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Cocaine (from French cocaïne, from Spanish coca, ultimately from Quechua kúka) [13] is a tropane alkaloid that acts as a central nervous system (CNS) stimulant. As an extract, it is mainly used recreationally and often illegally for its euphoric and rewarding effects.
The biosynthesis of the tropane alkaloids have attracted intense interest because of their high physiological activity as well as the presence of the bicyclic tropane core. [12] Final stages in the pathway for the biosynthesis of the tropane alkaloid cocaine.
Tropane is a nitrogenous bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include atropine and cocaine , among others. Tropane alkaloids occur in plants of the families Erythroxylaceae (including coca ) and Solanaceae (including mandrake , henbane , deadly nightshade , datura , potato , tomato ).
Of the approximately 200 members in the genus Erythroxylum, most species contain the central nervous system stimulant tropane alkaloid, known more commonly as cocaine.Because the plant is endemic ...
The tropane ring system undergoes hydrolysis, SAM-dependent methylation, and reduction via NADPH for the formation of methylecgonine. The benzoyl moiety required for the formation of the cocaine diester is synthesized from phenylalanine via cinnamic acid. [8] Benzoyl-CoA then combines the two units to form cocaine.
Ecgonine (tropane derivative) is a tropane alkaloid found naturally in coca leaves. It has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance in many jurisdictions, as are some substances which can be used as precursors to ecgonine itself.
Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. [2] [3] Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Its corresponding conjugate acid at pH 7.3 major species is known as tropiniumone. [4]
Within the scope of analogous compounds created from the structure of cocaine, so named "cocaine analogues" retain 3β-benzoyloxy or similar functionality (the term specifically used usually distinguishes from phenyltropanes, but in the broad sense generally, as a category, includes them) on a tropane skeleton, as compared to other stimulants ...