2-Naphthylmethcathinone

2-Naphthylmethcathinone (BMAPN), also known as βk-methamnetamine, is a stimulant drug of the cathinone and naphthylaminopropane families. It inhibits dopamine reuptake and has rewarding and reinforcing properties in animal studies.^[1][2] It is banned under drug analogue legislation in a number of jurisdictions. The drug was at one point marketed under the name NRG-3, although only a minority of samples of substances sold under this name have been found to actually contain BMAPN, with most such samples containing mixtures of other cathinone derivatives.^[3][4]

Monoamine release of BMAPN and related agents (EC₅₀Tooltip Half maximal effective concentration, nM)

Compound	NETooltip Norepinephrine	DATooltip Dopamine	5-HTTooltip Serotonin	Ref
d-Amphetamine	6.6–10.2	5.8–24.8	698–1,765	[5][6][7][8][9]
Naphthylaminopropane (NAP; PAL-287)	11.1	12.6	3.4	[10][7]
d-Methamphetamine	12.3–14.3	8.5–40.4	736–1,292	[5][11][7][9]
Methylnaphthylaminopropane (MNAP; PAL-1046)	34	10	13	[12][13]
l-Methcathinone	13.1	14.8	1,772	[14][8]
2-Naphthylmethcathinone (BMAPN; βk-MNAP)	94% at 10 μM	34	27	[15][16]
d-Ethylamphetamine	28.8	44.1	333.0	[17][18]
Ethylnaphthylaminopropane (ENAP; PAL-1045)	137	46 a	12 a	[12]
Phenmetrazine	29–50.4	70–131	7,765–>10,000	[19][7][20][21]
Naphthylmetrazine (PAL-704)	203	111	RI (105)	[21]
Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Footnotes: a ENAPTooltip Ethylnaphthylaminopropane is a partial releaser of serotonin (EmaxTooltip maximal efficacy = 66%) and dopamine (Emax = 78%). Refs: [22][23]

BMAPN

Clinical data
Other names	BMAPN; βk-Methamnetamine
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act
Identifiers
IUPAC name 2-(methylamino)-1-(naphthalene-2-yl) propan-1-one
CAS Number	109453-73-8
PubChem CID	112704365
ChemSpider	65998790
UNII	DL8RX8N8NK
CompTox Dashboard (EPA)	DTXSID601337020
Chemical and physical data
Formula	C14H15NO
Molar mass	213.280 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C(=O)C1=CC2=CC=CC=C2C=C1)NC
InChI InChI=1S/C14H15NO/c1-10(15-2)14(16)13-8-7-11-5-3-4-6-12(11)9-13/h3-10,15H,1-2H3 Key:QIMNQDXLKHGANJ-UHFFFAOYSA-N

See also

• 1-Naphthylmethcathinone (AMAPN)
• βk-Ephenidine
• Methamnetamine
• Methylnaphthidate
• Methylone
• Naphyrone
• WF-23