French
Deutsch1-Naphthylaminopropane
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| Other names | 1-NAP; 1-(1-Naphthyl)-2-aminopropane; α-Naphthylaminopropane; α-NAP; 1-Naphthylisopropylamine; α-Naphthylisopropylamine; Benzamphetamine |
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| Formula | C13H15N |
| Molar mass | 185.270 g·mol−1 |
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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
[edit]- 1-Naphthylmethcathinone (AMAPN)
References
[edit]- ^ a b c Mehes G (1952). "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. PMID 13050439.
- ^ a b c Glennon RA, Young R, Hauck AE, McKenney JD (December 1984). "Structure-activity studies on amphetamine analogs using drug discrimination methodology". Pharmacology, Biochemistry, and Behavior. 21 (6): 895–901. doi:10.1016/S0091-3057(84)80071-4. PMID 6522418. S2CID 36455297.
- ^ a b c d e Vilches-Herrera M, Miranda-Sepúlveda J, Rebolledo-Fuentes M, Fierro A, Lühr S, Iturriaga-Vasquez P, et al. (March 2009). "Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors". Bioorg Med Chem. 17 (6): 2452–2460. doi:10.1016/j.bmc.2009.01.074. PMID 19243954.
- ^ Rothman RB, Blough BE, Baumann MH (December 2006). "Dual dopamine-5-HT releasers: potential treatment agents for cocaine addiction". Trends Pharmacol Sci. 27 (12): 612–618. doi:10.1016/j.tips.2006.10.006. PMID 17056126.
- ^ Rothman RB, Blough BE, Baumann MH (January 2007). "Dual dopamine/serotonin releasers as potential medications for stimulant and alcohol addictions". The AAPS Journal. 9 (1): E1-10. doi:10.1208/aapsj0901001. PMC 2751297. PMID 17408232.
- ^ Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, et al. (February 2015). "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug Alcohol Depend. 147: 1–19. doi:10.1016/j.drugalcdep.2014.12.005. PMC 4297708. PMID 25548026.
- ^ Rothman RB, Partilla JS, Baumann MH, Lightfoot-Siordia C, Blough BE (April 2012). "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. doi:10.1124/jpet.111.188946. PMC 3364510. PMID 22271821.
- ^ a b Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol. 10: 1590. doi:10.3389/fphar.2019.01590. PMC 6989591. PMID 32038257.
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