2,N,N-TMT

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]

2,N,N-TMT

Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Class A
Identifiers
IUPAC name (2-(2-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine
CAS Number	1080-95-1 Y
PubChem CID	11820174
ChemSpider	9994827
UNII	P15UO6J3FK
ChEMBL	ChEMBL7580
CompTox Dashboard (EPA)	DTXSID801016967
Chemical and physical data
Formula	C13H18N2
Molar mass	202.301 g·mol−1
3D model (JSmol)	Interactive image
SMILES Cc1c(c2ccccc2[nH]1)CCN(C)C
InChI 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
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Effects

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-HT_2A 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

Its affinities (K_i) for the serotonin 5-HT_1A and 5-HT_2A 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-HT_1A and 5-HT_2A receptors compared to DMT.^[2][3] In addition, unlike DMT, 2-Me-DMT failed to activate the serotonin 5-HT_1A and 5-HT_2A 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]

Legal status

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

See also

• 2-Methyltryptamine (2-MT or 2-Me-T)
• 2-Methyl-N,N-diethyltryptamine (2-Me-DET)
• 2,α-Dimethyltryptamine (2,α-DMT or 2-Me-αMT)
• 5-Methoxy-2,N,N-trimethyltryptamine (5-MeO-2,N,N-TMT or 2-Me-5-MeO-DMT)
• 5,N,N-Trimethyltryptamine (5,N,N-TMT)
• 7,N,N-Trimethyltryptamine (7,N,N-TMT)