1-Naphthylaminopropane

1-Naphthylaminopropane
Clinical data
Other names	1-NAP; 1-(1-Naphthyl)-2-aminopropane; α-Naphthylaminopropane; α-NAP; 1-Naphthylisopropylamine; α-Naphthylisopropylamine; Benzamphetamine
Identifiers
	IUPAC name 1-naphthalen-1-ylpropan-2-amine;
CAS Number	12687-37-5;
PubChem CID	413939;
ChemSpider	366505;
ChEMBL	ChEMBL471838;
CompTox Dashboard (EPA)	DTXSID80925727 ;
Chemical and physical data
Formula	C13H15N
Molar mass	185.270 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC=CC2=CC=CC=C21)N;
	InChI InChI=1S/C13H15N/c1-10(14)9-12-7-4-6-11-5-2-3-8-13(11)12/h2-8,10H,9,14H2,1H3; Key: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. 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. 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) (IC₅₀Tooltip half-maximal effective concentration = 420 nM). 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. Neither 2-NAP or 1-NAP inhibited monoamine oxidase B (MAO-B) (IC₅₀ > 100,000 nM).

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