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2,4,6-Trimethoxyamphetamine
Pharmaceutical compound From Wikipedia, the free encyclopedia
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2,4,6-Trimethoxyamphetamine (2,4,6-TMA), also known as TMA-6 or ψ-TMA-2, is a psychedelic drug of the phenethylamine, amphetamine, and Ψ-PEA families.[1][2][3] It is one of the positional isomers of trimethoxyamphetamine (TMA).[1][2][3]
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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 50 mg and a duration of 12 to 16 hours.[1] Threshold effects occur at 20 mg, a full hallucinogenic state occurs at 30 to 40 mg, and erratic results have been reported for 40 to 80 mg.[3] The drug is said to have about 8 to 10 times the potency of mescaline.[4][5][6]
Its effects at 25 to 50 mg included 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".[1] Additional reported effects include enjoyable lightheadedness, euphoria, perceptual distortion, synesthesia, and nausea.[4][7]
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Interactions
Pharmacology
Summarize
Perspective
Pharmacodynamics
TMA-6 shows affinity for serotonin receptors in rat stomach fundus strips (A2 = 525 nM) as well as in rat brain membranes (IC50 = 25,000 nM).[2][8][9] In a later study, it showed no affinity for the serotonin 5-HT1A or dopamine D2 receptors (Ki = >10,000 nM).[10] It was inactive as a monoamine reuptake inhibitor and releasing agent in rat brain synaptosomes (IC50 and EC50 = >100,000 nM, respectively).[11][12][13] The drug is a potent monoamine oxidase A (MAO-A) inhibitor, with an IC50 of 400 nM.[14] This is in contrast to TMA (3,4,5-TMA) and TMA-2 (2,4,5-TMA), which are inactive in this regard.[14]
TMA-6 fully substitutes for the psychedelic drugs DOM and 5-MeO-DMT in rodent drug discrimination tests.[2][15][16] It also partially substitutes for dextroamphetamine in rodent drug discrimination tests.[2][17]
Chemistry
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.[1][18][19][20][21] Alexander Shulgin only limitedly explored the 2,4,6- substitution pattern.[22][20]
History
TMA-6 was first described in the scientific literature by 1954.[2][3][23] Alexander Shulgin discovered its psychedelic effects in 1964[3] 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.[24][5][25][26] Shulgin subsequently gave the drug the name TMA-6 in 1970.[25] He more thoroughly described TMA-6 in PiHKAL in 1991.[1] The drug was encountered as a novel designer drug in Europe in 2009.[27]
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Society and culture
Legal status
As a positional isomer of TMA, TMA-6 is said to be a Schedule I controlled substance in the United States.[2]
See also
- Substituted methoxyphenethylamine
- Trimethoxyamphetamine
- Ψ-PEA (psychedelics)
- 2,4,6-Trimethoxyphenethylamine (2,4,6-TMPEA; ψ-2C-O)
- Ψ-DOM (2,6-dimethoxy-4-methylamphetamine)
References
External links
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