Alkaloids: Classification
Alkaloids: Classification
Alkaloids: Classification
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. They occur naturally in seed bearing plants and are found in berries, bark, fruit, roots
and leaves. Often, they are bases which have some physiological effect.
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.
CLASSIFICATION
Alkaloids are generally classified by their common molecular precursors, based on the
biological pathway used to construct the molecule.
From a structural point of view, alkaloids are divided according to their shapes and
origins. There are three main types of alkaloids:
(1) true alkaloids,
(2) protoalkaloids, and
(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 form water-soluble salts.
Most of them are well-defined crystalline substances which unite with acids to form salts.
True alkaloids may occur in plants (1) in the free state, (2) as salts and (3) as N-oxides.
These alkaloids occur in a limited number of species and families, and are those
compounds in which decarboxylated amino acids are condensed with a nonnitrogenous
structural moiety.
The primary precursors of true alkaloids are such amino acids as L-ornithine, L-lysine, L-
phenylalanine/L-tyrosine, L-tryptophan and L-histidine. Examples of true alkaloids include such
biologically active alkaloids as cocaine, quinine, dopamine and morphine.
Protoalkaloids
Protoalkaloids are compounds, in which the N atom derived from an amino acid is not a
part of the heterocyclic.
Such kinds of alkaloid include compounds derived from L-ty-rosine and L-tryptophan.
Protoalkaloids are those with a closed ring, being perfect but structurally simple
alkaloids.
Hordenine, mescaline and yohimbine are good examples of these kinds of alkaloid.
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. They can also result from the amination and transamination reactions of the
different pathways connected with precursors or post-cursors of amino acids.
These alkaloids can also be derived from non-aminoacid precursors. The N atom is inserted into
the molecule at a relatively late stage, for example, in the case of steroidal or terpenoid skeletons.
Certainly, the N atom can also be donated by an amino acid source across a trans-amination
reaction, if there is a suitable aldehyde or ketone.
Pseudoalkaloids can be acetate and phenylala-nine derived or terpenoid, as well as steroidal
alkaloids. Examples of pseudoalkaloids include such compounds as coniine, capsaicin,
ephedrine, solanidine, caffeine and theobromine.
Alkaloids are mainly divided into two categories on the basis of their chemical structure,
that is, heterocyclic rings.
Atypical alkaloids
These are also known as nonheterocyclic alkaloids and contain nitrogen in aliphatic chain.
Typical alkaloids
These are also known as heterocyclic alkaloids and contain nitrogen in heterocyclic ring system.
Table : Classification of alkaloids
PROPERTIES
1. In general, they are colourless, crystalline solids which are basic, have a ring structure,
and have definite melting points.
2. They are also derived from plants and have a bitter taste.
3. Some alkaloids are not basic and others are brightly coloured (betanidine, beriberine,
sangui-narine) or liquid (nicotine).
4. Other alkaloids are produced synthetically.
5. Most alkaloids are also chiral molecules which mean they have nonsuperimposable
mirror images. This results in isomers that have different chemical properties. For
example, one isomer may have a physiological function while the other does not.
6. Generally free bases of alkaloids are soluble in organic solvents and insoluble in water,
where as alkaloidal salts are soluble in water and partially soluble in organic solvents. For
example, strychnine hydrochloride is much more soluble in water than strychnine as a
base.
EXTRACTION
The extraction of alkaloids is based on their basic character and solubility profiles.
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.
Volatile liquid alkaloids (nicotine and coniine) are isolated by distillation.
The powdered material that contains alkaloids is extracted with water and the aqueous extract is
made alkaline with sodium carbonate or ammonia and the alkaloid is distilled off in steam. This
could be collected and purified.
CHEMICAL TESTS
I. Dragendorff’s Test
Drug solution + Dragendroff’s reagent (Potassium Bismuth Iodide), formation of Orangish red
colour.
II. Mayer’s Test
Drug solution + few drops of Mayer’s reagent (potassium mercuric iodide), formation of
creamy-white precipitant.
