N-Methylphenethylamine

N-Methylphenethylamine
Clinical data
Other names	NMPEA; N-Methyl-2-phenylethanamine; N-Methylphenethylamine; N-Methyl-β-phenethylamine
Legal status
Legal status	CA: Schedule 1 as an isomer of amphetamine;
Identifiers
	IUPAC name N-methyl-2-phenylethan-1-amine;
CAS Number	589-08-2 ;
PubChem CID	11503;
ChemSpider	11019 ;
UNII	02N4V81704;
ChEMBL	ChEMBL45763 ;
CompTox Dashboard (EPA)	DTXSID10207629 ;
ECHA InfoCard	100.008.758
Chemical and physical data
Formula	C9H13N
Molar mass	135.210 g·mol−1
3D model (JSmol)	Interactive image;
Density	0.93 g/cm3
Boiling point	203 °C (397 °F)
	SMILES CNCCc1ccccc1;
	InChI InChI=1S/C9H13N/c1-10-8-7-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3 ; Key:SASNBVQSOZSTPD-UHFFFAOYSA-N ;
	(verify)

N-Methylphenethylamine (NMPEA) is a naturally occurring trace amine neuromodulator in humans that is derived from the trace amine, phenethylamine (PEA). It has been detected in human urine (<1 μg over 24 hours) and is produced by phenylethanolamine N-methyltransferase with phenethylamine as a substrate, which significantly increases PEA's effects. PEA breaks down into phenylacetaldehyde which is further broken down into phenylacetic acid by monoamine oxidase. When this is inhibited by monoamine oxidase inhibitors, it allows more of the PEA to remain present and produce psychoactive effects.

PEA and NMPEA are both alkaloids that are found in a number of different plant species as well. Some Acacia species, such as A. rigidula, contain remarkably high levels of NMPEA (~2300–5300 ppm). NMPEA is also present at low concentrations (< 10 ppm) in a wide range of foodstuffs.

NMPEA is a positional isomer of amphetamine.