Halogenated solvent interactions with N,N-dimethyltryptamine: formation of quaternary ammonium salts and their artificially induced rearrangements during analysis.
Simon D Brandt, Cláudia P B Martins, Sally Freeman, Nicola Dempster, Philip G Riby, Jochen Gartz, John F Alder
Forensic science international July 4, 2008 DOI: 10.1016/j.forsciint.2008.03.013 via PubMed
Summary
AI-generated from the abstractDMT, a psychoactive compound, reacts with common laboratory solvents like dichloromethane (DCM) to form a quaternary ammonium salt, which can rearrange during analysis into products including 3-(2-chloroethyl)indole and 2-methyltetrahydro-beta-carboline. This study extends these findings to other halogenated solvents—dibromomethane and 1,2-dichloroethane—characterizing the resulting derivatives. The DCE derivative produced at least six rearrangement products. Using deuterated compounds helped clarify the rearrangement mechanisms. These solvent-derived marker molecules could help identify which solvents were used in the manufacture of controlled substances, a factor often overlooked because solvents are assumed inert.
Study at a glance
| Characteristics | Laboratory study Peer reviewed |
|---|---|
| Interventions | dibromomethane and 1 2-dichloroethane |
| Citations | 10 |
| Key finding | DMT reacts with halogenated solvents such as DCM, dibromomethane, and 1,2-dichloroethane to form quaternary ammonium derivatives that can undergo rearrangement, producing marker molecules that may identify solvents used in controlled substance manufacture. |
Abstract
The psychoactive properties of N,N-dimethyltryptamine (DMT) 1a are known to induce altered states of consciousness in humans. This particular attribute attracts great interest from a variety of scientific and also clandestine communities. Our recent research has confirmed that DMT reacts with dichloromethane (DCM), either as a result of work-up or storage to give a quaternary N-chloromethyl ammonium salt 2a. Furthermore, this was observed to undergo rearrangement during analysis using gas chromatography-mass spectrometry (GC-MS) with products including 3-(2-chloroethyl)indole 3 and 2-methyltetrahydro-beta-carboline 4 (2-Me-THBC). This study further investigates this so far unexplored area of solvent interactions by the exposure of DMT to other halogenated solvents including dibromomethane and 1,2-dichloroethane (DCE). The N-bromomethyl- and N-chloroethyl quaternary ammonium derivatives were subsequently characterised by ion trap GC-MS in electron and chemical ionisation tandem MS mode and by NMR spectroscopy. The DCE-derived derivative formed at least six rearrangement products in the total ion chromatogram. Identification of mass spectrometry generated by-products was verified by conventional or microwave-accelerated synthesis. The use of deuterated DCM and deuterated DMT 1b provided insights into the mechanism of the rearrangements. The presence of potentially characteristic marker molecules may allow the identification of solvents used during the manufacture of controlled substances, which is often neglected since these are considered inert.