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).
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.
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-HT<sub>2A</sub> receptor but retained affinity for the serotonin 5-HT<sub>6</sub> receptor. It also retains significant affinity for the serotonin 5-HT<sub>1A</sub>, 5-HT<sub>1D</sub>, and 5-HT<sub>7</sub> 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).
The chemical synthesis of 5-MeO-2-TMT has been described.
5-MeO-2-TMT is not an explicitly nor implicitly controlled substance in Canada as of 2025.
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.