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3-APBT
| Column 1 |
|---|
| SKF-6678; SK&F-6678; 3-(2-Aminopropyl)benzo[β]thiophene; α-Methylbenzo[b]thiophene-3-ethylamine; 1-Thia-α-methyltryptamine; 1-Thia-AMT |
| Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT2 receptor agonist; Entactogen; Serotonergic psychedelic |
| IUPAC name |
| 1-(1-benzothiophen-3-yl)propan-2-amine |
| .mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}1201-27-0 |
| 517826 |
| 451800 |
| DTXSID501283721 |
| C11H13NS |
| 191.29 g·mol−1 |
| 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,6,12H2,1H3Key:NJJBOBSLFFUELD-UHFFFAOYSA-N |
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. 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 = 4,000–16,200 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.
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Substituted benzothiophene
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Substituted tryptamine § Related compounds
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S-DMT
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3-APB
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α-Methylisotryptamine (isoAMT)
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1ZP2MA (indolizine analogue of AMT)
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1Z2MAP1O (indolizine analogue of BK-NM-AMT)
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C-DMT
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2-APBT
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5-APBT
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6-APBT
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3-APBT - Isomer Design
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