4-Thioescaline

4-Thioescaline
Clinical data
Other names4-TE; Thioescaline; 3,5-Dimethoxy-4-ethylthiophenethylamine; 4-Ethylthio-3,5-dimethoxyphenethylamine
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action40 minutes[1]
Peak: 2 hours[1]
Duration of action9–12 hours (but up to 15 hours)[1][2]
Identifiers
  • 2-(4-ethylsulfanyl-3,5-dimethoxyphenyl)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)
  • CCSC1=C(C=C(C=C1OC)CCN)OC
  • InChI=1S/C12H19NO2S/c1-4-16-12-10(14-2)7-9(5-6-13)8-11(12)15-3/h7-8H,4-6,13H2,1-3H3
  • Key:JUZZKKJLOWQNPC-UHFFFAOYSA-N

4-Thioescaline (4-TE), or thioescaline, also known as 3,5-dimethoxy-4-ethylthiophenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline.[1][3][4][2] It is the analogue of escaline in which the methoxy group at the 4 position has been replaced with a methylthio group.[1][3][4][2] The drug is one of two possible thioescaline (TE) positional isomers, the other being 3-thioescaline (3-TE).[1][3][4][2]

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 4-thioescaline's dose as 20 to 30 mg orally and its duration as 9 to 12 hours (but up to 15 hours).[1][3][4][2] Its onset is 40 minutes and time to peak is 2 hours.[1] The drug has approximately 10 to 20 times the potency of mescaline and is among the most potent thioscalines.[3][4][2][1][5]

The effects of 4-thioescaline have been reported to include closed-eye imagery and fantasy, open-eye visuals, sensuousness, feelings of energy, clean experience, clear-headedness and clarity of thought, introspection and insights, easy talking and communication, cloudiness, feeling disconnected, feelings of complex depth without definition, feeling depleted, body awareness, body tingling, heavy body load, feeling jangly, body heaviness, pupil dilation, flushing, nausea, and lasting afterglow.[1][2] One person remarked that it was marvelous, very beautiful, joyous, and sensuous, while another said that there was not enough mental to balance the physical.[1] According to Shulgin, 4-thioescaline produces a state of perceptual distortion, tactile responsiveness, and mood enhancement like euphoria and easy humor that closely resembles that of mescaline.[2]

The chemical synthesis of 4-thioescaline has been described.[1][2]

4-Thioescaline was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1984.[2] 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 m n 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/pihkal151.shtml
  2. ^ a b c d e f g h i j 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ Blaazer AR, Smid P, Kruse CG (September 2008). "Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT(2A) receptors". ChemMedChem. 3 (9): 1299–1309. doi:10.1002/cmdc.200800133. PMID 18666267. In the case of 3,4,5-substituted phenethylamine, escaline (5) is 5–8 times more potent in humans than mescaline (4).[140] [...] Replacing the alkoxy substituents at the 4-position with alkylthio substituents leads to a further increase in potency. The potency of 4-thiomescaline (6) is an order of magnitude greater than the parent compound 4, and 4-thioescaline (7) is three times more potent than 5. [142, 143].
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