6-APBT

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| class = Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT2 receptor agonist; Entactogen; Serotonergic psychedelic

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| synonyms = 6-(2-Aminopropyl)-1-benzothiophene; 6-APBT; 6-APBTP

| IUPAC_name = 1-(1-benzothiophen-6-yl)propan-2-amine

| C=11 | H=13 | N=1 | S=1

| SMILES = CC(N([H])[H])CC1=CC2SC=CC=2C=C1

| StdInChI = InChI=1S/C11H13NS/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-5,7-8H,6,12H2,1H3

| StdInChIKey = QBWPJANWKXULQZ-UHFFFAOYSA-N

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6-(2-Aminopropyl)-1-benzothiophene (6-APBT) is a monoamine releasing agent and serotonin receptor agonist of the amphetamine and benzothiophene families.{{cite journal | vauthors = Brandt SD, Carlino L, Kavanagh PV, Westphal F, Dreiseitel W, Dowling G, Baumann MH, Sitte HH, Halberstadt AL | title = Syntheses and analytical characterizations of novel (2-aminopropyl)benzo[b]thiophene (APBT) based stimulants | journal = Drug Testing and Analysis | volume = 12 | issue = 8 | pages = 1109–1125 | date = August 2020 | pmid = 32372465 | doi = 10.1002/dta.2813 | pmc = 8281332 }}{{cite journal | vauthors = Rudin 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 | title = (2-Aminopropyl)benzo[β]thiophenes (APBTs) are novel monoamine transporter ligands that lack stimulant effects but display psychedelic-like activity in mice | journal = Neuropsychopharmacology | volume = 47 | issue = 4 | pages = 914–923 | date = March 2022 | pmid = 34750565 | pmc = 8882185 | doi = 10.1038/s41386-021-01221-0 }} It is related to MDA and other MDA bioisosteres like the benzofurans.

The drug acts as a potent and well-balanced serotonin–norepinephrine–dopamine releasing agent (SNDRA) and full agonist of the serotonin 5-HT2 receptors. 6-APBT does not increase locomotor activity in rodents and hence does not appear to have stimulant-like effects. However, it does produce the head-twitch response, a behavioral proxy of psychedelic effects, and hence may have hallucinogenic effects.

6-APBT was first described in the scientific literature by 2020.

See also

References

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