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QUININE

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

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QUININE

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  1. 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 , bicyclicquinuclidine.

  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 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.

  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

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

  10. 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.

  11. (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—redcolouration.

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

  13. Derivatives of quinine • Quinine Trihydrate • Quinine bisulphateheptahydrate • Quinine dihydrochloride • Quinine hydrochloride dehydrate • Quinine sulphate dehydrate

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

  15. Quinine bisulphateHeptahydrate • It is obtained as bitter crystals • Also known as Quinbisan, Dentojel.

  16. 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

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

  18. Quinine sulphatedihydrate • 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

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

  20. 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

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

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

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