOIDS

Pyridine
Piperidine
ARECA NUT

 Areca nut consist of pyridine and piperidine alkaloids.

SYNONYMS
 Betal nuts; Pinang; Semina Areacae, Supari (Hindi).
BIOLOGICAL SOURCE
 Areca nuts are the seeds of
Areca catechu Linn., belonging to family Palmaceae.
 CHEMICAL CONSTITUENTS

 Areca nut contains a number of alkaloids of a piperidine series, such as arecoline (methyl
ester of arecanine), arecaine (N-methyl guvacine), guvacine (tetrahydronicitinic acid),
arecaidine, guvacoline, arecolidine, leucocyanidine, (+)-catechin, (-)-epicatechin,
procyanidins A-l, B-l and B-2; phthalic, lauric, myristic, palmitic and stearic acids, β-sitosterol
and choline.
 Arecoline is present in about 0.1–0.5% yield and is medicinally important.
 In addition to alkaloids, areca nuts contain fat (14%) and amorphous red tannin (15%)
known as areca red of phlobaphene nature.
 The fat consists mainly of the glycerides of lauric, myristic and oleic acids.
CHEMICAL CONSTITUENTS
Uses

 Powdered Areca is used as anthelmintic, taenifuge and vermifuge for

dogs.
 It has found to useful in urinary disorders, as nervine tonic and
emmenagogue.
 The chewing of Areca nut may cause mouth cancer.
TROPANE ALKALOIDS

 The tropane alkaloids, which have the 8-azabicyclo octane nucleus, are
commonly found in plants of three families, the Solanaceae, Erythroxylaceae
and Convolvulaceae families.

Tropene
BELLADONNA

 SYNONYMS
 Belladonna herb; Belladonna leaf; Deadly night
shade.
 BIOLOGICAL SOURCE
 Belladonna consists of dried leaves and
flowering tops of Atropa belladonna Linn.
(European Belladonna), belonging to family
Solanaceae.
 It contains about 0.35% of total alkaloids
calculated as hyoscyamine.
CHEMICAL CONSTITUENTS

 Belladonna contains 0.3–1.0% total alkaloids.

 Atropine and scopolamine are the two most important belladonna alkaloids
 the prominent base is hyoscyamine and other components are apoatropine, choline,
belladonnine, cuscohygrine, chrysatropic acid, volatile bases, such as homatropine,
hyoscyamine.
 14% acid soluble ash and 4% acid-insoluble ash.
 Addition of ammonia to the alcoholic solution of scopoletin shows blue florescence.
 This test is useful to detect Belladonna poisoning.
 Atropine is formed by racemization during the extraction process.
 Atropine, a naturally occurring belladonna alkaloid, is a racemic mixture of equal parts
of d-and l-hyoscyamine; its activity is due almost entirely to the levo isomer of the drug.
USES

 The drug is used as adjunctive therapy in the treatment of peptic ulcer; functional
digestive disorders, including spastic, mucous and ulcerative colitis; diarrhoea,
diverticulitis and pancreatitis.
 Due to anticholinergic property, it is used to control excess motor activity of the
gastrointestinal tract and spasm of the urinary tract.
 Belladonna is anticholinergic, narcotic, sedative, diuretic, mydriatic and used as
anodyne and to check secretion.
 It relieves spasm of gut or respiratory tract.
 Belladonna acts as a parasympathetic depressant.
MARKETED PRODUCTS

 It is one of the ingredients of the preparation known as Belladona plaster

(Surgi Pharma) for backache, stiffness of muscles and boil, swollen joints.
HYOSCYAMUS

 SYNONYMS
 Common Henbane, Hyoscyamus, Hog’s-bean,
Jupiter’sbean, Symphonica, Cassila
 BIOLOGICAL SOURCE
 Hyoscyamus consists of the dried leaves and
flowering tops of Hyoscyamus niger Linn.,
belonging to family Solanaceae.
 It contains not less than 0.05% alkaloids,
calculated as hyoscyamine.ta, Cassilago, Deus
Caballinus
HISTORY

