2,3,4-Trimethoxyamphetamine

Pharmaceutical compound From Wikipedia, the free encyclopedia

2,3,4-Trimethoxyamphetamine (2,3,4-TMA), also known as TMA-3 or as α-methylisomescaline, is a putative psychedelic drug of the phenethylamine and amphetamine families.[1][2] It is one of the possible positional isomers of trimethoxyamphetamine and is a positional isomer of 3,4,5-trimethoxyamphetamine (TMA or TMA-1).[1]

Other names2,3,4-TMA; TMA-3; α-Methylisomescaline
Routes of
administrationOral[1]
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Quick facts Clinical data, Other names ...
TMA-3
Clinical data
Other names2,3,4-TMA; TMA-3; α-Methylisomescaline
Routes of
administration		Oral[1]
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown[1]
Identifiers
  • 1-(2,3,4-trimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H19NO3
Molar mass225.288 g·mol−1
3D model (JSmol)
  • CC(CC1=C(C(=C(C=C1)OC)OC)OC)N
  • InChI=1S/C12H19NO3/c1-8(13)7-9-5-6-10(14-2)12(16-4)11(9)15-3/h5-6,8H,7,13H2,1-4H3
  • Key:LWDQPPLPHGXYLG-UHFFFAOYSA-N
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Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2,3,4-TMA's dose as greater than 100 mg orally and its duration as unknown.[1][2][3][4] The drug produced no effects whatsoever at a dose of 100 mg in three separate individuals.[1] Higher doses were not tested, but 2,3,4-TMA could possibly be active at higher doses.[1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

2,3,4-TMA shows affinity for serotonin receptors.[5][2][6][7] It substituted for DOM in rodent drug discrimination tests.[2][8]

Chemistry

Synthesis

The chemical synthesis of 2,3,4-TMA has been described.[1][2]

History

2,3,4-TMA was first described in the scientific literature by Alexander Shulgin in 1964.[2][9][10] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1][2]

Society and culture

Canada

2,3,4-TMA is a controlled substance in Canada under phenethylamine blanket-ban language.[11]

United States

As a positional isomer of 3,4,5-trimethoxyamphetamine (TMA), 2,3,4-TMA is a Schedule I controlled substance in the United States.[2]

See also

References

External links

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