2-TOET

2-TOET.svg skin-invert-image 225px Oral Psychoactive drug None Unknown (but long-lasting) 779279-63-9 15915347 21106408 28GRS3DSL2 2-Methylthio-4-ethyl-5-methoxyamphetamine; 4-Ethyl-2-methylthio-5-methoxyamphetamine; 2-Thio-DOET; 2T-DOET; 2-Methylthio-DOET 1-(4-ethyl-5-methoxy-2-methylsulfanylphenyl)propan-2-amine 13 21 1 1 1 CCC1=CC(=C(C=C1OC)CC(C)N)SC 1S/C13H21NOS/c1-5-10-8-13(16-4)11(6-9(2)14)7-12(10)15-3/h7-9H,5-6,14H2,1-4H3 TZIBUOSWJBKVTA-UHFFFAOYSA-N 2-TOET, also known as 2-methylthio-4-ethyl-5-methoxyamphetamine or as 2-thio-DOET, is a psychoactive drug of the phenethylamine and amphetamine families related to the DOx psychedelic DOET. https://www.erowid.org/library/books_online/pihkal/pihkal169.shtml Shulgin AT Laing RR Basic Pharmacology and Effects Hallucinogens: A Forensic Drug Handbook 67–137 2003 Elsevier Science Forensic Drug Handbook Series 978-0-12-433951-4 https://books.google.com/books?id=l1DrqgobbcwC https://bibliography.maps.org/resources/download/12634 https://web.archive.org/web/20250713013624/https://bibliography.maps.org/resources/download/12634 13 July 2025 Nichols DE Cho AK, Segal DS Medicinal Chemistry and Structure-Activity Relationships Amphetamine and Its Analogs: Psychopharmacology, Toxicology, and Abuse 3–41 1994 Academic Press 978-0-12-173375-9 https://books.google.com/books?id=w99sAAAAMAAJ https://bitnest.netfirms.com/external/Books/AmphetamineAndItsAnalogs3 Biological activity is low in compounds in which the oxygen atom of either the 2- or the 5-methoxy group has been replaced with a sulfur, illustrating the difficulty in developing bioisosteres of the 2,5-dimethoxy-substituted aromatic nucleus. However, if relative importance were assigned to the two methoxy groups, the 2-methoxy group would appear to be more, critical for optimal activity (Jacob et al., 1977). For example, referring to Table l, when the 2-methoxy group of DOEt is replaced with a methylthio group, in vivo activity is reduced by more than one order of magnitude (Jacob and Shulgin, 1983; Shulgin and Shulgin, 1991). However, the replacement of the 5-methoxy oxygen with a sulfur reduces activity only 4- to 6-fold. Similarly, when the 2-methoxy group of DOM is replaced with a methylthio group, activity drops by a factor of 10–20, whereas similar replacement of the 5-methoxy only reduces activity 5- to 10-fold (Jacob et al., 1977; Shulgin and Shulgin, 1991). It is the analogue of DOET in which the methoxy group at the 2 position has been replaced with a methylthio group. The drug is one of two possible TOET (thio-DOET) positional isomers, the other being 5-TOET. In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2-TOET's dose as greater than 65mg orally and its duration as unknown (but long-lasting). The drug is more than 10-fold less potent than DOET, which has a listed dose range of 2 to 6mg orally. The effects of 2-TOET have been reported to include slight lightheadedness, feeling physically a bit fragile, possible appetite loss, possible erectile dysfunction, and next-day residual fragility. It was described as inactive as a hallucinogen at assessed doses, and higher doses were not tested. The chemical synthesis of 2-TOET has been described. The phenethylamine analogue, 2C-2-TOET (2-thio-2C-E), has been synthesized, but was not tested and its properties are unknown. 2-TOET was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1983. Jacob P, Shulgin AT Sulfur analogues of psychotomimetic agents. 2. Analogues of (2,5-dimethoxy-4-methylphenyl)-and (2,5-dimethoxy-4-ethylphenyl)isopropylamine J Med Chem 26 5 746–752 May 1983 6842515 10.1021/jm00359a021 Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991. See also Substituted methoxyphenethylamine 5-TOET and 2-TOM Ortho-DOT (2-thio-TMA-2) References External links 2-TOET - Isomer Design 2-TOET - PiHKAL - Erowid 2-TOET - PiHKAL - Isomer Design Category:Ethyl compounds Category:Methoxyphenethylamines Category:Methylthio compounds Category:PiHKAL Category:Psychedelic phenethylamines Category:Substituted amphetamines Category:Thio-2Cs and -DOx