 | |
| Clinical data | |
|---|---|
| Other names | 2-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 |
|
| Pharmacokinetic data | |
| Onset of action | 30 minutes[2] Peak: 4 hours[2] |
| Duration of action | 8–24 hours[1] |
| Identifiers | |
| |
| CAS Number | |
| PubChemCID | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| Chemical and physical data | |
| Formula | C13H21NOS |
| Molar mass | 239.38 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
5-TOET, also known as2-methoxy-4-ethyl-5-methylthioamphetamine or as5-thio-DOET, is apsychedelic drug of thephenethylamine andamphetamine families related to theDOx psychedelicDOET.[1][3][4][2] It is theanalogue of DOET in which themethoxy group at the 5 position has been replaced with amethylthio group.[1][3][4][2] The drug is one of two possibleTOET (thio-DOET)positional isomers, the other being2-TOET.[1][3][4][2]
In his bookPiHKAL (Phenethylamines I Have Known and Loved) and other publications,Alexander Shulgin lists 5-TOET's dose as 12 to 25 mgorally and itsduration as 8 to 24 hours.[1][3][2] Itsonset is about 30 minutes and its time to peak is about 4 hours.[2] The drug is around 5-fold lesspotent 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 includeclosed-eyeimagery andfantasy,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-dayafterglow as well aslethargy.[1][2] One user described it as "superb", "exquisite", and potentially "extraordinary".[1] It has much less physical discomfort than5-TOM.[1][2] There also appears to be significantinterindividual variability in intensity of 5-TOET, with two of eight people being roughly twice as sensitive as the others.[1][2] In addition, an unintentionaloverdose in one person, despite a similar dose taken as others, was described as intense, exhausting, and too long-lived.[1]
Thechemical synthesis of 5-TOET has been described.[1][2] Thephenethylamineanalogue,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 thescientific literature byAlexander Shulgin andPeyton Jacob III in 1983.[2] Subsequently, it was described in greater detail by Shulgin inPiHKAL in 1991.[1]
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).