 The medicinal uses of Henbane date from Ancients times, being

particularly commended by Dioscorides (first century A.D.), who used it to
procure sleep and allay pains
HISTORY

 Later it was not used, It was omitted from the London Pharmacopoeia of
1746 and 1788
 Restored in 1809; its reintroduction being chiefly due to experiments and
recommendations by Baron Storch, who gave it in the form of an extract,
in cases of epilepsy and other nervous and convulsive diseases.
CHEMICAL CONSTITUENTS

 The chief constituent of Henbane leaves is the alkaloid Hyoscyamine,

together with smaller quantities of Atropine and Hyoscine, also known as
Scopolamine.
 The proportion of alkaloid in the dried drug varies from 0.045% to 0.14%.
 USES

 It is used as antispasmodic, hypnotic and mild diuretic.

 The leaves have long been employed as a narcotic medicine.
 It is similar in action to belladonna and stramonium, though milder in its effects. The drug
combines the therapeutic actions of its two alkaloids, hyoscyamine and hyoscine.
 Because of the presence of the former, it tends to check excretion and to relax spasms of
the involuntary muscles, while through the narcotic effects of its hyoscine it lessens pain
and exercises a slight somnifacient action.
 It will also relieve pain in cystitis.
 It is used to relieve the griping caused by drastic purgatives
STRAMONIUM

 SYNONYMS
 Thorn apple leaves; Jimson or
Jamestown weed; Dhatura; Stinkweed;
Devil’s apple; Apple of Peru; Folia
stramonii.
 BIOLOGICAL SOURCE
 Stramonium consists of dried leaves and
flowering tops of Datura stramonium
Linn, or its variety D. tatula Linn.,
belonging to family Solanaceae.
CHEMICAL CONSTITUENTS

 Stramonium contains 0.2–0.6% alkaloids. The main alkaloids are hyoscyamine and
hyoscine (scopolamine).
 It also contains protein albumin and atropine.
 USES

 It is a narcotic, antispasmodic and anodyne drug and used to relieve the spasm of the
bronchioles in asthma.
 The leaves are ingredient of Pulvis stramonii compositus and other powders used for the
relief of asthma.
 The leaves may be made into cigarettes or smoked in a pipe to relieve asthma.
 They are also used in the treatment of parkinsonism, boils, sores and fish bites.
 The flower juice is used to treat earache.
 The fruit juice is applied to the scalp for curing dandruff and falling hair.
 Stramonium ointment, containing lanolin, yellow wax and petroleum, is employed to cure
haemorrhoids.
QUINOLINE ALKALOIDS
INTRODUCTION

 Quinoline is a double carbon ring containing one nitrogen atom.

 Quinoline alkaloids include quinine from the bark of Cinchona ledgeriana,
a South American tree in the coffee family (Rubiaceae).
 The alkaloid quinine is toxic to Plasmodium vivax and three additional
species, the one celled organisms (protozoans) that cause malaria.
CINCHONA

 SYNONYMS
 Cortex Cinchonae, Countess, Peruvian
or Jesuit’s bark, Cinchona.
 BIOLOGICAL SOURCE
 Cinchona is the dried bark of the stem
or of the root of Cinchona calisaya
Wedd., Cinchona ledgeriana Moens.,
Cinchona officinalis Linn., and
Cinchona succirubra Pavon., or hybrids
of any of the first two species with any
of the last two species, belonging to
family Rubiaceae.
USES

 It is mainly employed as antimalarial drug, but it is also used as analgesic,

antipyretic, protoplasmic, bitter stomachic and tonic.
 Quinidine is cardiac depressant and Cinchonidine is used in rheumatism
and neuralgia.
ISOQUINOLINE ALKALOIDS
ISOQUINOLINE ALKALOIDS

 Isoquinoline is a double carbon ring containing one nitrogen atom.

