TME (psychedelics)

TME, or thiometaescaline, is a series of lesser-known psychedelic drugs similar in structure to mescaline. Their structures are based on that of metaescaline. They were first synthesized by Alexander Shulgin and recorded in his book PiHKAL (Phenethylamines i Have Known And Loved). Very little is known about their dangers or toxicity.

TME
Chemical name Thiometaescaline or
Dimethoxy-ethoxy-1-aminoethane
Chemical formula C12H19NO2S

TME compounds
3-TME
Names
IUPAC name
2-[3-(Ethylsulfanyl)-4,5-dimethoxyphenyl]ethanamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • Key: WHUXWWJFRBXUOQ-UHFFFAOYSA-N
  • InChI=1S/C12H19NO2S/c1-4-16-11-8-9(5-6-13)7-10(14-2)12(11)15-3/h7-8H,4-6,13H2,1-3H3
  • CCSC1=CC(=CC(=C1OC)OC)CCN
Properties
C12H19NO2S
Molar mass 241.35 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Dosage: 60–100 mg
Duration: 10–15 hours
Effects: Strong entheogenic action, reduction of inhibition
4-TME
Names
IUPAC name
2-[3-Ethoxy-5-methoxy-4-(methylsulfanyl)phenyl]ethanamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • Key: ACLYMWAQSAEILP-UHFFFAOYSA-N
  • 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
  • CCOc1cc(cc(c1SC)OC)CCN
Properties
C12H19NO2S
Molar mass 241.35 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Dosage: 60–100 mg
Duration: 10–15 hours
Effects: Few to none
5-TME
Names
IUPAC name
2-[3-Ethoxy-4-methoxy-5-(methylsulfanyl)phenyl]ethanamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • Key: BRABKKMYSDDDCR-UHFFFAOYSA-N
  • 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
  • CCOc1cc(cc(c1OC)SC)CCN
Properties
C12H19NO2S
Molar mass 241.35 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Dosage: greater than 200 mg
Duration: unknown
Effects: Few to none

See also
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