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2C-5-TOET

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). It is the analogue of 2C-E in which the methoxy group at the 5 position has been replaced with a methylthio group. In addition, the compound is the phenethylamine (i.e., α-desmethyl) analogue of 5-TOET (the 5-methylthio analogue of DOET).

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

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

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