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Alkaloids

Dr Mohsina Zubair

Content of the Chapter

Nomenclature
Classification
Occurrance
Function of alkaloids
Isolation, properties of alkaloid, detection
of alkaloids
Quinine
Therapeutic uses of quinine
Morphine

introduction of alkaloids

The term alkaloids a alkalilike was


defined by a pharmacist Meissnei in 1819,
as the basic, nitrogenous organic
compounds of plant origin.
The alkaloids are now generally defined
now as physiologically active basic
compounds of plant origin, having one or
more basic nitro atoms in heterocyclic
system, which induce pronounced
physiological activity in animals and man.

Nomenclature

i.

A large no: of alkaloids are known and consist of such a variety of molecular
structure that their rational classification is very difficult. Alkaloids are often
classified according to plant from which they are isolated. e.g. cinchona,
opium etc.
Nowadays they are classified according to the heterocyclic ring system,
which is common group of alkaloids. They are classified as follows:
Phenylethylamine alkaloids

ii.
iii.
iv.
v.
vi.
vii.
viii.
ix.
x.

Pyrrolidine alkaloids e.g. hygrine etc.


Piperidine e.g. conine
Pyridine ..pyrrolidine e.g. Nicotine
Quinoline e.g. Quinine
Tropane e.g. atropine
Isoquinoline e.g. papaverine
Phenantherene isoquinoline e.g. Morphine
Indale e.g. strychnine
Tropolone

Occurrence of alkaloids

Alkaloids are cheifly found in plants of


dicotyledons families and occur in leaves, roots,
seeds and bark etc.
The alkaloid content of the plant varies with
season, age and its locality, closely related
alkaloids generally occur together in the same
plant e.g. nearly twenty alkaloids have been
isolated from opium.
Some alkaloids are found to occur as free amides
e.g. piperine, as esters e.g. tropine, and as
cocaine or organic acids.

Functions of alkaloids

The function of alkaloids in plant are uncertain and they are


regarded as by products of plant metabolism.
they may act as reservoir of protein synthesis. alkaloids are
also believed to act as protective substance against the
animal or insect attack.
They may function as plant stimulant or regulators like
hormones and regulates activities like growth, metabolism
and reproduction.
Alkaloids may function as detoxicating agents by
methylating, condensing and cyslising the compounds.

Isolation
alkaloids are isolated by a general
procedure, recommended by Manske,
is described here. The general
scheme for the extraction of
alkaloids is as follows.

Properties of alkaloids
1.

2.
3.
4.

5.
6.
7.

Alkaloids are generally colourless, crystalline, nonvolatile


solids through a few exceptions are there which occurs as
liquids e.g. coniine etc.
Alkaloids are insoluble in water but are soluble in most of
the organic solvents like ethanol, ether, chloroform.
Alkaloids are optically active compounds are a majority of
them are laevo rotatory.
Most of them posses marked physiological activity and are
of great value in medicine e.g. morphine, atropine, quinine
etc.
Alkaloids are bitter in taste.
They are poisonous in nature.
Alkaloids are precipitated by common alkaloid reagent
e.g. tannic acid, picric acid, perchloric acid.

Detection of alkaloids
Alkaloids are detected by physical methods as
well as by chemical methods.
Physical methods
1. Infra red spectroscopy
2. Ultra violet spectroscopy
3. X-ray analysis
4. NMR spectroscopy
5. Mass spectrometry
6. Optical rotatory dispersion (ORD) and circular
dichroism.

Detection of alkaloids
Infra red spectroscopy studies used to identifying the
several functional group like methylene groups, N-methyl
group, on C-methyl group, heterocyclic ring such as
pyridine, pyrrole etc.
UV spectroscopy are used to indicate the probable
structure of the alkaloids molecule.
X-ray analysis has been used for distinguishing the various
possible alternative structures.
Mass spectrometry has been recently used for determining
the types of nuclues (aromatic and heterocyclic) and the
size and structure of side chains in the various groups.
The stereochemistry of alkaloids is determined by X-ray
analysis, ORD and circular dichroism.

Detection of alkaloids

1.
2.
3.
4.

Chemical methods several important colour reaction are used for


detection of alkaloids. They following general reagents may be
used to detect the presence of alkaloids.
The reagent should be added to a cold solution of the substance in
the minimum quantity of dilute mineral acid.
These reagents precipitate the alkaloid from aqueous solution. In
many cases the presence of the trace of alkaloids can be detected
by adding a suitable reagent to its solution.
Mayers Reagent.
Dragendorffs Reagent
Wagners Reagent
Hagers Reagents. It is a saturated solution of picric acid in cold
water.

