Chemistry:1-Naphthylaminopropane

From HandWiki

1-Naphthylaminopropane (1-NAP), also known as 1-naphthylisopropylamine or as α-naphthylaminopropane (α-NAP), is a drug of the amphetamine and naphthylaminopropane families.[1][2][3] It is a positional isomer of 2-naphthylaminopropane (2-NAP; PAL-287).[1][2][3]

2-NAP and derivatives like methylnaphthylaminopropane (MNAP) are known to be potent serotonin–norepinephrine–dopamine releasing agents (SNDRAs) and/or serotonin receptor agonists, whereas 1-NAP has not been assessed in these regards.[4][5][6][7] Both 1-NAP and 2-NAP failed to substitute for dextroamphetamine in rodent drug discrimination tests, suggesting that they lack stimulant effects.[2]

2-NAP is a potent monoamine oxidase inhibitor (MAOI), specifically of monoamine oxidase A (MAO-A) (IC50 = 420 nM).[8][3] 1-NAP is an MAOI as well, also of MAO-A (IC50 = 5,630 nM), but was about 13-fold less potent than 2-NAP.[3] Neither 2-NAP or 1-NAP inhibited monoamine oxidase B (MAO-B) (IC50 > 100,000 nM).[8][3]

1-NAP was first described in the scientific literature by at least 1952.[1]

See also

  • 1-Naphthylmethcathinone (AMAPN)

References

  1. ↑ 1.0 1.1 1.2 "Uber die pharmakologische wirkung vom 1-(alpha-naphtyl)-, beziehungsweise 1-(beta-naphtyl)-2-aminopropan; Beiträge zum Zuzammenhang zwischen chemischer Struktur und Wirkung". Acta Physiologica Academiae Scientiarum Hungaricae 3 (1): 137–151. 1952. PMID 13050439. 
  2. ↑ 2.0 2.1 2.2 "Structure-activity studies on amphetamine analogs using drug discrimination methodology". Pharmacology, Biochemistry, and Behavior 21 (6): 895–901. December 1984. doi:10.1016/S0091-3057(84)80071-4. PMID 6522418. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors". Bioorg Med Chem 17 (6): 2452–2460. March 2009. doi:10.1016/j.bmc.2009.01.074. PMID 19243954. 
  4. ↑ "Dual dopamine-5-HT releasers: potential treatment agents for cocaine addiction". Trends Pharmacol Sci 27 (12): 612–618. December 2006. doi:10.1016/j.tips.2006.10.006. PMID 17056126. 
  5. ↑ "Dual dopamine/serotonin releasers as potential medications for stimulant and alcohol addictions". The AAPS Journal 9 (1): E1-10. January 2007. doi:10.1208/aapsj0901001. PMID 17408232. 
  6. ↑ "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug Alcohol Depend 147: 1–19. February 2015. doi:10.1016/j.drugalcdep.2014.12.005. PMID 25548026. 
  7. ↑ "Studies of the biogenic amine transporters. 14. Identification of low-efficacy "partial" substrates for the biogenic amine transporters". J Pharmacol Exp Ther 341 (1): 251–262. April 2012. doi:10.1124/jpet.111.188946. PMID 22271821. 
  8. ↑ 8.0 8.1 "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol 10. 2019. doi:10.3389/fphar.2019.01590. PMID 32038257. 





Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:1-Naphthylaminopropane&oldid=4035853"