 The isoquinoline alkaloids papaverine, sangumarine, protoverine, and
chelidonine are GI tract irritants and CNS stimulants.
 Isoquinoline alkaloids are found in varying quantities in the prickly poppy,
bloodroot and celandine poppy.
 Many have varying degrees of neurological effects, ranging from
relaxation and euphoria to seizures.
 They also cause vasodilation.
 ISOQUINOLINE ALKALOIDS

 Many of these plants have been used in herbal preparations. Scotch broom is smoked for
relaxation and has mild sedative-hypnotic effects.
 Prickly poppy is smoked as a euphoriant.
 Mescal bean is a hallucinogenic, which is used in Native American rituals and in medicine.
 Sanguinaria species (bloodroot) extract is used commercially as a dental plaque inhibitor.
 Papaverine, found in prickly poppy and bloodroot, has been used medically as a smooth muscle
relaxant.
 Prickly poppy extracts act as capillary dilators and have been implicated in epidemic glaucoma
in India.
 Celandine extracts are used as treatment of gastric and biliary disorders.
OPIUM

 SYNONYMS
 Crude Opium; Raw Opium; Gum Opium;
Afim; Post.
 BIOLOGICAL SOURCE
 Opium is the air dried milky latex obtained
by incision from the unripe capsules of
Papaver somniferum Linn, or its variety P.
album Decand., belonging to family
Papaveraceae.
HISTORY

 The cultivation of opium dates back to 3400 B.C.

 Hippocrates ‘the father of medicine’, (460–357 B.C.) prescribed drinking the juice of
the white poppy mixed with the seed of nettle and also acknowledged its use as
narcotic and styptic in internal diseases use as narcotic and styptic in internal
diseases.
 W. Seiturner (German pharmacist) isolated and identified the chief chemical
constituent of opium.
 The compound isolated was named morphium (morphine) after Morpheus, the god
of dreams.
CHEMICAL CONSTITUENTS

 Opium contains about 35 alkaloids among which morphine (10–16%) is the

most important base.
 The alkaloids are combined with meconic acid.
 The other alkaloids isolated from the drug are codeine (0.8–2.5%),
narcotine, thebaine (0.5–2%). noscapine (4–8%), narceine and papaverine
(0.5–2.5%).
 Morphine contains a phenanthrene nucleus.
 DIFFERENT TYPE OF ALKALOIDS
ISOLATED FROM MORPHINE

 MORPHINE TYPE
 Morphine, codeine, neopine, pseudo or oxymorphine, and thebaine
 Morphine consists of alkaloids which has phenanthrene nucleus.
 The morphine molecule has both a phenolic and an alcoholic
hydroxyl group and acetylated form is diacetyl morphine or heroin.
 Codeine is ether of morphine (methyl-morphine).
 Other morphine ethers which are used medicinally are ethylmorphine and
pholcodine.

PHENANTHRENE NUCLEUS
Chemical Tests

 1. Aqueous extract of Opium with FeCl3 solution gives deep reddish purple
colour which persists on addition of HCl. It indicates the presence of
meconic acid.
 2. Morphine gives dark violet colour with conc. H2SO4 and formaldehyde.
USES

 Opium and morphine have narcotic, analgesic and sedative action and used to
relieve pain, diarrhoea dysentery and cough.
 Poppy capsules are astringent, sedative and narcotic and used as anodyne and
emollient.
 Codeine is mild sedative and is employed in cough mixtures.
 Noscapine is not narcotic and has cough suppressant action acting as a central
antitussive drug.
 Papaverine has smooth muscle relaxant action and is used to cure muscle
spasms.
 Opium, morphine and the diacetyl derivative heroin, cause drug addiction
 INDOLE ALKALOIDS

 Indole (1-H-indole) is a benzopyrrole in which the benzene and pyrrole

rings are through the 2, 3-positions of the pyrrole.
 The indole nucleus is found in a large number of naturally occurring
compounds.
 It is of commercial importance as a component of perfumes.
HISTORY

 Indole was first obtained (and its structure elucidated) in 1866 by Adolf von
Baeyer.
 Interest in indole chemistry revived about 1930 when it was discovered that the
essential amino acid, tryptophan, the plant growth hormone, heteroauxin, and
several groups of important alkaloids are indole derivatives.
 Serotonin, which has been identified as a metabolite in brain chemistry; the
psychotomimetic indoles, psilocin and psilocybin from mushrooms; the tranquilizer
reserpine.
 ERGOT

