QUININE - PowerPoint Presentation

Slide1

QUININE

-chemistry behind the anti-malarial

drugSlide2

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

. Slide3

BIOLOGICAL SOURCES and HISTORY

Cinchona

species (

Rubiaceae

)

Obtained from cinchona or

peruvian

bark

First discovered by Quechua of Peru and Bolivia

First used

antimalarial

drugSlide4

CHEMICAL STRUCTURE

(

R

)-(6-Methoxyquinolin-4-yl)((2

S

,4

S

,8

R

)-8-vinylquinuclidin-2-yl)methanolSlide5

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.Slide6

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)Slide7

Types of bonds present in quinine

All the bonds present in quinine are covalent bonds.Slide8

R and S formsSlide9
Slide10

Rabe

and kindler process

In 1918 Paul

Rabe

and Karl Kindler obtained a three step preparation of quinine from d-

quinotoxineSlide11
Slide12

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 ethanol—

dark crystals

of

sulphate

of

iodoquinine

(

herpathite

) obtained

.Slide13

(c) Thalleioquin Test:

Br2 water+2-3 ml of weakly acidic solution of quinine salt+0.5-1 ml of strong ammonia

solution—

distinct emerald green

colouration

.

(d)

Erythroquinine

Test(

Rosequin

Test):

Quinine+ dil. Acetic acid+ freshly prepared Br2 water+ 10% solution of [K4Fe(CN)6]+ conc. NH4OH

soln

—

red

colouration

.Slide14

USES

Flavour

in carbonated beverages.

Antimalarial

agent.

Skeletal muscle relaxant.

Used to treat hemorrhoids and varicose veins

Oxytocic

agent.

Prophylactic for flu.Slide15

Derivatives of quinine

Quinine

Trihydrate

Quinine

bisulphate

heptahydrate

Quinine

dihydrochloride

Quinine hydrochloride dehydrate

Quinine

sulphate

dehydrateSlide16

Quinine

trihydrate

It has a melting point of 330 K

It becomes anhydrous at 398 KSlide17

Quinine

bisulphate

Heptahydrate

It

i

s obtained as bitter crystals

Also known as

Q

uinbisan

,

Dentojel

.Slide18

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 2.6Slide19

Quinine Hydrochloride

dihydrate

Obtained as silky needles of bitter taste

It effloresces on exposure to warm air.

Forms anhydrous solution at 373 K.Slide20

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 chloroformSlide21
Slide22

Quinine isomer : quinidine

(S)-(6-Methoxyquinolin-4-yl)((2R,4S,8R)-8-vinylquinuclidin-2-yl)methanolSlide23
Slide24

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 KSlide25

uses

It is an

antiarrhythmic agent

It helps in keeping the heart rate normal for the people with certain heart rhythm disorders.Slide26

….THANK YOU….

DONE BY

DHRUVI, RUTVI, SIDDHARTH