5-APBT

5-APBT
Clinical data
Other names	5-(2-Aminopropyl)-1-benzothiophene; 5-APBT; 5-APBTP
Drug class	Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT2 receptor agonist; Entactogen; Serotonergic psychedelic
Identifiers
	IUPAC name 1-(1-benzothiophen-5-yl)propan-2-amine;
CAS Number	1368128-53-3;
PubChem CID	82374371;
ChemSpider	26792704;
Chemical and physical data
Formula	C11H13NS
Molar mass	191.29 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC2=C(C=C1)SC=C2)N;
	InChI InChI=1S/C11H13NS/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11/h2-5,7-8H,6,12H2,1H3; Key:JBRWOJGXNBGRCE-UHFFFAOYSA-N;

Pharmaceutical compound

5-(2-Aminopropyl)-1-benzothiophene (5-APBT) is a monoamine releasing agent and serotonin receptor agonist of the amphetamine and benzothiophene families.^[1]^[2] It is related to MDA and other MDA bioisosteres like the benzofurans.^[1]^[2]

The drug acts as a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA) and full agonist of the serotonin 5-HT₂ receptors.^[2] It has approximately 4- and 9-fold preference for induction of serotonin release over norepinephrine and dopamine release, respectively, in rat brain synaptosomes.^[2] 5-APBT does not increase locomotor activity in rodents and hence does not appear to have stimulant-like effects.^[2] However, it does produce the head-twitch response, a behavioral proxy of psychedelic effects, and hence may have hallucinogenic effects.^[2] The drug is a potent monoamine oxidase inhibitor (MAOI), specifically of monoamine oxidase A (MAO-A) (IC₅₀Tooltip half-maximal inhibitory concentration = 400 nM).^[3]

5-APBT was first described in the scientific literature by 2020.^[1]^[2]

References

1 2 3 Brandt SD, Carlino L, Kavanagh PV, Westphal F, Dreiseitel W, Dowling G, et al. (August 2020). "Syntheses and analytical characterizations of novel (2-aminopropyl)benzo[b]thiophene (APBT) based stimulants". Drug Testing and Analysis. 12 (8): 1109–1125. doi:10.1002/dta.2813. PMC 8281332. PMID 32372465.
1 2 3 4 5 6 7 Rudin D, McCorvy JD, Glatfelter GC, Luethi D, Szöllősi D, Ljubišić T, et al. (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.
↑ Wagmann L, Brandt SD, Kavanagh PV, Meyer MR (January 2026). "In vivo and in vitro toxicokinetics including metabolism, isozyme mapping, and monoamine oxidase inhibition of three (2-aminopropyl)benzo[b]thiophene (APBT) psychedelics". Toxicology. 521 154402. doi:10.1016/j.tox.2026.154402. PMID 41519460.