III. Hager’s Test
Drug solution + few drops of Hagers reagent (Saturated aq. Solution of Picric acid), formation of
crystalline yellow precipitate.
IV. Wagner’s Test
Drug solution + few drops of Wagner’s reagent (dilute Iodine solution), formulation of reddish-
brown precipitate.
V. Tannic Acid Test
Drug solution + few drops of tannic acid solution, formation of buff coloured precipitate.
VI. Ammonia Reineckate Test
Drug solution + slightly acidified (HCl) saturated solution of ammonia reineckate, formation of
pink flocculent precipitate.
1. TROPANE ALKALOIDS
Tropane alkoloids are tropene derivatives. Tropane ring is composed of pyrrolidine and
piperidine rings.
A. BELLADONNA
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.
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.
Consumption of Belladonna checks excessive perspiration of patients suffering from
tuberculosis. Belladonna acts as a parasympathetic depressant.
b. DATURA HERB
Datura herb consists of the dried leaves and flowering tops of Datura metel Linn and Datura
metel var. fastuosa belonging to family Solanaceae.
Datura herb contains up to 0.5% of total alkaloids, among which hyoscine (scopolamine) is the
main alkaloid, while l-hyoscyamine (scopoline) and atropine are present in very less quantities.
scopolamine
Chemical Tests
1. Vitali-Morin test: The tropane alkaloid is treated with fuming nitric acid, followed by
evaporation to dryness and addition of methanolic potassium hydroxide solution to an acetone
solution of nitrated residue. Violet colouration takes place due to tropane derivative.
2. On addition of silver nitrate solution to solution of hyoscine hydrobromide, yellowish white
precipitate is formed, which is insoluble in nitric acid, but soluble in dilute ammonia.
Uses
In Ayurveda black datura is considered more efficacious or more toxic.
D. metel is used in the manufacture of hyoscine or scopolamine.
It exhibits parasympatholytic with anticholinergic and CNS depressant effects.
The drug is used in cerebral excitement, asthma and in cough.
Stramonium owes its activity to the same alkaloids as D. Stramonium, and its leaves are
also much used in the form of cigarettes as a remedy for spasmodic asthma.
D. ferox, Chinese Datura, is used in homoeopathy.
STRAMONIUM
Stramonium consists of dried leaves and flowering tops of Datura stramonium Linn, or its
variety D. tatula Linn., belonging to family Solanaceae.
The drug is required to contain not less than 0.25% of alkaloids calculated as hyoscyamine.
Prepared Stramonium is the finely powdered drug adjusted to an alkaloid content of 0.23–0.27%.
Stramonium contains 0.2–0.6% alkaloids. The main alkaloids are hyoscyamine and hyoscine
(scopolamine). It also contains protein albumin and atropine.
Atropine is formed from hyoscyamine by racemization. At the time of collection these alkaloids
are usually present in the proportion of about two parts of hyoscyamine to one part of hyoscine,
but in young plants hyoscine is the pre-dominant alkaloid. The larger stems contain small
amount of alkaloid and the official drug should contain not more than 3% stem with a diameter
exceeding 5 mm.
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 dan-druff and falling hair.
Stramonium ointment, containing lanolin, yellow wax and petroleum, is employed to cure
haemorrhoids.
HYOSCYAMUS
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.
The chief constituent of Henbane leaves is the alkaloid Hyoscyamine, together with smaller
quantities of Atropine and Hyoscine, also known as Scopolamine.
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 secretion 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, and is a common ingredient
of aperient pills, especially those containing aloes and colocynth.
COCA LEAVES
Coca consists of the dried leaves of various species of Eryth-mxylon, that is, Erythroxylon
coca Lam (Huanco or Bolivian coca) or Erythroxylon coca var. Spruceanum (Peruvian, Truxillo
or Java coca) also known as Erythroxylon truxillense Rusby., belonging to family
Erythroxylaceae.
Coca leaves contain the alkaloids Cocaine, Annamyl Cocaine, and Truxilline or Cocamine.
