3-Thiomescaline

Last updated
3-Thiomescaline
3-TM.png
Clinical data
Other names3-TM; 3-Methylthio-4,5-dimethoxyphenethylamine; 3,4-Dimethoxy-5-methylthiophenethylamine; 3-MeS-4-MeO-5-MeO-PEA
Routes of
administration 		Oral [1]
Drug class Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action ≤1 hour [1]
Duration of action 8–12 hours [1]
Identifiers
  • 2-(3,4-dimethoxy-5-methylsulfanylphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C11H17NO2S
Molar mass 227.32 g·mol−1
3D model (JSmol)
  • COC1=C(C(=CC(=C1)CCN)SC)OC
  • InChI=1S/C11H17NO2S/c1-13-9-6-8(4-5-12)7-10(15-3)11(9)14-2/h6-7H,4-5,12H2,1-3H3
  • Key:MASUNTXHOBXSNG-UHFFFAOYSA-N

3-Thiomescaline (3-TM), also known as 3-methylthio-4,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline (3,4,5-trimethoxyphenethylamine). [1] [2] [3] [4] It is the analogue of mescaline in which the methoxy group at the 3 position has been replaced with a methylthio group. [1] [2] [3] [4] The drug is one of two possible thiomescaline (TM) positional isomers, the other being 4-thiomescaline (4-TM). [1] [2] [3] [4]

Contents

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 3-TM's dose as 60 to 100 mg orally and its duration as 8 to 12 hours. [1] [2] [3] [4] Its onset is within 1 hour. [1] The drug has about 4 to 6 times the potency of mescaline. [1] [2] [3] [4] The effects of 3-TM have been reported to include color enhancement, closed-eye imagery and fantasy, no open-eye visuals, auditory–visual synaesthesia with music, intoxication, relaxation, feelings of sublimity and peacefulness, conflicting energy, tension, paranoia, irritability, and guardedness. [1] [4]

The chemical synthesis of 3-TM has been described. [1] [4]

3-TM was first described in the literature by Shulgin and colleagues by 1981. [4] 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 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/pihkal155.shtml
  2. 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.
  3. 1 2 3 4 5 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.
  4. 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 . Retrieved 20 January 2026.
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