Methylecgonine
From Wikipedia, the free encyclopedia
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| IUPAC name
methyl 3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate | |
Other names
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3D model (JSmol) |
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CompTox Dashboard (EPA) |
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| Properties | |
| C10H17NO3 | |
| Molar mass | 199.250 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methylecgonine, also known as ecgonine methyl ester is a prominent tropane alkaloid found in coca leaves.[1] It is metabolite of cocaine,[2] and may be used as a precursor for it. It also occurs as a minor alkaloid in roots of many Datura species such as Datura stramonium[3] and Datura innoxia.[4]
Cocamine[5] (a-Truxilline) aka isatropylcocaine [490-17-5] and isococamine (beta-Truxilline) [490-15-3] are alkaloids present in Erythroxylun truxillense Rusby. The Victorian era references disclosed in John Glasby's dictionary of alkaloids indicate the longevity of these compounds.[6][7][8][9] Although these citations are outdated, a newer citation proposes different structures.[10] These compounds are understood to be esters of truxillic acid and/or truxinic acid that are formed as a consequence of methylecgonine cinnamate photodimerizing. Cocamine was reported to be a heart poison in later work.[11]
Biosynthesis
It is the last step before cocaine is biosynthesized in coca plants with the help of BAHD acyltransferase.[12]