Truxillo or Peruvian leaves contain more alkaloid than the Bolivian, though the latter are
preferred for medicinal purposes.
Java Coca contains tropacocaine and four yellow crystalline glucosides in addition to the other
constituents.
Uses
The actions of Coca depend principally on the alkaloid Cocaine.
Cocaine has stimulant action on CNS.
The leaves are extensively chewed to relieve hunger and fatigue.
Coca alkaloids cause also hallucination.
Coca leaves are used as a cerebral and muscle stimulant, especially during convalescence,
to relieve nausea, vomiting and pains of the stomach without upsetting the digestion.
Cocaine also has local anesthetic action on skin and mucous membrane; and is used as
dental anaesthesia and minor local surgery of ophthalmic, ear, nose and throat.
Chemical structure of cocaine has lead to several synthetic annaesthetics like anaesthesia,
novocain, stovain, etc.
Adulterant
Jaborandi leaves are used as an adulterant of Coca leaves.
DUBOISIA
Duboisia consists of the dried leaves of Duboisia myoporoides R., Duboisia hopwoodii, D.
leichhardtii, belonging to family Solanaceae.
Chemical Constituents
Duboisia myoporoides is considered as the chief commercial source of scopolamine and
atropine. It contains hyoscyamine which is converted to atropine during extraction.
Atropine (C17H23O3N) occurs as colourless crystals, with a bitter taste and no odour. It is soluble
in chloroform and alcohol. It is a racemic form of hyoscyamine.
The chief constituent of Duboisia hopwoodii was found to be nicotine and nonnicotine, with
content reportedly up to 25% of the dried weight of the plant material.
Chemical Tests
1. The addition of gold chloride solution to atropine in water and hydrochloric acid gives lemon
yellow precipitate.
2. It gives positive Vitali Morin reaction.
Uses
Duboisia leaves are the main source of atropine and scopolamine.
Atropine is the parasympatholytic drug.
It also causes stimulant action on central, medullary and higher nerve centres.
It is used as an antidote for pilocarpine, physostigmine and other choline esters.
It relieves bronchial spasms in asthma.
As it suppresses the gastric secretions, it is used in peptic ulcer.
It has applications in ophthalmic practice, because of its dilatory effects on pupil of the
eye. It is also used to reduce tremor and rigidity in Parkinsonism.
Scopolamine is used as treatment for air and sea sickness and in the treatment of stomach
ulcers. Sedative, hypnotic and mydriatic (of variable strength), which augments the
activity of the respiratory system. Its alkaloid, Sulphate of Duboisia, is sometimes used as
a substitute for atropine.
The homoeopaths use the tincture and the alkaloid for paralysis and eye infections; a red
spot interfering with vision is an indication for its use.
It is antidoted by coffee and lemon juice.
2. 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.
Isoindole (I-H-isoindole), the isomer in which the benzene and pyrrole rings are fused through
the 3- and 4-positions of the pyrrole, is not stable. A few of its derivatives are known, the
simplest being N-methylisoindole.
Indole is a colourless crystalline solid (mp 52–54°C, bp 254°C).
The heat of combustion at constant volume is 4,268 MJ/mol (10–20 kcal/mol).
The molecule is planar and has only moderate polarity.
Indole has good solubility in a wide range of solvents including petroleum ether,
benzene, chloroform and hot water.
The solubility in cold water is only 1:540 at 25°C; thus, water is a good solvent for puri-
fication by recrystallization.
Indole forms salts with high concentrations of both strong bases and strong acids.
ERGOT
Ergot is the dried sclerotium of a fungus, Claviceps purpurea Tulasne, belonging to family
Clavicipitaceae, 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.
Cultivation and Collection
The life cycle of the fungus, Claviceps purpurea, which is a parasite, passes through the
following characteristic stages:
1) Sphacelia or honeydew or asexual stage
2) Sclerotium or ascigerous or sexual stage and
3) Ascospore stage.
