5-Methoxy-2,N,N-trimethyltryptamine (5-MeO-2,N,N-TMT, 5-MeO-TMT), also known as 2-methyl-5-methoxy-N,N-dimethyltryptamine (2-Me-5-MeO-DMT), is a serotonin receptor modulator and psychedelic drug of the tryptamine and 2-alkyltryptamine families. It is taken orally.
5-MeO-2-TMT was first synthesized by Alexander Shulgin and reported in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).Erowid Online Books : "TIHKAL" - #45 5-MEO-TMT
Use and effects According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), 5-MeO-TMT has a dose range of 75 to 150mg orally and a duration of 5 to 10hours. It produces effects including sexual stimulation, enhanced orgasm, relaxation, sedation, tingling, sleep disturbances, chills and cold sensations, time dilation, reduced heart rate, reduced respiratory rate, mild nausea, motor incoordination, visual waviness, mild to pronounced closed-eye visuals, emotional lability, crying, body temperature fluctuations, uncomfortableness, gastrointestinal disturbances, and abdominal pain. It has been said that 5-MeO-TMT at a dose of 150mg is definitely hallucinogenic and can be compared to a moderate 300mg dose of mescaline.
Interactions
Pharmacology Pharmacodynamics + Target Ki (nM) 5-HT1A 200 5-HT1B >10,000 5-HT1D 250 5-HT1E 1,800 5-HT1F 5-HT2A >10,000 (rat) 5-HT2B 5-HT2C 4,020 (rat) 5-HT3 5-HT4 5-HT5A 10,450 5-HT6 60–80 5-HT7 145 α1A–α2C β1–β3 D1–D5 >10,000 H1 >10,000 H2 H3, H4 >10,000 M1–M5 >10,000 I1 σ1, σ2 >10,000 6,380 >10,000 Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs:
The affinities of 5-MeO-TMT for numerous targets have been reported. 2-Methyltryptamines like 5-MeO-TMT show a loss of affinity for the serotonin 5-HT2A receptor but retained affinity for the serotonin 5-HT6 receptor. It also retains significant affinity for the serotonin 5-HT1A, 5-HT1D, and 5-HT7 receptors. In contrast to 5-MeO-DMT, 5-MeO-TMT is orally active, suggesting that the 2-methyl group blocks metabolism by monoamine oxidase (MAO).
Chemistry Synthesis The chemical synthesis of 5-MeO-2-TMT has been described.
Analogues 2-Methyltryptamine (2-MT or 2-Me-T) 2-Methyl-N,N-diethyltryptamine (2-Me-DET) 2,N,N-Trimethyltryptamine (2,N,N-TMT or 2-Me-DMT) 2,α-Dimethyltryptamine (2,α-DMT or 2-Me-αMT) 5-Methoxy-7,N,N-trimethyltryptamine (5-MeO-7-TMT or 7-Me-5-MeO-DMT) 2-Ethyl-5-methoxy-N,N-dimethyltryptamine (EMDT; 2-Et-5-MeO-DMT) BGC20-761 (5-MeO-2-phenyl-DMT)
Society and culture Legal status Canada 5-MeO-2-TMT is not an explicitly nor implicitly controlled substance in Canada as of 2025.
United States 5-MeO-2-TMT 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.
See also Substituted tryptamine
References
External links 2-Methyl-5-MeO-DMT - Isomer Design 5-MeO-TMT Experience Reports - Erowid The Big & Dandy 5-MeO-TMT Thread - Bluelight 5-MeO-TMT - TiHKAL - Erowid 5-MeO-TMT - TiHKAL - Isomer Design