Substituted benzothiophene

The substituted benzothiophenes are a class of chemical compounds based on benzothiophene.^[1][2] They are closely related to the substituted benzofurans, substituted tryptamines, and to other chemical groups such as the substituted benzodioxoles (or methylenedioxyphenyl compounds).^[1][2]

Benzothiophene.

Substituted benzothiophenes include the (2-aminopropyl)benzo[β]thiophenes (APBTs) 2-APBT, 3-APBT (SKF-6678), 4-APBT, 5-APBT, 5-MAPBT, 6-APBT, 6-MAPBT, and 7-APBT.^[1][2] These drugs have been found to act as serotonin–norepinephrine–dopamine releasing agents (SNDRAs) and, in some cases, as potent serotonin 5-HT₂ receptor agonists, analogously to the entactogen MDMA.^[2] They do not produce hyperlocomotion in rodents, suggesting that they lack psychostimulant effects.^[2] However, those acting as serotonin 5-HT₂ receptor agonists have been found to induce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.^[2]

These findings suggest that substituted benzothiophenes may have entactogenic and/or psychedelic effects in humans whilst lacking stimulant effects and possibly having reduced misuse potential.^[2] The substituted benzothiophenes have been little-encountered as designer drugs as of 2022.^[1][2]

Tactogen has patented a number of benzothiophenes as novel entactogens for use as potential medicines.^[3][4][5]

Chemical structures of selected APBTs

• 
  2-APBT
• 
  3-APBT
• 
  4-APBT
• 
  5-APBT
• 
  6-APBT
• 
  7-APBT

See also

• Substituted methylenedioxyphenethylamine § Related compounds