1-Naphthylaminopropane

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]

Other names1-NAP; 1-(1-Naphthyl)-2-aminopropane; α-Naphthylaminopropane; α-NAP; 1-Naphthylisopropylamine; α-Naphthylisopropylamine; Benzamphetamine

CAS Number

• 12687-37-5

PubChem CID

• 413939

ChemSpider

• 366505

Quick facts Clinical data, Other names ...

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

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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) (IC₅₀Tooltip half-maximal effective concentration = 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]