Stereochemical analysis of methorphan using (-)-menthyl chloroformate

Journal of Forensic Sciences
Christina KooMartin Johnston

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.

References

Jan 1, 1989·Journal of Pharmaceutical and Biomedical Analysis·L A Pieters, A J Vlietinck
Mar 1, 1995·The American Journal of Emergency Medicine·T R Wolfe, E M Caravati
Apr 23, 2003·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Howard P HendricksonWilliam D Wessinger
Jan 1, 1965·Tetrahedron Letters·H AUDIERT RUELL
Dec 23, 2006·Pharmacology, Biochemistry, and Behavior·Thomas MorganAlan Poling
Nov 21, 2007·The Journal of Organic Chemistry·Zemin Dong, Peter J Scammells
Dec 31, 2008·The Journal of Organic Chemistry·James R VyvyanBrian P Woods
Feb 21, 2009·Chirality·James D Swarbrick, Trent D Ashton
Oct 16, 2010·International Journal of Cardiology·Bonnie KaplanMori J Krantz

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Citations

May 1, 2013·Journal of Pharmaceutical and Biomedical Analysis·Daniele TedescoVincenza Andrisano
Oct 22, 2013·Drug Testing and Analysis·Federica BortolottiFranco Tagliaro
Aug 1, 2015·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Anna BertasoFranco Tagliaro
Jun 20, 2020·Critical Reviews in Analytical Chemistry·Cláudia RibeiroM E Tiritan

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