''N'',''N''-Dimethylphenethylamine (''N'',''N''-DMPEA) is a

substituted phenethylamine Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative (chemistry), derivative compounds of phenethylamine ...

that is used as a

flavoring agent A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive that is used to improve the taste or Sense of smell, smell of food. It changes the perceptual impression of food as determined primarily by the chem ...

. It is an

alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...

that was first isolated from the orchid ''

Pinalia ''Pinalia'', commonly known as gremlin orchids, is a genus of flowering plants in the family Orchidaceae. Orchids in this genus are large epiphytic or lithophytic plants with prominent pseudobulbs, each with up to three thin, flat leaves and cup ...

jarensis''. Its aroma is described as "sweet, fishy". It is mainly used in cereal, cheese, dairy products, fish, fruit and meat. It is also being used in pre-workout and bodybuilding supplements with claims of a stimulant effect. There is also evidence suggesting that ''N'',''N''-DMPEA acts as a

TAAR1 Trace amine-associated receptor 1 (TAAR1) is a trace amine-associated receptor (TAAR) protein that in humans is encoded by the ''TAAR1'' gene. TAAR1 is a primarily intracellular amine-activated and G protein-coupled receptor (GPCR) that is p ...

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

in humans, and as a

5-HT1A The serotonin 1A receptor (or 5-HT1A receptor) is a subtype of serotonin receptors, or 5-HT receptors, that binds serotonin, also known as 5-HT, a neurotransmitter. 5-HT1A is expressed in the brain, spleen, and neonatal kidney. It is a G protein ...

ligand In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...

in rats. Some less conclusive research also indicated that it had interaction with

MAO-B Monoamine oxidase B (MAO-B) is an enzyme that in humans is encoded by the ''MAOB'' gene. The protein encoded by this gene belongs to the flavin monoamine oxidase family. It is an enzyme located in the outer mitochondrial membrane. It catalyze ...

, most likely as an enzyme

substrate Substrate may refer to: Physical layers *Substrate (biology), the natural environment in which an organism lives, or the surface or medium on which an organism grows or is attached ** Substrate (aquatic environment), the earthy material that exi ...

and not an inhibitor. ''N'',''N''-DMPEA is a

positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

methamphetamine Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug use, recreational or Performance-enhancing substance, performance-enhancing drug and less commonly as a secon ...

. Instead of the methyl group attached to the alpha position of phenylethylamine, it is attached to the nitrogen group. Both substances have the chemical formula C₁₀H₁₅N.

Safety

N,N-DMPEA has been found to be safe for use as a flavoring agent by the

Flavor and Extract Manufacturers Association The Flavor and Extract Manufacturers Association (FEMA) is a food industry trade group based in the United States. FEMA was founded in 1909 by several flavor firms in response to the passage of the Pure Food and Drug Act of 1906. Founding members ...

(FEMA) Expert Panel and also by the Joint Expert Committee on Food Additives (JECFA)—a collaboration between the

Food and Agricultural Organization of the United Nations The Food and Agriculture Organization of the United Nations; . (FAO) is a specialized agency of the United Nations that leads international efforts to defeat hunger and improve nutrition and food security. Its Latin motto, , translates to ...

(FAO) and the

World Health Organization The World Health Organization (WHO) is a list of specialized agencies of the United Nations, specialized agency of the United Nations which coordinates responses to international public health issues and emergencies. It is headquartered in Gen ...

Legality

In the United States, N,N-DMPEA may be considered a Schedule II substance as a positional

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...

(C₁₀H₁₅N), due to the Schedule II definition of methamphetamine defined as "any quantity of methamphetamine, including its salts, isomers, and salts of isomers".

Notes

References

{{DEFAULTSORT:Dimethylphenethylamine, N,N- Phenethylamine alkaloids Food additives