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词条 4-Methylphenethylamine
释义

  1. References

{{chembox
| ImageFile=4-Methylphenethylamine.svg
| ImageSize=200px
| PIN = 2-(4-Methylphenyl)ethan-1-amine
| OtherNames= 2-(4-Methylphenyl)ethanamine
2-(p-Tolyl)ethan-1-amine
|Section1={{Chembox Identifiers
| CASNo=3261-62-9
| PubChem=76751
| ChemSpiderID=69207
| SMILES=CC1=CC=C(C=C1)CCN
|Section2={{Chembox Properties
| Formula= | C=9 | H=13 | N=1
| Appearance=Clear colorless to light yellow liquid[1]
| Density=0.93 g/mL[1]
| MeltingPt=
| BoilingPtC=214
| BoilingPt_notes =[1]
| Solubility=
|Section3={{Chembox Hazards
| MainHazards=Corrosive[1]
| FlashPt={{convert|91|C|F}}[1]
| AutoignitionPt =
}}4-Methylphenethylamine (4MPEA), also known as para-methylphenethylamine, is an organic compound with the chemical formula of {{chemical formula|C|9|H|13|N}}. 4MPEA 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), {{nowrap|β-methylphenethylamine}}, and {{nowrap|N-methylphenethylamine}} (a trace amine).[2] 4MPEA also appears to inhibit the human cytochrome P450 enzymes CYP1A2 and CYP2A6, based upon the published literature.[3]

References

1. ^{{cite web|title=4-Methylphenethylamine|url=http://www.chemicalbook.com/ProductChemicalPropertiesCB3299377_EN.htm|work=Chemical Book|accessdate=21 July 2014}}
2. ^{{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 |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.}}
3. ^{{cite web | title=4-Methylphenethylamine | url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=76751 | work=PubChem Compound | publisher = National Center for Biotechnology Information | accessdate=21 July 2014 }}
{{TAAR ligands}}{{DEFAULTSORT:Methylphenethylamine, 4-}}{{amine-stub}}

2 : Phenethylamines|TAAR1 agonists

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