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| Other names | 5-Thio-2C-E; 5T-2C-E; 4-Ethyl-2-methoxy-5-methylthiophenethylamine; 2-Methoxy-4-ethyl-5-methylthiophenethylamine |
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| Chemical and physical data | |
| Formula | C12H19NOS |
| Molar mass | 225.35 g·mol−1 |
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2C-5-TOET, also known as2-methoxy-4-ethyl-5-methylthiophenethylamine or as5-thio-2C-E, is achemical compound and possiblepsychedelic drug of thephenethylamine andthio-2C families related to the psychedelics2C-E and5-TOET (5-thio-DOET).[1][2][3][4] It is theanalogue of 2C-E in which themethoxy group at the 5 position has been replaced with amethylthio group.[1][2][4] In addition, the compound is the phenethylamine (i.e., α-desmethyl) analogue of 5-TOET (the 5-methylthio analogue ofDOET).[1][2][3][4]
2C-5-TOET was first described in thescientific literature byAlexander Shulgin andPeyton Jacob III in 1983.[4] Subsequently, it was also described by Shulgin in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved).[1][2][3] However, he onlysynthesized 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 lesspotent than DOET.[1][5] Thechemical synthesis of 2C-5-TOET has been described.[1][4] Other related compounds include2C-2-TOM (2-thio-DOM),2C-5-TOM (5-thio-DOM), and2C-2-TOET (2-thio-DOET).[1][2][3][4]
2C-5-TOET and/orprecursors orintermediates have reportedly been encountered as noveldesigner 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 notcontrolled substances inCanada as of 2025.[10]
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.
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).
[...] 2C-5-TOET PROP. 5-TOET TFA. [...]
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 [...]
Table 1 NPSfinder® psychedelic phenethylamines and comparisons with EMCDDA and UNODC databases. [...] 11 2C-2-TOET [...] 12 2C-2-TOM [...]