2-TOM

2-TOM.svg skin-invert-image 215px Oral Serotonergic psychedelic; Hallucinogen None 8–10 hours 207740-44-1 15915345 21106409 PWF2TYB2Z5 123914 2-Methylthio-4-methyl-5-methoxyamphetamine; 5-Methoxy-4-methyl-2-methylthioamphetamine; 2-Thio-DOM; 2T-DOM; 2-Methylthio-DOM 1-(5-methoxy-4-methyl-2-methylsulfanylphenyl)propan-2-amine 12 19 1 1 1 CC1=CC(=C(C=C1OC)CC(C)N)SC 1S/C12H19NOS/c1-8-5-12(15-4)10(6-9(2)13)7-11(8)14-3/h5,7,9H,6,13H2,1-4H3 CROYZNIEESCKGY-UHFFFAOYSA-N 2-TOM, also known as 2-methylthio-4-methyl-5-methoxyamphetamine or as 2-thio-DOM, is a psychedelic drug of the phenethylamine and amphetamine families related to the DOx psychedelic DOM. https://www.erowid.org/library/books_online/pihkal/pihkal171.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 DOM in which the methoxy group at the 2 position has been replaced with a methylthio group. The drug is one of two possible TOM (thio-DOM) positional isomers, the other being 5-TOM. In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2-TOM's dose as 60 to 100mg orally and its duration as 8 to 10hours. Whereas 2-TOM has a fully effective dose of around 80mg, DOM has a fully effective dose of about 5mg, and so there is around a 15-fold loss of potency with the drug. Marcher-Rørsted E, Halberstadt AL, Klein AK, Chatha M, Jademyr S, Jensen AA, Kristensen JL Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists ACS Chem Neurosci 11 9 1238–1244 May 2020 32212672 10.1021/acschemneuro.0c00129 Shulgin observed that replacement of either the 2-position (10, Figure 2) or the 5- position (11, Figure 2) oxygen in 9 with a sulfur atom reduces its hallucinogenic potency by approximately 15- or 10-fold, respectively.13 Replacing both oxygen atoms with sulfur (12, Figure 2) completely abolished activity. In addition, it has a shorter duration than DOM, with DOM having a listed duration of 14 to 20hours. The effects of 2-TOM have been reported to include closed-eye visuals, feeling strange, "superb body feeling", pleasantness, bodily awareness, and feeling heavy. It has none of the neurological or physical "roughness" that was observed with 5-TOM. The chemical synthesis of 2-TOM has been described. The phenethylamine analogue, 2C-2-TOM (2-thio-2C-D), has been synthesized, but was not tested and its properties are unknown. Bis-TOM, the 2,5-dimethylthio analogue of DOM, was synthesized and tested, but was inactive at doses of up to 160mg orally or approximately 50times the minimum effective dose of DOM. 2-TOM 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-TOM and 2-TOET Ortho-DOT (2-thio-TMA-2) References External links 2-TOM - Isomer Design 2-TOM - PiHKAL - Erowid 2-TOM - PiHKAL - Isomer Design Category:Methoxyphenethylamines Category:Methyl compounds Category:Methylthio compounds Category:PiHKAL Category:Psychedelic phenethylamines Category:Substituted amphetamines Category:Thio-2Cs and -DOx