Coca and Cocaine

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Coca is a plant from the genus Erythroxylum and is native to northwestern South America. For the purposes of a plant of abuse, coca leaves are used. Cocaine is the most important psychoactive alkaloid in the plant. The chemical structure of cocaine (2) is shown in Fig. 19.1. The leaves contain up to 2% cocaine in a dried state [6]. Although the genus Erythroxylum includes several hundred species, only E. coca and E. novogratense contain significant amounts of cocaine [6]. Trace amounts of cocaine have recently been detected in 23 species of Erythroxylum, with content below 0.001% [11].

Drugs Chemicals Structure Collection
Fig. 19.1 Chemical structures of most important active compounds of common herbal drugs of abuse
Kavapyrone Fig. 19.1 (continued)

The use of coca has a long tradition in South America. Hair analysis of mummies dated to at least 1000 CE has proven the consumption of coca via detection of cocaine and its metabolites in hair [12]. The first European description of coca is from Amerigo Vespucci from 1499. He described how South American aboriginals would chew the leaves together with a white powder [6]. The main psychoactive compound, cocaine, was first isolated in 1859 by Albert Niemann, a German chemist [13].

In 1863, the Italian chemist Angelo Mariani introduced a coca extract in sweet wine as a tonic, the so-called Vin Mariani. This tonic was copied in 1884 in the USA by John Pemberton. One year later, Pemberton responded to the American Prohibition legislation by developing a nonalcoholic carbonated coca extract, called Coca-Cola, which contained an estimated amount of 9 mg of cocaine and on the market until 1903.

The use of coca leaves as a local anesthetic was first proposed by Samuel Percy in 1856 [13]. After the isolation of cocaine, the Austrian pharmacologist Karl Damian Ritter described narcotic effects after application on the skin. About 25 years later, cocaine was used in clinical practice as a local anesthetic in ophthalmic surgery. The advantage of cocaine as a local anesthetic is its unique combination of local anesthesia and intense vasoconstriction. Therefore, cocaine is still used for topical anesthesia by otorhinolaryngologists [13].

The anesthetic effects are pharmacologically caused by blocking of sodium channels, whereas the vasoconstriction is caused by sympathetic activation [14]. Cocaine inhibits the reuptake of catecholamines, which increases the activity of sympathetic synapses. This stimulation also occurs in the brain; therefore cocaine causes euphoria, garrulousness, and increased motor activity [14]. Cocaine also decreases fatigue and is abused as a stimulant.

In some communities coca leaves are typically mixed with an alkaline substance (such as lime) and chewed like a gum. Alternatively, coca leaves can be infused in liquid and consumed like tea such as mate de coca. This is a traditional method of consumption to treat altitude sickness, reduce fatigue, and increase energy and has been practiced for many centuries by some natives of South America [6].

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