Chemistry:2C-5-TOET

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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]

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

  • Substituted methoxyphenethylamine
  • 2-TOET (2-thio-DOET) and 5-TOET (5-thio-DOET)
  • 2T-2CTFM-3PIP (2-thio-LPH-5)

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 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.  "#170 5-TOET". https://erowid.org/library/books_online/pihkal/pihkal170.shtml. "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. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. 2011. pp. 108. ISBN 978-0-9630096-3-0. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 (in de) Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. 2013. pp. 823–824. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 4.7 "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. May 1983. doi:10.1021/jm00359a021. PMID 6842515. 
  5. ↑ "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)." 
  6. ↑ "New psychoactive substances in the Volga Federal District.". Scientific and practical conference with international participation "Chemical and toxicological studies in the Volga Federal District". September 2025. pp. 41. doi:10.13140/RG.2.2.12993.42088. Ufa, KDL GBUZ RKND MZ RB] (presentation of the report in Russian). https://www.researchgate.net/doi/10.13140/RG.2.2.12993.42088. Retrieved 21 January 2026. "[...] 2C-5-TOET PROP. 5-TOET TFA. [...]" 
  7. ↑ "2C-5-TOET". https://dev.spectrabase.com/compound/9tCCQhZhq99. "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". https://www.chemograph.de/dd2023/dd2023-16159.html. 
  9. ↑ "Psychonauts' psychedelics: A systematic, multilingual, web-crawling exercise". European Neuropsychopharmacology 49: 69–92. August 2021. 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". 5 December 2025. https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 



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