Journal Article

GC-MS Analysis of Methamphetamine Impurities: Reactivity of (+)-or (−)-Chloroephedrine and <i>cis</i>- or <i>trans</i>-1,2-Dimethyl-3-phenylaziridine

Veeravan Lekskulchai, Karen Carter, Alphonse Poklis and William Soine

in Journal of Analytical Toxicology

Volume 24, issue 7, pages 602-605
Published in print October 2000 | ISSN: 0146-4760
Published online October 2000 | e-ISSN: 1945-2403 | DOI:
GC-MS Analysis of Methamphetamine Impurities: Reactivity of (+)-or (−)-Chloroephedrine and cis- or trans-1,2-Dimethyl-3-phenylaziridine

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S-(+)-Methamphetamine is frequently found as the only isomer in urine specimens from methamphetamine abuseres. Enantiomerically pure S-(+)-methamphetamine can be synthesized from ephedrine or pseudoephedrine via chloroephedrine intermediates. These intermediates are unstable and capable of cyclizing to form cis- and trans-1,2-dimethyl-3-phenyl aziridine. Studies were done to determine if these intermediates could be detected when using a common gas chromatographic-mass spectrometric analytical method (derivatization with heptafluorobutyric anhydride, HFBA) for toxicological screening of methamphetamine. Analysis of (+)- or (−)-chloroephedrine after extraction into hexane and derivatization with HFBA indicated that both pseudoephedrine and ephedrine were the major compounds detected. Direct derivatization of a hexane solution of cis-1,2-dimethyl-3-phenyl aziridine yielded only the derivatives of ephedrine and pseudoephedrine, indicating that the aziridine intermediate is responsible for the formation of the ephedrine or pseudoephedrine. These studies indicate that the aziridine intermediates would not be detected in methamphetamine samples following HFBA derivatization.

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Subjects: Medical Toxicology ; Toxicology (Non-medical)

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