N,N-Dimethylphenethylamine

N,N-Dimethylphenethylamine

Names
Preferred IUPAC name N,N-Dimethyl-2-phenylethan-1-amine
Other names N,N-Dimethyl-2-phenylethanamine N,N-Dimethyl-β-phenylethylamine N,N-DMPEA
Identifiers
CAS Number	1126-71-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:188983
ChEMBL	ChEMBL46278
ChemSpider	23470
ECHA InfoCard	100.156.869
EC Number	628-613-4
PubChem CID	25125
UNII	I4C10U12C8 Y
CompTox Dashboard (EPA)	DTXSID40150114
InChI InChI=1S/C10H15N/c1-11(2)9-8-10-6-4-3-5-7-10/h3-7H,8-9H2,1-2H3 Key: TXOFSCODFRHERQ-UHFFFAOYSA-N
SMILES CN(C)CCC1=CC=CC=C1
Properties
Chemical formula	C10H15N
Molar mass	149.237 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

N,N-Dimethylphenethylamine (N,N-DMPEA) is a substituted phenethylamine that is used as a flavoring agent. It is an alkaloid that was first isolated from the orchid Pinalia jarensis.^[1][a] Its aroma is described as "sweet, fishy". It is mainly used in cereal, cheese, dairy products, fish, fruit and meat.^[3] It is also being used in pre-workout and bodybuilding supplements with claims of a stimulant effect.^[4]

There is also evidence suggesting that N,N-DMPEA acts as a TAAR1 agonist in humans,^[5] and as a 5-HT1A ligand in rats. Some less conclusive research also indicated that it had interaction with MAO-B, most likely as an enzyme substrate and not an inhibitor.^[6]

N,N-DMPEA is a positional isomer of methamphetamine. Instead of the methyl group attached to the alpha position of phenylethylamine, it's attached to the nitrogen group. Both substances have the chemical formula C₁₀H₁₅N.

N,N-DMPEA has been found to be safe for use as a flavoring agent by the Flavor and Extract Manufacturers Association (FEMA) Expert Panel^[7] and also by the Joint Expert Committee on Food Additives (JECFA)^[8]—a collaboration between the Food and Agricultural Organization of the United Nations (FAO) and the World Health Organization.^[9]

In the United States, N,N-DMPEA may be considered a Schedule II substance as a positional isomer of methamphetamine (C₁₀H₁₅N), due to the Schedule II definition of methamphetamine defined as "any quantity of methamphetamine, including its salts, isomers, and salts of isomers".^{[10] [11][12]}