5-Thioasymbescaline

Pharmaceutical compound From Wikipedia, the free encyclopedia

5-Thioasymbescaline (5-TASB), also known as 3,4-diethoxy-5-methylthiophenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline.[1][2][3][4] It is the analogue of asymbescaline in which the methoxy group at the 5 position has been replaced with a methylthio group.[1][2][3][4] The drug is one of three possible thioasymbescaline (TASB) positional isomers, the others being 3-thioasymbescaline (3-TASB) and 4-thioasymbescaline (4-TASB).[1][2][3][4]

Other names5-TASB; 3,4-Diethoxy-5-methylthiophenethylamine; 3-Ethoxy-4-ethoxy-5-methylthiophenethylamine; 3-EtO-4-EtO-5-MeS-PEA
ATC code
  • None
Quick facts Clinical data, Other names ...
5-Thioasymbescaline
Clinical data
Other names5-TASB; 3,4-Diethoxy-5-methylthiophenethylamine; 3-Ethoxy-4-ethoxy-5-methylthiophenethylamine; 3-EtO-4-EtO-5-MeS-PEA
Routes of
administration
Oral[1][2][3]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action~8 hours[1]
Identifiers
  • 2-(3,4-diethoxy-5-methylsulfanylphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H21NO2S
Molar mass255.38 g·mol−1
3D model (JSmol)
  • CCOC1=C(C(=CC(=C1)CCN)SC)OCC
  • InChI=1S/C13H21NO2S/c1-4-15-11-8-10(6-7-14)9-12(17-3)13(11)16-5-2/h8-9H,4-7,14H2,1-3H3
  • Key:WEGXTQPSIDDJRM-UHFFFAOYSA-N
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In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 5-TASB's dose as approximately 160 mg orally and its duration as about 8 hours.[1] The drug has been variously described as having lower potency than mescaline to having twice the potency of mescaline.[4][2][3][1]

The effects of 5-TASB have been reported to include hints of strangeness, neurological hyperactivity, slight physical effects, extremities feeling warm, slight lightheadedness, slight hyperreflexia, slight diarrhea, and extended physical malaise.[1][3][4] It was said that there was more physical than mental and that it was not all entirely nice.[1] In addition, it was said that the effects are real, but the person didn't want to go any higher.[1] It was concluded that the drug's somatic effects overshadowed the psychological effects.[1] Besides hints of strangeness, no hallucinogenic or other perceptual effects were described.[1]

The chemical synthesis of 5-TASB has been described.[1][4]

5-TASB was first described in the scientific literature by 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

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