N,N-Dimethylphenethylamine

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N,N-Dimethylphenethylamine
N,N-Dimethylphenethylamine.svg
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)
ChemSpider
Properties
C10H15N
Molar mass 149.24 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 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][unreliable source?]

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]

References[edit]

  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. In contrast to a methyl substitution on the β-carbon, an α-methyl substitution reduced potency by ∼10-fold for d-amphetamine and 16-fold for l-amphetamine relative to β-PEA (Table 4). N-Methyl substitution was fairly well tolerated; however, N,N-dimethyl substitution was not.
    Link to Table 4
  5. ^ Pubchem. "N,N-Dimethylphenethylamine | C10H15N - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2016-10-05.