 Synonyms
 Ergot; Rye Ergot; Secale cornutum; Spurred rye; Ergot
of rye; Ergota.
 Biological Source
 Ergot is the dried sclerotium of a fungus, Claviceps
purpurea
 developing in the ovary of rye plant, Secale cereale
(Family Poaceae).
 Ergot should yield about 0.15% of the total alkaloids
calculated as ergotoxine and water-soluble alkaloids
equivalent to about 0.01% of ergonovine.
CHEMICAL CONSTITUENTS

 A large number of alkaloids have been isolated from the Ergot.

 The most important alkaloids are ergonovine and ergotamine.
 On the basis of solubility in water the alkaloids are divided into two groups:
 1. water-soluble ergometrine (or ergonovine) group
 2. water-insoluble (ergotamine and ergotoxine) group
• Alkaloids of Group II and II are polypeptides in which lysergic acid or isolysergic acid is linked
to amino acids.
• Alkaloids obtained from lysergic acid are physiologically active compounds.
Chemical Tests

 1. Ergot under UV light shows a red-colored fluorescence.

 2. Ergot powder is extracted with a mixture of CHCl3 and sodium
carbonate.
 The CHCl3 layer is separated and a mixture of p-
dimethylaminobenzaldehyde (0.1 g), H2SO4 (35%, v/v, 100 ml) and 5%
ferric chloride (1.5 ml) is added. A deep blue color is produced.
Uses

 Ergot is oxytocic, vasoconstrictor and abortifacient and used to assist

delivery and to reduce post-partum hemorrhage.
 Lysergic acid diethylamide (LSD-25), obtained by partial synthesis from
lysergic acid, is a potent specific psychotomimetic.
 Ergometrine is oxytocic and used in delivery.
 It stimulates the tone of uterine muscles and prevents postpartum
hemorrhage.
 Ergotamine and the semisynthetic dihydroergotamine salts are used as
specific analgesics for the treatment of migraine.
RAUWOLFIA

 Synonyms
 Indian snake root.
 Biological Source
 Rauwolfia consists of dried roots of
Rauwolfia serpentine Benth., belonging to
family Apocynaceae.
CHEMICAL CONSTITUENTS

 Rauwolfia contains about 0.7–2.4% total alkaloidal bases from which more
than 80 alkaloids have been isolated.
 The prominent alkaloids isolated from the drug are reserpine,
rescinnamine, rescidine, raubescine and deserpidine.
 The other alkaloidal components are ajmalinine, ajmaline, ajmalicine (8-
yohimbine), serpentine, serpentinine, tetrahydroreserpine, raubasine,
reserpinine, isoajamaline and yohambinine.
BIOSYNTHETIC PATHWAY

 Reserpine is one of dozens of indole alkaloids isolated from the plant

Rauvolfia serpentine.
 In the rauwolfia plant, tryptophan is the starting material in the biosynthetic
pathway of reserpine, and is converted to tryptamine by tryptophan
decarboxylase enzyme.
 Tryptamine is combined with secologanin in the presence of strictosidine
synthetase enzyme and yields strictosidine.
 Various enzymatic conversion reactions lead to the synthesis of reserpine
from strictosidine.
 USES

 Rauwolfia in used as hypnotic, sedative and antihypertensive.

 It is specific for insanity, reduces blood pressure and cures pain due to affections of the bowels.
 It is given in labors to increase uterine contractions and in certain neuropsychiatric disorders.
 Ajmaline, is marketed in Japan for the treatment of cardiac arrhythmias
 The antihypertensive actions of reserpine are largely due to it antinoradrenergic effects, which
are a result of its ability to deplete catecholamines (among other monoamine neurotransmitters)
from peripheral sympathetic nerve endings.
 These substances are normally involved in controlling heart rate, force of cardiac contraction
and peripheral vascular resistance.
 Reserpine is recommended as an alternative drug for treating hypertension.
NUX VOMICA

