2-TOET

Last updated
2-TOET
2-TOET.png
Clinical data
Other names2-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
  • None
Pharmacokinetic data
Duration of action Unknown (but long-lasting) [1]
Identifiers
  • 1-(4-ethyl-5-methoxy-2-methylsulfanylphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C13H21NOS
Molar mass 239.38 g·mol−1
3D model (JSmol)
  • CCC1=CC(=C(C=C1OC)CC(C)N)SC
  • InChI=1S/C13H21NOS/c1-5-10-8-13(16-4)11(6-9(2)14)7-12(10)15-3/h7-9H,5-6,14H2,1-4H3
  • Key:TZIBUOSWJBKVTA-UHFFFAOYSA-N

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]

Contents

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

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 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
  2. 1 2 3 4 5 6 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.
  3. 1 2 3 4 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).
  4. 1 2 3 4 5 6 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.
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