5-TOET

Last updated
5-TOET
5-TOET.png
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 class Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action 30 minutes [2]
Peak: 4 hours [2]
Duration of action 8–24 hours [1]
Identifiers
  • 1-(4-ethyl-2-methoxy-5-methylsulfanylphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C13H21NOS
Molar mass 239.38 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]

Contents

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. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 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. 1 2 3 4 5 6 7 8 9 10 11 12 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. 1 2 3 4 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. 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).
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