''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
3D model (JSmol)	Interactive image;
ChemSpider	23470;
PubChem CID	25125;
	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	149.24 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]

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

↑ 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.
↑ Burdock, G.A. (2016). Fenaroli's Handbook of Flavor Ingredients, Sixth Edition. CRC Press. p. 499. ISBN 9781420090864. Retrieved 2016-09-13.
↑ "Eria Jarensis Extract / N-phenethyl dimethylamine: The Next Big Thing?". blog.priceplow.com. Retrieved 2016-10-05.
↑ 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
↑ Pubchem. "N,N-Dimethylphenethylamine | C10H15N - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2016-10-05.

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[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.

[google-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.

[Wainscott_2007-4] 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.