Chemical Tests
1. Ergot under UV light shows a red-coloured fluores-cence.
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 colour is produced.
Uses
Ergot is oxytocic, vasoconstrictor and abortifacient and used to assist delivery and to
reduce post-partum haemorrhage.
Lysergic acid diethylamide (LSD-25), obtained by partial synthesis from lysergic acid, is
a potent specific psychoto-mimetic.
Ergometrine is oxytocic and used in delivery. It stimulates the tone of uterine muscles
and prevents post-partum haemorrhage.
Only ergometrine produces an oxytocic effect, ergotoxine and ergotamine having quite a
different action. Ergometrine is soluble in water or in dilute alcohol. It is known as
ergonovine.
Ergotamine and the semisynthetic dihydroergotamine salts are used as specific analgesics
for the treatment of migraine.
Lysergic acid diethylamide (LSD-25), prepared by partial synthesis from lysergic acid, is
a potent specific psychotomimetic.
RAUWOLFIA
Rauwolfia consists of dried roots of Rauwolfia serpentina Benth., belonging to family
Slight odour is felt in recently dried drug which decreases with age; taste is bitter.
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, ψ-reserpine, rescidine, raubescine and deserpidine.
The other alkaloidal components are ajmalinine, ajmaline, ajmalicine (8-yohimbine), serpentine,
serpentinine, tetrahydroreserpine, raubasine, reserpinine, isoajamaline and yohambinine.
Reserpine is a white or pale buff to slightly yellow, odourless, crystalline powder that darkens
slowly when exposed to light and rapidly when in solution.
The other substances present are phytosterols, fatty acids, unsaturated alcohols and sugars.
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 labours to increase uterine contractions and in certain
neuropsychiatric disorders. Ajmaline, which has pharmacological properties similar to
those of quinidine, is marketed in Japan for the treatment of cardiac arrhythmias.
Reserpine is an antihypertensive and tranquilizer. Rescinnamine is the methyl reserpate
ester of 3,4,5-trimethoxy cinnamic acid. The usual antihypertensive dose of rescinnamine
is 500 μg, two times a day. Higher doses may cause serious mental depression.
Deserpidine is 11-des-methoxyreserpine. It is a wide-range tranquilizer and
antihypertensive and is free from the side effects.
NUX VOMICA
Nux vomica consists of the dried ripe seeds of Strychnos nux vomica Linn, belonging to family
Loganiaceae; containing not less than 1.2% strychnine.
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. It contains about 2.5–3.5% bitter indole alkaloids.
Strychnine is therapeutically active and toxic alkaloid and is located in central portion of
endosperm.
Brucine is chemically 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.
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.
4. Hemicellulose Test: To a thick section add iodine and sulphuric acid. The cell walls are
stained blue.
Uses
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 and sex tonic.
The senses of smell, touch, hearing and vision are rendered more acute, it improves the
pulse and raises blood pressure and is of great value as a tonic to the circulatory system
in cardiac failure.
In toxic doses strychnine causes violent tetanus like convulsions and death takes place
due to asphyxia and respiratory failure.
Brucine closely resembles strychnine in its action, but is slightly less poisonous; it
paralyses the peripheral motor nerves.
It is said that the convulsive action characteristic of strychnine is absent in brucine
almost entirely.
It is used in pruritis and as a local anodyne in inflammations of the external ear.
Nux vomica is also known as vomiting nut but it has no vomiting properties.
However Strychnos potatorum has emetic action.
VINCA
Vinca is the dried entire plant of Catharanthus roseus Linn., belonging to family 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.
It also contains monoterpenes, sesquiterpene, indole and indoline glycoside.
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, it may also be used as
a gargle.
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
Calabar beans are the dried ripe seeds of Physostigma veneno-sum 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 coloured, 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%, .
Calabar beans also contain stigmasterol.
Uses
Mainly used for diseases of the eye; it causes rapid con-traction 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.
LOBELIA
Lobelia consists of the dried aerial parts of Lobelia inflata Linn, belonging to family
Lobeliaceae.
