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2,N,N-TMT

Chemical compound


Chemical compound

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2,N,N-Trimethyltryptamine (2,N,N-TMT or 2-TMT), also known as 2-methyl-N,N-dimethyltryptamine (2-methyl-DMT), is a tryptamine derivative. It is not a conventional psychedelic, but instead produces tactile enhancement and auditory distortion. The drug was described by Alexander Shulgin and reported in his book TiHKAL (Tryptamines I Have Known and Loved).

Use and effects

2-Me-DMT is claimed to show psychoactive effects at a dose of 50 to 100mg orally, but these are relatively mild compared to other similar drugs. This suggests that while the 2-methyl group has blocked the binding of metabolic enzymes, it is also interfering with binding to the 5-HT2A receptor target that mediates the hallucinogenic effects of these drugs. The duration of 2-Me-DMT is 4 to 6hours.

The specific effects produced by 2-Me-DMT included tingling, mild stomach rumbling, mild relaxation, skin "alerting" especially on the head and neck, bodily/tactile activation and heightened sensitivity, auditory distortion, and altered tonal perception. There were no visuals, no cloudiness of thought processes, no motor impairment, but sexual activity was said to be enhanced. There were no changes in appetite, no gastrointestinal problems, and no after-effects the next day. The drug was described as not being a psychedelic or psychostimulant, but instead being a specific "tactile stimulant" and sexual enhancer.

Interactions

Pharmacology

Pharmacodynamics

Its affinities (Ki) for the serotonin 5-HT1A and 5-HT2A receptor were 4,598nM and 15,037nM, respectively. These affinities were dramatically lower than those of dimethyltryptamine (DMT) in the same study, which were 87nM and 1,513nM, respectively. Hence, 2-Me-DMT appears to show approximately 53- and 10-fold lower affinities for the serotonin 5-HT1A and 5-HT2A receptors compared to DMT. In addition, unlike DMT, 2-Me-DMT failed to activate the serotonin 5-HT1A and 5-HT2A receptors. Despite the preceding findings however, 2-Me-DMT induces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, and does so to a similar magnitude as 5-MeO-DMT.

In studies of other 2-methyltryptamines, specifically 2-methyl-5-MeO-DALT and 2-methyl-5-F-DALT, these compounds had variably reduced affinities for serotonin receptors and, in contrast to 2-Me-DMT, did not produce the head-twitch response.

Chemistry

Synthesis

The chemical synthesis of 2,N,N-TMT has been described.

Analogues

Analogues of 2,N,N-TMT include dimethyltryptamine (DMT), 2-methyltryptamine, 2-methyl-DET, 2-methyl-AMT, 2-Me-5-MeO-DMT (5-MeO-2,N,N-TMT), 4-methyl-DMT, 5-methyl-DMT, 6-methyl-DMT, and 7-methyl-DMT.

Society and culture

Canada

2-Me-DMT is not an explicitly nor implicitly controlled substance in Canada as of 2025.

Sweden

Sweden's public health agency suggested classifying 2-Me-DMT as a hazardous substance, on May 15, 2019.

United States

2-Me-DMT is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

References

References

  1. "#34 2-ME-DMT". Erowid Online Books : "TIHKAL".
  2. (October 2023). "A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines". J Biol Chem.
  3. (10 March 2023). "Bioproduction platform using a novel cane toad (Rhinella marina) N-methyltransferase for psychedelic-inspired drug discovery".
  4. (November 2018). "Receptor binding profiles and behavioral pharmacology of ring-substituted N,N-diallyltryptamine analogs". Neuropharmacology.
  5. (5 December 2025). "Controlled Drugs and Substances Act".
  6. (15 May 2019). "Folkhälsomyndigheten föreslår att 20 ämnen klassas som narkotika eller hälsofarlig vara". Folkhälsomyndigheten.
  7. "2-Me-DMT".
  8. (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.
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