quinine
DESCRIPTION
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 - PowerPoint PPT PresentationTRANSCRIPT
![Page 1: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/1.jpg)
QUININE-CHEMISTRY BEHIND THE ANTI-MALARIAL
DRUG
![Page 2: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/2.jpg)
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.
![Page 3: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/3.jpg)
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
![Page 4: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/4.jpg)
CHEMICAL STRUCTURE
(R)-(6-Methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanol
![Page 5: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/5.jpg)
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.
![Page 6: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/6.jpg)
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)
![Page 7: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/7.jpg)
TYPES OF BONDS PRESENT IN QUININE
• All the bonds present in quinine are covalent bonds.
![Page 8: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/8.jpg)
R AND S FORMS
![Page 9: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/9.jpg)
Powdered Bark- Alk. CaO + NaOH + H2O- Reflux with benzene &- Filtration while hot
Benzene filtrate (Alkaloidal bases)dilute H2SO4
Acidic aqueous layer(Alkaloidal bisulphates)
pH to 6.5 with Na2CO3
PrecipitateQuinine quinidine,
cinchonine & cinchonidine Hot water, Na2CO3
Quinine NaOH, ether
Aqueous layerEther layerCinchonineQuinidine & Cinchonidine
-HCl PH=7, Na, K Tart. salt- filter
Precipitate Filtrate
Cinchonidine tartrate Quinidine tartrate
Aqueous solution (Monosulphates)(monosulphate)
![Page 10: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/10.jpg)
RABE AND KINDLER PROCESS
• In 1918 Paul Rabe and Karl Kindler obtained a three step preparation of quinine from d- quinotoxine
![Page 11: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/11.jpg)
![Page 12: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/12.jpg)
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.
![Page 13: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/13.jpg)
(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.
![Page 14: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/14.jpg)
USES
• Flavour in carbonated beverages.• Antimalarial agent.• Skeletal muscle relaxant.• Used to treat hemorrhoids and varicose veins• Oxytocic agent.• Prophylactic for flu.
![Page 15: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/15.jpg)
DERIVATIVES OF QUININE
1)Quinine Trihydrate2)Quinine bisulphate heptahydrate3)Quinine dihydrochloride4)Quinine hydrochloride dehydrate5)Quinine sulphate dehydrate
![Page 16: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/16.jpg)
QUININE TRIHYDRATE
• It has a melting point of 330 K • It becomes anhydrous at 398 K
![Page 17: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/17.jpg)
QUININE BISULPHATE HEPTAHYDRATE
• It is obtained as bitter crystals• Also known as Quinbisan, Dentojel.
![Page 18: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/18.jpg)
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
![Page 19: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/19.jpg)
QUININE HYDROCHLORIDE DIHYDRATE
• Obtained as silky needles of bitter taste• It effloresces on exposure to warm
air.• Forms anhydrous solution at 373 K.
![Page 20: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/20.jpg)
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
![Page 21: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/21.jpg)
![Page 22: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/22.jpg)
QUININE ISOMER : QUINIDINE
(S)-(6-Methoxyquinolin-4-yl)((2R,4S,8R)-8-vinylquinuclidin-2-yl)methanol
![Page 23: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/23.jpg)
Powdered Bark- Alk. CaO + NaOH + H2O- Reflux with benzene &- Filtration while hot
Benzene filtrate (Alkaloidal bases)dilute H2SO4
Acidic aqueous layer(Alkaloidal bisulphates)
pH to 6.5 with Na2CO3
PrecipitateQuinine quinidine,
cinchonine & cinchonidine Hot water, Na2CO3
Quinine NaOH, ether
Aqueous layerEther layerCinchonineQuinidine & Cinchonidine
-HCl PH=7, Na, K Tart. salt- filter
Precipitate Filtrate
Cinchonidine tartrate Quinidine tartrate
Aqueous solution (Monosulphates)(monosulphate)
![Page 24: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/24.jpg)
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
![Page 25: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/25.jpg)
USES
• It is an antiarrhythmic agent • It helps in keeping the heart rate normal
for the people with certain heart rhythm disorders.
![Page 26: QUININE](https://reader031.vdocument.in/reader031/viewer/2022013012/56816720550346895ddba21c/html5/thumbnails/26.jpg)
….THANK YOU….DONE BY DHRUVI, RUTVI, SIDDHARTH