It has an irritating odour and taste is unpleasant, acrid and burning.
Lobelia contains about 0.4% crystalline alkaloids of which lobeline is the important active
alkaloid.
Other alkaloids are lobelidine, lobelanidine, lobelanine and isolobinine chemically related to
lobeline. Also, gum, resin, chlorophyll, fixed oil, lignin, salts of lime and potassium with ferric
oxide are present.
Uses
It is mainly used as expectorant, diaphoretic, antiasthmatic.
Some authorities attach great value to it as an expectorant in bronchitis, others as a
valuable counterirritant when combined with other ingredients in ointment form.
It is sometimes given in convulsive and inflammatory disorders, such as epilepsy,
tetanus, diphtheria and tonsillitis.
Lobeline is a respiratory stimulant and is used in asphyxia of the newborn, in gas,
alcohol and narcotic poisoning and in drowning in water, electric shock and collapse.
It has relaxant and dilatory action and is used in asthma and dyspnoea.
Lobelia is also used to discontinue smoking habit.
Externally, an infusion has been found useful in ophthalmia, and the tincture can be used
as a local application for sprains, bruises, or skin diseases, alone, or in powder combined
with an equal part of slippery elm bark and weak lye water in a poultice.
The oil of Lobelia is valuable in tetanus.
TOBACCO
It consists of dried leaves of Nicotiana tobaccum, belonging to family Solanaceae.
Characteristics
Chemical Constituents
The most important constituent is the alkaloids nicotine, nicotianin, nicotinine, nicoteine,
nicoteline.
After leaves are smoked the nicotine decomposes into pyridine, furfurol, collidine, hydrocyanic
acid, carbon monoxide, etc. The poisonous effects of Tobacco smoke are due to these substances
of decomposed nicotine.
Uses
Nicotine is very like coniine and lobeline in its pharmacological action, and the pyridines
in the smoke modify very slightly its action.
It is used as a sedative, diuretic, expectorant, discutient and sialagogue.
The leaves in combination with the leaves of belladonna or stramonium make an
excellent application for obstinate ulcers, painful tremors and spasmodic affections.
Tobacco leaves are made wet and applied for piles.
Externally nicotine is an antiseptic.
Nicotine exerts stimulant effects on heart and nervous system.
ARECA NUTS
Areca nuts are the seeds of Areca catechu Linn., belonging to family Palmaceae.
Uses
o
Powdered Areca is used as anthelmintic, taenifuge and vermifuge for dogs.
It has aphrodisiac action and useful in urinary disorders, as nervine tonic and
emmenagogue.
The chewing of Areca nut may cause mouth cancer.
4. IMIDAZOLE ALKALOIDS
Imidazole is a heterocyclic aromatic organic compound. This ring system is present in important
biological build-ing blocks such as histidine and histamine.
Imidazoles can act as bases (Pka = 7.0) and as a weak acids (pK = 14.5).
Imidazole exists in two tautomeric forms with a hydrogen atom moving between the two
nitrogens.
PILOCARPUS
The drug consists of the leaves of Pilocarpus jaborandi, belonging to family Rutaceae
Chemical Test
To the drug containing pilocarpine, small quantities of dilute sulphuric acid, hydrogen peroxide
solution, benzene and potassium chromate solution is added and shaken, organic layer gives
bluish-violet colour and yellow colour appears in aqueous layer.
Uses
Pilocarpine is antagonistic to atropine, stimulating the nerve endings paralysed 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.
5. QUINOLINE ALKALOIDS
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
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.
The chiefly identified alkaloids are quinidine, quinine, cinchonine and cinchonidine.
Chemical Test
1)Thalleioquin test: To the extract of cinchona powder add one drop of dilute sulphuric acid and
1 ml of water. Add bromine water drop wise till the solution acquires per-manent yellow colour
and add 1 ml of dilute ammonia solution, emerald green colour is produced.
