Lesser Alkaloids of Cocaine-Bearing Plants. Part I: Nicotinoyl-, 2′-Pyrroloyl, and 2′- and 3′-Furanoylecgonine Methyl Ester—Isolation and Mass Spectral Characterization of Four New Alkaloids of South American Erythroxylum coca Var. coca

Abstract

Four new trace-level alkaloids of South American coca leaf, Erythroxylum coca var. coca, have been isolated from the bulk leaf/alkaloids matrix and characterized by gas chromatography-mass spectrometry and synthesis. These alkaloids, nicotinoyl, 2'-pyrroloyl- and 2'- and 3'-furanoylecgonine methyl ester, were detected in Peruvian coca leaf and/or in a commercial, industrial-grade extract of South American coca. Alkaloid isolation methodology included toluene extraction of the leaf followed by dilute acid/Celite and alumina column chromatography and recrystallization. This methodology also allowed for the detection and partial characterization of an additional 125-150 new tropane alkaloids in coca leaf. Forensic implications are discussed.