2,3,5-Trimethoxyphenethylamine

2,3,5-Trimethoxyphenethylamine
Clinical data
Other names2,3,5-TMPEA; TMPEA-4; 2C-TMA-4
ATC code
  • None
Identifiers
  • 2-(2,3,5-trimethoxyphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC11H17NO3
Molar mass211.261 g·mol−1
3D model (JSmol)
  • COC1=CC(=C(C(=C1)OC)OC)CCN
  • InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)11(15-3)10(7-9)14-2/h6-7H,4-5,12H2,1-3H3
  • Key:GERNGXILVRWWGB-UHFFFAOYSA-N

2,3,5-Trimethoxyphenethylamine (2,3,5-TMPEA), also known as TMPEA-4 or as 2C-TMA-4, is a chemical compound of the phenethylamine family related to mescaline (3,4,5-trimethoxyphenethylamine).[1][2][3][4][5] It is one of the possible positional isomers of trimethoxyphenethylamine and is a positional isomer of mescaline.[1][2][3][4] According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved), 2,3,5-TMPEA has never been tested in humans.[1] Unlike mescaline, 2,3,5-TMPEA does not appear to be a substrate for amine oxidase.[3][1][2][5] The chemical synthesis of 2,3,5-TMPEA has been described.[4] The 2,3,5- substitution pattern, as in 2,3,5-TMPEA, is said to be the most difficult tri-substitution pattern in terms of synthesis.[1] 2,3,5-TMPEA was first described in the scientific literature by J. R. Merchant and A. J. Mountwala in 1958.[2][1][4] As a positional isomer of mescaline, it is a Schedule I controlled substance in the United States.[2]

See also

References

  1. ^ a b c d e f Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "This 2,3,5-orientation of the methoxy groups on the aromatic ring is far and away the most difficult tri-substitution pattern known to chemists. There just isn’t any simple way to put it together. The 2-carbon phenethylamine (2,3,5-trimethoxyphenethylamine) had been synthesized quite a while ago. Its role as a substrate for liver amine oxidase in in vitro studies has been explored, but it has never been tried in man."
  2. ^ a b c d e Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
  3. ^ a b c Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 663, 883. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
  4. ^ a b c d Merchant J, Mountwala A (1958). "Notes - Synthesis of Some β-Phenethylamine Derivatives. I.". The Journal of Organic Chemistry. 23 (11): 1774–1776. doi:10.1021/jo01105a601. ISSN 0022-3263. Retrieved 29 November 2025.
  5. ^ a b Clark LC, Benington F, Morin RD (May 1965). "The Effects of Ring-Methoxyl Groups on Biological Deamination of Phenethylamines". Journal of Medicinal Chemistry. 8 (3): 353–355. doi:10.1021/jm00327a016. PMID 14323146.
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