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2,N,N-TMT

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2,N,N-TMT
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Identifiers
  • (2-(2-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H18N2
Molar mass202.301 g·mol−1
3D model (JSmol)
  • Cc1c(c2ccccc2[nH]1)CCN(C)C
  • InChI=1S/C13H18N2/c1-10-11(8-9-15(2)3)12-6-4-5-7-13(12)14-10/h4-7,14H,8-9H2,1-3H3
  • Key:NDGCOWDSLVNLGE-UHFFFAOYSA-N
  (verify)

2,N,N-Trimethyltryptamine (2,N,N-TMT), also known as 2-methyl-N,N-dimethyltryptamine (2-Me-DMT), is a tryptamine derivative.[1] It is not a psychedelic, but instead produces tactile enhancement and auditory distortion.[1] The drug was invented by Alexander Shulgin and reported in his book TiHKAL (#34).[1]

Effects

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2-Me-DMT is claimed to show psychoactive effects at a dosage of 50–100 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 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.[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]

Pharmacology

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Its 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-Me-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-Me-DMT failed to activate the serotonin 5-HT1A and 5-HT2A receptors.[3] 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.[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-Me-DMT, did not produce the head-twitch response.[4]

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Sweden's public health agency suggested classifying 2-Me-DMT as a hazardous substance, on May 15, 2019.[5]

See also

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References

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  1. ^ a b c d e f g h "#34 2-ME-DMT". Erowid Online Books : "TIHKAL".
  2. ^ a b c 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.
  3. ^ a b c d e 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
  4. ^ 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.
  5. ^ "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.
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