2,3,4,5-Tetramethoxyamphetamine

Tetramethoxyamphetamine (TeMA), or 2,3,4,5-tetramethoxyamphetamine (2,3,4,5-TeMA), is a drug of the phenethylamine and amphetamine families related to mescaline (3,4,5-trimethoxyphenethylamine).^[1][2]

2,3,4,5-Tetramethoxyamphetamine

Clinical data
Other names	TeMA; TA; 2,3,4,5-TeMA; 2,3,4,5-Tetramethoxyamphetamine; 2,3,4,5-Tetramethoxyphenylisopropylamine
ATC code	None
Legal status
Legal status	CA: Schedule I UK: Class A
Identifiers
IUPAC name 1-(2,3,4,5-tetramethoxyphenyl)propan-2-amine
CAS Number	23693-26-7
PubChem CID	44350147
ChemSpider	23206528 Y
UNII	W39F9G7WET
ChEMBL	ChEMBL124969 Y
CompTox Dashboard (EPA)	DTXSID601027160
Chemical and physical data
Formula	C13H21NO4
Molar mass	255.314 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(Cc1cc(c(c(c1OC)OC)OC)OC)N
InChI InChI=1S/C13H21NO4/c1-8(14)6-9-7-10(15-2)12(17-4)13(18-5)11(9)16-3/h7-8H,6,14H2,1-5H3 Y Key:WVNJEHORYAZBRZ-UHFFFAOYSA-N Y
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In Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known And Loved), the minimum dose is listed as 50 mg, and the duration as unknown but has been said to be relatively long-lived.^[1][2] TeMA is said to produce a threshold, disinhibited intoxication, mydriasis, and a headache.^[1][2] It is said to be roughly 6 times as potent as mescaline.^[3]

TeMA has been said to be the only amphetamine with more than three methoxy groups known to be hallucinogenic.^[2] However, subsequently, the psychedelic properties of TeMA were questioned.^[4] Limited data exists about its pharmacological properties, metabolism, and toxicity.^[5][6][7] It was first described in the scientific literature by at least 1975.^[3][2]

See also

• Substituted methoxyphenethylamine
• 2,3,4,5-Tetramethoxyphenethylamine (TeMPEA)
• 2,5-Dimethoxy-3,4-methylenedioxyamphetamine (DMMDA)