2,3,4,5-Tetramethoxyamphetamine

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2,3,4,5-Tetramethoxyamphetamine
Clinical data
Other namesTeMA; TA; 2,3,4,5-TeMA; 2,3,4,5-Tetramethoxyamphetamine; 2,3,4,5-Tetramethoxyphenylisopropylamine; 2-Methoxy-TMA; 2-Methoxy-3,4,5-TMA; 3-Methoxy-TMA-2; 3-Methoxy-2,4,5-TMA
ATC code
  • None
Legal status
Legal status
Identifiers
  • 1-(2,3,4,5-tetramethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC13H21NO4
Molar mass255.314 g·mol−1
3D model (JSmol)
  • CC(Cc1cc(c(c(c1OC)OC)OC)OC)N
  • InChI=1S/C13H21NO4/c1-8(14)6-9-7-10(15-2)12(17-4)13(18-5)11(9)16-3/h7-8H,6,14H2,1-5H3 checkY
  • Key:WVNJEHORYAZBRZ-UHFFFAOYSA-N checkY
  (verify)

Tetramethoxyamphetamine (TeMA), or 2,3,4,5-tetramethoxyamphetamine (2,3,4,5-TeMA), also known as 2-methoxy-TMA or 3-methoxy-TMA-2, is a drug of the phenethylamine and amphetamine families related to mescaline (3,4,5-trimethoxyphenethylamine).[1][2]

In Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known And Loved), the minimum dose is listed as 50 mg, and the duration as unknown but has been said to be relatively long-lived.[1][2] TeMA is said to produce a threshold, disinhibited intoxication, mydriasis, and a headache.[1][2] It is said to be roughly 6 times as potent as mescaline.[3]

TeMA has been said to be the only amphetamine with more than three methoxy groups known to be hallucinogenic.[2] However, subsequently, the psychedelic properties of TeMA were questioned.[4] Limited data exists about its pharmacological properties, metabolism, and toxicity.[5][6][7] It was first described in the scientific literature by at least 1975.[3][2]

See also

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References

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