 SYNONYMS
 Nux vomica Seed, Poison Nut, Semen.
 BIOLOGICAL SOURCE
 Nux vomica consists of the dried ripe seeds of
Strychnos nux vomica Linn, belonging to family
Loganiaceae; containing not less than 1.2% strychnine
Chemical Constituents

 Nux vomica contains the alkaloids, Strychnine (1.25%) and Brucine (1.5%), also traces
of strychnicine, and a glucoside Loganin, about 3% fatty matter, caffeotannic acid
and a trace of copper.
 Strychnine is therapeutically active and toxic alkaloid and is located in central
portion of endosperm.
 Brucine ischemically dimethoxystrychnine and is less toxic and has very little
physiological action.
 It is intensely bitter and is used as a standard for determining the bitter value, of
many bitter drugs. Brucine is more in the outer part.
 Vomicine and pseudostrychnine are minor alkaloids.
Chemical Tests

 1. Strychnine Test:
 To a section of endosperm add ammonium vanadate and sulphuric acid.
Strychnine in the middle portion of endosperm is stained purple.
 2. Potassium dichromate test:
 Strychnine gives violet colour with potassium dichromate and conc.
Sulphuric acid.
 3. Brucine Test:
 To a thick section add concentrated nitric acid. Outer part of endosperm
is stained yellow to orange because of brucine.
USES

 The properties of nux vomica are substantially those of the alkaloid Strychnine.
 In the mouth it acts as a bitter, increasing appetite; it stimulates peristalsis, in chronic
constipation due to atony of the bowel it is often combined with cascara and other
laxatives with good effects.
 Strychnine, the chief alkaloid constituent of the seeds, also acts as a bitter, increasing
the flow of gastric juice; it is rapidly absorbed as it reaches the intestines, after which it
exerts its characteristic effects upon the CNS.
 The movements of respiration are deepened and quickened and the heart slowed
through excitation of the vagal centre.
 Strychnine has a stimulant action on spinal cord and reflex movements are better.
 It is considered as nervine tonic.
USES

 it improves the pulse and raises blood pressure and is of great value as a tonic to the
circulatory system in cardiac failure.
 Brucine closely resembles strychnine in its action, but is slightly less poisonous; it
paralyses the peripheral motor nerves
VINCA ROSEA

 SYNONYMS
 Vinca rosea, Catharanthus, Madagascar periwinkle.
 BIOLOGICAL SOURCE
 Vinca is the dried entire plant of Catharanthus roseus Linn.,
belonging to family Apocynaceae.
CHEMICAL CONSTITUENTS

 Alkaloids are present in entire shrub but leaves and roots contain more
alkaloids.
 About 90 alkaloids have been isolated from Vinca from which some like
Ajmalicine, Serpentine and Tetrahydroalstonine are known and are
present in other species of Apocynaceae.
 The important alkaloids in Catharanthus are the dimer indole indoline
alkaloids Vinblastine and Vincristine and they possess definite anticancer
activity.
 Vindoline and Catharanthine are indole monomeric alkaloids.
VINCRISTINE (ONCOVIN)

 Vincristine, also known as leurocristine and marketed under the brandname Oncovin
among others, is a chemotherapy medication used to treat a number of types of
cancer.
 This includes acute lymphocytic leukemia, acute myeloid leukemia, Hodgkin's
disease, neuroblastoma, and small cell lung cancer among others.
 It is given intravenously
 Vincristine works partly by binding to the tubulin protein, stopping the tubulin dimers
from polymerizing to form microtubules, causing the cell to be unable to separate
its chromosomes during the metaphase.
 The cell then undergoes apoptosis.
 The vincristine molecule inhibits leukocyte production and maturation.
 A downside, however, to Vincristine is that it does not only affect the division of
cancer cells. It affects all rapidly dividing cell types, making it necessary for the very
specific administration of the drug
 Uses

 Vinblastin is an antitumour alkaloid used in the treatment of Hodgkin’s disease.

