Chemistry:Substituted benzothiophene

From HandWiki
Short description: Class of chemical compounds
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]

Substituted benzothiophenes include S-DMT (1-thia-DMT)[3] and the (2-aminopropyl)benzo[β]thiophenes (APBTs) 2-APBT, 3-APBT (1-thia-AMT; 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] Some APBTs, such as 5-APBT and 6-APBT, have additionally been found to be potent monoamine oxidase inhibitors (MAOIs), specifically of monoamine oxidase A (MAO-A).[4]

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.[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.[5][6][7]

Chemical structures of selected benzothiophenes

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 "Syntheses and analytical characterizations of novel (2-aminopropyl)benzo[bthiophene (APBT) based stimulants"]. Drug Test Anal 12 (8): 1109–1125. August 2020. doi:10.1002/dta.2813. PMID 32372465. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 "(2-Aminopropyl)benzo[βthiophenes (APBTs) are novel monoamine transporter ligands that lack stimulant effects but display psychedelic-like activity in mice"]. Neuropsychopharmacology 47 (4): 914–923. March 2022. doi:10.1038/s41386-021-01221-0. PMID 34750565. 
  3. ↑ Nichols, David E. (2012). "Structure–activity relationships of serotonin 5‐HT2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling 1 (5): 559–579. doi:10.1002/wmts.42. ISSN 2190-460X. https://onlinelibrary.wiley.com/doi/10.1002/wmts.42. Retrieved 9 January 2026. "Early work with benzo[b]thiophenes 6 and 3-indenalkylamines 7 (Figure 5) demonstrated that for compounds lacking ring substituents, the ability to act as agonists in the rat fundus was about the same as for the tryptamines themselves.8 That is, the indole NH was not essential to activate the 5-HT2 receptor in the rat fundus. No modern studies have been carried out to assess affinity at 5-HT2A receptors.". 
  4. ↑ "In vivo and in vitro toxicokinetics including metabolism, isozyme mapping, and monoamine oxidase inhibition of three (2-aminopropyl)benzo[b]thiophene (APBT) psychedelics". Toxicology. January 2026. doi:10.1016/j.tox.2026.154402. PMID 41519460. 
  5. ↑ "Tactogen patents 5-HT1B receptor agonists and MAO-A inhibitors". 7 February 2022. https://www.bioworld.com/articles/687206-tactogen-patents-5-ht1b-receptor-agonists-and-mao-a-inhibitors. 
  6. ↑ "Advantageous benzothiophene compositions for mental disorders or enhancement". 6 July 2021. https://patents.google.com/patent/EP4175638A1/. 
  7. ↑ "2-ethylamine substituted benzofuran and benzothiophene compositions for mental disorders or enhancement". 17 November 2023. https://patents.google.com/patent/WO2024108179A2/. 



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Substituted_benzothiophene&oldid=4309046"