3-Thioescaline

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
PubChem CID
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 as 3-methoxy-4-ethoxy-5-methylthiophenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline.[1][2][3][4] It is the analogue of escaline 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 thioescaline (TE) positional isomers, the other being 4-thioescaline (4-TE).[1][2][3][4]

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 3-thioescaline's dose as 60 to 80 mg orally and its duration as 8 to 12 hours.[1][2][3] The drug has approximately 5 or 6 times the potency of mescaline.[2][3][4][1] The effects of 3-thioescaline have been reported to include closed-eye imagery and fantasy, sounds having a deeper pitch, introspection, enhanced appreciation of art and music, time dilation, body load, and sleep disturbances.[1] It was said to be psychedelic rather than just intoxicating.[1] The desired psychoactive effects were said to outweigh its physical side effects.[1]

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

3-Thioescaline 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. ^ a b c d e f g h i j k l 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/pihkal150.shtml
  2. ^ a b c d e 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 e 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 f 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.