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QUININE

-CHEMISTRY BEHIND THE ANTI-MALARIAL


DRUG
WHAT IS QUININE?
Natural, white crystalline alkaloid
Possesses antipyretic, antimalarial ,
analgesic and anti-inflammatory
properties
Bitter taste
Stereoisomer of quinidine
Possesses 2 major ring systems:
aromatic quinoline , bicyclic
quinuclidine.
BIOLOGICAL SOURCES
AND HISTORY
Cinchona species (Rubiaceae)
Obtained from cinchona or
peruvian bark
First discovered by Quechua of
Peru and Bolivia
First used antimalarial drug
CHEMICAL STRUCTURE

(R)-(6-Methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-
yl)methanol
CHARACTERISTICS
Fluoresces in direct sunlight
Sublimes in vacuum at 443-453k.
Dissociation constants Pk1=5.07
and pK2=9.7
pH of saturated solution=8.8
Fluoresces with a blue colour
especially in sulphuric acid.
FUNCTIONAL GROUPS
It's functional groups are:

* alkene
* tertiary amine (the quinuclidine bicyclic
system)
* secondary alcohol
* quinoline (an aromatic system,
specifically 1- azanaphthalene)
* phenolic ether (or perhaps simply an
aromatic ether)
TYPES OF BONDS
PRESENT IN QUININE

All the bonds present in quinine are


covalent bonds.
R AND S FORMS
RABE AND KINDLER
PROCESS

In 1918 Paul Rabe and Karl Kindler


obtained a three step preparation of
quinine from d- quinotoxine
IDENTIFICATION TESTS
( a)Colour Tests:
1.Oxygenated Acids : Strong, blue
fluorescence in sulphuric acid, acetic
acid,etc.
2. Herpathite Test: boiling mixture of
quinine(0.3g)+ 7.5ml glacial acetic acid+
5 drops of conc. H2SO4 in 3ml
ethanol(0.9v/v)+3.5 ml of I2
solution(0.01w/v) in ethanoldark
crystals of sulphate of iodoquinine
(herpathite) obtained.
( c) Thalleioquin Test: Br2 water+2-3
ml of weakly acidic solution of
quinine salt+0.5-1 ml of strong
ammonia solutiondistinct
emerald green colouration.
(d) Erythroquinine Test(Rosequin
Test): Quinine+ dil. Acetic acid+
freshly prepared Br2 water+ 10%
solution of [K4Fe(CN)6]+ conc.
NH4OH solnred colouration.
USES
Flavour in carbonated beverages.
Antimalarial agent.
Skeletal muscle relaxant.
Used to treat hemorrhoids and
varicose veins
Oxytocic agent.
Prophylactic for flu.
DERIVATIVES OF QUININE

1)Quinine Trihydrate
2)Quinine bisulphate heptahydrate
3)Quinine dihydrochloride
4)Quinine hydrochloride dehydrate
5)Quinine sulphate dehydrate
QUININE TRIHYDRATE

It has a melting point of 330 K


It becomes anhydrous at 398 K
QUININE BISULPHATE
HEPTAHYDRATE

It is obtained as bitter crystals


Also known as Quinbisan, Dentojel.
QUININE DIHYDROCHLORIDE

Also known as quinine dichloride,


Quinine bimuriate
Slightly soluble in chloroform and
very slightly soluble in ether
Aqueous solutions are found to be
higly acidic with a pH of 2.6
QUININE HYDROCHLORIDE
DIHYDRATE

Obtained as silky needles of


bitter taste
It effloresces on exposure to
warm air.
Forms anhydrous solution at
373 K.
QUININE SULPHATE
DIHYDRATE
Also known as Quinsan, Quine and
Quinate
Its is obtained as dull needles or
rods making a light and readily
compressible mass.
Losses water of crystallization at
383 K.
Slightly soluble in ether and
chloroform
QUININE ISOMER :
QUINIDINE

(S)-(6-Methoxyquinolin-4-yl)((2R,4S,8R)-8-
vinylquinuclidin-2-yl)methanol
PROPERTIES
It is optical isomer of quinine
It is a diastereomer of quinidine
It is found as white powder or
crystals
Insoluble in water
It melts at 441 K
USES

It is an antiarrhythmic agent
It helps in keeping the heart rate
normal for the people with
certain heart rhythm disorders.
.THANK
YOU.
DONE BY
DHRUVI, RUTVI, SIDDHARTH