Palmitoylethanolamide

Palmitoylethanolamide (PEA) is an endogenous fatty acid amide, and lipid modulator PEA has been studied in in vitro and in vivo systems using exogenously added or dosed compound; there is evidence that it binds to a nuclear receptor, through which it exerts a variety of biological effects, some related to chronic inflammation and pain.

Palmitoylethanolamide
Names
Preferred IUPAC name
N-(2-Hydroxyethyl)hexadecanamide
Other names
  • Hydroxyethylpalmitamide
  • Palmidrol
  • N-Palmitoylethanolamine
  • Palmitylethanolamide
Identifiers
3D model (JSmol)
Abbreviations PEA
ChEMBL
ChemSpider
ECHA InfoCard 100.008.062
EC Number
  • 208-867-9
KEGG
MeSH palmidrol
UNII
  • InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)19-16-17-20/h20H,2-17H2,1H3,(H,19,21) N
    Key: HXYVTAGFYLMHSO-UHFFFAOYSA-N N
  • CCCCCCCCCCCCCCCC(=O)NCCO
Properties
C18H37NO2
Molar mass 299.499 g·mol−1
Appearance White crystals
Density 910 mg mL−1
Melting point 93 to 98 °C (199 to 208 °F; 366 to 371 K)
log P 5.796
Hazards
Flash point 323.9 °C (615.0 °F; 597.0 K)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

A main target of PEA is proposed to be the peroxisome proliferator-activated receptor alpha (PPAR-α). PEA also has affinity to cannabinoid-like G-coupled receptors GPR55 and GPR119. PEA cannot strictly be considered a classic endocannabinoid because it lacks affinity for the cannabinoid receptors CB1 and CB2. However, primary research supports the conclusion that the presence of PEA (or other structurally related N-acylethanolamines) enhances anandamide activity by an "entourage effect".

Some primary research reports support the conclusion that PEA levels are altered and that the endocannabinoid system (ECS) is "imbalanced" in acute and chronic inflammation. A primary research article, for instance, has reported that the deregulation of cannabinoid receptors and their endogenous ligands accompanies the development and progression of β-amyloid-induced neuroinflammation.

In some primary research studies, PEA has been shown to have anti-inflammatory, anti-nociceptive, neuroprotective, and anticonvulsant properties.

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