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Stereochemical Analysis of Methorphan Using (-)-Menthyl Chloroformate

NCJ Number
242519
Journal
Journal of Forensic Sciences Volume: 57 Issue: 6 Dated: November 2012 Pages: 1549-1555
Author(s)
Christina Koo, B.Sc.; Matthew Cox, Ph.D.; Gunter Klass, Ph.D.; Martin Johnston, Ph.D.
Date Published
November 2012
Length
7 pages
Annotation
Forensic laboratories around the world have seen an increase in the number of drug seizures containing methorphan.
Abstract
Forensic laboratories around the world have seen an increase in the number of drug seizures containing methorphan. Levomethorphan is a narcotic and a controlled substance, and its enantiomer dextromethorphan is an antitussive agent used in over-the-counter medications. For the forensic analysis of seized drugs containing methorphan, it is important to report the stereochemical composition of the drug. Ideally, a method based on common forensic laboratory instrumentation is desirable. The use of the chiral derivatizing agent (-)-menthyl chloroformate followed by routine gas chromatography-mass spectrometry analysis of the derivative was shown to successfully determine the stereochemical composition of methorphan. This approach was applied to a street seizure containing methorphan proving that it was pure dextromethorphan. The derivatives of dextro- and levomethorphan were subjected to mass spectroscopic and nuclear magnetic resonance analysis, which confirmed that the structure of the derivatives remained unchanged as a result of the derivatization process. Abstract published by arrangement with John Wiley & Sons.