2,3,6-Trimethoxyphenethylamine

Last updated

2,3,6-Trimethoxyphenethylamine
2,3,6-Trimethoxyphenethylamine.svg
Clinical data
Other names2,3,6-TMPEA; TMPEA-5; 2C-TMA-5
ATC code
  • None
Identifiers
  • 2-(2,3,6-trimethoxyphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C11H17NO3
Molar mass 211.261 g·mol−1
3D model (JSmol)
  • COC1=C(C(=C(C=C1)OC)OC)CCN
  • InChI=1S/C11H17NO3/c1-13-9-4-5-10(14-2)11(15-3)8(9)6-7-12/h4-5H,6-7,12H2,1-3H3
  • Key:SOARXDWNNULVNL-UHFFFAOYSA-N

2,3,6-Trimethoxyphenethylamine (2,3,6-TMPEA), also known as TMPEA-5 or as 2C-TMA-5, is a chemical compound of the phenethylamine family related to mescaline (3,4,5-trimethoxyphenethylamine). [1] [2] [3] [4] 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), 2,3,6-TMPEA is not known to have ever been tested in humans. [1] [3] It is either a competitive substrate or inhibitor of monoamine oxidase (MAO). [3] [1] [2] The chemical synthesis of 2,3,6-TMPEA has been described. [4] 2,3,6-TMPEA was first described in the scientific literature by J. R. Merchant and A. J. Mountwala in 1958. [2] As a positional isomer of mescaline, it is a Schedule I controlled substance in the United States. [2]

Contents

See also

References

  1. 1 2 3 4 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628. "The two-carbon analogue of TMA-5 is 2,3,6-trimethoxyphenethylamine (or 2C-TMA-5 or 2,3,6-TMPEA). This is a known material, although there has been some controversy as to its physical properties. It has been studied in monoamine oxidase systems, and appears to be either a competitive substrate or an inhibitor of that enzyme. But as far as I know, no one has nibbled it, so its human activity is unknown."
  2. 1 2 3 4 5 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. 1 2 3 4 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. 669, 883. ISBN   978-3-03788-700-4. OCLC   858805226. Archived from the original on 21 August 2025.
  4. 1 2 3 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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.