2,4,5-Trimethoxyamphetamine

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), 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 (3,4,5-TMA, TMA, or TMA-1), which is said to be active at doses of 100 to 250mg orally and to have a duration of 6 to 8hours. However, DOM (2,5-dimethoxy-4-methylamphetamine), 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.

Interactions

Pharmacology

Pharmacodynamics

TMA-2's affinity (Ki) 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 (Ki) 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 (TAAR1), whereas it bound to the rat TAAR1 with an affinity (Ki) 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 (Phenethylamines I Have Known and Loved).

Society and culture

Legal status

Canada

TMA-2 is a controlled substance in Canada.

United States

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 (TMA), and thus is a Schedule I controlled substance in this country similarly.

References

References

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