Chemistry:3-APBT

From HandWiki

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) (IC50 = 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. ↑ 1.0 1.1 1.2 1.3 1.4 "Syntheses and analytical characterizations of novel (2-aminopropyl)benzo[bthiophene (APBT) based stimulants"]. Drug Testing and Analysis 12 (8): 1109–1125. August 2020. doi:10.1002/dta.2813. PMID 32372465. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 "(2-Aminopropyl)benzo[βthiophenes (APBTs) are novel monoamine transporter ligands that lack stimulant effects but display psychedelic-like activity in mice"]. Neuropsychopharmacology 47 (4): 914–923. March 2022. doi:10.1038/s41386-021-01221-0. PMID 34750565. 
  3. ↑ "Heteroarylisopropylamines as MAO inhibitors". Bioorganic & Medicinal Chemistry 13 (14): 4450–4457. July 2005. doi:10.1016/j.bmc.2005.04.045. PMID 15908219. 
  4. ↑ 4.0 4.1 "Improvements in or relating to β-aminoalkylthianaphthene and β-aminoalkylbenzofuran derivatives" GB patent 855115A
  5. ↑ "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. September 1968. doi:10.1021/jm00311a031. PMID 5697069. 

Template:Psychedelics



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:3-APBT&oldid=4180460"