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Stereochemical Analysis of Methorphan Using (−)‐Menthyl Chloroformate
Author(s) -
Koo Christina,
Cox Matthew,
Klass Gunter,
Johnston Martin
Publication year - 2012
Publication title -
journal of forensic sciences
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.715
H-Index - 96
eISSN - 1556-4029
pISSN - 0022-1198
DOI - 10.1111/j.1556-4029.2012.02162.x
Subject(s) - chloroformate , chemistry , derivatization , enantiomer , forensic toxicology , chromatography , mass spectrometry , derivative (finance) , adulterant , dextromethorphan , organic chemistry , pharmacology , medicine , financial economics , economics
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 dextro methorphan. The derivatives of dextro ‐ and levo methorphan 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.