3-Methylphenethylamine

3-Methylphenethylamine
Names

Preferred IUPAC name 2-(3-Methylphenyl)ethan-1-amine
Other names 2-(3-Methylphenyl)ethanamine 3-Methylbenzeneethanamine 2-(m-Tolyl)ethan-1-amine
Identifiers
CAS Number	55755-17-4^Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL448576^Y
ChemSpider	362941^Y
ECHA InfoCard	100.189.789
PubChem	410085
SMILES CC1=CC(=CC=C1)CCN
Properties
Chemical formula	C₉H₁₃N
Molar mass	135.20622
Appearance	clear liquid at room temp.
Density	1.0±0.1 g/cm3
Boiling point	110 °C (230 °F; 383 K) / 20 mmHg 240.9519 °C / 760 mmHg Experimental^[1]
Hazards
Main hazards	Corrossive
Flash point	90.5 ± 6.3 °C (194.9 ± 11.3 °F; 363.6 ± 6.3 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

3-Methylphenethylamine (3MPEA) is an organic compound with the chemical formula of C₉H₁₃N. 3MPEA is a human trace amine associated receptor 1 (TAAR1) agonist,^[2] a property which it shares with its monomethylated phenethylamine isomers, such as amphetamine (α-methylphenethylamine), β-methylphenethylamine, and N-methylphenethylamine (a trace amine).^[2]

Very little data, even on toxicity, is available about its effects on humans other than the fact that it is corrosive and activates the human TAAR1 receptor.^[1]

References

1 2 "2-(3-Methylphenyl)ethanamine". Chemspider. Retrieved 30 May 2014.
1 2 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): 475–85. doi:10.1124/jpet.106.112532. PMID 17038507. 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.

Human trace amine-associated receptor ligands

TAAR1

Agonists

Endogenous^†	Classical monoamine neurotransmitters Dopamine Histamine Norepinephrine Serotonin Trace amines 3-Iodothyronamine 3-Methoxytyramine N-Methylphenethylamine N-Methyltyramine m-Octopamine p-Octopamine Phenethylamine Phenylethanolamine Synephrine Tryptamine m-Tyramine p-Tyramine

Synthetic^‡	Amphetamine DOB DOET 4-Hydroxyamphetamine Isoprenaline MDA MDMA 2-Methylphenethylamine 3-Methylphenethylamine 4-Methylphenethylamine β-Methylphenethylamine Methamphetamine 3-MMA Norfenfluramine Phentermine o-PIT Propylhexedrine RO5166017 N,N-Dimethylphenethylamine

Antagonists

EPPTB (RO5212773)

TAAR2

Agonists^‡	3-Iodothyronamine Phenethylamine Tyramine

Antagonists

TAAR5

Agonists^‡	Dimethylethylamine Trimethylamine

Antagonists^‡	3-Iodothyronamine

^†References for all endogenous human TAAR1 ligands are provided at List of trace amines

^‡References for synthetic TAAR1 agonists can be found at TAAR1 or in the associated compound articles. For TAAR2 and TAAR5 agonists and antagonists, see TAAR for references.

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