Alkaloids

By Dr.Saima Rubab
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•Definition
• Alkaloids are the nitrogenous basic compounds usually
of plants origin having definite pharmacological
activities.
•Distribution
• Alkaloids are present in plants, animals, bacteria and
fungi. They are mostly present in family of angiosperm
like Leguminosae, Solanaceae, Papaveraceae and
Ranunculaceae. As per chemical rules, the name of
alkaloids should end in “ine” e.g. Nicotine

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• Properties of alkaloids
• Alkaloids possess carbon, nitrogen and hydrogen.
• They are crystalline solid but sometime are liquid.
Example Nicotine
• They are insoluble or sparingly in water but soluble in
organic solvents like ether, chloroform etc.
• They form salt in acids which are soluble in water not
in organic solvents.
• Alkaloids are generally colorless but few are colored
e.g. Sanguinarine is red in color.

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• Functions in plants
• They are metabolic waste products.
• They also control metabolism in plants.
• They have defensive mechanism against pathogenic
substances in plants, they protect plants from insect
and herbivores.
• They have storage property of nitrogen.
• They regulate growth factors in plants.
• They occur as pigment such as pyridine and attract
animals for pollination.

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• Pharmacological functions
• Alkaloids have different pharmacological actions like,
• Analgesic ( Morphine)
• Emetic (Emetine)
• Antimalarial (Quinine, Cinchonine)
• Antitussive (Codine)
• Antitumor (Vincristine and Vinblastine)
• Oxytocic (Ergotamine which decrease uterus contraction)
• Ophthalmic (Pilocarpine)
• Cholinergic action (Physostigmine)
• Muscle relaxant (Tubercurarine and Papaverine)
• CNS stimulant (Strychnine, Brucine, Caffeine and Nicotine)

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 •Chemical Test
Group tests
•Wanger’s reagent
It is the solution of potassium iodide with iodine. It is prepared
by dissolving 2g of potassium iodide in 5ml of water and add
1.27g of iodine. Stir it until dissolved and makeup to 100ml with
distilled water (Reddish brown ppt. formed)
•Mayer’s reagent
It is solution of potassium iodide and mercuric chloride. It is
prepared by taking 1.36g of mercuric chloride and dissolve in
60ml of water. Take potassium iodide 10g and add 20ml of
water. Mix both the solution together and makeup volume to
100ml with distilled water. (Cream colored ppt.)
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 •Chemical Test
Group tests
•Hager’s reagent
It is the saturated solution of picric acid. It is prepared
by taking 1g of picric acid in 100ml of distilled water
and dissolves properly. (Yellow color ppt. formed)
•Dragendroff’s reagent
Dissolve 0.11g potassium iodide and 0.18g bismuth
nitrate (BiNO3) in 20ml acetic acid and make up to
100ml (Reddish brown ppt. formed)

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 •Individual Tests
•Lieberman burshads reagent
10% KMnO4 + H2SO4 treated with alkaloids
• Atropine, Hyoscine, Hyoscyamine gives orange
color
Papaverine, Emetine gives black color
Physostigmine gives red color
Colchicine gives yellow color

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 Extraction of alkaloid from powdered plants
•Method I
The powder is treated with alkali to liberate the free bases that can
then be extracted with water immiscible organic solvents.
•Method II
The powder material is extracted with water or aqueous alcohol
containing dilute acid. Alkaloids are extracted as their salts
together with accompanying soluble impurities.
•Method III
The powder is extracted with water soluble organic solvents such
as Methyl alcohol or Ethyl alcohol which are good solvents for both
salts and free bases.

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 •Types of alkaloids
•True alkaloids
These are basic nitrogenous compounds which are derived
from amino acids and nitrogen is present in the ring. e.g.
Nicotine.
•Proto alkaloids
In these alkaloids, nitrogen is present outside the ring and
they are derived from amino acids. e.g. Colchicine.
•Pseudo alkaloids
They are not derived from amino acids and nitrogen may or
may not present in ring. e.g. Aconitine and Caffeine.
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 Classification of alkaloids
A) On the basis of basic ring structure
1. Pyridine and Piperidine alkaloids
e.g. Nicotine, Lobeline and Arecoline
2. Tropane alkaloids
e.g. Atropine, Hyoscine and Hyoscyamine
3. Quinoline alkaloids
e.g. Quinine, Cinchonine, Quinidine and Cinchonidine
4. Isoquinoline alkaloids
e.g. Emetine, Cephaeline, Hydrastine, Morphine and
Codeine
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5.Indole alkaloids
e.g. Reserpine, Vincristine, Vinblastine, Strychnine,
Brucine, Serpentine, Physostigmine and Ergotamine
6.Imidaziole alkaloids
e.g. Pilocarpine, Isopilocarpine
7.Steroidal alkaloids
e.g. Veratidine, Veratrosine
8.Alkaloidal amines
e.g. Colchicine, Ephedrine
9.Purine bases
e.g. Caffeine, Theophylline, Theobromine 12
 B) On the basis of Plants
1. Pyridine and Piperidine alkaloids
e.g. Areca nut, Lobelia,Tobacco
2. Tropane alkaloids
e.g. Belladona, Hyoscyamus, Stramonium
3. Quinoline alkaloids
e.g. Cinchona
4. Isoquinoline alkaloids
e.g. Ipecacuanha, Opium
5. Indole alkaloids
e.g. Rauwolfia, Catharanthus, Nux Vomica, Physostigma, Ergot
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 B) On the basis of Plants
6. Imidaziole alkaloids
e.g. Pilocarpus

