1-Naphthylaminopropane (1-NAP), also known as 1-naphthylisopropylamine or as ñ-naphthylaminopropane (ñ-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 serotoninâÂÂnorepinephrineâÂÂdopamine 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) ( = 420nM). 1-NAP is an MAOI as well, also of MAO-A ( = 5,630nM), but was about 13-fold less potent than 2-NAP. Neither 2-NAP or 1-NAP inhibited monoamine oxidase B (MAO-B) ( > 100,000nM).
1-NAP was first described in the scientific literature by at least 1952.