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 M. Dempster, Philip G Riby, Jochen Gartz, John F. Alder
Forensic Science International July 4, 2008 DOI: 10.1016/j.forsciint.2008.03.013 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Laboratory study Peer reviewed |
|---|---|
| Interventions | dibromomethane and 1 2-dichloroethane |
| Topics | 5-MeO-DMT DMT |
| Citations | 10 |
| Key points | 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.
Comparable studies
Other experimental studies on 5-MeO-DMT, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Short term changes in the proteome of human cerebral organoids induced by 5-MeO-DMT. Human cerebral organoids | 2017 | Experimental study | |
| Bufo alvarius: a potent hallucinogen of animal origin. Bufo alvarius toad venom | 1994 | Experimental study | |
| Prospective examination of synthetic 5-methoxy-N,N-dimethyltryptamine inhalation: effects on salivary IL-6, cortisol levels, affect, and non-judgment Volunteers | 2019 | Within-subjects experimental study | n = 11 |
| Unmasking of a neonatal somatovesical reflex in adult cats by the serotonin autoreceptor agonist 5-methoxy-N,N-dimethyltryptamine. Adult cats | 1990 | Experimental study | n = 10 |
| Studies on the Mechanism of Action of Monoamine Oxidase: Metabolism of N,N-Dimethyltryptamine and N,N-Dimethyltryptamine-N-Oxide | 1962 | Experimental study |
Citations in the library
Cited by 5
- A critical review of reports of endogenous psychedelic N, N-dimethyltryptamines in humans: 1955-2010. Drug Testing and Analysis 2012
- Synthesis and Characterization of 5-MeO-DMT Succinate for Clinical Use ACS Omega December 2, 2020
- Reaction of N,N‑Dimethyltryptamine with Dichloromethane Under Common Experimental Conditions ACS Omega May 7, 2018
- Characterization of the synthesis of N,N‐dimethyltryptamine by reductive amination using gas chromatography ion trap mass spectrometry Drug Testing and Analysis July 1, 2010
- Ayahuasca characterization, metabolism in humans, and relevance to endogenous N,N-dimethyltryptamines June 8, 2012
Cites 8
- Analytical chemistry of synthetic routes to psychoactive tryptamines : Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR The Analyst 2005
- Analytical chemistry of synthetic routes to psychoactive tryptamines : Part I. Characterisation of the Speeter and Anthony synthetic route to 5-methoxy-N,N-diisopropyltryptamine using ESI-MS-MS and ESI-TOF-MS The Analyst 2004
- N,N-Dimethyltryptamine and dichloromethane: Rearrangement of quaternary ammonium salt product during GC–EI and CI-MS–MS analysis Journal of Pharmaceutical and Biomedical Analysis December 28, 2007
- Analytical chemistry of synthetic routes to psychoactive tryptamines : Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS The Analyst 2005
- Hallucinogens. Pharmacology & Therapeutics February 1, 2004
and 3 more in the library