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3-Thiometaescaline

From Wikipedia, the free encyclopedia
Pharmaceutical compound
3-Thiometaescaline
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 classSerotonergic psychedelic;Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action"Quite early"[1]
Duration of action10–15 hours[1]
Identifiers
  • 2-(3-ethylsulfanyl-4,5-dimethoxyphenyl)ethanamine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC12H19NO2S
Molar mass241.35 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 as3-ethylthio-4,5-dimethoxyphenethylamine, is apsychedelic drug of thephenethylamine andscaline families related tomescaline.[1][2][3][4] It is theanalogue ofmetaescaline in which theethoxy group at the 3 position has been replaced with anethylthio group.[1][2][3][4] The drug is one of three possiblepositional isomers ofthiometaescaline (TME), the others being4-thiometaescaline (4-TME) and5-thiometaescaline (5-TME).[1][2][3][4]

In his bookPiHKAL (Phenethylamines I Have Known and Loved) and other publications,Alexander Shulgin lists 3-TME's dose as 60 to 100 mgorally and itsduration as 10 to 15 hours.[1][2][3] Itsonset is "quite early" and substantial effects occur by 1.5 hours.[1] The drug is approximately 4 to 6 times aspotent as mescaline.[2][3][4] The effects of 3-TME have been reported to includeintrospection andinsights,disinhibition, easyhumor,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] Novisual or otherperceptual effects were mentioned.[1]

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

3-TME was first described in thescientific literature byAlexander Shulgin andPeyton Jacob III in 1984.[4] Subsequently, it was described in greater detail by Shulgin inPiHKAL in 1991.[1]

See also

[edit]

References

[edit]
  1. ^abcdefghijklmShulgin, 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. ^abcdeJacob 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 fromthe original on 13 July 2025.
  3. ^abcdeShulgin 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 fromthe original on 13 July 2025.
  4. ^abcdefJacob 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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