2,3,4,5-Tetramethoxyamphetamine

Chemical compound 477210028 TeMA TeMA structure.svg skin-invert-image 225px None Schedule I Class A 23693-26-7 W39F9G7WET 44350147 correct chemspider 23206528 correct EBI 124969 TeMA; TA; 2,3,4,5-TeMA; 2,3,4,5-Tetramethoxyamphetamine; 2,3,4,5-Tetramethoxyphenylisopropylamine; 2-Methoxy-TMA; 2-Methoxy-3,4,5-TMA; 3-Methoxy-TMA-2; 3-Methoxy-2,4,5-TMA 1-(2,3,4,5-tetramethoxyphenyl)propan-2-amine 13 21 1 4 CC(Cc1cc(c(c(c1OC)OC)OC)OC)N correct chemspider 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 correct chemspider WVNJEHORYAZBRZ-UHFFFAOYSA-N Tetramethoxyamphetamine (TeMA), or 2,3,4,5-tetramethoxyamphetamine (2,3,4,5-TeMA), also known as 2-methoxy-TMA or 3-methoxy-TMA-2, is a drug of the phenethylamine and amphetamine families related to mescaline (3,4,5-trimethoxyphenethylamine). https://www.erowid.org/library/books_online/pihkal/pihkal145.shtml Shulgin AT Iversen LL, Iversen SD, Snyder SH Psychotomimetic Drugs: Structure-Activity Relationships Stimulants 243–333 1978 10.1007/978-1-4757-0510-2_6 Springer US Boston, MA 978-1-4757-0512-6 https://bitnest.netfirms.com/external/10.1007/978-1-4757-0510-2_6 https://books.google.com/books?id=h0_uBwAAQBAJ&pg=PA261 3.1.11. 2,3,4,5-Tetramethoxyphenylisopropylamine: Only one substituted phenylisopropylamine with more than three methoxyl groups has been established as being psychotomimetic. This is 2,3,4,5-tetramethoxyphenylisopropylamine (44, 2,3,4,5-tetramethoxyamphetamine). A threshold level of central activity is evident at a 30 mg dose orally, and a relatively long-lived disinhibited intoxication is produced by a 50-mg dosage. Compound (44) has been recorded as having six times the potency of mescaline (Shulgin et ai., 1969), but additional studies will be needed to establish the qualitative nature of its action. In his book PiHKAL (Phenethylamines I Have Known And Loved), Alexander Shulgin lists TeMA's "probably above 50mg" orally and its duration as unknown. In an earlier publication, it was said to produce threshold effects at a dose of 30mg orally and long-lived effects at a dose of 50mg orally. The effects of TeMA have been reported to include disinhibition, intoxication, pupil dilation, and headache. It is said to be roughly 6times as potent as mescaline. Brimblecombe RW, Pinder RM Phenylalkylamines and Their Derivatives 55–97 Hallucinogenic Agents 1975 Bristol Wright-Scientechnica https://bitnest.netfirms.com/external/Books/978-0-85608-011-1#page=38 TeMA has been said to be the only amphetamine with more than three methoxy groups known to be hallucinogenic. However, the psychedelic properties of TeMA were subsequently questioned. Nichols DE Medicinal Chemistry and Structure–Activity Relationships 3–41 https://bitnest.netfirms.com/external/Books/AmphetamineAndItsAnalogs3 Cho AK, Segal DS Amphetamine and Its Analogs: Psychopharmacology, Toxicology, and Abuse 1994 Academic Press 978-0-12-173375-9 https://books.google.com/books?id=w99sAAAAMAAJ Finally, 2,3,4,5-tetramethoxyamphetamine was reported earlier to be active in humans (Shulgin, 1978). However, the more recent description of its effects leaves some doubt about this conclusion (Shulgin and Shulgin, 1991). The chemical synthesis of TeMA has been described. TeMA was first described in the scientific literature by at least 1975. Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991. The drug is a controlled substance in Canada under phenethylamine blanket-ban language.Controlled Drugs and Substances Act Department of Justice Canada https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html 19 January 2026 See also Substituted methoxyphenethylamine Tetramethoxyamphetamine 2,3,4,5-Tetramethoxyphenethylamine (TeMPEA) 2,5-Dimethoxy-3,4-methylenedioxyamphetamine (DMMDA) 2-Bromo-TMA References External links TeMA - Isomer Design TeMA - PiHKAL - Erowid TeMA - PiHKAL - Isomer Design Category:DOx (psychedelics) Category:Methoxyphenethylamines Category:PiHKAL