1. -chemistry behind the anti-malarial drug
QUININE
-chemistry behind the anti-malarial
drug

2. 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.

3. 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

4. CHEMICAL STRUCTURE
(R)-(6-Methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanol

5. CHARACTERISTICS Fluoresces in direct sunlight
Sublimes in vacuum at k.
Dissociation constants Pk1=5.07 and pK2=9.7
pH of saturated solution=8.8
Fluoresces with a blue colour especially in sulphuric acid.

6. 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)

7. Types of bonds present in quinine
All the bonds present in quinine are covalent bonds.

8. R and S forms

10. Rabe and kindler process
In 1918 Paul Rabe and Karl Kindler obtained a three step preparation of quinine from d- quinotoxine

12. 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.

13. (c) Thalleioquin Test: Br2 water+2-3 ml of weakly acidic solution of quinine salt 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.

14. USES Flavour in carbonated beverages. Antimalarial agent.
Skeletal muscle relaxant.
Used to treat hemorrhoids and varicose veins
Oxytocic agent.
Prophylactic for flu.

15. Derivatives of quinine
Quinine Trihydrate
Quinine bisulphate heptahydrate
Quinine dihydrochloride
Quinine hydrochloride dehydrate
Quinine sulphate dehydrate

16. Quinine trihydrate It has a melting point of 330 K
It becomes anhydrous at 398 K

17. Quinine bisulphate Heptahydrate
It is obtained as bitter crystals
Also known as Quinbisan, Dentojel.

18. 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

19. Quinine Hydrochloride dihydrate
Obtained as silky needles of bitter taste
It effloresces on exposure to warm air.
Forms anhydrous solution at 373 K.

20. 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

22. Quinine isomer : quinidine
(S)-(6-Methoxyquinolin-4-yl)((2R,4S,8R)-8-vinylquinuclidin-2-yl)methanol

24. 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

25. uses It is an antiarrhythmic agent
It helps in keeping the heart rate normal for the people with certain heart rhythm disorders.

26. ….THANK YOU….
DONE BY
DHRUVI, RUTVI, SIDDHARTH