2,3,5,6-Tetramethoxyphenethylamine

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]

2,3,5,6-Tetramethoxyphenethylamine

Clinical data
Other names	2,3,5,6-TeMPEA; TeMPEA-3
Identifiers
IUPAC name 2-(2,3,5,6-tetramethoxyphenyl)ethanamine
PubChem CID	121008955
ChemSpider	62993366
Chemical and physical data
Formula	C12H19NO4
Molar mass	241.287 g·mol−1
3D model (JSmol)	Interactive image
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

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

• Substituted methoxyphenethylamine
• Tetramethoxyphenethylamine (TeMPEA)
• 2,3,4,5-Tetramethoxyphenethylamine (TeMPEA, TeMPEA-1)
• 2,3,4,6-Tetramethoxyphenethylamine (TeMPEA-2)
• 2,3,5,6-Tetramethoxyamphetamine (TeMA-3)
• Pentamethoxyphenethylamine (PeMPEA)
• Trimethoxyphenethylamine (TMPEA)