1|Rajesh Kumar Sharma,Asso.
Prof,TMU,Moradabad
Alkaloids are the complex compound generally produces from plant. They are basic in nature and contain
one or more nitrogen atom (usually present in heterocyclic ring) and have pronounced pharmacological
action on man or animals.
CLASSIFICATION
Alkaloids are generally classified by their common molecular precursors, based on the biological pathway
used to construct the molecule.
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. Moreover, most of them are well-defined crystalline
substances which unite with acids to form salts.
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-tyrosine and L-tryptophan.
Protoalkaloids are those with a
closed ring, being perfect but structurally simple alkaloids. They form a minority of all alkaloids. Hordenine,
mescaline and yohimbine are good examples of these kinds of alkaloid. Chini et al. have found new alkaloids,
stachydrine and 4-hydroxystachydrine, derived from Boscia angustifolia, a plant belonging to the
Capparidacea family. These alkaloids have a pyrroline nucleus and are basic alkaloids in the genus Boscia. The
species from this genus have been used in folk medicine in East and South Africa. Boscia angustifolia is used
for the treatment of mental illness, and occasionally to combat pain and neuralgia.
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 trans-amination reactions of the different pathways connected with
precursors or post-cursors of amino acids.
These alkaloids can also be derived from non amino acid 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 phenylalanine derived or terpenoid, as well as
steroidal alkaloids.
Examples of pseudoalkaloids include such compounds as coniine, capsaicin, ephedrine, solanidine, caffeine
and theobromine.
PROPERTIES
Although numerous alkaloids exist, they have similar properties when separated. In general, they are
colourless, crystalline solids which are basic, have a ring structure, and have definite melting points. They are
also derived from plants and have a bitter taste. However, some exceptions are known. For instance, some
alkaloids are not basic and others are brightly coloured (betanidine, beriberine, sanguinarine)
or liquid (nicotine). Other alkaloids are produced synthetically. 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. Generally free bases of alkaloids are soluble in organic solvents and
2|Rajesh Kumar Sharma,Asso.Prof,TMU,Moradabad
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 of Alkaloids
Alkaloids can be isolated by any one of the following method
Method A
Powder Material
A) Keep moisten with water
B) Mixed with lime(Acids, Tannins and other phenolic compound combined with lime)
C) Extracted with organic solvent such as ether or pet. Spirit
Powder (discarded) Organic phase(containing alkaloidal extract)
A) Concentrated the above extract
B) Shake with aqueous acid
C) Allow to stand
Organic Phase discarded (containing impurities) Aqueous Phase containing alkaloidal salt
Method B
Powder Materials
a) Extract with water and aqueous alcohol containing dilute acid.
Shake with chloroform and other organic solvent
Chloroform layer (pigment Aqueous layer (Alkaloidal salt present)
and other unwanted material) Added Excess of solution bicarbonate or ammonia
Free alkaloid precipitated
a) Extract with organic solvent
b) Concentrate the solution
Concentrated organic solvent contain alkaloid
Alkaloid is purified by crystallization using suitable solvent.
Identification test for Alkaloid
i. Mayer’s reagent (Potassium mercuric iodide solution): It gives creamy precipitate.
ii. Wagner’s reagent (Aqueous iodine solution): Reddish brown precipitate.
iii. Dragendorff’s reagent (Potassium Bismuth iodine solution): Gives reddish precipitate.
iv. Hager’s reagent (Saturated solution of picric acid): Gives yellow precipitate.
Caffeine and some other alkaloids do not give test with mayer’s reagent, wagner’s reagent, dragendorff’s
reagent and hager’s reagent
Murexide test: Alkaloid is digested with potassium chloride and a drop of hydrochloric acid and this is expose
to vapour of ammonia – purple colour is form with caffeine and Purine group of alkaloid.
