2,3,4,5-Tetramethoxyamphetamine

Chemical compound From Wikipedia, the free encyclopedia

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]

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
Quick facts Clinical data, Other names ...
TeMA
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
CompTox Dashboard (EPA)
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
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In his book PiHKAL (Phenethylamines I Have Known And Loved), Alexander Shulgin lists TeMA's "probably above 50 mg" orally and its duration as unknown.[1][2] In an earlier publication, it was said to produce threshold effects at a dose of 30 mg orally and long-lived effects at a dose of 50 mg orally.[2] The effects of TeMA have been reported to include disinhibition, intoxication, pupil dilation, and 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, the psychedelic properties of TeMA were subsequently questioned.[4]

The chemical synthesis of TeMA has been described.[1]

TeMA was first described in the scientific literature by at least 1975.[3][2] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.[1] The drug is a controlled substance in Canada under phenethylamine blanket-ban language.[5]

See also

References

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