2-TOET

{{Infobox drug | drug_name = | image = 2-TOET.svg | image_class = skin-invert-image | width = 225px | caption =

| legal_status =

| IUPAC_name = 1-(4-ethyl-5-methoxy-2-methylsulfanylphenyl)propan-2-amine | C=13 | H=21 | N=1 | O=1 | S=1 | SMILES = CCC1=CC(=C(C=C1OC)CC(C)N)SC | StdInChI = 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 | StdInChIKey = 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.<ref name="PiHKAL">{{CitePiHKAL}} https://www.erowid.org/library/books_online/pihkal/pihkal169.shtml</ref><ref name="Shulgin2003">{{cite book | vauthors = Shulgin AT | veditors = Laing RR | chapter = Basic Pharmacology and Effects | title = Hallucinogens: A Forensic Drug Handbook | pages = 67–137 | year = 2003 | publisher = Elsevier Science | series = Forensic Drug Handbook Series | isbn = 978-0-12-433951-4 | url = https://books.google.com/books?id=l1DrqgobbcwC | chapter-url = https://bibliography.maps.org/resources/download/12634 | archive-url = https://web.archive.org/web/20250713013624/https://bibliography.maps.org/resources/download/12634 | archive-date = 13 July 2025 }}</ref><ref name="Nichols1994">{{cite book | vauthors = Nichols DE | veditors = Cho AK, Segal DS | chapter = Medicinal Chemistry and Structure-Activity Relationships | title = Amphetamine and Its Analogs: Psychopharmacology, Toxicology, and Abuse | pages = 3–41 | date = 1994 | publisher = Academic Press | isbn = 978-0-12-173375-9 | url = https://books.google.com/books?id=w99sAAAAMAAJ | chapter-url = https://bitnest.netfirms.com/external/Books/AmphetamineAndItsAnalogs3 | quote = 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).}}</ref><ref name="JacobShulgin1983" /> It is the analogue of DOET in which the methoxy group at the 2 position has been replaced with a methylthio group.<ref name="PiHKAL" /><ref name="Shulgin2003" /><ref name="Nichols1994" /><ref name="JacobShulgin1983" /> The drug is one of two possible TOET (thio-DOET) positional isomers, the other being 5-TOET.<ref name="PiHKAL" /><ref name="Shulgin2003" /><ref name="Nichols1994" /><ref name="JacobShulgin1983" />

In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'') and other publications, Alexander Shulgin lists 2-TOET's dose as greater than 65{{nbsp}}mg orally and its duration as unknown (but long-lasting).<ref name="PiHKAL" /><ref name="Shulgin2003" /><ref name="JacobShulgin1983" /> The drug is more than 10-fold less potent than DOET, which has a listed dose range of 2 to 6{{nbsp}}mg orally.<ref name="PiHKAL" /><ref name="Shulgin2003" /><ref name="Nichols1994" />

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.<ref name="PiHKAL" /> It was described as inactive as a hallucinogen at assessed doses, and higher doses were not tested.<ref name="PiHKAL" /><ref name="Shulgin2003" />

The chemical synthesis of 2-TOET has been described.<ref name="PiHKAL" /><ref name="JacobShulgin1983" /> The phenethylamine analogue, 2C-2-TOET (2-thio-2C-E), has been synthesized, but was not tested and its properties are unknown.<ref name="PiHKAL" />

2-TOET was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1983.<ref name="JacobShulgin1983">{{cite journal | vauthors = Jacob P, Shulgin AT | title = Sulfur analogues of psychotomimetic agents. 2. Analogues of (2,5-dimethoxy-4-methylphenyl)-and (2,5-dimethoxy-4-ethylphenyl)isopropylamine | journal = J Med Chem | volume = 26 | issue = 5 | pages = 746–752 | date = May 1983 | pmid = 6842515 | doi = 10.1021/jm00359a021 | url = }}</ref> Subsequently, it was described in greater detail by Shulgin in ''PiHKAL'' in 1991.<ref name="PiHKAL" />

==See also== * Substituted methoxyphenethylamine * 5-TOET and 2-TOM * Ortho-DOT (2-thio-TMA-2)

==References== {{Reflist}}

==External links== * [https://isomerdesign.com/pihkal/explore/169 2-TOET - Isomer Design] * [https://erowid.org/library/books_online/pihkal/pihkal169.shtml 2-TOET - PiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/pk/169 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