Characterisation of a proposed internet synthesis of N,N-dimethyltryptamine using liquid chromatography/electrospray ionisation tandem mass spectrometry.
Cláudia P B Martins, Sally Freeman, John F Alder, Simon D Brandt
Journal of chromatography. A August 14, 2009 Peer reviewed DOI: 10.1016/j.chroma.2009.06.060 via PubMed
Summary
The study characterizes the second step of a two-step methodology for preparing N,N-dimethyltryptamine (DMT) involving methylation of tryptamine. The analysis revealed that instead of DMT, the products included 11.1% tryptamine, 21.0% N,N,N-trimethyltryptammonium iodide, and 47.4% 1-N-methyl-TMT, with a trace of 0.5% monomethylated N-methyltryptamine. This highlights the issues with product purity in questionable synthetic methods found online.
Study at a glance
| Key finding | The reaction did not yield DMT but produced several other compounds, indicating poor product purity from the discussed synthetic methodology. |
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Abstract
The psychoactive properties of N,N-dimethyltryptamine (DMT) are known to induce altered states of consciousness in humans. These properties attract great interest from clinical, neuroscientific, clandestine and forensic communities. The Breath of Hope Synthesis was reported on an internet website as a convenient two-step methodology for the preparation of DMT. The analytical characterisation of the first stage was the subject of previous publications by the authors and involved the thermal decarboxylation of tryptophan and the formation of tryptamine. The present study reports on the characterisation of the second step of this procedure which was based on the methylation of tryptamine. This employed methyl iodide and benzyltriethylammonium chloride/sodium hydroxide as a phase transfer catalyst. The reaction product was characterised by liquid chromatography/electrospray ionisation tandem mass spectrometry and orthogonal acceleration time-of-flight mass spectrometry. Quantitative evaluation was carried out in positive multiple reaction monitoring mode (MRM), which included synthesis of the identified reaction products. MRM screening of the product did not lead to the detection of DMT. Instead, 11.1% tryptamine starting material, 21.0% N,N,N-trimethyltryptammonium iodide (TMT) and 47.4% 1-N-methyl-TMT were detected. A 0.5% trace of the monomethylated N-methyltryptamine was also detected. This study demonstrated the impact on product purity of doubtful synthetic methodologies discussed on the internet.