Description
From the leaves of Erythroxylon truxillense Rusby, Hesse isolated an amorphous
alkaloid which he designated Cocamine. This was subsequently shown by
Liebermann to be a mixture of two isomeric bases and, although the pure
alkaloids have not yet been obtained from the alkaloidal mixture owing to
difficulties in their separation, each has been prepared synthetically. This
particular alkaloid is an amorphous white powder which is soluble in all
organic solvents except light petroleum and also insoluble in H20. Solutions of
the base are alllaevorotatory and have an intensely bitter taste. Acid hydrolysis
with dilute HCl yields MeOH, (-)-ecgonine and Q-truxillic acid, m.p. 228°C. The
alkaloid is synthesized by the action of α-truxillic anhydride on (-)-ecgonine
followed by methylation of the resulting α-truxilloylecgonine.
Uses
?-Truxillin is an alkaloid found in coca leaves. It is an impurity of illicit Cocaine (C633500), which inhibits the dopamine, norepinephrine, and serotonin transporters.
References
Hesse., Pharm. Zeit., 407,668 (1887)
Liebermann., Ber., 21,2342 (1888)
Hesse., ibid, 22, 665 (1889)
Liebermann, Drory., ibid, 22,682 (1889)
