2,3,5,6-Tetramethoxyphenethylamine

2,3,5,6-Tetramethoxyphenethylamine
Clinical data
Other names2,3,5,6-TeMPEA; TeMPEA-3
Identifiers
IUPAC name
  • 2-(2,3,5,6-tetramethoxyphenyl)ethanamine
PubChem CID
ChemSpider
Chemical and physical data
FormulaC12H19NO4
Molar mass241.287 g·mol−1
3D model (JSmol)
SMILES
  • COC1=CC(=C(C(=C1OC)CCN)OC)OC
InChI
  • InChI=1S/C12H19NO4/c1-14-9-7-10(15-2)12(17-4)8(5-6-13)11(9)16-3/h7H,5-6,13H2,1-4H3
  • Key:MRCWRNATBFUERI-UHFFFAOYSA-N

2,3,5,6-Tetramethoxyphenethylamine (2,3,5,6-TeMPEA), also known as TeMPEA-3, is a drug of the phenethylamine family related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine).[1] It is one of the possible positional isomers of tetramethoxyphenethylamine (TeMPEA).[1]

The in-vitro metabolism and effects of TeMPEA-3 on behavior in animals have been studied.[1][2][3] Unlike mescaline, TeMPEA-3 was inactive in the conditioned avoidance response test in rats.[1][4] The effects of TeMPEA-3 in humans have not been reported and are unknown.[1]

The drug was first described in the scientific literature by 1955.[1][5] TeMPEA-3 was included as an entry in Alexander Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds.[1]

See also

References

  1. ^ a b c d e f g 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. ^ 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.
  3. ^ 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.
  4. ^ Smythies JR, Bradley RJ, Johnston VS, Benington F, Morin RD, Clark LC (1967). "Structure-activity relationship studies on mescaline. 3. The influence of the methoxy groups". Psychopharmacologia. 10 (5): 379–387. doi:10.1007/BF00403978. PMID 5588333.
  5. ^ 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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