N,N-Dimethyltryptamine and dichloromethane: Rearrangement of quaternary ammonium salt product during GC-EI and CI-MS-MS analysis

Simon D. Brandt, Cláudia P B Martins, Sally Freeman, Nicola Dempster, Mark Wainwright, Philip G. Riby, John F. Alder

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    N,N-Dimethyltryptamine (DMT) 1 is a simple tryptamine derivative with powerful psychoactive properties. It is abundant in nature and easily accessible through a variety of synthetic routes. Most work-up procedures require the use of organic solvents and halogenated representatives are often employed. DMT was found to be reactive towards dichloromethane, either during work-up or long term storage therein, which led to the formation of the quaternary ammonium salt N-chloromethyl-DMT chloride 2. Analysis of this side-product by gas chromatography ion trap mass spectrometry (GC-MS), both in electron and chemical ionisation tandem MS modes, gave only degradation products. For example, 2 could not be detected but appeared to have rearranged to 3-(2-chloroethyl)indole 3 and 2-methyltetrahydro-β-carboline 4, whereas HPLC analysis enabled the detection of 2. GC-MS is a standard tool for the fingerprinting of drug products. The identification of a particular synthetic route is based on the analysis of impurities, provided these side products can be established to be route-specific. The in situ detection of both 3 and 4 within a DMT sample may have led to erroneous conclusions with regards to the identification of the synthetic route. © 2007 Elsevier B.V. All rights reserved.
    Original languageEnglish
    Pages (from-to)207-212
    Number of pages5
    JournalJournal of Pharmaceutical and Biomedical Analysis
    Issue number1
    Publication statusPublished - 12 May 2008


    • Analysis
    • Forensic
    • Hallucinogens
    • Mass spectrometry
    • Tryptamines


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