2C-5-TOET

Last updated

2C-5-TOET
2C-5-TOET structure.svg
Clinical data
Other names5-Thio-2C-E; 5T-2C-E; 4-Ethyl-2-methoxy-5-methylthiophenethylamine; 2-Methoxy-4-ethyl-5-methylthiophenethylamine
ATC code
  • None
Identifiers
  • 2-(4-ethyl-2-methoxy-5-methylsulfanylphenyl)ethanamine
PubChem CID
ChemSpider
Chemical and physical data
Formula C12H19NOS
Molar mass 225.35 g·mol−1
3D model (JSmol)
  • CCC1=CC(=C(C=C1SC)CCN)OC
  • InChI=1S/C12H19NOS/c1-4-9-7-11(14-2)10(5-6-13)8-12(9)15-3/h7-8H,4-6,13H2,1-3H3
  • Key:NMFLGCDBOWGERA-UHFFFAOYSA-N

2C-5-TOET, also known as 2-methoxy-4-ethyl-5-methylthiophenethylamine or as 5-thio-2C-E, is a chemical compound and possible psychedelic drug of the phenethylamine and thio-2C families related to the psychedelics 2C-E and 5-TOET (5-thio-DOET). [1] [2] [3] [4] It is the analogue of 2C-E in which the methoxy group at the 5 position has been replaced with a methylthio group. [1] [2] [4] In addition, the compound is the phenethylamine (i.e., α-desmethyl) analogue of 5-TOET (the 5-methylthio analogue of DOET). [1] [2] [3] [4]

Contents

2C-5-TOET was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1983. [4] Subsequently, it was also described by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). [1] [2] [3] However, he only synthesized the compound and did not test it. [1] [2] [3] [4] As such, its properties and effects are unknown. [1] [2] [3] [4] The related drug 5-TOET is known to be robustly active as a psychedelic but to be about 5-fold less potent than DOET. [1] [5] The chemical synthesis of 2C-5-TOET has been described. [1] [4] Other related compounds include 2C-2-TOM (2-thio-DOM), 2C-5-TOM (5-thio-DOM), and 2C-2-TOET (2-thio-DOET). [1] [2] [3] [4]

2C-5-TOET and/or precursors or intermediates have reportedly been encountered as novel designer drugs. [6] [7] [8] Similarly, 2C-2-TOM and 2C-2-TOET have reportedly been encountered as designer drugs. [9] Thio-2Cs like 2C-5-TOET are not controlled substances in Canada as of 2025. [10]

See also

References

  1. 1 2 3 4 5 6 7 8 9 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628. "#170 5-TOET". As with the other members of the TOM's and TOET's, the phenethylamine homologue of 5-TOET was synthesized, but had never been started in human evaluation. The aldehyde from above, 4-ethyl-2-methoxy-5-(methylthio)benzaldehyde, was condensed with nitroethane (as reagent and as solvent) and with ammonium acetate as catalyst to give the nitrostyrene as spectacular canary-yellow electrostatic crystals with a mp of 91-92 °C. Anal. (C12H15NO3S) C,H. This was reduced with aluminum hydride (from cold THF-dissolved lithium aluminum hydride and 100% sulfuric acid) to the phenethylamine 4-ethyl-2-methoxy-5-methylthiophenethylamine (2C-5-TOET) which, when totally freed from water of hydration by drying at 100 °C under a hard vacuum, had a mp of 216-217 °C. Anal. (C12H20ClNOS) C,H.
  2. 1 2 3 4 5 6 7 Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley: Transform Press. p. 108. ISBN   978-0-9630096-3-0.
  3. 1 2 3 4 5 6 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 823–824. ISBN   978-3-03788-700-4. OCLC   858805226. Archived from the original on 21 August 2025.
  4. 1 2 3 4 5 6 7 8 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". Journal of Medicinal Chemistry. 26 (5): 746–752. doi:10.1021/jm00359a021. PMID   6842515.
  5. ↑ 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).
  6. ↑ Yurchenko R, Zayats M, Piatsetskaya A, Yurchenko V (September 2025). New psychoactive substances in the Volga Federal District. Scientific and practical conference with international participation "Chemical and toxicological studies in the Volga Federal District". p. 41. doi:10.13140/RG.2.2.12993.42088. Ufa, KDL GBUZ RKND MZ RB] (presentation of the report in Russian). Retrieved 21 January 2026. [...] 2C-5-TOET PROP. 5-TOET TFA. [...]
  7. ↑ "2C-5-TOET". spectrabase.com. 2C-5-TOET. Compound with spectra: 3 MS (GC) [...] SpectraBase Compound ID: 9tCCQhZhq99 [...] This compound is available in the following databases: Mass Spectra of Designer Drugs 2025. Author: Peter Rösner [...]
  8. ↑ "Designer Drugs 2023 :: 2C-5-TOET AC". Chemograph Plus. Retrieved 21 January 2026.
  9. ↑ Catalani V, Corkery JM, Guirguis A, Napoletano F, Arillotta D, Zangani C, et al. (August 2021). "Psychonauts' psychedelics: A systematic, multilingual, web-crawling exercise". European Neuropsychopharmacology. 49: 69–92. doi:10.1016/j.euroneuro.2021.03.006. PMID   33857740. Table 1 NPSfinder® psychedelic phenethylamines and comparisons with EMCDDA and UNODC databases. [...] 11 2C-2-TOET [...] 12 2C-2-TOM [...]
  10. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. 5 December 2025. Retrieved 20 January 2026.
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