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2,3,5-Trimethoxyamphetamine

Pharmaceutical compound From Wikipedia, the free encyclopedia

2,3,5-Trimethoxyamphetamine (2,3,5-TMA), also known as TMA-4, is a 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][2]

Other names2,3,5-TMA; TMA-4
Routes of
administrationOral[1]
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Quick facts Clinical data, Other names ...
TMA-4
Clinical data
Other names2,3,5-TMA; TMA-4
Routes of
administration		Oral[1]
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action~6 hours[1]
Identifiers
  • 1-(2,3,5-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(=CC(=C1)OC)OC)OC)N
  • InChI=1S/C12H19NO3/c1-8(13)5-9-6-10(14-2)7-11(15-3)12(9)16-4/h6-8H,5,13H2,1-4H3
  • Key:MJIBJXKJBRLSQA-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 2,3,5-TMA's dose as greater than 80 mg orally and its duration as perhaps or about 6 hours.[1][3][4] Based on limited testing, it produced threshold effects including much introspection among others, along with no subjective physical symptoms.[1][2] The drug at 80 mg was described as comparable to 50 μg LSD or 120 mg TMA and as being roughly 4-fold as potent as mescaline.[1][2] Per Shulgin, more testing is needed to fully characterize the drug in humans.[1]

Interactions

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

Pharmacology

Pharmacodynamics

2,3,5-TMA shows affinity for serotonin receptors.[2][5][6] The drug substitutes for DOM in rodent drug discrimination tests.[2][7]

Chemistry

Synthesis

The chemical synthesis of 2,3,5-TMA has been described.[1][2]

History

2,3,5-TMA was first described in the scientific literature by Alexander Shulgin in 1966.[8] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]

Society and culture

Canada

2,3,5-TMA is a controlled substance in Canada under phenethylamine blanket-ban language.[9]

United States

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

See also

References

External links

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