2)The powdered drug when heated with glacial acetic acid in dry test tube, evolves red fumes,
which con-dense in the top portion of the tube.
3)Cinchona bark, when moistened with sulphuric acid and observed under ultraviolet light shows
a blue fluorescence due to the methoxy group of Quinine and quinidine.
Uses
It is mainly employed as antimalarial drug,
it is also used as analgesic,
antipyretic,
protoplasmic,
bitter stomachic and tonic.
Quinidine is cardiac depressant
Cinchonidine is used in rheumatism and neuralgia.
6. ISOQUINOLINE ALKALOIDS
Isoquinoline is a double carbon ring containing one nitrogen atom.
Plants containing isoquinoline alkaloids are Argemone species (Prickly poppy)
Chelidonium species (Celandine poppy)
Corydalis species (Fitweed)
Dicentra species (Dutch-man’s breeches)
Papaver species (Poppy)
Sanguinera species (Bloodroot).
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.
IPECAC
Ipecac consists of the dried root or rhizome of Cephaelis ipecacuanha (Brot.) A. Rich. (Rio or
Brazilian Ipecac) or of Cephaelis acuminata Karst), family Rubiaceae.
It should contain about 2% of ether soluble alkaloids calculated as emetine.
Chemical constituents include emetine, cephaeline, psychotrine and psychotrine methyl ether.
Chemical Test of Emetine
Powdered drug (0.5 g) is mixed with HCl (20 ml) and water (5 ml), filtered and to the filtrate (2
ml) potas-sium chloride (0.01) is added. If emetine is present, a yellow colour develops which on
standing for 1 hour gradually changes to red.
Uses
Ipecac is emetic and used as an expectorant and diaphoretic and in the treatment of
amoebic dysentery.
The alkaloids have local irritant action.
Emetine has a more expectorant and less emetic action than cephaeline.
In the treatment of amoebic dysentery emetine hydrochloride is given by injection and
emetine and bismuth iodide by mouth.
Psychotrine and its methyl ether are selective inhibitors of human immunodeficiency
virus.
OPIUM
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.
Opium is required to contain not less than 10% of morphine and not less than 2.0% of codeine.
The thebaine content is limited to 3%.
Internal surface is coarsely granular, reddish-brown, lustrous; odour is characteristic; taste is
bitter and distinct.
Opium is intended only as a starting material for the manufacture of galenical preparations and is
not dispensed as such.
Chemical Constituents
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, the-baine (0.5–
2%). noscapine (4–8%), narceine and papaverine (0.5–2.5%).
Morphine contains a phenanthrene nucleus. The different types of alkaloids isolated are:
1. Morphine Type: Morphine, codeine, neopine, pseudo or oxymorphine, thebaine and
porphyroxine. Morphine consists of alkaloids which has phenanthrene nucleus whereas those of
the papaverine group has benzyliso-quinoline structure. Protopine and hydrocotamine are of
different structural types. 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.
2. Phthalide Isoquinoline Type: Hydrocotarnme, narcotoline, 1-narcotine, noscapine,
oxynarcotine, narceine, and 5’-O-demethyl-narcotine.
3. Benzyl Isoquinoline Type: Papaverine, dl-laudanine, lau-danidine, codamine and
laudanosine.
4. Cryptopine Type: Protopine, cryptopine.
5. Unknown Constituents: Aporeine, diodeadine, meconidine, papaveramine and lanthopine.
The drug also contains sugars, sulphates, albuminous compounds, colouring matter and moisture.
In addition to these anisaldehyde, vanillin, vanillic acid, β-hydroxystyrene, fumaric acid, lactic
acid, benzyl alcohol, 2-hydroxycinchonic acid, phthalic acid, hemipinic acid, meconin and an
odorous compound have also been reported.
Chemical Tests
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.
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, somniferous, soporific,
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.
CURARE
Curare is a crude dried extract from stems of Strychnos castelnaei Wedd., S. toxifiera Benth, S.
crevauxii G. Planchon, S. gubleri G. Planchon, belonging to family Loganiaceae. The extract is
also prepared from Chondodendron tomentosum Ruiz et Par and C.
microphylla (Menispermaceae).
