Methamnetamine

Methamnetamine (also known as methylnaphetamine, MNA, MNT, MNAP, PAL-1046, and MY-10) is a triple monoamine releasing agent of the amphetamine and naphthylaminopropane families. It is the N-methyl analog of the non-neurotoxic experimental drug naphthylaminopropane and the naphthalene analog of methamphetamine.^[2][3][4] It has been sold online as a designer drug between 2015 and 2016.^[5][6][7]

Methamnetamine

Clinical data
Other names	Methylnaphetamine; MNA; MNT; MNAP; PAL-1046; MY-10;[1] N-Methylnaphthylaminopropane; N-Methylnaphthylisopropylamine
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act Illegal in Japan
Identifiers
IUPAC name N-Methyl-1-(naphthalen-2-yl)propan-2-amine
CAS Number	1178720-66-5 Y
PubChem CID	17802040
ChemSpider	38754167
UNII	CAS64BB01B
CompTox Dashboard (EPA)	DTXSID801032850
Chemical and physical data
Formula	C14H17N
Molar mass	199.297 g·mol−1
3D model (JSmol)	Interactive image
SMILES CNC(C)Cc1ccc2ccccc2c1
InChI InChI=1S/C14H17N/c1-11(15-2)9-12-7-8-13-5-3-4-6-14(13)10-12/h3-8,10-11,15H,9H2,1-2H3 Key:BWWWOLYZMKACSB-UHFFFAOYSA-N

Pharmacology

Pharmacodynamics

Methamnetamine acts as a releasing agent of serotonin, norepinephrine, and dopamine, with EC₅₀ values of 13 nM, 34 nM, and 10 nM, respectively.^[2] It is also a lower-potency partial agonist of the serotonin 5-HT_2A receptor.^[8]

Monoamine release of methamnetamine 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	[9][10][11][12][13]
Naphthylaminopropane (NAP; PAL-287)	11.1	12.6	3.4	[14][11]
d-Methamphetamine	12.3–14.3	8.5–40.4	736–1,292	[9][15][11][13]
Methylnaphthylaminopropane (MNAP; PAL-1046)	34	10	13	[16][17]
l-Methcathinone	13.1	14.8	1,772	[18][12]
2-Naphthylmethcathinone (BMAPN; βk-MNAP)	94% at 10 μM	34	27	[19][20]
d-Ethylamphetamine	28.8	44.1	333.0	[21][22]
Ethylnaphthylaminopropane (ENAP; PAL-1045)	137	46 a	12 a	[16]
Phenmetrazine	29–50.4	70–131	7,765–>10,000	[23][11][24][25]
Naphthylmetrazine (PAL-704)	203	111	RI (105)	[25]
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:[26][27]

Society and culture

Legal status

Methamnetamine is illegal in Japan.^[28]

See also

• 2-MAPB
• 5-MAPBT
• BMAPN
• Naphthylaminopropane
• Ethylnaphthylaminopropane
• Naphthylpropylaminopentane
• HDEP-28
• HDMP-28
• Naphyrone
• WF-23