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3-Thioescaline

From Wikipedia, the free encyclopedia
Pharmaceutical compound
3-Thioescaline
Clinical data
Other names3-TE; 3-Methoxy-4-ethoxy-5-methylthiophenethylamine; 4-Ethoxy-3-methoxy-5-methylthiophenethylamine; 4-Ethoxy-5-methoxy-3-methylthiophenethylamine
Routes of
administration
Oral[1]
Drug classSerotonergic psychedelic;Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action8–12 hours[1]
Identifiers
  • 2-(4-ethoxy-3-methoxy-5-methylsulfanylphenyl)ethanamine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC12H19NO2S
Molar mass241.35 g·mol−1
3D model (JSmol)
  • CCOC1=C(C=C(C=C1SC)CCN)OC
  • InChI=1S/C12H19NO2S/c1-4-15-12-10(14-2)7-9(5-6-13)8-11(12)16-3/h7-8H,4-6,13H2,1-3H3
  • Key:LRYPRFGBZRIFIX-UHFFFAOYSA-N

3-Thioescaline (3-TE), also known as3-methoxy-4-ethoxy-5-methylthiophenethylamine, is apsychedelic drug of thephenethylamine andscaline families related tomescaline.[1][2][3][4] It is theanalogue ofescaline in which themethoxy group at the 3 position has been replaced with amethylthio group.[1][2][3][4] The drug is one of two possiblethioescaline (TE)positional isomers, the other being4-thioescaline (4-TE).[1][2][3][4]

In his bookPiHKAL (Phenethylamines I Have Known and Loved) and other publications,Alexander Shulgin lists 3-thioescaline's dose as 60 to 80 mgorally and itsduration as 8 to 12 hours.[1][2][3] The drug has approximately 5 or 6 times thepotency of mescaline.[2][3][4][1] The effects of 3-thioescaline have been reported to includeclosed-eyeimagery andfantasy, sounds having a deeperpitch,introspection, enhanced appreciation ofart andmusic,time dilation,body load, andsleep disturbances.[1] It was said to be psychedelic rather than just intoxicating.[1] The desired psychoactive effects were said to outweigh its physicalside effects.[1]

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

3-Thioescaline 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. ^abcdefghijklShulgin, 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/pihkal150.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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