 Vincristine is a cytotoxic compound and used to treat leukaemia in children.
 Vinca is used in herbal practice for its astringent and tonic properties in menorrhagia and in
haemorrhages generally.
 In cases of scurvy and for relaxed sore throat and inflamed tonsils.
 For bleeding piles, it may be applied externally, as well as taken internally.
 It is also used in the treatment of diabetes.
 The flowers of the Periwinkle are gently purgative, but lose their effect on drying.
 If gathered in the spring and made into a syrup, they impart all their virtues, and this, it is
stated, is excellent as a gentle laxative for children and also for overcoming chronic
constipation in grown persons
PHYSOSTIGMA

 SYNONYMS
Calabar bean, Ordeal bean, Chop nut.
 BIOLOGICAL SOURCE
 Calabar beans are the dried ripe seeds of
Physostigma venenosum half containing not less than
0.15% alkaloids, belonging to family Leguminosae
(Papilionaecae).
Chemical Constituents

 Drug contains 0.1–0.2% indole alkaloids of which half is physostigmine

known also as eserine (a crystalline solid, white or pinkish colored, readily
soluble in alcohol, sparingly soluble in water) and is the important alkaloid.
 The other alkaloids are eseramine, geneserine and physovenine.
 Physostigmine the major alkaloid is present in cotyledons up to 0.04–0.3%,
Physostigmine is methyl carbamide acid ester of eroline.
 These alkaloids are pyrrolidineindoline derivatives.
 Calabar beans also contain stigmasterol
PHYSOSTIGMINE

 is a highly toxic parasympathomimetic alkaloid, specifically, a reversible

cholinesterase inhibitor. It occurs naturally in the Calabar bean and the
Manchineel tree.
 Physostigmine is used to treat glaucoma and delayed gastric emptying.
 Because it enhances the transmission of acetylcholine signals in the brain and
can cross the blood–brain barrier, physostigmine salicylate is used to
treat anticholinergic poisoning (that is, poisoning by substances that interfere with
the transmission of acetylcholine signaling, such as atropine, scopolamine, and
other anticholinergic drug overdoses).
 Physostigmine is the antidote of choice for Datura stramonium poisoning. It is also
an antidote for Atropa belladonna poisoning, the same as for atropine
USES

 Mainly used for diseases of the eye; it causes rapid contraction of the pupil
and disturbed vision.
 Also used as a stimulant to the unstriped muscles of the intestines in
chronic constipation.
 Its action on the circulation is to slow the pulse and raise blood pressure; it
depresses the CNS, causing muscular weakness; it has been employed
internally for its depressant action.
IMIDAZOLE ALKALOIDS

 Imidazole is a heterocyclic aromatic organic compound.

 This ring system is present in important biological building blocks such as
histidine and histamine.
PILOCARPUS

 SYNONYMS
 Jaborandi, Arruda do Mato, Arruda brava,
Jamguarandi, Juarandi.
 BIOLOGICAL SOURCE
 The drug consists of the leaves of
Pilocarpus jaborandi,
 belonging to family Rutaceae.
HISTORY

 Dr. Coutinho in 1874 sent the plant to Europe from Pernambuco, hence
the name Pernambuco jaborandi or Pilocarpus jaborandi.
 Later, Byasson in 1875 showed it alkaloidal nature and further Gerrard and
Hardy isolated the main alkaloid pilocarpine.
CHEMICAL CONSTITUENTS

 The drug contains imidazole alkaloids among, which pilocarpine is most

important.
 Other alkaloids are isopilocarpine, pilocarpidine, pilosine,
pseudopilocarpine and isopilosine.
 The range of total alkaloids in different species is between 0.5% and 1%.
USES

 Pilocarpine is antagonistic to atropine, stimulating the nerve endings

paralyzed by that drug, and contracting the pupil of the eye.
 Its principal use is as a powerful and rapid diaphoretic.
 It induces also free salivation and excites most gland secretions, some
regarding it as a galactagogue.
 It is also used in ophthalmic practice in the treatment of glaucoma.
STEROIDAL ALKALOIDS

