3-Thioescaline

Last updated
3-Thioescaline
3-TE.png
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 class Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action 8–12 hours [1]
Identifiers
  • 2-(4-ethoxy-3-methoxy-5-methylsulfanylphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C12H19NO2S
Molar mass 241.35 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]

Contents

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. 1 2 3 4 5 6 7 8 9 10 11 12 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. 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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