7. Steroidal alkaloids
e.g. Veratrum

8. Alkaloidal amines
e.g. Ephedra, Colchicum

9. Purine bases
e.g. Tea, Coffee

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 Pyridine and piperidine alkaloids
a) Areca nut
Botanical origin: Areca catechu
Family: Palmae
Part used: Dried ripened seeds

Constituents: Arecoline, Arecadine, Guvacine,

Guvacoline, Lipids, Volatile oils, Tannins and Gums
Uses: Anthelmetic in veterinary medicines,
Vermicides, Expel tapeworm.

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 Pyridine and piperidine alkaloids
b) Lobelia
Botanical origin: Lobelia inflata
Family: Lobeliaceae

Part used: Dried leaves and flowering tops

Constituents: It contain 14 alkaloids but most important is
Lobeline, Lipids, Resins, Volatile oils, Gums.
Uses: Expectorant, Respiratory stimulant, Smoking inhibitor.
Some effects are similar to nicotine, 0.5-1.5mg doses of
lobiline sulfate are given in the form of tablets and lozenges
to inhibit smoking
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c) Tobacco
Botanical origin: Nicotiana tobaccum
Family: Solanaceae
Part used: Liquid obtained
from leaves

Constituents: Nicotine, Nor-nicotine, Nicotianine

Uses: Nicotine chewing gums for given up smoking.
Finely divided powders of leaves are used as contact
poison, 40% solution of nicotine used as insecticide.
This become more toxic on addition of alkali.
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 Tropane alkaloids
a) Belladona
• Botanical origin: Atropa belladona
Family: Solanaceae
•
Part used: Dried leaves, flowering tops and roots
Constituents: Atropine, Hyoscyamine. Drug also contain 0.3-
0.6% alkaloids, the chief of which is hyoscyamine, also
contain volatile base pyridine, scopalitin (a florescent
substance) and calcium oxalate
Uses: Anti-cholinergic, GIT inflammation, Mushroom
poisning, Metal poisning

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 Tropane alkaloids
b) Hyoscyamus

• Botanical origin: Hyoscyamus niger

Family: Solanaceae
Part used: Dried leaves and flowering tops
Constituents: Scopolamine, Hyoscyamine, Hyocine.
(Petiole contain more alkaloids than stem or lamina)
Uses: Anti-cholinergic, GIT inflammation

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atropine

Hysocyamine

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 c) Stramonium
Botanical origin: Datura stramonium

Family: Solanaceae
Part used: Dried leaves and flowering tops
Constituents: Scopolamine, Hyoscyamine, traces of
atropine. It is required to contain not less than
0.25% of alkaloids calculated as hyoscyamine
Uses: Asthma, Treatment of burns
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d) Coca leaves
•Botanical origin: Erythroxylum coca
Family: Erythroxylaceae

Part used: Dried leaves

Constituents: Cocaine, cinnamyl cocaine, tropa
cocaine
Uses: Local anesthetics, CNS stimulant

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cocaine

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 Quinoline Alkaloids
These are alkaloids which contain basic quinolone nucleus. They are also
known as cinchona alkaloids.
a) Cinchona

Botanical origin: Cinchona succiruba (pure)

Cinchona calisaya (pure)
Cinchona officinalis (hybrid)
Family: Rubiaceae
Part used: Dried bark
Constituents: Yellow cinchona contain alkaloids quinine and quinidine,
cinchonine and cinchonidine
Uses: Anti-malarial, Anti-pyretic, Mild anesthetic and bitter tonic. Also
used in autoimmune disorder like rheumatoid arthritis (quinine
bisulphate)
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 Isoquinoline alkaloids
a) Ipecac
• Botanical origin: Cephaelis ipecacuanha
Family: Rubiaceae
Part used: Dried root and rhizome