 The active chemical principles of such drugs contain mainly steroidal

(cyclopentenophenanthrene) entity, along with basic nitrogen.
 They belong to C21 or C27 group of steroids.
 Either they are used as medicines or as a precursor for synthesis of various
other steroids.
 Steroidal alkaloids contain a tetracyclic (4-ring) triterpene compound
called the steroid nucleus or steroidal backbone.
VERATRUM

 SYNONYMS
 American Hellebore; Green Hellebore;
American Veratrum; Indian poke.
 Biological Source
 Veratrum consists of dried roots and rhizomes
of the perennial herbs, Veratrum viride Aiton
and Veratrum album Linn., belonging to family
Liliaceae.
Chemical Constituents

 Various steroidal alkaloids have been isolated from Veratrums.

 The important alkaloids are jervine, pseudojervine, rubijervine, cevadine,
germitrine, germidine, veratralbine, veratroidine, neogermitrine,
neoprotoveratrine, protoveratrine A and B and veratridine.
USES

 Veratrum is used as antihypertensive, cardiac depressant, sedative and

insecticides.
 It is also used for relief in irritation of the nervous system, in convulsions, mania,
neuralgia, headache, febrile and inflammatory affections of the respiratory organs
and acute tonsillitis.
 The rhizomes are also used for insecticidal purposes in the form of sprays and in
dusts.
 The alkaloids, especially proveratrines A and B, are effective in reducing blood
pressure.
 American veratrum is used for the preparation of Veriloid, a mixture of the
hypotensive alkaloids.
 European veratrum is used for the preparation of the protoveratrines.
 The drugs are used as insecticides.
ALKALOIDAL AMINES

 One or more carbon rings with a nitrogen atom on a carbon side chain.
 One of the most interesting alkaloids in this group is mescaline from
Lophophora williamsii.
 Mescaline has a molecular structure that is remarkably similar to the brain
neurotransmitter dopamine.
 It is also structurally similar to the neurohormone norepinephrine
(noradrenalin) and to the stimulant amphetamine.
 DOPAMINE

NOREPINEPHRINE
MESCALINE

AMPHETAMINE
ALKALOIDAL AMINES

 Dopamine and its precursor L-dopa are also derived from a tyrosine
pathway, Mescaline also occurs in several other cactus species, including
the commonly cultivated, night-blooming, South American San Pedro
cactus.
 Another alkaloid called ephedrine has a molecular structure similar to that
of mescaline. Since ephedrine has a chemical structure similar to
epinephrine (adrenalin), it works like a powerful cardiac stimulant that may
cause cardiac arrest in infants and heart patients.
EPHEDRA

 SYNONYMS
Ma Huang.
 BIOLOGICAL SOURCE
 Ephedra consists of the dried aerial parts
of Ephedra gerardiana Wall, Ephedra sinica
belonging to family Ephadreaceae.
Chemical Constituents

 Ephedra contains alkaloids Ephedrine (water-soluble salt of an alkaloid),

Pseudoephedrine (analog of ephedrine), Norpseudoephedrine (An
analog of ephedrine).
 The leaves and stems of ephedra also contain many potentially active
compounds, such as tannins, saponin, flavone and volatile oils.
USES

 Ephedrine is antiallergenic, antiasthmatic, antispasmodic, decongestant,

cough suppressant, stimulant and vasoconstrictor.
 Pseudoephedrine is decongestant, cough suppressant.
 norpseudoephedrine is peripheral vasodilator used to treat angina.
 As a whole it is decongestant; it opens sinuses, increases sweating, dilates
bronchioles (antiasthmatic use), diuretic, CNS stimulant, raises blood
pressure, alleviates aches and rheumatism, alleviates hay fever/colds, etc.
COLCHICUM

 SYNONYMS
 Autumn Crocus, Meadow Saffron.
 BIOLOGICAL SOURCE
 Colchicum consists of dried ripe seeds and
corms of Colchicum
 autumnale Linn., belonging to family Liliaceae.
Chemical Constituents

 The active principle is said to be an alkaline substance of a very poisonous

nature called Colchicine.
 Besides colchicine, demecolcine and other alkaloids are present.
 They also contain resin, called colchicoresin, fixed oil, glucose and starch.
MECHANISM OF COLCHICINE.

