1-Naphthylmethcathinone

1-Naphthylmethcathinone (AMAPN) is a monoamine releasing agent of the cathinone and naphthylaminopropane families.^[1][2] It is an analogue of methcathinone in which the phenyl ring has been replaced with a 1-naphthalene ring.^[1][2]

Other namesAMAPN

Drug classSerotonin–norepinephrine–dopamine releasing agent

CAS Number

• 854674-62-7

PubChem CID

• 112704364

Quick facts Clinical data, Other names ...

1-Naphthylmethcathinone

Clinical data
Other names	AMAPN
Drug class	Serotonin–norepinephrine–dopamine releasing agent
Identifiers
IUPAC name 2-(methylamino)-1-naphthalen-1-ylpropan-1-one
CAS Number	854674-62-7
PubChem CID	112704364
ChemSpider	72080032
UNII	DM7M36B5BS
Chemical and physical data
Formula	C14H15NO
Molar mass	213.280 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C(=O)C1=CC=CC2=CC=CC=C21)NC
InChI InChI=1S/C14H15NO/c1-10(15-2)14(16)13-9-5-7-11-6-3-4-8-12(11)13/h3-10,15H,1-2H3 Key:QIACKSHQBOUATI-UHFFFAOYSA-N

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The drug acts as a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA).^[1][2] Its EC₅₀Tooltip half-maximal effective concentration values for induction of monoamine release are 21.6 nM for serotonin and 55.2 nM for dopamine, whereas the EC₅₀ for norepinephrine was not reported.^[1] However, AMAPN induced 92% release of norepinephrine at a concentration of 10,000 nM, indicating that it is an effective norepinephrine releaser as well.^[1]