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; 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;

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.¹² It is an analogue of α-methyltryptamine (AMT) in which the indole ring has been replaced with a benzothiophene ring.¹²

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).²³⁴

3-APBT was developed by Smith, Kline & French (SKF) as a potential pharmaceutical drug in the late 1950s.¹⁵ 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".¹⁵ 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.¹⁶

References

Brandt SD, Carlino L, Kavanagh PV, Westphal F, Dreiseitel W, Dowling G, et al. (August 2020). "Syntheses and analytical characterizations of novel (2-aminopropyl)benzo[b]thiophene (APBT) based stimulants". Drug Testing and Analysis. 12 (8): 1109–1125. doi:10.1002/dta.2813. PMC 8281332. PMID 32372465.
Rudin D, McCorvy JD, Glatfelter GC, Luethi D, Szöllősi D, Ljubišić T, et al. (March 2022). "(2-Aminopropyl)benzo[β]thiophenes (APBTs) are novel monoamine transporter ligands that lack stimulant effects but display psychedelic-like activity in mice". Neuropsychopharmacology. 47 (4): 914–923. doi:10.1038/s41386-021-01221-0. PMC 8882185. PMID 34750565.
Vallejos G, Fierro A, Rezende MC, Sepúlveda-Boza S, Reyes-Parada M (July 2005). "Heteroarylisopropylamines as MAO inhibitors". Bioorganic & Medicinal Chemistry. 13 (14): 4450–4457. doi:10.1016/j.bmc.2005.04.045. PMID 15908219.
Wagmann L, Brandt SD, Kavanagh PV, Meyer MR (January 2026). "In vivo and in vitro toxicokinetics including metabolism, isozyme mapping, and monoamine oxidase inhibition of three (2-aminopropyl)benzo[b]thiophene (APBT) psychedelics". Toxicology. 521 154402. doi:10.1016/j.tox.2026.154402. PMID 41519460.
GB 855115A, "Improvements in or relating to β-aminoalkylthianaphthene and β-aminoalkylbenzofuran derivatives", assigned to Smith Kline and French Laboratories Ltd.
Campaigne E, Neiss ES, Pfeiffer CC, Beck RA (September 1968). "Benzo[b]thiophen derivatives. XII. Synthesis of some 3-benzo[b]thienylalkylamines and comparison of their central nervous system activity with tryptamine isosteres". Journal of Medicinal Chemistry. 11 (5): 1049–1054. doi:10.1021/jm00311a031. PMID 5697069.

External links

3-APBT - Isomer Design

[BrandtCarlinoKavanagh2020-1] Brandt SD, Carlino L, Kavanagh PV, Westphal F, Dreiseitel W, Dowling G, et al. (August 2020). "Syntheses and analytical characterizations of novel (2-aminopropyl)benzo[b]thiophene (APBT) based stimulants". Drug Testing and Analysis. 12 (8): 1109–1125. doi:10.1002/dta.2813. PMC 8281332. PMID 32372465.

[RudinMcCorvyGlatfelter2022-2] Rudin D, McCorvy JD, Glatfelter GC, Luethi D, Szöllősi D, Ljubišić T, et al. (March 2022). "(2-Aminopropyl)benzo[β]thiophenes (APBTs) are novel monoamine transporter ligands that lack stimulant effects but display psychedelic-like activity in mice". Neuropsychopharmacology. 47 (4): 914–923. doi:10.1038/s41386-021-01221-0. PMC 8882185. PMID 34750565.

[VallejosFierroRezende2005-3] Vallejos G, Fierro A, Rezende MC, Sepúlveda-Boza S, Reyes-Parada M (July 2005). "Heteroarylisopropylamines as MAO inhibitors". Bioorganic & Medicinal Chemistry. 13 (14): 4450–4457. doi:10.1016/j.bmc.2005.04.045. PMID 15908219.

[WagmannBrandtKavanagh2026-4] Wagmann L, Brandt SD, Kavanagh PV, Meyer MR (January 2026). "In vivo and in vitro toxicokinetics including metabolism, isozyme mapping, and monoamine oxidase inhibition of three (2-aminopropyl)benzo[b]thiophene (APBT) psychedelics". Toxicology. 521 154402. doi:10.1016/j.tox.2026.154402. PMID 41519460.

[GB855115A-5] GB 855115A, "Improvements in or relating to β-aminoalkylthianaphthene and β-aminoalkylbenzofuran derivatives", assigned to Smith Kline and French Laboratories Ltd.

[CampaigneNeissPfeiffer1968-6] Campaigne E, Neiss ES, Pfeiffer CC, Beck RA (September 1968). "Benzo[b]thiophen derivatives. XII. Synthesis of some 3-benzo[b]thienylalkylamines and comparison of their central nervous system activity with tryptamine isosteres". Journal of Medicinal Chemistry. 11 (5): 1049–1054. doi:10.1021/jm00311a031. PMID 5697069.

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References

External links