2,3,5-Trimethoxyamphetamine (2,3,5-TMA), also known as TMA-4, is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the possible positional isomers of trimethoxyamphetamine and is a positional isomer of 3,4,5-trimethoxyamphetamine (TMA or TMA-1).
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2,3,5-TMA's dose as greater than 80mg orally and its duration as perhaps or about 6hours. Based on limited testing, it produced threshold effects including much introspection among others, along with no subjective physical symptoms. The drug at 80mg was described as comparable to 50üg LSD or 120mg TMA and as being roughly 4-fold as potent as mescaline. Per Shulgin, more testing is needed to fully characterize the drug in humans.
2,3,5-TMA shows affinity for serotonin receptors. The drug substitutes for DOM in rodent drug discrimination tests.
The chemical synthesis of 2,3,5-TMA has been described.
2,3,5-TMA was first described in the scientific literature by Alexander Shulgin in 1966. Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).
2,3,5-TMA is a controlled substance in Canada under phenethylamine blanket-ban language.
As a positional isomer of 3,4,5-trimethoxyamphetamine (TMA), 2,3,5-TMA is a Schedule I controlled substance in the United States.