Alkaloids
Prof. S.Hemalatha
Department of Pharm. Engg. & Technology
IIT (BHU), Varanasi
U.P.-221005
Definition
• Derived from plant sources
• Basic in nature
• Contain one or more nitrogen atoms (usually in heterocycle ring) derived
from biogenetic amines
• Have significant physiological effect
• Mostly solid and crystalline in nature
• Exception:
❑ Liquid alkaloids: Nicotine,Coniine
❑ Coloured alkaloids: Berberine (Yellow), Sanguinarine (Copper red)
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• True alkaloid —Nitrogen derived from
biogenetic amine and present in heterocyclic
ring
eg. Quinine, Morphine and Strychnine
• Pseudo alkaloid- Nitrogen not derived from
biogenetic amine, and may or may not present
in heterocyclic ring
eg. Solanidine
• Proto alkaloid - Nitrogen derived from
biogenetic amine and Nitrogen not present in
heterocyclic ring
eg. Ephedrine
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Distribution
•Berberidaceae
•Menispermaceae
•Papaveraceae
•Chenopodiaceae
•Berberidaceae
•Rutaceae
•Solanaceae
•Ranunculaceae
•Rubiaceae
•Apocynaceae
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Distribution in Plant
All Parts e.g. Datura.
Barks e.g. Cinchona Barks
Seeds e.g. Nux vomica Seeds
Roots e.g. AconiteRoots
Fruits e.g. Black pepperFruits
Leaves e.g. Tobacco Leaves
Latex e.g. Opium Latex
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Forms of Alkaloids
• Free bases
• Salts with Organic acids e.g. Oxalic, acetic acids
• Salts with inorganic acids e.g. HCl, H2SO4.
• Salts with special e.g. Meconic acid in Opium
• Quinic acid in Cinchona
• Glycosidal form e.g. Solanine in Glycosidal form
e.g. Solanine in Solanum tubarosum.
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Physical properties
• Nature/Condition:
• Most alkaloids are crystalline alkaloids are crystalline
solids
• Few alkaloids are amorphous solids e.g.
• Some are liquids that are either Volatile e.g. nicotine and
coniine, or Non-volatile e.g. pilocarpine and e.g.
pilocarpine and hyoscine.
• Color:
• The majorityof alkaloids are colorless but some are
colored e.g.: Colchicine and berberine are yellow.
Canadine is orange.
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Physical Properties
• Solubility: Both alkaloidal bases and their salts are
soluble in alcohol Generally, the are soluble in
organic solvents and insoluble in water
• Exceptions:Bases soluble in water : caffeine,
ephedrine, codeine, colchicine, pilocarpine and
quaternary ammonium Bases insoluble or
sparingly soluble in certain organic solvents
• morphine in ether, theobromine and theophylline
in benzene.
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• Salts are usually soluble in waters, and,
insoluble or sparingly soluble in organic
solvents. Exceptions: Salts insoluble in water :
quinine monosulphate.:
• Salts soluble in organic solvents: lobeline and
apoatropine hydrochlorides are soluble in
chloroform.
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Isomerization
• Optically active isomers may show different physiological
activities.
• L-ephedrine is 3.5 times more active than-ephedrine
d-ephedrine.-
• l-ergotamine is 3-4 times more active
d-ergotamine.-ergotamine.
• d- Tubocurarine is more active than the corresponding- l-
form.
• Quinine (l-form) is antimalarial and its-d form is quinidine is
antiarrythmic.
• The racemic (optically inactive)dl-atropine is-atropine is
physiologically active.
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Chemical Properties
• Nitrogen:
• Primary amines –R-NH2 - e.g. Norephedrine
• Secondary amines R2-NH e.g. Ephedrine
• Tertiary amines R3-N e.g. Atropine
• Quaternary ammonium salts R4 e.g-
d-Tubocurarine
• Basicity:R2-NH> R-NH2 >R3-N
• Saturated hexacyclic amines is more basic than
aromatic amines.
