4-Thiometaescaline

Last updated
4-Thiometaescaline
4-TME.svg
Clinical data
Other names4-TME; 3-Ethoxy-4-methylthio-5-methoxyphenethylamine; 3-Ethoxy-5-methoxy-4-methylthiophenethylamine
Routes of
administration 		Oral [1]
Drug class Psychoactive drug
ATC code
  • None
Pharmacokinetic data
Duration of action 10–15 hours [1]
Identifiers
  • 2-(3-ethoxy-5-methoxy-4-methylsulfanylphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H19NO2S
Molar mass 241.35 g·mol−1
3D model (JSmol)
  • CCOC1=CC(=CC(=C1SC)OC)CCN
  • InChI=1S/C12H19NO2S/c1-4-15-11-8-9(5-6-13)7-10(14-2)12(11)16-3/h7-8H,4-6,13H2,1-3H3
  • Key:ACLYMWAQSAEILP-UHFFFAOYSA-N

4-Thiometaescaline (4-TME), also known as 3-ethoxy-4-methylthio-5-methoxyphenethylamine, is a psychoactive drug of the phenethylamine and scaline families related to mescaline. [1] [2] [3] It is the analogue of metaescaline in which the methoxy group at the 4 position has been replaced with a methylthio group. [1] [2] [3] The drug is one of three possible positional isomers of thiometaescaline (TME), the others being 3-thiometaescaline (3-TME) and 5-thiometaescaline (5-TME). [1] [2] [3]

Contents

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 4-TME's dose as 60 to 100 mg orally and its duration as 10 to 15 hours. [1] [2] The drug has approximately 4 times the potency of mescaline, though its effects are very different. [2] [1] [3] The effects of 4-TME have been reported to include mild mental changes that were neither visual nor particularly interesting, a strange off-baseness, feeling sad and morbid, mild gastrointestinal disturbances, sleep disturbances, and subsequent-day negative effects like lethargy and emotional disconnection. [1] It was described as being more toxic than joyous. [1] No clear hallucinogenic or perceptual effects were described. [1]

The chemical synthesis of 4-TME has been described. [1] [3] It is said to have a very small yield. [1]

4-TME was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1984. [3] 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 13 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/pihkal164.shtml
  2. 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.
  3. 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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