Classification of Alkaloids

Md. Zahidul Islam Zahid

Lecturer
Department of Pharmaceutical Sciences
North South University
What are alkaloids?

• Alkaloids are basic heterocyclic nitrogenous compounds

derived from plant sources that are physiologically active
• They are derived from amino acids
• Remain in solution in the cell sap of many plant drugs
• Possess a significant physiological action on man and other
animals
Some deviations/ exceptions:
• Some alkaloids are not basic e.g. piperine
• The nitrogen is not in a heterocyclic ring e.g. ephedrine
• Some alkaloids derive from micro-organisms, frogs, insects
• Some alkaloids does not derive from amino acids e.g.
steroidal alkaloid
Physical properties of alkaloids
1. Alkaloids are colorless crystalline solids and contain C, H, N
and O
2. A small number of them are liquids and oxygen free
3. Alkaloid bases are soluble in most organic solvent and
sparingly soluble or insoluble in water
4. Alkaloid salts are more soluble in water and other aqueous
solution and sparingly soluble or insoluble in organic
solvents
5. Majority of alkaloids are colorless except few like colchicine
is yellow
Chemical properties
1. Most are basic in nature due to presence of lone pair
of electrons on nitrogen
2. The alkaloid turns neutral or acidic if the adjacent
functional group are electron withdrawing like
amide group which reduces the availability of the
lone pair of electron
3. In natural form alkaloids exist either in free state, as
amine or as salt with acid or alkaloid N-oxides
 Pharmacological action of some important alkaloids

Most of the natural drugs used in pharmacy and medicine

are obtained from the alkaloid containing plants
- As analgesic: cocaine, morphine, codeine
- As anti amoebic and emetic: emetin
- As anti cholinergic: atropine, hyoscyamine, scopolamine
- As anti hypertensive: reserpine, deserpine
- As anti malarial: quinine, cinchonine
- As anti tumor: vinblastine, vincristine
- As anti tussive: codeine, noscapine
Pharmacological action of some important alkaloids

- As cardiac depressant: quinidine

- As central nervous stimulant: caffeine, strychnine, brucine
- As diuretic: theobromine, theophyllene
- As oxytocic: ergometrine, ergotamine
- As ophthalmic and cholinergic: physostigmine,
pilocarpine
- As skeletal muscle relaxant: tubocurarine
- As smooth muscle relaxant: papaverine, theophylline
Types of alkaloids

Simple amines Derived from acyl CoA units

Types cont..
1. True alkaloids include: pyrrole and pyrrolidine,
pyridine and piperidine, pyrrolizdine, tropane,
quinoline, isoquinoline, indole, imidazole,
norlupinane, piporphine
2. Protoalkaloids include alkylamine
3. Pseudoalkaloids include purine, steroidal,
diterpene
Classification of alkaloids
On the basis of various ring structure alkaloids are broadly
divided into the following major groups:
1) Pyridine-piperidine alkaloids:
- possess pyrrolidine, pyridine, piperidine ring structure or a combination of
these rings as their basic nuclei
- alkaloids of this group are used as anthelmintic, respiratory stimulants and as
insecticides
Examples are : Lobelia, Ricinus, Nicotine
N
N N H
H
Pyridine Piperidine Pyrrolidine
Classification of alkaloids
2) Tropane alkaloids:
- possess a dicyclic compound, tropane, as their basic nuclei which is formed by
the condensation of piperidine and N-methyl pyrrolidine ring
- alkaloids of this group are used as spasmolytic and anticholinergic and mydriatic
agents
Examples are: Atropine, Hyoscine, Hyoscyamine, littorone, tigloidine, cocaine

N-CH3

Tropane
Classification of alkaloids
3) Quinoline alkaloids:
- possess quinoline as their basic nuclei
- alkaloids of this group are used in the treatment of
malaria
Examples are: quinine, quinidine, cinchonine,
cinchonidine

N
Quinoline
Classification of alkaloids
4) Isoquinoline alkaloids :
- possess an isoquinoline basic structure
- alkaloids of this group are used as anti-amoebic, skeletal muscle relaxants,
analgesics, hypnotics and astringents
Examples are:
- Alkaloids in Ipecac( emetine, cephaeline, psychotrine)
- Alkaloids of opium( morphine, codeine, thebaine)

Isoquinoline
Classification of alkaloids
5) Indole alkaloids :
- possesses an indole ring as a part of structure
- alkaloids of this group are used in the treatment of high
blood pressure, Hodgkin’s disease, leukemia and
as oxytocics
Examples are: Rauwolfia and its alkaloids( reserpine, deserpidine, rescinnamine)
- Ergot and its alkaloids( ergotamine, ergometrine)

N
H Indole
Classification of alkaloids

6) Imidazole alkaloids :
- possesses an imidazole ring as the principal nucleus
- alkaloid of this group is used as cholinergic drug
Example:
- Pilocarpine
NH

Imidazole
Classification of alkaloids
7) Steroidal alkaloids:
- possess a cyclopentanoperhydrophenanthrene nucleus
- alkaloids of this group are used as hypotensives,
cardiac depressants, sedatives and anti-dysenteric
agents
Examples are:
- protoveratrine, veretramin, veratridin and germidine

Cyclopentenoperhydrophenanthrene
Classification of alkaloids
8) Alkaloidal amines:
- possess nitrogen atoms in side chains and called non-
heterocyclic alkaloids
- alkaloids of this group are used as bronchodilator,
vasoconstrictor and cardiac stimulant and as a
suppressant for gout
Examples are:

_
H-C-OH
- ephedrine, colchicine
H-C-NH-CH3
CH3
ephedrine
Qualitative chemical tests for alkaloids
1. Dragendorff’s test
2. Mayer’s test
3. Hager’s test
4. Wagner’s test

• Mayer’s test: To 2-3 ml of alkaloid solution few drops of Mayer’s

reagent (potassium mercuric iodide solution) is added. White brown
precipitate shows positive result.
Thank You 