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| Other names | 2-Methylthio-4-ethyl-5-methoxyamphetamine; 4-Ethyl-2-methylthio-5-methoxyamphetamine; 2-Thio-DOET; 2T-DOET; 2-Methylthio-DOET |
| Routes of administration | Oral1 |
| Drug class | Psychoactive drug |
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| Pharmacokinetic data | |
| Duration of action | Unknown (but long-lasting)1 |
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| Chemical and physical data | |
| Formula | C13H21NOS |
| Molar mass | 239.38 g·mol−1 |
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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.1234 It is the analogue of DOET in which the methoxy group at the 2 position has been replaced with a methylthio group.1234 The drug is one of two possible TOET (thio-DOET) positional isomers, the other being 5-TOET.1234
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2-TOET's dose as greater than 65 mg orally and its duration as unknown (but long-lasting).124 The drug is more than 10-fold less potent than DOET, which has a listed dose range of 2 to 6 mg orally.123
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.1 It was described as inactive as a hallucinogen at assessed doses, and higher doses were not tested.12
The chemical synthesis of 2-TOET has been described.14 The phenethylamine analogue, 2C-2-TOET (2-thio-2C-E), has been synthesized, but was not tested and its properties are unknown.1
2-TOET 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/pihkal169.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.