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
IUPAC name
  • 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)
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]

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-HT2A, 5-HT2B, and 5-HT2C 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

References

  1. 1 2 3 4 5 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. PMID 32372465.
  2. 1 2 3 4 5 6 7 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.
  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.
  4. 1 2 GB 855115A, "Improvements in or relating to β-aminoalkylthianaphthene and β-aminoalkylbenzofuran derivatives", assigned to Smith Kline and French Laboratories Ltd.
  5. ↑ 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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