Professional Documents
Culture Documents
Lecture-1
(Introduction)
By
Dr. Ahmed Metwaly
Objectives
Definition
Function
Nomenclature
Classification
Physical properties
Chemical properties
Qualitative chemical tests
Isolation
Quantitative chemical assay
Definition:
Alkaloids, which means alkali-like substances , are
basic nitrogenous compounds of plant or animal origin
and generally possessing a marked physiological
action on man or animals.
The nitrogen is usually contained in a heterocyclic
ring system and it mainly derived from amino acids.
Function of alkaloids in plants
1. They may act as protective against insects and herbivores
due to their bitterness and toxicity.
2. They are, in certain cases, the final products of
detoxification in metabolic reactions, therefore considered
as waste products of metabolism.
3. They may provide nitrogen to the plant organs in case of
nitrogen deficiency (source of nitrogen).
4. They, sometimes, act as growth regulators in certain
metabolic systems.
5. They may be utilized as a source of energy in case of
deficiency in carbon dioxide assimilation, especially those
alkaloids containing a sugar moiety.
Some alkaloids are extremely poisonous e.g.:
H H
H H
HO H
H N HO N
H H
R R
N N
(-)-Quinine R = OCH3 (+)-Quinidine R = OCH3
(-)-Cinchonidine R = H (+)-Cinchonine R = H
Classification
N CH3
N N N
N H
N N N
N CH3
3- Alkaloids are classified according to the amino acid that provides both the
nitrogen atom and the fundamental portion of the alkaloid skeleton.
H R R1 R1 R1
R3
N N N N N
H H H H R2 H R2 R3 R2 R4
Exceptions:
Bases soluble in water: caffeine, ephedrine, codeine,
colchicine, pilocarpine and quaternary ammonium bases.
Bases insoluble or sparingly soluble in certain organic
solvents:
Morphine and psychotrine in ether,
Theobromine and theophylline in benzene.
Salts
are usually soluble in water and, insoluble or sparingly
soluble in organic solvents.
Exceptions:
Salts insoluble In water:
e.g. quinine monosulphate
Salts soluble in organic solvents:
e.g. Lobeline hydrochlorides
soluble in chloroform.
Optical activity:
Many alkaloids are optically active due to the
presence of one or more asymmetric carbon atom
(chiral) in their molecule.
Optically active isomers show different
physiological activities.
Usually, the l (-) isomer is more active than the d (+)
isomer
e.g.:
l-ephedrine is 3 times more active than d-ephedrine
l-ergotamine is 3 times more active than d-ergotamine.
Exceptions:
d-Tubocurarine is more active than the corresponding l- form.
Both quinine (l-form) and its d- isomer quinidine are active.
The racemic dl-atropine is physiologically active.
Chemical characters:
Basicity:
The unshared electron pairs on the nitrogen atom is
responsible for alkaloidal basicity.
Strong basic alkaloids can form salts even with very weak
acids. While weak bases require more acidic medium.
1) Heat:
Alkaloids generally decompose on heating while some
of them sublime e.g. caffeine.
2) Acids:
Cold conc. acids may cause dramatic changes
(meanwhile heating with dil. acids may cause similar
changes) e.g.:
Dehydration:
Some alkaloids lose water molecule to from the anhydro-or apo
alkaloids
e.g. Morphine to Apomorphine,
Atropine to Apoatropine.
Demethylation:
N -or O-demethylation of certain alkaloids can take place upon
heating with mineral acids
e.g.: Quinine, Narcotine, Codeine, and Papaverine.
Chemical properties
In addition to carbon, hydrogen and nitrogen, most alkaloids
contain oxygen in their molecules.
Few alkaloids are oxygen-free such as nicotine and coniine.
Salt formation
Due to their basic character, alkaloids with acids make salts.
Strong bases form salts with very weak acids.
Weak bases require stronger acids.
Dibasic alkaloids may form two series of salts.
Very weak bases form unstable salts, e.g. piperine,
papaverine, narcotine and caffeine.
Amphoteric alkaloids (e.g. containing phenolic or carboxylic
groups) can form salts with both acids and alkalis.
Alkaloids showing acidic characters do not form salts with
acids e.g. ricinine.
Tests for detection and identification
Name of Composition Remarks
reagent
1) Volumetric methods.
a) Aqueous titration.
b) Non-aqueous titration.
2) Gravimetric methods.
3) Colorimetric and spectrophotometric methods.
Summary
Definition
Function
Nomenclature
Classification
Physical properties
Chemical properties
Qualitative chemical tests
Isolation
Quantitative chemical assay