4-Thiomescaline
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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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| 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 |
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4-Thiomescaline (4-TM), or simply thiomescaline, also known as 3,5-dimethoxy-4-methylthiophenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline (3,4,5-trimethoxyphenethylamine).[1][3][4][2][5] It is the analogue of mescaline in which the methoxy group at the 4 position has been replaced with a methylthio group.[1][3][4][5] The drug is one of two possible thiomescaline (TM) positional isomers, the other being 3-thiomescaline (3-TM).[1][3][4][5]
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 4-TM's dose as 20 to 40 mg orally and its duration as 10 to 15 hours.[1][3][4][2][5] Its onset is 30 to 60 minutes.[1][2] The drug has about 10 times the potency of mescaline.[1][3][4][5][6][7][8] The effects of 4-TM have been reported to include little color enhancement, closed-eye imagery, fantasy, feeling strange, feelings of unreality, seeing reality like a Möbius strip, introspection, insights, lightheadedness, physical uneasiness, tremor, abdominal cramps, walking difficulty, appetite loss, and some tactile numbness.[1][2][5] Shulgin described it as a "mixed bag of responses".[1] It was described as being more similar in its effects to LSD than to mescaline and as being similar in effects to the Aleph series.[1][2]
The chemical synthesis of 4-TM has been described.[1][5][2]
4-TM was first synthesized 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 in PiHKAL in 1991.[1]
See also
References
- ^ a b c d e f g h i j k l m n Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. https://erowid.org/library/books_online/pihkal/pihkal156.shtml
- ^ a b c d e f g h Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT (1978). "Mescaline analogs: substitutions at the 4-position". NIDA Research Monograph (22): 27–37. PMID 101882.
- ^ a b c d e Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived from the original on 13 July 2025.
- ^ a b c d e f Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025.
- ^ a b c d e f g h Jacob P, Shulgin AT (November 1981). "Sulfur analogues of psychotomimetic agents. Monothio analogues of mescaline and isomescaline". Journal of Medicinal Chemistry. 24 (11): 1348–1353. doi:10.1021/jm00143a017. PMID 7310812.
- ^ Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.
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]
- ^ Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2021). "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines". Frontiers in Pharmacology. 12 794254. doi:10.3389/fphar.2021.794254. PMC 8865417. PMID 35222010.
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).
- ^ Shulgin AT (1982). "Chemistry of Psychotomimetics". In Hoffmeister F, Stille G (eds.). Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. Vol. 55. Berlin: Springer Berlin Heidelberg. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916.