N,N-Dimethylphenethylamine

{{DISPLAYTITLE:N,N-Dimethylphenethylamine}}

{{Chembox

| Name = N,N-Dimethylphenethylamine

| ImageFile = N,N-Dimethylphenethylamine.svg

| ImageSize = 200px

| PIN = N,N-Dimethyl-2-phenylethan-1-amine

| OtherNames = N,N-Dimethyl-2-phenylethanamine
N,N-Dimethyl-β-phenylethylamine
N,N-DMPEA

| Section1 = {{Chembox Identifiers

| CASNo = 1126-71-2

| ChEBI = 188983

| ChEMBL = 46278

| ChemSpiderID = 23470

| EC_number = 628-613-4

| PubChem = 25125

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = I4C10U12C8

| StdInChI = 1S/C10H15N/c1-11(2)9-8-10-6-4-3-5-7-10/h3-7H,8-9H2,1-2H3

| StdInChIKey = TXOFSCODFRHERQ-UHFFFAOYSA-N

| SMILES = CN(C)CCC1=CC=CC=C1

}}

| Section2 = {{Chembox Properties

| C=10|H=15|N=1

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

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| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

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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.{{Cite journal | author = K. Hedman, K. Leander and B. Luning | journal = Acta Chem. Scand. | volume = 23 | pages = 3261 | date = 1969 | doi = 10.3891/acta.chem.scand.23-3261 | title = Studies on Orchidaceae Alkaloids. XV. Phenethylamines from Eria jarensis Ames| doi-access = free }}{{efn|Formerly placed in Eria.{{Cite POWO|id=77098891-1|title=Pinalia jarensis|access-date=2024-11-26}}}} Its aroma is described as "sweet, fishy". It is mainly used in cereal, cheese, dairy products, fish, fruit and meat.{{cite book|title=Fenaroli's Handbook of Flavor Ingredients, Sixth Edition|author=Burdock, G.A.|date=2016|publisher=CRC Press|isbn=9781420090864|url=https://books.google.com/books?id=pUEqBgAAQBAJ&pg=PA499|page=499|access-date=2016-09-13}} It is also being used in pre-workout and bodybuilding supplements with claims of a stimulant effect.{{Cite web|url=https://blog.priceplow.com/eria-jarensis-extract-n-phenethyl-dimethylamine|title=Eria Jarensis Extract / N-phenethyl dimethylamine: The Next Big Thing?|website=blog.priceplow.com|access-date=2016-10-05}}

There is also evidence suggesting that N,N-DMPEA acts as a TAAR1 agonist in humans,{{cite journal | vauthors = Wainscott DB, Little SP, Yin T, Tu Y, Rocco VP, He JX, Nelson DL | title = Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1 | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 320 | issue = 1 | pages = 475–485 | date = January 2007 | pmid = 17038507 | doi = 10.1124/jpet.106.112532 | s2cid = 10829497 | url = http://jpet.aspetjournals.org/content/320/1/475.long| url-access = subscription }} 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.{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/N_N-Dimethylphenethylamine#section=Biological-Test-Results|title=N,N-Dimethylphenethylamine {{!}} C10H15N - PubChem|last=Pubchem|website=pubchem.ncbi.nlm.nih.gov|access-date=2016-10-05}}

N,N-DMPEA is a positional isomer of methamphetamine. 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.