3-APBT

3-APBT
Clinical data
Other names	SKF-6678; SK&F-6678; 3-(2-Aminopropyl)benzo[β]thiophene; α-Methylbenzo[b]thiophene-3-ethylamine
Drug class	Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT2 receptor agonist; Entactogen; Serotonergic psychedelic
Identifiers
	IUPAC name 1-(1-benzothiophen-3-yl)propan-2-amine;
CAS Number	1201-27-0;
PubChem CID	517826;
ChemSpider	451800;
Chemical and physical data
Formula	C11H13NS
Molar mass	191.29 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CSC2=CC=CC=C21)N;
	InChI InChI=1S/C11H13NS/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8H,6,12H2,1H3; Key:NJJBOBSLFFUELD-UHFFFAOYSA-N;

3-APBT (former developmental code name SKF-6678), also known as 3-(2-aminopropyl)benzo[β]thiophene, is a monoamine releasing agent and serotonin receptor agonist of the benzothiophene group.^[1]^[2] It is an analogue of α-methyltryptamine (AMT) in which the indole ring has been replaced with a benzothiophene ring.^[1]^[2]

Quick Facts Clinical data, Other names ...

The drug acts as a potent and well-balanced serotonin–norepinephrine–dopamine releasing agent (SNDRA).^[2] It is also a full agonist of the serotonin 5-HT₂ receptors, including of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.^[2] 3-APBT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.^[2] It does not stimulate locomotor activity in rodents, suggesting that it does not possess stimulant-type effects.^[2] The drug has been reported be a weak monoamine oxidase inhibitor (MAOI), specifically of monoamine oxidase A (MAO-A) (IC₅₀Tooltip half-maximal inhibitory concentration = 16,200 nM).^[2]^[3]

3-APBT was developed by Smith, Kline & French (SKF) as a potential pharmaceutical drug in the late 1950s.^[1]^[4] The drug and its positional isomer 2-APBT were reported to produce various central nervous system (CNS) effects and to be useful as a "ataractics, psychic energizers, and analgetics".^[1]^[4] 3-APBT has also been reported to have appetite suppressant effects in rodents, but to have considerably lower potency than AMT as an "analeptic" in rodents.^[1]^[5]

See also