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

5-(2-Aminopropyl)-1-benzothiophene (5-APBT) is a monoamine releasing agent and serotonin receptor agonist of the amphetamine and benzothiophene families.¹² It is related to MDA and other MDA bioisosteres like the benzofurans.¹²

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 2020.¹²