 inhibits microtubule polymerization by binding to its constitutive protein,

tubulin
 as availability of tubulin is essential to mitosis, colchicine may inhibit mitosis
 inhibits activation and migration of neutrophils to sites of inflammation
 interferes with the inflammasome complex found in neutrophils and
monocytes that mediate interleukin-1β activation, a component of
inflammation
 inhibits superoxide anion production in response to urate crystals
 interrupts mast cell degranulation
Uses

 Both the corm and the seeds are analgesic, antirheumatic, cathartic and
emetic.
 They are used mainly in the treatment of gout and rheumatic complaints,
usually accompanied with an alkaline diuretic.
 Leukaemia has been successfully treated with autumn crocus, and the
plant has also been used with some success to treat Bechet’s syndrome, a
chronic disease marked by recurring ulcers and leukaemia.
 A very toxic plant, it should not be prescribed for pregnant women or
patients with kidney disease, and should only be used under the
supervision of a qualified practitioner.
PURINE ALKALOIDS

 Purine contains double carbon ring containing four nitrogen atoms.

 Purine alkaloids have a molecular structure remarkably similar to the
nitrogenous purine base adenine, which is found in DNA, RNA and ATP.
COFFEE

 SYNONYMS
 Coffee bean, coffee seed, Arabica coffee,
Arabian coffee, Abyssinian coffee, Brazilian coffee.
 Biological Source
 It is the dried ripe seeds of Coffea arabica Linn,
belonging to family Rubiaceae.
CHEMICAL CONSTITUENTS

 The main constituents of coffee are caffeine, tannin, fixed oil and proteins.
 It contains 2–3% caffeine, 3–5% tannins, 13% proteins, 10–15% fixed oils.
 In the seeds, caffeine is present as a salt of chlorogenic acid.
 Also it contains oil and wax.
CAFFIENE

 Caffeine is most commonly used to improve mental alertness, but it has many other
uses.
 Caffeine is used by mouth or rectally in combination with painkillers (such as aspirin
and acetaminophen) and a chemical called ergotamine for treating migraine
headaches.
 It is also used with painkillers for simple headaches and preventing and treating
headaches after epidural anesthesia.
 Caffeine is one of the most commonly used stimulants among athletes. Taking
caffeine, within limits, is allowed by the National Collegiate Athletic Association
(NCAA).
 Caffeine creams are applied to the skin to reduce redness and itching in dermatitis.
 Healthcare providers sometimes give caffeine intravenously (by IV) for headache
after epidural anesthesia
USES

 Coffee is widely used as a flavoring agent, as in ice cream, pastries,

candies and liquors.
 Source of caffeine, dried ripe seeds are used as a stimulant, nervine and
diuretic, acting on CNS, kidneys, heart and muscles.
 Very valuable in cases of snake-bite, helping to ward off the terrible
coma.
 It also exerts a soothing action on the vascular system, preventing a too
rapid wasting of the tissues of the body;
 these effects are not only due to the volatile oil but to the caffeine it
contains.
TEA

 BIOLOGICAL SOURCE
 It contains the prepared leaves and leaf buds
of Thea sinensis (Linne) kuntz., belonging to
family Theaceae.
Chemical Constituents

 The leaves are a rich source of caffeine (1–5%).

 It also contains theobromine and theophylline in minor quantities.
 The color of tea leaves is due to tannin (10–20% gallotannic acid).
 The agreeable odor is due to presence of a yellow volatile oil.
 Tea leaves also contain protein, wax, resin and ash.
THEOPHYLLINE

 Theophylline is used to treat lung diseases such as asthma and COPD

(bronchitis, emphysema).
 It must be used regularly to prevent wheezing and shortness of breath. This
medication belongs to a class of drugs known as xanthine.
 It works in the airways by relaxing muscles, opening breathing passages,
and decreasing the lungs' response to irritants.
 Controlling symptoms of breathing problems can decrease time lost from
work or school.
USES

 It is used as stimulant, astringent and also as diuretic.