Cocaine Erythroxylum

The amount of cuscohygrine is the main difference between the two commercial varieties of coca leaves Erythroxylum coca Lam. var. coca and var. spru-ceanum (Erythroxylaceae). Coca leaves collected in Bolivia and in Peru have cuscohygrine as the main alkaloid besides cocaine, whereas the opposite situation occurs with material collected in Java (35). 

When we look at another tropane alkaloid, cocaine, we get a different scenario. Cocaine is obtained from the coca plant Erythroxylum coca, and is a powerfnl local anaesthetic, bnt now known primarily as a dmg of abuse. There is no chiral centre in the acid portion, which is benzoic acid, but the optical activity of cocaine comes from the alcohol methylecgonine. Because of the ester function in methylecgonine, the tropane system is no longer symmetrical, and the four chiral centres all contribute towards optical activity. 

Cocaine (8) Erythroxylum coca Lam. (coca leaves) Local anesthetic... 

Cocaine (8), from Erythroxylum coca Lam., besides causing euphoria by inhibiting the dopamine transport protein (DAT) responsible for its recreational and illegal use, exerts a local anesthetic activity through blocking sodium channels and is still used as a probe for this target. 

Erythroxylum coca Lam. Guo Yi (leaf) 1-cocaine, cinnamylococaine, alpha-trevilline, beta-trevilline, ecgonine, benzoylecgonine.33 For local anesthetic, has vasoconstriction effect. 

The stimulant narcotic cocaine (benzoylmethylecgonine) from Erythroxylum coca (coca) and other Erythroxylum species (Erythroxylaceae) inhibits serotonin (5HT) and dopamine reuptake. Related bioactive tropane alkaloids from Erythroxylum species include benzoylecgonine, benzoyltropeine (tropine benzoate), cinnamoylcocaine (cinnamoylmethylecgonine) and ecgonine. 

Cocaine (= Benzoyl- Erythroxylum coca [coca leaf], GABAA-R current block... 

Gas chromatography of cocaine of plant origin has mainly involved the analysis of the coca plant [77-79]. Identification and quantitation GC methods of minor naturally occurring tropane alkaloids in illicit cocaine samples have also been reviewed [80]. Moore et al. presented an in-depth methodology for the analysis of the coca plant by GC-FID, GC-ECD, and GC-MS for the identification of alkaloids of unknown structure [81]. Recently, Casale et al. [82] have analyzed the seeds from Erythroxylum coca for their alkaloidal content. Several tropane alkaloids were detected and characterized and it appeared that methylecgonidine (MEG) was the primary constituent and not an analytical artifact. 

During a screening of tropane alkaloids in Erythroxylum species from Southern Brazil, Zuanazzi et al. [83] identified a new alkaloid as 3p,6p-ditigloyloxynortropane. The five investigated species were also screened for MEG, tropacocaine, and cocaine. Tropacocaine and MEG were present in two plants but no cocaine was detected in any species. 

Leaf samples of various Erythroxylum species have been investigated for their cocaine content by a fast GC-MS method [29]. Amongst the 51 analyzed species, 28 had not been examined previously and cocaine was detected in 23 wild species. Cocaine content was less than 0.001 % for all wild species, except for Erythroxylum laetevirens in which a 10-fold higher concentration was determined. The qualitative... 

CO-beneldopa benserazide levodopa. cocaine (ban, usan] (cocaine hydrochloride (jan, usan)) is an ester of benzoic acid and methylecgonine and the principal alkaloid of Erythroxylum coca and other Erythroxylum spp. (Erythroxylaceae). It is a LOCAL ANAESTHETIC (used topically because of toxicity), and has pronounced indirect-acting SYMPATHOMIMETIC actions by virtue of being an UPTAKE INHIBITOR (interferes with Uj active uptake of noradrenaline into noradrenergic nerve terminals). It is a VASOCONSTRICTOR and can be used as a topical mydriatic and ocular diagnostic agent. It is a powerful CNS stimulant (similar in action to amphetamine), with considerable abuse potential, cocaine hydrochloride cocaine. 

Distribution of cocaine and cinnamoylcocaine in Erythroxylum coca Lam (from various origins) [243]... 

Tropane alkaloids mainly occur in the Solanaceae family but are also found in other families such as Convolvulaceae, Erythroxylaceae, Proteaceae and Rhizophoraceae. Less frequently, tropane alkaloids have been mentioned in the Euphorbiaceae, Brassicaceae and Olacaceae families which show no taxonomic relationships with Solanaceae. In several species of Erythroxylum, the tropane alkaloids are characterized by a 3 3-hydroxy function and a carboxyl group at C-2 of the tropane nucleus. The most famous representant of this group is cocaine (Fig. 2). In Table 1 the distribution of tropane alkaloids in the plant kingdom is indicated. 

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