2,4,5-Trimethoxyamphetamine
2,4,5-Trimethoxyamphetamine, also known as TMA-2 or as 2,5-dimethoxy-4-methoxyamphetamine, is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the trimethoxyamphetamine series of positional isomers. The drug is also notable in being the 4-methoxylated member of the DOx series of drugs.
Use and effects
In his book PiHKAL, Alexander Shulgin lists TMA-2's dose as 20 to 40mg orally and its duration as 8 to 12hours. It is much more potent than its positional isomer 3,4,5-trimethoxyamphetamine, which is said to be active at doses of 100 to 250mg orally and to have a duration of 6 to 8hours. However, DOM, the analogue of TMA-2 in which its 4-methoxy group has been replaced with a more lipophilic 4-methyl group, is about 10times more potent than TMA-2.
The effects of TMA-2 have been reported to include closed-eye imagery like kaleidoscopic images, visuals such as visual distortion and movement, auditory enhancement, cosmic thinking, time dilation, music and erotic enhancement, confusion, lethargy, laziness, sleepiness, lightheadedness, feeling faintish, pupil dilation, nausea, abdominal cramps, diarrhea, and muscle tremors, among others. The drug was described as a "seminal" or "archetypal" psychedelic.
Pharmacology
Pharmacodynamics
TMA-2's affinity for the serotonin 5-HT2A receptor has been found to be 1,300nM. Its at the receptor was 190nM and its was 84%. The drug was also active at the serotonin 5-HT2B receptor and, to a much lesser extent, at the serotonin 5-HT2C receptor. In an earlier study, its affinities were 1,650nM at the serotonin 5-HT2 receptor and 46,400nM at the serotonin 5-HT1 receptor. TMA-2 is inactive at the monoamine transporters. It was inactive at the mouse trace amine-associated receptor 1, whereas it bound to the rat TAAR1 with an affinity of 3,100nM and was not assessed at the human TAAR1.
Chemistry
Synthesis
The chemical synthesis of TMA-2 has been described.
Derivatives
A variety of derivatives of TMA-2 have been developed and studied.
History
TMA-2 was first described in the scientific literature by Bruckner in 1933. Subsequently, Alexander Shulgin first described the hallucinogenic effects of TMA-2 in 1964. It was later described in further detail by Shulgin in his 1991 book PiHKAL.
Legal status
Canada
TMA-2 is a controlled substance in Canada.
As of 2011, TMA-2 is not an explicitly controlled substance in the United States. However, it is a positional isomer of 3,4,5-trimethoxyamphetamine, and thus is a Schedule I controlled substance in this country similarly.