3-APBT

3-APBT
Clinical data
Other namesSKF-6678; SK&F-6678; 3-(2-Aminopropyl)benzo[β]thiophene; α-Methylbenzo[b]thiophene-3-ethylamine
Drug classSerotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT2 receptor agonist; Entactogen; Serotonergic psychedelic
Identifiers
  • 1-(1-benzothiophen-3-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC11H13NS
Molar mass191.29 g·mol−1
3D model (JSmol)
  • CC(CC1=CSC2=CC=CC=C21)N
  • 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. It is an analogue of α-methyltryptamine (AMT) in which the indole ring has been replaced with a benzothiophene ring.

The drug acts as a potent and well-balanced serotonin–norepinephrine–dopamine releasing agent (SNDRA). It is also a full agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. 3-APBT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. It does not stimulate locomotor activity in rodents, suggesting that it does not possess stimulant-type effects. 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).

3-APBT was developed by Smith, Kline & French (SKF) as a potential pharmaceutical drug in the late 1950s. 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". 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.