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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.156.869 Edit this at Wikidata
EC Number
  • 628-613-4
UNII
  • 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
  • CN(C)CCC1=CC=CC=C1
Properties
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).

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 Eria jarensis.[1] Its aroma is described as "sweet, fishy". It is mainly used in cereal, cheese, dairy products, fish, fruit and meat.[2] It is also being used in pre-workout and bodybuilding supplements with claims of a stimulant effect.[3]

There is also evidence suggesting that N,N-DMPEA acts as a TAAR1 agonist in humans,[4] 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.[5]

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.

Safety

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[6] and also by the Joint Expert Committee on Food Additives (JECFA)[7]—a collaboration between the Food and Agricultural Organization of the United Nations (FAO) and the World Health Organization.[8]

Legality

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"[9][10][11]

References

  1. ^ K. Hedman, K. Leander and B. Luning (1969). "Studies on Orchidaceae Alkaloids. XV. Phenethylamines from Eria jarensis Ames". Acta Chem. Scand. 23: 3261. doi:10.3891/acta.chem.scand.23-3261.
  2. ^ Burdock, G.A. (2016). Fenaroli's Handbook of Flavor Ingredients, Sixth Edition. CRC Press. p. 499. ISBN 9781420090864. Retrieved 2016-09-13.
  3. ^ "Eria Jarensis Extract / N-phenethyl dimethylamine: The Next Big Thing?". blog.priceplow.com. Retrieved 2016-10-05.
  4. ^ Wainscott DB, Little SP, Yin T, Tu Y, Rocco VP, He JX, Nelson DL (January 2007). "Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1". The Journal of Pharmacology and Experimental Therapeutics. 320 (1): 475–485. doi:10.1124/jpet.106.112532. PMID 17038507. S2CID 10829497.
  5. ^ Pubchem. "N,N-Dimethylphenethylamine | C10H15N - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2016-10-05.
  6. ^ "Flavor and Extract Manufacturers Association (FEMA) GRAS Flavoring Substances 22". www.femaflavor.org. Retrieved 2019-01-14.
  7. ^ "Evaluations of the Joint FAO/WHO Expert Committee on Food Additives (JECFA)". apps.who.int. Retrieved 2019-01-14.
  8. ^ "The Joint FAO/WHO Expert Committee on Food Additives (JECFA)". www.fao.org. Retrieved 2019-01-14. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) is an international expert scientific committee that is administered jointly by the Food and Agriculture Organization of the United Nations (FAO) and the World Health Organization (WHO).
  9. ^ http://isomerdesign.com/Cdsa/FR/36FR12734.pdf [bare URL PDF]
  10. ^ "21 U.S. Code § 812 - Schedules of controlled substances".
  11. ^ https://www.govinfo.gov/content/pkg/STATUTE-84/pdf/STATUTE-84-Pg1236.pdf [bare URL PDF]