3′,4′,5′-Trimethoxy-Substituted Analogs of Cocaine, <i>Cis-/Trans</i>-Cinnamoylcocaine and Tropacocaine: Characterization and Quantitation of New Alkaloids in Coca Leaf, Coca Paste and Refined Illicit Cocaine

Abstract

Abstract Four new alkaloids have been detected in South American coca leaf, coca paste and refined illicit cocaine. The compounds 3′,4′,5′-trimethoxycocaine (TMC), 3′,4′,5′-trimethoxytropacocaine (TMT), 3′,4′,5′-trimethoxy-cis-cinnamoylcocaine (cTMCC) and 3′,4′,5′-trimethoxy-trans-cinnamoylcocaine (tTMCC) were isolated from the coca leaf matrix and other alkaloids by toluene extraction followed by trap and ion-pair column chromatography. The identity of each alkaloid was verified via comparison of its mass spectrum with a synthesized standard. All four alkaloids were quantitated in leaf, paste and refined samples at levels of less than 0.1% relative to cocaine via capillary gas chromatography—flame ionization detection (cGC-FID).