4-Thiotrisescaline

4-Thiotrisescaline
Clinical data
Other names4-T-TRIS; 4-Thiotrescaline; 4-Ethylthio-3,5-diethoxyphenethylamine; 3,5-Diethoxy-4-ethylthiophenethylamine
Routes of
administration
Oral[1]
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown[1]
Identifiers
  • 2-(3,5-diethoxy-4-ethylsulfanylphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H23NO2S
Molar mass269.40 g·mol−1
3D model (JSmol)
  • CCOC1=CC(=CC(=C1SCC)OCC)CCN
  • InChI=1S/C14H23NO2S/c1-4-16-12-9-11(7-8-15)10-13(17-5-2)14(12)18-6-3/h9-10H,4-8,15H2,1-3H3
  • Key:VFCYKJRATPCSED-UHFFFAOYSA-N

4-Thiotrisescaline (4-T-TRIS), also known as 4-thiotrescaline or as 4-ethylthio-3,5-diethoxyphenethylamine, is a chemical compound of the phenethylamine and scaline families related to mescaline.[1][2][3][4] It is the analogue of trisescaline (TRIS; trescaline) in which the ethoxy group at the 4 position has been replaced with an ethylthio group.[1][2][3][4] The drug is one of two possible thiotrisescaline (T-TRIS; thiotrescaline) positional isomers, the other being 3-thiotrisescaline (3-T-TRIS; 3-thiotrescaline).[1][2][3][4]

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 4-T-TRIS's dose as greater than 200 mg orally and its duration as unknown.[1][2][3] The effects of 4-T-TRIS have been reported to include possibly some physical effects, slight tingling or numbing of hands and fingers, gas, and no mental effects at a dose of 120 mg orally in one report.[1] However, in another report in which a higher dose of 200 mg orally was used, there were, aside from a brief passing awareness, no physical or mental effects whatsoever.[1] Shulgin concluded that the compound is inactive.[1]

The chemical synthesis of 4-T-TRIS has been described.[1][4]

4-T-TRIS was first described in the scientific literature by 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. ^ a b c d e f g h i j k 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/pihkal179.shtml
  2. ^ a b c d 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. ^ a b c d 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. ^ a b c d e 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.