4-Thiomescaline

Last updated
4-Thiomescaline
4-TM.png
Clinical data
Other names4-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
ATC code
  • None
Pharmacokinetic data
Onset of action 30–60 minutes [1] [2]
Duration of action 10–15 hours [1]
Identifiers
  • 2-(3,5-dimethoxy-4-methylsulfanylphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H17NO2S
Molar mass 227.32 g·mol−1
3D model (JSmol)
  • COC1=CC(=CC(=C1SC)OC)CCN
  • InChI=1S/C11H17NO2S/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3
  • Key:FYTOAZIRBXNPKZ-UHFFFAOYSA-N

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]

Contents

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

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Shulgin, Alexander; Shulgin, Ann (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
  2. 1 2 3 4 5 6 7 8 Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT (1978). "Mescaline analogs: substitutions at the 4-position" (PDF). NIDA Res Monogr (22): 27–37. PMID   101882.
  3. 1 2 3 4 5 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.
  4. 1 2 3 4 5 6 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.
  5. 1 2 3 4 5 6 7 8 Jacob, Peyton; Shulgin, Alexander T. (1981). "Sulfur analogues of psychotomimetic agents. Monothio analogs of mescaline and isomescaline". Journal of Medicinal Chemistry. 24 (11): 1348–1353. doi:10.1021/jm00143a017. ISSN   0022-2623. PMID   7310812 . Retrieved 20 January 2026.
  6. ↑ Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Test Anal. 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]
  7. ↑ 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". Front Pharmacol. 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).
  8. ↑ 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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.