5-Thiometaescaline

Last updated
5-Thiometaescaline
5-TME.svg
Clinical data
Other names5-TME; 3-Ethoxy-4-methoxy-5-methylthiophenethylamine; 3-EtO-4-MeO-5-MeS-PEA
Routes of
administration 		Oral [1]
ATC code
  • None
Pharmacokinetic data
Duration of action Unknown [1]
Identifiers
  • 2-(3-ethoxy-4-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(=CC(=C1)CCN)SC)OC
  • InChI=1S/C12H19NO2S/c1-4-15-10-7-9(5-6-13)8-11(16-3)12(10)14-2/h7-8H,4-6,13H2,1-3H3
  • Key:BRABKKMYSDDDCR-UHFFFAOYSA-N

5-Thiometaescaline (5-TME), also known as 3-ethoxy-4-methoxy-5-methylthiophenethylamine, 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 5 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 4-thiometaescaline (4-TME). [1] [2] [3]

Contents

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 5-TME's dose as greater than 200 mg orally and its duration as unknown. [1] [2] The effects of 5-TME have been reported to include possible tinnitus, a possible brush of lightheadedness, and nothing else, but these changes could not be clearly ascribed to the drug. [1]

The chemical synthesis of 5-TME has been described. [1] [3]

5-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 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/pihkal165.shtml
  2. 1 2 3 4 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 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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