Quinine

Quinine is a cinchona alkaloids. It occurs a along with other


cinchona akaloids like quinidine, cinchoninie, cinchonidine
etc., in the cinchona bark.
Among these alkaloids quinine is the most important.
All the alkaloids are present in the bark in combination with
various complex organic acids such as quinic acids,
cinchotannic acid etc.
Quinine is widely used as an antimalarial drug.
Malaria is a protozoan infection caused by plasmodium
faiciprun, plasmodium vivax, plasmodium malaria and
plasmodium ovale.

Quinine
Sources. It is obtained from cinchona
ledgeriana and its hybrids.
Extraction. The bark is powdered and mixed
with sodium hydroxide solution and slaked
lime and the librated alkaloids are extracted
with hot petroleum. The separated extract is
shaken with hot dilute sulphuric acid. The
alkaloids passes into the aqueous layer as
sulphate. The solution is then cooled and the
sparingly soluble quinine sulphate crystallizes.

Structure

Properties of Quinine
1.

2.
3.

4.
5.
6.

Quinine crystallizes as colourless needles containing 3HO. It is


sparingly soluble in water but readily soluble in most organic
solvents. It is better in taste and is laevo-rotatory.
It is derivative of quinoline.
It is a di-acid tertiary base and forms salts with two
equivalents of an acid. The dihydrochloride is more soluble
than monohydrochloride.
on oxidation quinine gives quininic acid.
A dilute solution of quinine or quinine salt in dilute sulphuric
acid shows a characteristic blue fluorescence.
Another characteristic test is thalloquin reaction which is as
follows: then 2 ml of dilute ammonia solution is added to it
when it gives bright green colouration.

Structure and activity of quinine and


related Antimalarials
1.

2.
3.

The antimalarial activity of the cinchona alkaloids has


been studied. Depending on the infection the biological
activity of quinine, quinidine, cinchonidine , cinchonine
differ both qualitatively and quantitatively.
Quinidine is more active than quinine against plasmodium
falciperum plasmodium vivex.
Quinine has many adverse side effects such as blurred
vision, deafness etc. it requires dosing and quinine
sulphate is poorly absorbed from the gastro intestinal
tract.

Therapeutic activity of cinchona


alkaloids
Until the early 1930 quinine and the
related alkaloids were the sole
chemotherapeutic agents available
for the treatment of malaria. Despite
its limitation it is still frequently used
because of its low cost.
It is effective as a suppressive and in
the control of acute attacks of
malaria due to P. falciperum, P. vivax
etc.

Therapeutic uses of Quinine


It is mainly used in the treatment of malaria. Quinine is
termed as general protoplasmic poison. It can depress a
large no: of enzymatic processes. Quinine has local
anaesthetic activity. It can also depress the myocardium
by reducing its conductivity, excitability.
Quinine is also used in hereditary myopathy ( disease
of a muscle).
Chloroquine is effective against malaria due to P. vivax
and P. falcipurum. These are also useful in the
treatment of an acute attack of malaria.
Intravenous injection of quinine has a relaxant effect on
vascular smooth muscle causing a fall in blood pressure.

Morphine

Morphine is one of the narcotic analgesic. it is obtained


opium there are three important opium alkaloids namely
morphine, codeine and thebaine which contain
phenanthrene nucleus.
Morphine is the chief alkaloid obtained from opium which is
the dried sap of the unripe fruit capsules of papaver
somniferum.
Structure of morphine
morphine is C17H19NO3 and contains a phenanthrene
nuclues and has a tertiary nitrogen. it has a secondary
hydroxyl group position 6 and a phenolic group at position
3.

Properties of Morphine
i.
ii.
iii.
iv.
v.

vi.

It is a solid having m.p at 254C and natural morphine is


levo rotatory, has a specific rotation of - 131C.
Morphine forms a diactetate salt showing the presence of
two hydroxylic group on alcoholic and on phenolic.
It gives ferric chloride test for phenols due to the
presence of phenolic hydroxylic group.
It dissolves in aqueous NaOH to give mono Na Salts.
On treatment with halogen acids morphine forms monohalogen product indicating that an alcoholic hydroxyl
group is present in morphine.
Morphine has stimulant and depressant effects on central
nervous system and procedures a sense of euphoria, and
is a valuable analgesic.

Question
Q1. explain the nomenclature and classification of
alkaloids ?
Q2. Describe the function and isolation of alkaloids?
Q3. Quinine structure and properties?
Q4. Describe Morphine structure and properties ?
Q5. Define the detection method of alkaloids?