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Substituted benzothiophene

From Wikipedia, the free encyclopedia
Class of chemical compounds
Benzothiophene.

Thesubstituted benzothiophenes are a class ofchemical compounds based onbenzothiophene.[1][2] They are closely related to thesubstituted benzofurans,substituted tryptamines, and to otherchemical groups such as thesubstituted benzodioxoles (ormethylenedioxyphenyl compounds).[1][2]

Substituted benzothiophenes include the (2-aminopropyl)benzo[β]thiophenes (APBTs)2-APBT,3-APBT (SKF-6678),4-APBT,5-APBT,5-MAPBT,6-APBT, and7-APBT.[1][2] These drugs have been found to act asserotonin–norepinephrine–dopamine releasing agents (SNDRAs) and, in some cases, aspotentserotonin5-HT2 receptoragonists, analogously to the entactogenMDMA.[2] They do not producehyperlocomotion in rodents, suggesting that they lackpsychostimulant effects.[2] However, those acting as serotonin 5-HT2 receptor agonists have been found to induce thehead-twitch response, a behavioral proxy ofpsychedelic 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 reducedmisuse potential.[2] The substituted benzothiophenes have been little-encountered asdesigner drugs as of 2022.[1][2]

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

Chemical structures of selected APBTs

See also

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References

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  1. ^abcdBrandt SD, Carlino L, Kavanagh PV, Westphal F, Dreiseitel W, Dowling G, Baumann MH, Sitte HH, Halberstadt AL (August 2020)."Syntheses and analytical characterizations of novel (2-aminopropyl)benzo[b]thiophene (APBT) based stimulants".Drug Test Anal.12 (8):1109–1125.doi:10.1002/dta.2813.PMC 8281332.PMID 32372465.
  2. ^abcdefghRudin D, McCorvy JD, Glatfelter GC, Luethi D, Szöllősi D, Ljubišić T, Kavanagh PV, Dowling G, Holy M, Jaentsch K, Walther D, Brandt SD, Stockner T, Baumann MH, Halberstadt AL, Sitte HH (March 2022)."(2-Aminopropyl)benzo[β]thiophenes (APBTs) are novel monoamine transporter ligands that lack stimulant effects but display psychedelic-like activity in mice".Neuropsychopharmacology.47 (4):914–923.doi:10.1038/s41386-021-01221-0.PMC 8882185.PMID 34750565.
  3. ^"Tactogen patents 5-HT1B receptor agonists and MAO-A inhibitors".BioWorld. 7 February 2022. Retrieved29 January 2025.
  4. ^"Advantageous benzothiophene compositions for mental disorders or enhancement".Google Patents. 6 July 2021. Retrieved29 January 2025.
  5. ^"2-ethylamine substituted benzofuran and benzothiophene compositions for mental disorders or enhancement".Google Patents. 17 November 2023. Retrieved29 January 2025.


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