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| Other names | 4-TM; Thiomescaline; 3,5-Dimethoxy-4-methylthiophenethylamine; 4-Methylthio-3,5-dimethoxyphenethylamine; 3-MeO-4-MeS-5-MeO-PEA |
| Routes of administration | Oral[1] |
| Drug class | Serotonergic psychedelic;Hallucinogen |
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| Pharmacokinetic data | |
| Onset of action | 30–60 minutes[1][2] |
| Duration of action | 10–15 hours[1] |
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| Chemical and physical data | |
| Formula | C11H17NO2S |
| Molar mass | 227.32 g·mol−1 |
| 3D model (JSmol) | |
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4-Thiomescaline (4-TM), or simplythiomescaline, also known as3,5-dimethoxy-4-methylthiophenethylamine, is apsychedelic drug of thephenethylamine andscaline families related tomescaline (3,4,5-trimethoxyphenethylamine).[1][3][4][2][5] It is theanalogue of mescaline in which themethoxy group at the 4 position has been replaced with amethylthio group.[1][3][4][5] The drug is one of two possiblethiomescaline (TM)positional isomers, the other being3-thiomescaline (3-TM).[1][3][4][5]
In his bookPiHKAL (Phenethylamines I Have Known and Loved) and other publications,Alexander Shulgin lists 4-TM's dose as 20 to 40 mgorally and itsduration as 10 to 15 hours.[1][3][4][2][5] Itsonset is 30 to 60 minutes.[1][2] The drug has about 10 times thepotency of mescaline.[1][3][4][5][6][7][8] The effects of 4-TM have been reported to include little color enhancement,closed-eyeimagery,fantasy, feeling strange,feelings of unreality, seeing reality like aMöbius strip,introspection,insights,lightheadedness, physical uneasiness,tremor,abdominal cramps,walking difficulty,appetite loss, and sometactilenumbness.[1][2][5] Shulgin described it as a "mixed bag of responses".[1] It was described as being more similar in its effects toLSD than to mescaline and as being similar in effects to theAleph series.[1][2]
Thechemical synthesis of 4-TM has been described.[1][5][2]
4-TM was firstsynthesized and tested in 1977 and was described in the literature by Shulgin and colleagues in 1978.[4][2][5] Subsequently, it was described in greater detail by Shulgin inPiHKAL in 1991.[1]
With the simple transformation of the 4-MeO in mescaline (22) to a 4-EtO group, i.e. escaline (70), a five times more potent analogue is obtained (Figure 5).[3] An even more dramatic increase of human potency has been observed with a 4-O to 4-S substitution. 4-Thiomescaline (4-TM, 71) is one order of magnitude more potent than mescaline.[3] It seems that the 5-HT2A receptor affinities do not increase sufficiently by these structural modifications to explain the increased human potency; the enhanced lipophilicity and receptor activation could also play an important role.[85]
A simple substitution of the 4-MeO group on mescaline (5; Figure 2) to a 4-S group, leads to 4-thiomescaline (4-TM; 10), an analogue that has been shown to increase human potency 10-fold compared to 5 (active dose of 10 in humans = 20–40 mg) (Shulgin and Shulgin 1991).
