 | |
| Clinical data | |
|---|---|
| Other names | 2-Methoxy-4-methyl-5-methylthioamphetamine; 5-Methylthio-4-methyl-2-methoxyamphetamine; 5-Thio-DOM; 5T-DOM; 5-Methylthio-DOM |
| Routes of administration | Oral[1] |
| Drug class | Serotonergic psychedelic;Hallucinogen |
| ATC code |
|
| Pharmacokinetic data | |
| Onset of action | 30 minutes[2][1] Peak: ~3 hours[2][1] |
| Duration of action | 6–10 hours (but up to 12–16 hours)[1][2] |
| Identifiers | |
| |
| CAS Number | |
| PubChemCID | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| Chemical and physical data | |
| Formula | C12H19NOS |
| Molar mass | 225.35 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
5-TOM, also known as2-methoxy-4-methyl-5-methylthioamphetamine or as5-thio-DOM, is apsychedelic drug of thephenethylamine andamphetamine families related to theDOx psychedelicDOM.[1][3][4][2] It is theanalogue of DOM in which themethoxy group at the 5 position has been replaced with amethylthio group.[1][3][4][2] The drug is one of two possibleTOM (thio-DOM)positional isomers, the other being2-TOM.[1][3][4][2]
In his bookPiHKAL (Phenethylamines I Have Known and Loved) and other publications,Alexander Shulgin lists 5-TOM's dose as 30 to 50 mgorally and itsduration as 6 to 10 hours (but up to 12–16 hours).[1][3][2] Itsonset is about 30 minutes and its time to peak is a little over 3 hours.[2] Whereas 5-TOM has an effective dose of around 40 mg, DOM has a fully effective dose of about 5 mg, and so there is around an 8-fold loss ofpotency with the drug.[1][3][4][5] In addition, it has a shorter duration than DOM, with DOM having a listed duration of 14 to 20 hours.[1]
The effects of 5-TOM have been reported to includesensory enhancement,closed-eyeimagery andfantasy, substantialopen-eye visuals and somevisual distortions,catatonia-like state, "pretty heavy-duty experience",body load, generalized discomfort ormalaise, neurological discoordination,gastrointestinal disturbance such ascramping andnausea,irritability,anger,sleep disturbance, and next-daylethargy.[1][2] According to Shulgin, there were no completely positive experiences, more negative reports than positive ones, not even many neutral reports, and the consensus being that the drug wasn't worth the struggle.[1] There also appears to be significantinterindividual variability in intensity of 5-TOM.[1][2]
Thechemical synthesis of 5-TOM has been described.[1][2] Thephenethylamineanalogue,2C-5-TOM (5-thio-2C-D), has been synthesized, but was not tested and its properties are unknown.[1][2]Bis-TOM, the 2,5-dimethylthio analogue of DOM, was synthesized and tested, but was inactive at doses of up to 160 mg orally or approximately 50 times the minimum effective dose of DOM.[1][3][5][2]TOMSO is thesulfoxide of 5-TOM, and produced few effects on its own at doses of up to 150 mg orally.[1][3][2]
5-TOM 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).
Shulgin observed that replacement of either the 2-position (10, Figure 2) or the 5- position (11, Figure 2) oxygen in 9 with a sulfur atom reduces its hallucinogenic potency by approximately 15- or 10-fold, respectively.13 Replacing both oxygen atoms with sulfur (12, Figure 2) completely abolished activity.