1-Naphthylmethcathinone

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

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]}

The drug acts as a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA). ^{[1] [2]} Its EC₅₀ Tooltip 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]

See also

• 1-Naphthylaminopropane (1-NAP)
• 2-Naphthylmethcathinone (BMAPN)
• 2,3-Methylenedioxyamphetamine (2,3-MDA)
• 2,3-Methylenedioxymethamphetamine (2,3-MDMA)

References

1. Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, et al. (March 2019). "The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes". Psychopharmacology (Berl). 236 (3): 915–924. doi:10.1007/s00213-018-5063-9. PMC   6475490 . PMID   30341459.
2. Yadav BJ (16 July 2019). Understanding Structure–Activity Relationship of Synthetic Cathinones (Bath Salts) Utilizing Methylphenidate. VCU Scholars Compass (Thesis). doi:10.25772/MJQW-8C64 . Retrieved 24 November 2024.