3-Thiometaescaline

Last updated
3-Thiometaescaline
3-TME.svg
Clinical data
Other names3-TME; 3-Ethylthio-4,5-dimethoxyphenethylamine; 4,5-Dimethoxy-3-ethylthiophenethylamine; 3-EtS-4-MeO-5-MeO-PEA
Routes of
administration 		Oral [1]
Drug class Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action "Quite early" [1]
Duration of action 10–15 hours [1]
Identifiers
  • 2-(3-ethylsulfanyl-4,5-dimethoxyphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H19NO2S
Molar mass 241.35 g·mol−1
3D model (JSmol)
  • CCSC1=CC(=CC(=C1OC)OC)CCN
  • InChI=1S/C12H19NO2S/c1-4-16-11-8-9(5-6-13)7-10(14-2)12(11)15-3/h7-8H,4-6,13H2,1-3H3
  • Key:WHUXWWJFRBXUOQ-UHFFFAOYSA-N

3-Thiometaescaline (3-TME), also known as 3-ethylthio-4,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. [1] [2] [3] [4] It is the analogue of metaescaline in which the ethoxy group at the 3 position has been replaced with an ethylthio group. [1] [2] [3] [4] The drug is one of three possible positional isomers of thiometaescaline (TME), the others being 4-thiometaescaline (4-TME) and 5-thiometaescaline (5-TME). [1] [2] [3] [4]

Contents

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 3-TME's dose as 60 to 100 mg orally and its duration as 10 to 15 hours. [1] [2] [3] Its onset is "quite early" and substantial effects occur by 1.5 hours. [1] The drug is approximately 4 to 6 times as potent as mescaline. [2] [3] [4] The effects of 3-TME have been reported to include introspection and insights, disinhibition, easy humor, sleep disturbances, and increased psychological strength after the experience. [1] One person reported it as producing a "remarkable state" and another remarked that it was a kind of experience that should be had once a year if not more often. [1] No visual or other perceptual effects were mentioned. [1]

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

3-TME was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1984. [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 13 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628. https://www.erowid.org/library/books_online/pihkal/pihkal163.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 Jacob P, Shulgin AT (July 1984). "Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothio analogues". J Med Chem. 27 (7): 881–888. doi:10.1021/jm00373a013. PMID   6737431.
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