Constituents: Cephaeline, Emetine, Psychotrine, psychotrine

methyl ether.
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 Isoquinoline alkaloids
• It also contains glucosidal tannins ipecacuanhic acid
(ipecacuahin).
A monoterpinoid isoquinoline glycoside (ipecoside), starch
and calcium oxalate. It require to contain not less than 2%
ether soluble alkaloids
Uses:
• Expectorant in small doses
• Emetic in the case of drug over dosage. It acts on CTZ and
stimulate it.
• Also act as Anti-amoebic
• Also used as antitumor

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 Isoquinoline alkaloids
b) Hydrastis

• Botanical origin: Hydrastis canadensis

Family: Ranunculaceae
Part used: Dried root and rhizome
Constituents: Hydrastine, berberine, canadine
Uses: Astringent, GIT, Nasal and Vaginal
inflammation

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Canadine

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 c) Opium
Botanical origin: Papaver somniferum
Family: Papaveraceae
Part used: Air dried milky exudate from ripened poppy capsule
Cultivation: The cultivation of opium is controlled
internationally by “International Narcotic Control Board of
United Nation”. The poppy blossom in April to May and capsule
mature in May or June. Each plant contains 5-8 capsules.

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Collection: The unripened capsule changes from green to
yellowish color. This time is critical for collection of latex. The
capsules are incised with the knife which is usually three bladed
and incision is made around circumference of endocarp. The
latex flows outside the capsule the latex which is at first white,
rapidly coagulates and turns brown to blackish in color.

It is collected at very first morning with the help of scraper

and then wrapped in poppy leaves and dried in shade.

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Constituents: Morphine, Papaverine, Codeine, Noscopine.
Thebaine is therapeutically inactive.
• It also contain Meconic acid which gives red color with FeCl3
(Detection test for Opium)
Uses: CNS stimulant, Analgesic, Hypotonic, Narcotics,
Antitussive (Codiene), Anti-diarrheal, Antipyretic contract
the eye pupil.

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Papeverine

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 Semi synthetic Compounds
They are more active than parent compounds,e.g. Heroine,
Hydromorphone (Analgesic), Hydrocodon (Antitussive)
•Opioids
They are natural or synthetic compounds that produce
morphine like effects, e.g. morphine, codeine (Natural) and
Dextropropoxyphene, Dextromethorphin (synthetic)
•Opiates
This term is reserved for drugs obtained naturally from
opium, e.g. morphine and codeine.
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 •Indole alkaloids
a) Rauwolfia
Botanical origin: Rauwolfia serpentina
Family: Apocynaceae
Part used: Dried roots
Constituents: Reserpine, Ajmaline,
Ajmalicine, Serpentine, Serpentinine, Rescinnamine. It
is required to contain not less than 0.25% of total
alkaloids calculated as reserpine, phytosterol fatty
acids.
Uses: Anti-hypertensive, Cardiac arrhythmias
(Ajmaline), mild anxiety, tranquillizer and neuro-
psychotic disorders 34
 •Indole alkaloids
b) Catharanthus
• Botanical origin: Catharanthus roseus
Vinca roseus
Family: Apocynaceae
Part used: Whole dried plant
Constituents: Vincristine, Vinblastine
Uses: Vinblastine use in Hodgkin disease (cancer),
lymphocytic lymphoma, Breast cancer
Vincristine use in Hodgkin disease, lymphocytic
leukemia, Wilm’s tumor (cancer of kidney that
typically occurs in children) and lymphosarcoma.
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Cantharidin
Rauwolfia

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 c) Nux vomica
• Botanical origin: Strychnous nuxvomica
Family: Loganiaceae

Part used: Dried ripened seeds

Constituents: Strychnine, Brucine, α-calubrin, β-
calubrin, novacine, loganin and chlorogenic acid
Uses: Strychnine used as CNS stimulant, Respiratory
stimulant, act as poison and germicide
Brucine: Alcohol denaturant 37
d) Pysostigmine
• Botanical origin: Physostigma venenosum
Family: Leguminosae
Part used: Dried ripened seed

Constituents: Physostigmine, Isophysostigmine, eseramine,

calabatine. It is derived from tryptophan on the exposure to
air. It oxidized into red color compound rubricerine and
should therefore be protected from light and air. Its salicylate
salts is more commonly used and rubrecerine more stable
and non-deliquescent.
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d) Pysostigmina
Uses:
• Reversible anticholinesterase, use in glucoma.
• Used topically to produce miosis and spasm of
accommodation to lower the intraocular pressure of eye.
• Given intravenously it reverses the effect of many sedatives.

