Wiki Article
2-TOET
Nguồn dữ liệu từ Wikipedia, hiển thị bởi DefZone.Net
 | |
| Clinical data | |
|---|---|
| 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 | Oral[1] |
| Drug class | Psychoactive drug |
| ATC code |
|
| Pharmacokinetic data | |
| Duration of action | Unknown (but long-lasting)[1] |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| Chemical and physical data | |
| Formula | C13H21NOS |
| Molar mass | 239.38 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
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.[1][2][3][4] It is the analogue of DOET in which the methoxy group at the 2 position has been replaced with a methylthio group.[1][2][3][4] The drug is one of two possible TOET (thio-DOET) positional isomers, the other being 5-TOET.[1][2][3][4]
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).[1][2][4] The drug is more than 10-fold less potent than DOET, which has a listed dose range of 2 to 6 mg orally.[1][2][3]
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.[1][2]
The chemical synthesis of 2-TOET has been described.[1][4] 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]
See also
[edit]- Substituted methoxyphenethylamine
- 5-TOET and 2-TOM
- Ortho-DOT (2-thio-TMA-2)
References
[edit]- ^ a b c d e f g h i j k l 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
- ^ a b c d e f 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.
- ^ a b c d 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).
- ^ a b c d e f 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.