title: Four new illicit cocaine impurities from the oxidation of crude cocaine base: formation and characterization of the diastereomeric 2,3-dihydroxy-3-phenylpropionylecgonine methyl esters from cis- and trans-cinnamoylcocaine.
abstract: Four new impurities have recently been detected in the gas chromatographic signature profiles of many illicit cocaine hydrochloride exhibits. These impurities are only seen in exhibits that have been oxidized and are most prominent in samples that have been highly oxidized. Exhibits containing these compounds were subjected to gas and liquid chromatographic-mass spectrometric analyses to determine the identity of the impurities. These impurities were subsequently synthesized to verify their structures. Four diastereomeric diols formed from the oxidation of cis- and trans-cinnamoylcocaine were characterized by nuclear magnetic resonance spectrometry, mass spectrometry, and synthesis. Oxidation of cis-cinnamoylcocaine in neutral conditions yielded (2R,3R)-dihydroxy-3-phenylpropionylecgonine methyl ester and (2S,3S)-dihydroxy-3-phenylpropionylecgonine methyl ester, while trans-cinnamoylcocaine produced (2R,3S)-dihydroxy-3-phenylpropionylecgonine methyl ester and (2S,3R)-dihydroxy-3-phenylpropionylecgonine methyl ester. The recent appearance of these new impurities suggests that some illicit cocaine processors have modified their oxidation procedures of crude cocaine base for transformation into illicit refined cocaine hydrochloride.
authors.affiliation: Special Testing and Research Laboratory, Drug Enforcement Administration, U.S. Department of Justice, Dulles, VA 20166-9509, USA. john.f.casale@usdoj.gov
authors.forename: John F
authors.initials: JF
authors.lastname: Casale
authors.forename: Patrick A
authors.initials: PA
authors.lastname: Hays
authors.forename: Steven G
authors.initials: SG
authors.lastname: Toske
authors.forename: Arthur L
authors.initials: AL
authors.lastname: Berrier
mesh_terms: D003042:Cocaine / Q000031:analogs & derivatives* / Q000737:chemistry; D004340:Drug Contamination; D008401:Gas Chromatography-Mass Spectrometry; D013287:Illicit Drugs / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D013287:Illicit Drugs; D003042:Cocaine; C034029:cinnamoylcocaine