Chemistry:2-TOET
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
- Substituted methoxyphenethylamine
- 5-TOET and 2-TOM
- Ortho-DOT (2-thio-TMA-2)
References
- ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml. https://www.erowid.org/library/books_online/pihkal/pihkal169.shtml
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://bibliography.maps.org/resources/download/12634.
- ↑ 3.0 3.1 3.2 3.3 "Medicinal Chemistry and Structure-Activity Relationships". Amphetamine and Its Analogs: Psychopharmacology, Toxicology, and Abuse. Academic Press. 1994. pp. 3–41. ISBN 978-0-12-173375-9. 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)."
- ↑ 4.0 4.1 4.2 4.3 4.4 4.5 "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. doi:10.1021/jm00359a021. PMID 6842515.
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