Naphthylpropylaminopentane

1-(2-Naphthyl)-2-propylaminopentane (NPAP), also known as 2-naphthyl-α,N-dipropylphenethylamine, is a monoaminergic activity enhancer (MAE) of the α-propylphenethylamine and naphthylaminopropane families related to phenylpropylaminopentane (PPAP).^[1] It is the analogue of PPAP in which the phenyl ring has been replaced with a naphthalene ring.^[1] MAEs are agents that enhance the action potential-mediated release of monoamine neurotransmitters.^[2][3][4] NPAP is a MAE of norepinephrine and dopamine but not of serotonin.^[1] Its potency is similar to that of PPAP.^[1] As with PPAP, the (–)-enantiomer of NPAP is more potent as a MAE.^[1] Like PPAP, it is inactive as a classical monoamine releasing agent.^[1] NPAP was developed by József Knoll and colleagues and was first described in 2001.^[1]

Other names1-(2-Naphthyl)-2-propylaminopentane; NPAP; 2-Naphthyl-α,N-dipropylphenethylamine

Drug classMonoaminergic activity enhancer

ATC code

• None

PubChem CID

• 9926059

Quick facts Clinical data, Other names ...

NPAP

Clinical data
Other names	1-(2-Naphthyl)-2-propylaminopentane; NPAP; 2-Naphthyl-α,N-dipropylphenethylamine
Drug class	Monoaminergic activity enhancer
ATC code	None
Identifiers
IUPAC name 1-naphthalen-2-yl-N-propylpentan-2-amine
PubChem CID	9926059
ChemSpider	8101694
Chemical and physical data
Formula	C18H25N
Molar mass	255.405 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCC(CC1=CC2=CC=CC=C2C=C1)NCCC
InChI InChI=1S/C18H25N/c1-3-7-18(19-12-4-2)14-15-10-11-16-8-5-6-9-17(16)13-15/h5-6,8-11,13,18-19H,3-4,7,12,14H2,1-2H3 Key:GKNKHAOHVXOYDS-UHFFFAOYSA-N

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