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 e) Ergot

• It is dried sclerotium of fungus Claviceps purpurea

Family: Claviptaceae
It is arising in the ovary of rye plant (Secale cereal; Family:
Graminae)
Ergot is required to yield not less than 0.15% of total
alkaloid calculated as ergotoxin.
• How sclerosium is formed??
• Sclerosium is dark purple color solidified metabolic product
of fungus in the ovary of spine of rye plant. 40
 e) Ergot
Rye plant become infected in spring or early summer by the
Ascospores of fungus. These are carried by wind or by insect
to the base of young ovary where in damp wheather, They
germinate forming filamentous hyphae, which enter the wall
of ovary by the enzyme action and form a soft white mass
over its surface. This mycelium produce a yellowish
saccharin (sweet) secretion “honey dew”. At the same time
some hyphael strands produce asexual spores
“Conidiophores” which are suspended in honey dew and can
be carried to other plant by insect and bees (sexual stage). In
the next stage of development hyphae penetrate deeper and
deeper feeding on ovarian tissue and finally replace it by a
compact tissue which gradually hardens, becomes dark
purple and form a resting body (final product) Scleroscium.
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 e) Ergot

This may fall to the ground over winter and in the spring produces
Ascospores (sexual spores) that repeat the entire cycle.
Constituents: Ergot contains or produce large number of alkaloids
which fall into 2 catageries depending upon their solubility in water
(i) Water soluble alkaloid: Ergometrine (Ergonovin), Ergometrinine
(ii) Water insoluble alkaloid: Ergotamine, Ergotaminine, Ergosine,
Ergocristine, Ergocriptine, Ergocornine. These are also called peptide
alkaloids
Other constituents are histamine, tyramine, acetyl choline, coloring
matter, sterol, fats.

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• Significant semisynthetic alkaloids includes methyl
ergonovine, dihydroergotamine, methyl surgid, lysergic acid
diethyl amide (LSD)
Uses: Whole ergot preparation are rarely used but isolated
alkaloid are widely used
o Labor to assist delivery and to reduce postpartum
hemorrhage
o Ergotamine is used in combination with caffeine to
treat migraine
o Dihydroergotamine is used in lowering B.P and in
bradycardia
o LSD is potent psycomimetic agent

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 Imidazole alkaloids
•a) Pilocarpine
• Botanical origin: Pilocarpus jaborandi
Pilocarpus microphyllus
Family: Rutaceae
Part used: Freshly dried leaves
Constituents: Pilocarpine, isopilocarpine
Uses:
• Used in the form of pilocarpine HCl ans pilocarpine nitrate
are cholinergic drugs and used in treatment of glaucoma.
• stimulate oral secretions, cholinergic agonist, have
parasympathomimetic effect.
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Pilocarpine

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 Steroidal alkaloids
a) Veratrum
• Botanical origin: Veratrum viride
Family: Liliaceae
Part used: Dried rhizome and root
Constituents:Drug contain numerous steroidal
alkaloids, which can be divided into three groups,
• Group I : Consisting of esters of steroidal bases
(alkamines) with organic acid.
• Cevadine, Geramidine, Protoveratrine and
veratridine.
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 Steroidal alkaloids
a) Veratrum
• Group II :Glucosides of alkamines
• Pseudojeravine, veratrosides
• Group III: Alkamines in free state
• Germine, jervine veratramine
Uses: Cardiac depressant, decrease B.P, sedative and
insecticide

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Alkaloidal amines
• They have homocyclic ring and nitrogen is attached
outside the ring.
a) Colchicum
• Botanical origin: Colchicum luteum
Colchicum autumnale
Family: Liliaceae
Part used: Dreid ripened seeds
Constituents: Colchicine, is an amorphous yellowish
white alkaloid, which is darken on exposure to light
and give yellow coloration with strong mineral acid
Uses: Gout, Rheumatism and polyploidy
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Alkaloidal amines
b) Ephedra
• Botanical origin: Ephedra sinica
Family: Ephedraceae
Part used: Dried whole plant
Constituents: Ephedrine, Pseudoephedrine,
Ephedrodine in roots only.
Uses: Anti-tussive used in asthma,
Bronchodilator, used in hay fever, potent
sympathomimetic, ephedra herb has
sudorific action
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Protoveratrine
Colchicine

Ephidrine 50
 Purine bases
• These are heterocyclic compounds with five
membered imidazole ring.

a) Coffee
• Botanical origin: Coffea arabica
Family: Rubiaceae
Part used: Dried ripened seeds
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 Purine bases

Constituents: Caffeine (1-2%), Trigonelline, Tannins,

Glucoside, Dextrin, Fatty oils, consisting of oleine,
palmitine. Aroma of roasted coffee is caused by an oil
known as caffeol.
Uses: CNS stimulant, Diuretics
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 Purine bases
b) Tea
•Botanical origin: Camellia sinensis
Family: Theaceae
Part used: Dried leaves and leaf buds
Constituents: Caffeine, adenine, theobromine,
theophylline, xanthine
Uses: CNS stimulant, Diuretics, smooth muscle
relaxant, prevent asthma.

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Oleanolinic
acid

Caffeine

Theophillin
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