C20H24N2O2
Exact Mass: 324.18
Mol. Wt.: 324.42
C, 74.04; H, 7.46; N, 8.64; O, 986
Legatrin; Quin-260; Quin-amino; Quinamm; Quindan; Quiphile; Q-VEL; 6'-Methoxycinchonan-9-ol;
6'-Methoxychinchonan-9-ol sulfate (2:1) (salt); Novoquinine;
Strema;
6-Methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol;
Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)-
PROPERTIES
Quinine was introduced into Europe around 1640 by Peruvian Jesuits. Natural quinine is an alkaloid that comes from the bark of the cinchona tree ( named for the Countess of Chinchon, Spain) found in the Andes mountains of Ecuador and Peru. The alkaloid is stored in the parenchyma of the bark, with the most quinine found in the bark of the truck. It is a white powder used in tonic water to give the water a bitter taste. On September 11, 1820, pure quinine was isolated for the first time by Joseph Caventou and Joseph Pelletier in a lab in Paris. Quinine gained prominence in Europe as the first anti malarial drug and was used to control the severe malarial fevers. The increased need for quinine nearly destroyed the cinchona tree, so synthetic means were sought to obtain quinine. In 1944, Robert Woodward and William Doering discovered a way of synthesizing quinine from coal tar.
USES
Medicinal-
Medicinal
forms of quinine include quinine dihydrochloride and quinine sulfate.
Quinine is used as a fever reducer and anti malarial drug. Hydrogenation
of the vinyl group increases the antimalarial properties. Esterification
of the carboxylic group make the anti malarial action reappear if the
side chain to the carboxyl group has been previously oxidized. However,
it is not as effective as an antimalarial agent after this process, possibly
due to saponification.
Quinine is also used as a treatment for leg cramps. The FDA banned the sale of over-the-counter quinine sulfate, commonly prescribed for muscle cramps, after studies failed to find quinine effective in reducing leg cramps. However, other studies have indicated that quinine does significantly control cramping. Side effects of quinine sulfate use include rashes, vision/hearing loss, dizziness, fever, nausea, vomiting, diarrhea, and the destruction of blood platelets.
Quinine is rapidly absorbed by the body and can be distributed throughout the body in 1 to 3 hours. Quinine is metabolized in the liver and the metabolites are excreted in the urine. Quinine is available by prescription, however, over 20 deaths have been linked to quinine between 1969 and 1992. Quinine cannot be administered in doses of over 430 mg if taking Hismanal.
Commercial-
Quinine
is found in tonic water. The quinine in the water gives it a bitter
taste. No more than 2.45 mg/ounce of quinine is allowed in a carbonated
beverage by the FDA.
Research-
Quinine
can be used to polarize light. E. H. Land invented the Polaroid sheet
polarizer, which has microcrystals of quinine iodosulfate embedded in it.
OTHER INTERESTING WEB SITES
How to brew quinine sulate periodide and use it to make herpathite.
REFERENCES
"Leg Cramps and Quinine". PharmInfoNet Homepage, 1997.
Lenthall, Joe. "Quinine". Magdalen College School, Oxford, 1999.
"MedWatch Safety Summaries - Hismanal". USFDA, 1996.
"Molecular Fluorescence: Quinine Assay". UK Chemistry Homepage, 1997.
Nelson, Lewis, MD. "Blindness after an unkown ingestion". New York City Poison Center, 1995.
"Nocturnal Leg Cramps". Bandolier, 1999.
Taylor, Norman. Cinchona in Java: The Story of Quinine. Greenberg: New York, 1945.
von Oettingen, W.F., M.D, PhD.The
Therapeutic Agents of the Quinoline Group. Chemical Catalog
Company, Inc: New York, 1933.
"Why it's harder to get quinine to treat leg cramps". Mayo Clinic, 1999.
Prepared by Laura E. Teany