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According to basicity
• Alkaloids are classified into: Weak bases e.g.
Caffeine
• Strong bases e.g. Atropine
• Amphoteric
• Phenolic Alkaloids e.g. Morphine
• Alkaloids with Carboxylic groups e.g.
Narceine
• Neutral alkaloids e.g. Colchicine
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• Oxygen:
• Most alkaloids contain Oxygen and are solid in
nature e.g. Atropine.
• Some alkaloids are free from Oxygen are mostly
liquids e.g. Nicotine, Coniine.
• Stability: Effect of heat:
• Alkaloids are decomposed by heat, except
Strychnine and caffeine (sublimable). Reaction
with acids: 1- Salt formation. 2- Dil acids
hydrolyze Ester Alkaloids e.g. Atropine
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Classification
Sl. Type of alkaloid Name of Plant Name
No. (basic ring structure) alkaloid
1. Tropane Atropine Belladona
(Atropha belladonna)
2. Quinoline Quinine Cinchona
(Cinchona officinalis)
3. Isoquinoline Papaverine Opium
Narcotine (Papaver somniferum)
Emetine Ipecac
Berberine (Cephaelis ipecacuanha)
Berberis
(Berberis species)
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Sl. Type of alkaoid Name of Plant Name
No. (basic ring structure) alkaloid
4. Indole Strychnine Nux-vomica
Brucine (Strychnos nux vomica)
Reserpine Sarpagandha(Rauwolfia
Vincristine serpentina)
Vinca
(Catharanthus roseus)
5. Phenanthrene Morphine Opium
Codeine (Papaver somniferum)
6. Purine Caffeine Tea
Theobromine (Thea sinensis)
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Sl. Type of alkaoid Name of Plant Name
No. (basic ring structure) alkaloid
7. Pyrrole Pyrrolidine Hygrine Tobacco
Trigonelline Coca
Nicotine (Theobroma cacao)
8. Pyridine Piperidine Coniine Hemlock
Lobeline Lobelia
(Lobelia nicotianefolia)
9. Imidazole Pilocarpine Pilocarpus
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Sl. Type of alkaoid Name of Plant Name
No. (basic ring structure) alkaloid
10. Steroidal Conessine Kurchi
Solanidine (Holarrhena antidysenterica)
Protoveratrine Solanum species, Potato
11. Terpenoid Aconitine Aconite
C20H32 Aconine (Aconitum napellus)
12. Alkylamine Ephedrine Ephedra
(Amino alkaloid) (Ephedra gerardiana,
E.equisetina, E.sinica)
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Chemical Test
Sl. Name test Reagent/ Procedure Observation
No.
1. Dragendroff test Potassium bismuth iodide Brown
2. Mayer’s test Potassium mercuric iodide Cream
3. Hager’s test Picric acid Yellow
4. Wagner’s test Iodine (I + KI) Red brown
5. Murexide test for Extract+ Pot. chlorate+ drops of Purple colour
Caffeine HCl Expose to ammonia vapour
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Isolation of Alkaloids
• Plant material (macerated with alkai)
• Extract with Organic solvent (Alcohol)
• Alcoholic extract (contains alkaloid) treated
with acid to get alkaloid in salt form.
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Pharmacological Actions
S.No Category Examples
1 Anti cancer Vinca, Taxus(taxol)
2 Anti inflammatory Colchicine
3 Anti amoebic Ipecac, Kurchi
4 Anthelmintic Artemisia,Quassia
5 Antiasthmatic Vasaka, Ephedra
6 Anti spasmodic Belladonna( Atropine), Datura,
Hyosyamus
7 Analgesic Opium(Morphine), caffeine
8 Antimalarial Quinine(Cinchona)
9 Anti hypertensive/ Tranquliser Rauwolfia (reserpine)
10 Anti arrhythmic Quinidine(Cinchona)
11 CNS action Strychinine (Nuxvomica)
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