3-APBT

3-APBT, also known by its former developmental code name SKF-6678 and as 3-(2-aminopropyl)benzo[β]thiophene, as well as 1-thia-α-methyltryptamine (1-thia-AMT), 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]

Other namesSKF-6678; SK&F-6678; 3-(2-Aminopropyl)benzo[β]thiophene; α-Methylbenzo[b]thiophene-3-ethylamine; 1-Thia-α-methyltryptamine; 1-Thia-AMT

Drug classSerotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT₂ receptor agonist; Entactogen; Serotonergic psychedelic

CAS Number

• 1201-27-0

PubChem CID

• 517826

Quick facts Clinical data, Other names ...

3-APBT

Clinical data
Other names	SKF-6678; SK&F-6678; 3-(2-Aminopropyl)benzo[β]thiophene; α-Methylbenzo[b]thiophene-3-ethylamine; 1-Thia-α-methyltryptamine; 1-Thia-AMT
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
CompTox Dashboard (EPA)	DTXSID501283721
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

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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 = 4,000–16,200 nM).^[2][3][4]

3-APBT was developed by Smith, Kline & French (SKF) as a potential pharmaceutical drug in the late 1950s.^[1][5] 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][5] 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][6]