R-Palmitoyl-(1-methyl) Ethanolamide

- Overview
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    Background
    
    R-Palmitoyl-(1-methyl) ethanolamide, a synthetic analog of Palmitoyl ethanolamide (PEA), incorporates the (R)-methyl group vicinal to the alcohol on the ethanolamine moiety. The analogous modification to arachidonoyl ethanolamide (AEA) protects the molecule from hydrolysis by fatty acid amide hydrolase, prolongs duration of action and enhances potency in vivo [1]. PEA is an endogenous cannabinoid existed in mammalian tissues, such as liver and brain. PEA has also been isolated from egg yolk [2, 3]. PEA is a compound with documented anti-nociceptive and anti-inflammatory effects. During inflammation, PEA is accumulated and exihibits anti-inflammatory effects, including beneficial effects in clinically relevant animal models of inflammatory pain [4].
    
    [1] Abadji V, Lin S, Taha G, et al. (R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability[J]. Journal of medicinal chemistry, 1994, 37(12): 1889-1893.
    [2] Bachur N R, Masek K, Melmon K L, et al. Fatty acid amides of ethanol-amine in mammalian tissues[J]. Journal of Biological Chemistry, 1965, 240: 1019-1024.
    [3] Ganley O H, Graessle O E, Robinson H J, et al. Anti-inflammatory activity of compounds obtained from egg yolk, peanut oil, and soybean lecithin[J]. Journal of Laboratory and Clinical Medicine, 1958, 51: 709-714.
    [4] Lambert D M, Vandevoorde S, Jonsson K O, et al. The palmitoylethanolamide family: a new class of anti-inflammatory agents [J]. Current medicinal chemistry, 2002, 9(6): 663-674.
- Properties
  - Categories
    
    synthetic analog of palmitoyl ethanolamide (PEA)
    
    Alternative Name
    
    R-1 PMA; N-(2-hydroxy-1R-methylethyl)-hexadecanamide
    
    CAS Number
    
    142128-47-0
    
    Molecular Formula
    
    C19H39NO2
    
    Molecular Weight
    
    313.5
    
    Appearance
    
    A crystalline solid
    
    Purity
    
    98.00%
    
    Solubility
    
    ≤10mg/ml in ethanol;25mg/ml in DMSO;3.3mg/ml in dimethyl formamide
    
    Storage
    
    Store at -20°C
    
    SMILES
    
    CCCCCCCCCCCCCCCC(=O)N[[email protected]](C)CO
    
    * For Research Use Only