EPHEDRINE

INTRODUCTION
 It is an important drug which occurs along with
five other alkaloids namely pseudo ephedrine,
methyl ephedrine , methyl pseudo-ephedrine ,
nor ephedrine and nor pseudo-ephedrine in the
genus Ephedra
 It is a species that occur in temperate and
subtropical mediteranean region
 Physiologically the action of ephedrine has been
found to be similar to that of adrenaline and it
can be taken orally
 Ephedrine has been used sucessfully in the
treatment of bronchial asthma, hay fever and
other allergic conditions.
 It also decreases blood pressure, it is a stronger
stimulant than caffiene
 These are phenylamine type of derivatives and
their concentration varies from different species.
CONSTITUTION
 MOLECULAR FORMULA:-
From the analytical data, the molecular
formula of ephedrine has been found to be
C10H15NO
 PRESENCE OF SECONDARY AMINO
GROUP:-
When ephedrine is treated with nitrous acid
it yields a nitroso compound, this reaction
reveals that ephedrine is a secondary amine.
 PRESENCE OF HYDROXYL GROUP:-
When it is benzolyated it forms a dibenzyl
derivative indicating that oxygen atom is present as
hydroxyl group because one benzoyl group is
introduced at NH group while the other at OH-group
NATURE OF CARBON SKELETON:-
When ephedrine is oxidised, it yields benzoic
acid, indicating the ephedrine contains a benzene
ring with a side chain, thus ephedrine may be
represented as C4
H19ON
 NATURE OF SIDE CHAIN:-
 When ephedrine is heated with
concentrated hydrochloric acid it forms
methylamine and propiophenone.This reaction
reveals the presence of an-NH-CH3 group in
ephedrine
 C10H15NO HCL CH3NH2 C6H5COCH2CH3
STERIOCHEMISTRY OF EPHEDRINE
 OPTICAL ISOMERISM:-
 As there are two dissimilar chiral centres in the
ephedrine, four optical active forms are theoritically
possible…..(two pairs of enantiomers)
 Freudenberg gave the following configuration of
ephedrine and pseudoephedrine.
BIOSYNTHESIS OF EPHEDRINE
 These alkaloids are formed by a union of a C6-C1 unit
and a C2 unit.
 Phenylalanine is the orginator of the C6-C1 moiety ,which
is being converted to benzaldehyde or benzoic acid.
 The benzoic acid combines with the intact CH3CO group
of pyruvic acid to form ephedrine and related alkaloids
with 1-phenylpropane-1,2-dione and (s)-(-) 2-amino-1-
phenyl propane-1-one (cathione) which serves as
intermediates
BASICITY
 The pseudoephedrine is a stronger base than ephedrine.
 This is due to the stabilisation of the conjugate acid in
the former case by the internal hydrogen bonding
between the neighbouring –OH and -NH2CH3 groups.
 In case of ephedrine the conformation necessary for such
hydrogen bonding would be strongly opposed by
interferance between the bulky methyl group and phenyl
group.
USES

 It is used in cough mixtures to relieve asthma and hay

fever due to its bronchodilator activity.

 It is a potent nasal decongestant

 It has similar action to that of adrenaline and it can be
taken orally
REFERENCE
 Organic chemistry of natural products by
 Gurudeep chatwal

 Pharmacognosy and phytochemistry of natural products

by
 Jean brueneton
 Text book of pharmacognosy by

 Trese and Evans

 www.inchem.org
THANK YOU