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| Other names | 2-Methylthio-4-methyl-5-methoxyamphetamine; 5-Methoxy-4-methyl-2-methylthioamphetamine; 2-Thio-DOM; 2T-DOM; 2-Methylthio-DOM |
| Routes of administration | Oral1 |
| Drug class | Serotonergic psychedelic; Hallucinogen |
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| Pharmacokinetic data | |
| Duration of action | 8–10 hours1 |
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| Chemical and physical data | |
| Formula | C12H19NOS |
| Molar mass | 225.35 g·mol−1 |
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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.1234 It is the analogue of DOM in which the methoxy group at the 2 position has been replaced with a methylthio group.1234 The drug is one of two possible TOM (thio-DOM) positional isomers, the other being 5-TOM.1234
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2-TOM's dose as 60 to 100 mg orally and its duration as 8 to 10 hours.12 Whereas 2-TOM has a fully effective dose of around 80 mg, DOM has a fully effective dose of about 5 mg, and so there is around a 15-fold loss of potency with the drug.1235 In addition, it has a shorter duration than DOM, with DOM having a listed duration of 14 to 20 hours.1
The effects of 2-TOM have been reported to include closed-eye visuals, feeling strange, "superb body feeling", pleasantness, bodily awareness, and feeling heavy.1 It has none of the neurological or physical "roughness" that was observed with 5-TOM.1
The chemical synthesis of 2-TOM has been described.14 The phenethylamine analogue, 2C-2-TOM (2-thio-2C-D), has been synthesized, but was not tested and its properties are unknown.14 Bis-TOM, the 2,5-dimethylthio analogue of DOM, was synthesized and tested, but was inactive at doses of up to 160 mg orally or approximately 50 times the minimum effective dose of DOM.1254
2-TOM was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1983.4 Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.1
References
References
- Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. https://www.erowid.org/library/books_online/pihkal/pihkal171.shtml
- Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025.
- Nichols DE (1994). "Medicinal Chemistry and Structure-Activity Relationships". In Cho AK, Segal DS (eds.). Amphetamine and Its Analogs: Psychopharmacology, Toxicology, and Abuse. Academic Press. pp. 3–41. ISBN 978-0-12-173375-9.
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).
- Jacob P, Shulgin AT (May 1983). "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. doi:10.1021/jm00359a021. PMID 6842515.
- Marcher-Rørsted E, Halberstadt AL, Klein AK, Chatha M, Jademyr S, Jensen AA, Kristensen JL (May 2020). "Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists". ACS Chem Neurosci. 11 (9): 1238–1244. doi:10.1021/acschemneuro.0c00129. PMID 32212672.
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.