:2-Methylphenethylamine

{{chembox

| Watchedfields = changed

| verifiedrevid =

| ImageFile =2-Methylphenethylamine.svg

| ImageSize =

| PIN = 2-(2-Methylphenyl)ethan-1-amine

| OtherNames = 2-(2-Methylphenyl)ethanamine
2-Methylbenzeneethanamine
2-(o-Tolyl)ethan-1-amine

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo =55755-16-3

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

| UNII = B2VHM2W3X9

| PubChem =2063868

| SMILES =CC1=CC=CC=C1CCN

| Abbreviations =

| ChEBI =

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 451372

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 1554538

}}

|Section2={{Chembox Properties

| C=9 | H=13 | N=1

| Appearance =Clear colorless liquid at room temp{{cite web|title=2-Methylphenethylamine|url=https://pubchem.ncbi.nlm.nih.gov/compound/2063868|access-date=24 June 2023|publisher=National Library of Medicine}}

| Density = 0.96 g/cm3

| MeltingPt =

| MeltingPt_notes =

| BoilingPtC = 97

| BoilingPt_notes = / 5 mmHg (270.7984 °C / 760 mmHg) Experimental{{cite web|title=2-(2-Methylphenyl)ethanamine|url=http://www.chemspider.com/Chemical-Structure.1554538.html|work=Chemspider|access-date=27 May 2014}}

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards = Corrosive; causes burns

| FlashPt =

| AutoignitionPt =

}}

}}

2-Methylphenethylamine (2MPEA) is an organic compound with the chemical formula of {{Chem2|C9H13N|auto=yes}}. 2MPEA is a human trace amine associated receptor 1 (TAAR1) agonist,{{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=475–85 |date=January 2007 |pmid=17038507 |doi=10.1124/jpet.106.112532 |s2cid=10829497 |quote=Several series of substituted phenylethylamines were investigated for activity at the human TAAR1 (Table 2). A surprising finding was the potency of phenylethylamines with substituents at the phenyl C2 position relative to their respective C4-substituted congeners. In each case, except for the hydroxyl substituent, the C2-substituted compound had 8- to 27-fold higher potency than the C4-substituted compound. The C3-substituted compound in each homologous series was typically 2- to 5-fold less potent than the 2-substituted compound, except for the hydroxyl substituent. The most potent of the 2-substituted phenylethylamines was 2-chloro-β-PEA, followed by 2-fluoro-β-PEA, 2-bromo-β-PEA, 2-methoxy-β-PEA, 2-methyl-β-PEA, and then 2-hydroxy-β-PEA.
The effect of β-carbon substitution on the phenylethylamine side chain was also investigated (Table 3). A β-methyl substituent was well tolerated compared with β-PEA. In fact, S-(−)-β-methyl-β-PEA was as potent as β-PEA at human TAAR1. β-Hydroxyl substitution was, however, not tolerated compared with β-PEA. In both cases of β-substitution, enantiomeric selectivity was demonstrated.
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.}} a property which it shares with its monomethylated phenethylamine isomers, such as amphetamine (α-methylphenethylamine), {{nowrap|β-methylphenethylamine}}, and {{nowrap|N-methylphenethylamine}} (a trace amine).

Very little data, even on toxicity, is available about its effects on humans other than that it activates the human TAAR1 receptor.