2,3,4,6-Tetramethoxyphenethylamine

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2,3,4,6-Tetramethoxyphenethylamine
2,3,4,6-Tetramethoxyphenethylamine.svg
Clinical data
Other names2,3,4,6-TeMPEA; TeMPEA-2
ATC code
  • None
Identifiers
  • 2-(2,3,4,6-tetramethoxyphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C12H19NO4
Molar mass 241.287 g·mol−1
3D model (JSmol)
  • COC1=CC(=C(C(=C1CCN)OC)OC)OC
  • InChI=1S/C12H19NO4/c1-14-9-7-10(15-2)12(17-4)11(16-3)8(9)5-6-13/h7H,5-6,13H2,1-4H3
  • Key:BIJGTHTWKBFOCK-UHFFFAOYSA-N

2,3,4,6-Tetramethoxyphenethylamine (2,3,4,6-TeMPEA), also known as TeMPEA-2, is a drug of the phenethylamine family related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine). [1] [2] It is one of the possible positional isomers of tetramethoxyphenethylamine (TeMPEA). [1] [2] The in-vitro metabolism and effects of TeMPEA-2 on behavior in animals have been studied. [1] [3] [4] The drug showed little or no activity as a norepinephrine releasing agent in vitro. [1] [5] It does not seem to have been tested in humans. [1] TeMPEA-2 was first described in the scientific literature by 1955. [1] [6]

Contents

See also

References

  1. 1 2 3 4 5 6 Shulgin A, Manning T, Daley PF (2011). "#115. TeMPEA-3". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley, CA: Transform Press. pp. 282–283. ISBN   978-0-9630096-3-0. OCLC   709667010.
  2. 1 2 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. 883, 923. ISBN   978-3-03788-700-4. OCLC   858805226.
  3. ↑ Clark LC, Benington F, Morin RD (October 1964). "The enzymatic oxidative deamination and effect on cat behavior mescaline and structurally-related β-phenethylamines". The Alabama Journal of Medical Sciences. 1: 417–429. PMID   14230671.
  4. ↑ 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.
  5. ↑ Daly JW, Creveling CR, Witkop B (May 1966). "The chemorelease of norepinephrine from mouse hearts. Structure-activity relationships. I. Sympathomimetic and related amines". Journal of Medicinal Chemistry. 9 (3): 273–280. doi:10.1021/jm00321a001. PMID   5960887.
  6. ↑ Benington F, Morin RD, Clark LC (1955). "Mescaline Analogs. II. Tetra- and Penta-Methoxy-β-Phenethylamines". The Journal of Organic Chemistry. 20 (1): 102–108. doi:10.1021/jo01119a017. ISSN   0022-3263.
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