5-TOET

5-TOET
Clinical data
Other names2-Methoxy-4-ethyl-5-methylthioamphetamine; 4-Ethyl-2-methoxy-5-methylthioamphetamine; 5-Thio-DOET; 5T-DOET; 5-Methylthio-DOET
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action30 minutes[2]
Peak: 4 hours[2]
Duration of action8–24 hours[1]
Identifiers
  • 1-(4-ethyl-2-methoxy-5-methylsulfanylphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC13H21NOS
Molar mass239.38 g·mol−1
3D model (JSmol)
  • CCC1=CC(=C(C=C1SC)CC(C)N)OC
  • InChI=1S/C13H21NOS/c1-5-10-7-12(15-3)11(6-9(2)14)8-13(10)16-4/h7-9H,5-6,14H2,1-4H3
  • Key:CBSUPAQTEZIWSK-UHFFFAOYSA-N

5-TOET, also known as 2-methoxy-4-ethyl-5-methylthioamphetamine or as 5-thio-DOET, is a psychedelic drug of the phenethylamine and amphetamine families related to the DOx psychedelic DOET.[1][3][4][2] It is the analogue of DOET in which the methoxy group at the 5 position has been replaced with a methylthio group.[1][3][4][2] The drug is one of two possible TOET (thio-DOET) positional isomers, the other being 2-TOET.[1][3][4][2]

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 5-TOET's dose as 12 to 25 mg orally and its duration as 8 to 24 hours.[1][3][2] Its onset is about 30 minutes and its time to peak is about 4 hours.[2] The drug is around 5-fold less potent than DOET, which has a listed dose range of 2 to 6 mg orally.[1][4]

The effects of 5-TOET have been reported to include closed-eye imagery and fantasy, open-eye visuals such as brightness around objects and visual movement, feelings of joy, beauty, love, and serenity, erotic enhancement, restlessness, lightheadedness, pupil dilation, sleep disturbances, and next-day afterglow as well as lethargy.[1][2] One user described it as "superb", "exquisite", and potentially "extraordinary".[1] It has much less physical discomfort than 5-TOM.[1][2] There also appears to be significant interindividual variability in intensity of 5-TOET, with two of eight people being roughly twice as sensitive as the others.[1][2] In addition, an unintentional overdose in one person, despite a similar dose taken as others, was described as intense, exhausting, and too long-lived.[1]

The chemical synthesis of 5-TOET has been described.[1][2] The phenethylamine analogue, 2C-5-TOET (5-thio-2C-E), has been synthesized, but was not tested and its properties are unknown.[1]

5-TOET was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1983.[2] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.[1]

See also

References

  1. ^ a b c d e f g h i j k l m n o 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/pihkal170.shtml
  2. ^ a b c d e f g h i j k l 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.
  3. ^ a b c d 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.
  4. ^ 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).
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