I know alot of people use DCM, so can any of our local chemist comment on this little ditty. Seems like it would be a problem.
Journal of Pharmaceutical and Biomedical Analysis xxx (2008) xxx–xxx
Short communication
N,N-Dimethyltryptamine and dichloromethane: Rearrangement of quaternary ammonium salt product during GC–EI and CI-MS–MS analysis
Simon D. Brandt a,∗, Cl´audia P.B. Martins b, Sally Freeman c, Nicola Dempster a,
Mark Wainwright a, Philip G. Riby a, John F. Alder b
a School of Pharmacy and Chemistry, Liverpool John Moores University, Byrom Street, Liverpool, L3 3AF, UK
b Centre for Instrumentation and Analytical Science, The University of Manchester, Sackville Street, P.O. Box 88, M60 1QD, UK
c School of Pharmacy and Pharmaceutical Sciences, The University of Manchester, Oxford Road, Manchester, M13 9PT, UK
Received 11 October 2007; received in revised form 30 November 2007; accepted 12 December 2007
Abstract
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- -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.