2,4,6-Trimethoxyamphetamine

Use and effects

In his 1991 book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin gave a dose range for TMA-6 of 25 to 50mg and a duration of 12 to 16hours. Threshold effects occur at 20mg, a full hallucinogenic state occurs at 30 to 40mg, and erratic results have been reported for 40 to 80mg. The drug is said to have about 8 to 10times the potency of mescaline.

The effects of TMA-6 have been reported to include ease with concepts and writing, body tingling, walking unsteadiness, thinking difficulty or intoxication, difficulty with tasks, funniness, hilarity, and laughter, difficulty sleeping, inner chill, visual sparkle, stomach queasiness, diarrhea, reduced appetite, fluctuating emotions, personal insights, visuals, colors, and feelings of "energy flow". Additional reported effects include enjoyable lightheadedness, euphoria, perceptual distortion, synesthesia, and nausea.

Interactions

Pharmacology

Pharmacodynamics

TMA-6 shows affinity for serotonin receptors in rat stomach fundus strips (A2 = 525nM) as well as in rat brain membranes ( = 25,000nM). In a later study, it showed no affinity for the serotonin 5-HT1A or dopamine D2 receptors (Ki = 10,000nM). Subsequently, it was reported to be a potent serotonin 5-HT2A receptor full agonist, with an of 29.2nM and an of 107%. The drug was inactive as a monoamine reuptake inhibitor and releasing agent in rat brain synaptosomes ( and = 100,000nM, respectively). The drug is a potent monoamine oxidase A (MAO-A) inhibitor, with an of 400nM. This is in contrast to TMA (3,4,5-TMA) and TMA-2 (2,4,5-TMA), which are inactive in this regard.

TMA-6 fully substitutes for the psychedelic drugs DOM and 5-MeO-DMT in rodent drug discrimination tests. It also partially substitutes for dextroamphetamine in rodent drug discrimination tests.

Chemistry

Synthesis

The chemical synthesis of TMA-6 has been described.

Analogues

A number of analogues of TMA-6 with a 2,4,6- substitution pattern have been described, such as Ψ-DOM and ψ-2C-T-4, among others. Alexander Shulgin only limitedly explored the 2,4,6- substitution pattern.

History

TMA-6 was first described in the scientific literature by 1954. Alexander Shulgin discovered its psychedelic effects in 1964 and first described its hallucinogenic effects in the literature in 1969, where he stated its potency relative to mescaline and noted that these findings were previously unpublished. Shulgin subsequently gave the drug the name TMA-6 in 1970. He more thoroughly described TMA-6 in PiHKAL in 1991. The drug was encountered as a novel designer drug in Europe in 2009.

Society and culture

Legal status

Canada

TMA-6 is a controlled substance in Canada under phenethylamine blanket-ban language.

United States

As a positional isomer of TMA, TMA-6 is a Schedule I controlled substance in the United States.

References

References

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