2-Methyl-DMT, or 2-Me-DMT, also known as 2-methyl-N,N-dimethyltryptamine or as 2,N,N-trimethyltryptamine (2,N,N-TMT or 2-TMT), is a psychoactive drug of the tryptamine family related to the psychedelic drug dimethyltryptamine (DMT).[1] It is not a conventional psychedelic, but instead produces tactile enhancement and auditory distortion.[1] The drug was described by Alexander Shulgin and reported in his book TiHKAL (Tryptamines I Have Known and Loved).[1]
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| Other names | 2-Me-DMT; 2-Methyl-N,N-dimethyltryptamine; 2,N,N-Trimethyltryptamine; 2,N,N-TMT; 2-TMT; Desmethoxy-Indapex; 3-[2-(Dimethylamino)ethyl]-2-methylindole; |
| Routes of administration | Oral[1] |
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| Duration of action | 4–6 hours[1] |
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| Formula | C13H18N2 |
| Molar mass | 202.301 g·mol−1 |
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Use and effects
edit2-Methyl-DMT is claimed to show psychoactive effects at a dose of 50 to 100 mg orally, but these are relatively mild compared to other similar drugs.[1] 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-methyl-DMT is 4 to 6 hours.[1]
The specific effects produced by 2-methyl-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.[1] There were no visuals, no cloudiness of thought processes, no motor impairment, but sexual activity was said to be enhanced.[1] There were no changes in appetite, no gastrointestinal problems, and no after-effects the next day.[1] The drug was described as not being a psychedelic or psychostimulant, but instead being a specific "tactile stimulant" and sexual enhancer.[1]
Interactions
editPharmacology
editPharmacodynamics
editIts affinities (Ki) for the serotonin 5-HT1A and 5-HT2A receptor were 4,598 nM and 15,037 nM, respectively.[2][3] These affinities were dramatically lower than those of dimethyltryptamine (DMT) in the same study, which were 87 nM and 1,513 nM, respectively.[2][3] Hence, 2-methyl-DMT appears to show approximately 53- and 10-fold lower affinities for the serotonin 5-HT1A and 5-HT2A receptors compared to DMT.[2][3] In addition, unlike DMT, 2-methyl-DMT failed to activate the serotonin 5-HT1A and 5-HT2A receptors.[3] Similarly, 2-methyl-DMT showed profoundly reduced serotonin receptor agonism in the rat uterus and fundus strip.[4] Despite the preceding findings however, 2-methyl-DMT robustly induces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, and does so to a similar magnitude as psilocin and 5-MeO-DMT.[2][3]
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-methyl-DMT, did not produce the head-twitch response.[5]
Chemistry
editSynthesis
editThe chemical synthesis of 2-methyl-DMT has been described.[1]
Analogues
editAnalogues of 2-methyl-DMT include dimethyltryptamine (DMT), 2-methyltryptamine (2-methyl-T), 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.[1]
History
edit2-Methyl-DMT was first described in the scientific literature by R. B. Barlow and I. Khan by 1959.[4] Subsequently, it was described in greater detail by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved) in 1997.[1]
Society and culture
editLegal status
editCanada
edit2-Methyl-DMT is not an explicitly nor implicitly controlled substance in Canada as of 2025.[6]
Sweden
editUnited States
edit2-Methyl-DMT is not an explicitly controlled substance in the United States.[9] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.
See also
editReferences
edit- 1 2 3 4 5 6 7 8 9 10 11 12 13 14 "#34 2-ME-DMT". Erowid Online Books : "TIHKAL".
- 1 2 3 4 Chen X, Li J, Yu L, Maule F, Chang L, Gallant JA, et al. (October 2023). "A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines". J Biol Chem. 299 (10) 105231. doi:10.1016/j.jbc.2023.105231. PMC 10570959. PMID 37690691.
- 1 2 3 4 5 Chen X, Li J, Yu L, Dhananjaya D, Maule F, Cook S, et al. (10 March 2023), Bioproduction platform using a novel cane toad (Rhinella marina) N-methyltransferase for psychedelic-inspired drug discovery (PDF), doi:10.21203/rs.3.rs-2667175/v1, retrieved 17 March 2025
- 1 2 Barlow RB, Khan I (March 1959). "Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations". Br J Pharmacol Chemother. 14 (1): 99–107. doi:10.1111/j.1476-5381.1959.tb00934.x. PMC 1481812. PMID 13651585.
- ↑ Klein LM, Cozzi NV, Daley PF, Brandt SD, Halberstadt AL (November 2018). "Receptor binding profiles and behavioral pharmacology of ring-substituted N,N-diallyltryptamine analogs". Neuropharmacology. 142: 231–239. doi:10.1016/j.neuropharm.2018.02.028. PMC 6230509. PMID 29499272.
- ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. 5 December 2025. Retrieved 20 January 2026.
- ↑ "Folkhälsomyndigheten föreslår att 20 ämnen klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 15 May 2019. Archived from the original on 20 October 2021. Retrieved 11 November 2019.
- ↑ "2-Me-DMT". АИПСИН (in Russian). Retrieved 7 January 2026.
- ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026