Characteristics
Earlier curare has been imported in earthen pots and bamboos, now it is being imported in tins.
It is dark brown or black in colour. It is odourless and very bitter in taste.
Chemical Constituents
Curare contains several alkaloids, and quaternary compounds.
The most important alkaloid is curarine and two quaternary bases, calabashcurarine I and
calabashcurarine
Though the drug contains Strychnos, but strychnine is not present.
Uses
Curare has been used in the treatment of hydrophobia, cholera and tetanus.
It is used as a source of alkaloids.
It has muscular relaxation in surgery and is used to control convulsions of strychnine
poisoning and of tetanus.
7. STEROIDAL ALKALOIDS
They are formed by the addition of nitrogen on the similar point in the steroidal molecule, for
example kurchi and veratrum.
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 pre-cursor for synthesis of various other
steroids. Steroidal alkaloids contain a tetracyclic (4-ring) triterpene compound called the steroid
nucleus or steroidal backbone.
SOLANUM
These compounds generally appear as their corresponding glycoside in plants of
the genus Solanum. Solanum nigrum, solanum tuberosum .;
Solanum includes plants like potatoes, tomatoes, and various nightshades..
Starting with cholesterol, the biosynthesis of these compounds follow a similar general
mechanism including hyroxylation, oxidation, and transamination before
differentiating. Alkaloids found in these plants include chaconine, solanine, solasodine,
tomatidine, tomatine, and solanidine.
Typically they are used in plants as a protection mechanism against animals. Due to the typical
anti-cholinesterase activity, they can be used as poisons against the plants' predators.
They can be used as starting materials for steroidal drugs.
There are various tests for identifying these alkaloids.
The characteristic test involves dissolving the compound in hot amyl alcohol or ethanol and
watching for the formation of a jelly-like product as the mixture cools.
VERATRUM
Veratrum consists of dried roots and rhizomes of the peren-nial 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. Pseudojervine and veratrosine are glycosides of alkamine.
Germine, jervine, rubijervine and veratramine are alkamines.
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.
KURCHI BARK
Kurchi bark consists of dried stem bark of Holarrhena antidysenterica Wall,
belonging to family Apocynaceae.
Chemical Constituents
The main steroidal alkaloid is conessine (20–30%).
The other alkaloids isolated include conarrhimine, conimine, conamine,
conessimine, isoconessimine, dimethyl conkurchine and holarrhimine. In addition
to alkaloids the bark also contains gum, resin, tannin, lupeol and digitenol
glycoside holadysone.
Uses
The bark is considered to be stomachic, astringent, tonic, antidysenteric, febrifuge
and anthelmintic.
The dried bark is rubbed over the body in dropsy. Kurchi bark is used to cure
amoebic dysentery and diarrhoea.
8. 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.
They have a CNS; stimulant effect, relax bronchial smooth muscles and have a
diuretic effect. Mode of action is via inhibition of phosphodiesterase, this increases
production of cAMP causing release of adrenaline.
Caffeine occurs naturally in many beverage plants, including
coffee (Coffea arabica) belonging to the family Rubiaceae,
tea (Thea sinensis) belonging to the tea family (Theaceae),
yerba mate (Ilex paraguariensis) in the holly family (Aquifoliaceae) and
cola (Cola nitida) in the chocolate family (Sterculiaceae).
The primary source of theobromine is from the seeds of Cacao (Theobroma
cacao), another member of the chocolate family (Sterculiaceae)
.
COFFEE
Chemical Tests
1. Caffeine and other purine alkaloids, gives murexide colour reaction. Caffeine is
taken in a petridish to which hydrochloric acid and potassium chlorate crystals are
added and heated to dryness. A purple colour is obtained by exposing the residue
to vapours of dilute ammonia. In addition of fixed alkali the purple colour
disappears.
