QUININE - (130-95-0)

introduction

prénom: quinine; (R)-(6-methoxyquinolin-4-yl)((2S,4S,8R)- 8-vinylquinuclidin-2-yl)methanol
* IUPAC
Numero CAS: 130-95-0
Formule chimique: C20H24N2O2
Masse molaire: 324.41676 g
Pourcentage de masse: C 74.044 %; H 7.4566 %; N 8.6350 %; O 9.8634 % 
isomères:  quinidine

Classification

Usages / Fonction

• "When the quinine molecules in tonic water are exposed to ultraviolet radiation, they absorb high-energy photons and fluoresce, emitting lower-energy photons in the visible region of the spectrum." 1

• "Flavor in carbonated beverages. Antimalarial; muscle relaxant (skeletal). Antiprotozoal for fish." 2

• "Quinine occurs naturally in the bark of the Cinchona tree. Until World War II it served as the chief combatant of malaria. Japanese occupation of the East Indies, however, cut off this major are of production, and a synthetic substitute was urgently needed. Atebrin, first announced in 1930 but little used until the war, was found to be effective. It was adopted by the U.S. forces with very satisfactory results. The complete synthesis of quinine was accomplished in 1944, but this chemical feat had no essential import on wartime malarial therapy." 3

Bonding

Obligations doubles: 6
Obligations Triple: 0
Obligations Sigma: 51
Obligations Pi: 6
Total: 57
carboxyl Groupes: 0
Les groupes hydroxylés: 1
Hybridation: aromatic carbons are sp2; heterocyclic carbons are sp3; carbon attached to the hydroxyl group is sp3; methyl carbon (off the quinolone) is sp3; double bonded carbons (off the piperidine) are sp2; pyridine nitrogen is sp2; piperidine nitrogen is sp3; oxygens are sp3

Thermochimie

ΔHf° (s): -37.1 kcal/mol 4 = -155.23 kJ/mol

Pour plus d'informations

Wikipédia
Journaux:
Ronald Fayer, J. Parasitol. 57, 901-905 (1971)
A. O. Seeler, O. Graessle and W. H. Ott, J. Infect. Dis. 79, 156-158 (1946)
Malcolm Man-Son-Hing and George Wells, BMJ 310, 13-17 (1995)
James W. Moulder, J. Infect. Dis. 83, 262-270 (1948)

Sources

(1) - Gillespie, Ronald J., Eaton, Donald R., Humphreys, David A., and Robinson, Edward A. Atoms, Molecules, and Reactions; Prentice-Hall: Englewood Cliffs, NJ, 1994; p 592.
(2) - The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 13th ed.; Budavari, S.; O'Neil, M.J.; Smith, A.; Heckelman, P. E.; Kinneary, J. F., Eds.; Merck & Co.: Whitehouse Station, NJ, 2001; entry 8151.
(3) - Estok, George K. Organic Chemistry: A Short Text; W.B. Saunders: Philadelphia, 1959; p 242.
(4) - Dean, John A. Lange's Handbook of Chemistry, 12th ed.; McGraw-Hill Book Company: New York, NY, 1979; p 9:89.
(5) - Dean, John A. Lange's Handbook of Chemistry, 12th ed.; McGraw-Hill Book Company: New York, NY, 1979; p 9:89.
(6) - Dean, John A. Lange's Handbook of Chemistry, 12th ed.; McGraw-Hill Book Company: New York, NY, 1979; p 9:89.