1-Naphthylaminopropane

vanc 6 Naphthylaminopropane 1-Naphthylaminopropane.svg skin-invert-image 215px 12687-37-5 413939 366505 471838 1-NAP; 1-(1-Naphthyl)-2-aminopropane; α-Naphthylaminopropane; α-NAP; 1-Naphthylisopropylamine; α-Naphthylisopropylamine; Benzamphetamine 1-naphthalen-1-ylpropan-2-amine 13 15 1 CC(CC1=CC=CC2=CC=CC=C21)N 1S/C13H15N/c1-10(14)9-12-7-4-6-11-5-2-3-8-13(11)12/h2-8,10H,9,14H2,1H3 ODTJDLMNBKMVGR-UHFFFAOYSA-N 1-Naphthylaminopropane (1-NAP), also known as 1-naphthylisopropylamine or as α-naphthylaminopropane (α-NAP), is a drug of the amphetamine and naphthylaminopropane families. Mehes G Uber die pharmakologische wirkung vom 1-(alpha-naphtyl)-, beziehungsweise 1-(beta-naphtyl)-2-aminopropan; Beiträge zum Zuzammenhang zwischen chemischer Struktur und Wirkung On the pharmacological effects of 1-(alpha-naphthyl)-, and 1-(beta-naphthyl)-2-aminopropane; a contribution on the problem of chemical structure and effect Acta Physiologica Academiae Scientiarum Hungaricae 3 1 137–151 1952 13050439 Glennon RA, Young R, Hauck AE, McKenney JD Structure-activity studies on amphetamine analogs using drug discrimination methodology Pharmacology, Biochemistry, and Behavior 21 6 895–901 December 1984 6522418 10.1016/S0091-3057(84)80071-4 36455297 Vilches-Herrera M, Miranda-Sepúlveda J, Rebolledo-Fuentes M, Fierro A, Lühr S, Iturriaga-Vasquez P, Cassels BK, Reyes-Parada M Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors Bioorg Med Chem 17 6 2452–2460 March 2009 19243954 10.1016/j.bmc.2009.01.074 10533/142511 free It is a positional isomer of 2-naphthylaminopropane (2-NAP; PAL-287). 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. Rothman RB, Blough BE, Baumann MH Dual dopamine-5-HT releasers: potential treatment agents for cocaine addiction Trends Pharmacol Sci 27 12 612–618 December 2006 17056126 10.1016/j.tips.2006.10.006 Rothman RB, Blough BE, Baumann MH Dual dopamine/serotonin releasers as potential medications for stimulant and alcohol addictions The AAPS Journal 9 1 E1-10 January 2007 17408232 2751297 10.1208/aapsj0901001 Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, Partilla JS, Rothman RB, Katz JL Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter Drug Alcohol Depend 147 1–19 February 2015 25548026 4297708 10.1016/j.drugalcdep.2014.12.005 Rothman RB, Partilla JS, Baumann MH, Lightfoot-Siordia C, Blough BE 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 22271821 3364510 10.1124/jpet.111.188946 Both 1-NAP and 2-NAP failed to substitute for dextroamphetamine in rodent drug discrimination tests, suggesting that they lack stimulant effects. 2-NAP is a potent monoamine oxidase inhibitor (MAOI), specifically of monoamine oxidase A (MAO-A) (IC50 half-maximal effective concentration = 420nM). Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK Amphetamine Derivatives as Monoamine Oxidase Inhibitors Front Pharmacol 10 1590 2019 32038257 6989591 10.3389/fphar.2019.01590 free 1-NAP is an MAOI as well, also of MAO-A (IC50 half-maximal effective concentration = 5,630nM), but was about 13-fold less potent than 2-NAP. Neither 2-NAP or 1-NAP inhibited monoamine oxidase B (MAO-B) (IC50 half-maximal effective concentration > 100,000nM). 1-NAP was first described in the scientific literature by at least 1952. See also 1-Naphthylmethcathinone (AMAPN) References Category:Monoamine oxidase inhibitors Category:1-Naphthyl compounds Category:Naphthylethylamines Category:Substituted amphetamines