Substituted benzothiophene
The substituted benzothiophenes are a class of chemical compounds based on benzothiophene. They are closely related to the substituted benzofurans, substituted tryptamines, and to other chemical groups such as the substituted benzodioxoles.
Substituted benzothiophenes include S-DMT and the benzothiophenes 2-APBT, 3-APBT, 4-APBT, 5-APBT, 5-MAPBT, 6-APBT, 6-MAPBT, and 7-APBT. These drugs have been found to act as serotonin–norepinephrine–dopamine releasing agents and, in some cases, as potent serotonin 5-HT2 receptor agonists, analogously to the entactogen MDMA. They do not produce hyperlocomotion in rodents, suggesting that they lack psychostimulant effects. 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. Some APBTs, such as 5-APBT and 6-APBT, have additionally been found to be potent monoamine oxidase inhibitors, specifically of monoamine oxidase A.
The preceding findings suggest that substituted benzothiophenes may have entactogenic and/or psychedelic effects in humans whilst lacking stimulant effects and possibly having reduced misuse potential. The substituted benzothiophenes have been little-encountered as designer drugs as of 2022.
Tactogen has patented a number of benzothiophenes as novel entactogens for use as potential medicines.