2. Caffeine also produces white precipitate with tannic acid solution.
Uses
a) Coffee is widely used as a flavoring agent, as in ice cream, pastries, candies
and liquors.
b) Source of caffeine, dried ripe seeds are used as a stimulant, nervine and
diuretic, acting on CNS, kidneys, heart and muscles.
c) Very valuable in cases of snake-bite, helping to ward off the terrible coma.
d) 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.
Geographical Source
It is mainly cultivated in India (Assam), Ceylon, Japan and Java.
The leaves are a rich source of caffeine (1–5%). It also contains theobromine and theophylline in
minor quantities. The colour of tea leaves is due to tannin (10–20% gallotannic acid).
The agreeable odour is due to presence of a yellow volatile oil. Tea leaves also contain protein,
wax, resin and ash.
Chemical Tests
1. Caffeine and other purine alkaloids, gives murexide colour reaction. Caffeine is taken in a
petridish to which hydrochloric acid and potassium chlorate are added and heated to dryness. A
purple colour is obtained by exposing the residue to vapours of dilute ammonia. In addition of
fixed alkali the purple colour disappears.
2. Caffeine also produces white precipitate with tannic acid solution.
Uses
It is used as stimulant, astringent and also as diuretic.
COCOA
It is obtained from seeds of Theobroma cocoa, belonging to family Sterculiaceae.
Chemical Constituents
Cocoa beans mainly contain theobromine and cocoa butter. The percentage of caffeine is less in
this, various volatile compounds, polyphenols, together with mucilage, etc., are also present.
Uses
It is used as an ingredient in cosmetic ointments and in pharmacy for coating pills and
preparing suppositories.
It has excellent emollient properties and is used to soften and protect chapped hands and
lips. Theobromine, the alkaloid in the beans, resembles caffeine in its action, but its effect
on the CNS is less powerful.
It is also used as diuretic.
It is also employed in high blood pressure as it dilates the blood-vessels. Cocoa is also
used as nutritive.
9. DITERPENE ALKALOIDS
Diterpene alkaloids are selectively accumulated in plants of the Aconitum, Delphinium, Carrya
and Thalictrum genera.
Diterpene bases are subdivided into two categories: the ones based on C19 skeleton and those
based on C20 skeleton.
ACONITE
Aconite is the dried roots of Aconitum napellus Linn, collected from wild or cultivated plants.,
belonging to family Ranunculaceae.
The odour is slight. Taste is sweet at first followed by tingling and numbness.
Uses
a) It is used externally as a local analgesic in liniments and to treat neuralgia, rheumatism
and inflammation.
b) Tincture Aconite is antipyretic in small doses.
c) Aconitine in amount 2–3 mg can lead respiratory failure, heart failure and in the end
death.
d) The drug is used for the preparation of an antineuralgic liniment.
EPHEDRA
Ephedra consists of the dried aerial parts of Ephedra gerardiana Wall, Ephedra
sinica Stapf, Ephedra equisetina Bunge, Ephedra nebrodensis Tineo and other Ephedra species,
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.
Chemical Test
To the drug (10 mg) in water (1 ml) dilute HCl (0.2 ml), copper sulphate solution (0.1 ml) and
sodium hydroxide solution (2 ml) are added; the liquid turns violet. On adding solvent ether (2
ml) and shaking vigorously, the ethereal layer turns purple and the aqueous layer becomes blue.
Uses
Ephedrine is antiallergenic, antiasthmatic, antispasmodic, decongestant, cough
suppressant, stimulant and vasoconstrictor.
Pseudoephedrine is decongestant, cough suppressant and 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
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.
Chemical Test
Colchicum corm with sulphuric acid (70%) or conc. HCl produces yellow colour due to the
presence of colchicines.
Uses
a) Both the corm and the seeds are analgesic, antirheumatic, cathartic and emetic.
b) They are used mainly in the treatment of gout and rheumatic complaints, usually
accompanied with an alkaline diuretic.
c) Leukaemia has been successfully treated with autumn crocus,
d) 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.