22798242-Total-synthesis-of-Cocaine - Cocaine chemistry...

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GABRIEL TOJO 1 * RABIH JAOUHARI 2 * JACOBO CRUCES 1 JOHN O’CALLAGHAN 2 1. GalChimia, S.L. Cebreiro, s/n O Pino 15823 A Coruña, Spain E-mail gogatogo@usa.es www.galchimia.com 2. PR euroCHEM, Ballyvolane Business Park, Unit C, Spring Lane, Ballyvolane, Cork, Ireland E-mail rabih.jaouhari@preurochem.com www.preurochem.com PHARMACEUTICALS PHARMACEUTICALS MARCH 2002 9 PROPERTIES AND HISTORY F ew chemicals have caused such undesirable political and social consequences as cocaine. Its consumption in some developed countries is reaching epidemic level and the stability of the governments in some producing countries is threatened by the enormous power of those trafficking illegally with this drug. Cocaine is an alkaloid found in the leaves of the small tree Erythroxylon coca , which is native to the tropical mountains of Peru, Bolivia and Colombia. Indians in this area place in the cheek a mixture of coca leaves and basic material like ground seashell or ashes, so that the saliva extracts the free base that is ingested. Consumers of the drug are easily spotted by their hump in the cheek. There is evidence of very ancient consumption of coca leaves. Ceramics depicting human figures with a cheek bulge were found in archaeological sites from Peru, dated from 1900-1750 B.C. Remains of coca leaves were encountered in 2000 years-old mummies from Nazca in Peru. As the content of cocaine in dry coca leaves is only 0.4-0.8%, it is very doubtful that its traditional ingestion causes any serious threat for the health, producing a damage akin to moderate tobacco smoking (1). The Incas consumed coca leaves for religious and ceremonial purposes. In 1533, the Incas were conquered by the troops of the Spanish conquistador Pizarro. A few years later in 1551, the Bishop of Cuzco prohibited the cultivation and consumption of coca, and its possession was punished by death. Coca ingestion was viewed as an obstacle for the conversion of the Indians into Christianity, for it was a tie with their past religion. Nevertheless, later it was found that coca increased the stamina of Indian laborers and in 1569 King Philip II decreed that coca was not devilish. As the long journey by ship to Spain caused coca leaves to deteriorate, the effects of coca ingestion were not experienced in Europe for a long time. Following the isolation of pure cocaine form coca leaves in 1862 (2), the pure drug became available in Europe from the Merck Company. At the same time coca extracts began to be added to beverages that were sold as tonics. One of the most popular was the so-called Mariani´s Coca Wine, which was advertised as a drink able to lift spirits and alleviate fatigue. The original recipe for the preparation of Coca- Cola, which was invented in 1886 as a “tonic” medicine by John Pemberton, included an extract of coca leaves, and sugar was added to abate the bitterness of cocaine. By 1903 the alkaloid was removed and substituted for caffeine in order to keep the tonic properties of the
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22798242-Total-synthesis-of-Cocaine - Cocaine chemistry...

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