Palmitoylethanolamide

Palmitoylethanolamide
Skeletal formula of palmitoylethanolamide
Names
Preferred IUPAC name
N-(2-Hydroxyethyl)hexadecanamide[1]
Other names
  • Hydroxyethylpalmitamide
  • Palmidrol
  • N-Palmitoylethanolamine
  • Palmitylethanolamide
Identifiers
3D model (JSmol)
Abbreviations PEA
ChEMBL
ChemSpider
ECHA InfoCard 100.008.062 Edit this at Wikidata
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).
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Palmitoylethanolamide (PEA) is an endogenous fatty acid amide, and lipid modulator.[2]

A main target of PEA is proposed to be the peroxisome proliferator-activated receptor alpha (PPAR-α).[3][4] PEA also has affinity to cannabinoid-like G-coupled receptors GPR55 and GPR119.[5] PEA cannot strictly be considered a classic endocannabinoid because it lacks affinity for the cannabinoid receptors CB1 and CB2.[6]

  1. ^ NCBI-PubChem Staff (25 March 2005). "Compound Summary: Palmitoylethanolamide" (database entry). PubChem.NCBI.NLM.NIH.gov. Bethesda, MD: US NLM-National Center for Biotechnology Information (NCBI). Retrieved 26 February 2020.
  2. ^ Petrosino S, Di Marzo V (2017). "The pharmacology of palmitoylethanolamide and first data on the therapeutic efficacy of some of its new formulations". British Journal of Pharmacology. 174 (11): 1349–1365. doi:10.1111/bph.13580. PMC 5429331. PMID 27539936.
  3. ^ O'Sullivan SE (November 2007). "Cannabinoids go nuclear: evidence for activation of peroxisome proliferator-activated receptors". British Journal of Pharmacology. 152 (5): 576–82. doi:10.1038/sj.bjp.0707423. PMC 2190029. PMID 17704824.
  4. ^ Lo Verme J, Fu J, Astarita G, La Rana G, Russo R, Calignano A, Piomelli D (January 2005). "The nuclear receptor peroxisome proliferator-activated receptor-alpha mediates the anti-inflammatory actions of palmitoylethanolamide". Molecular Pharmacology. 67 (1): 15–9. doi:10.1124/mol.104.006353. PMID 15465922. S2CID 12671741.
  5. ^ Godlewski G, Offertáler L, Wagner JA, Kunos G (September 2009). "Receptors for acylethanolamides-GPR55 and GPR119". Prostaglandins & Other Lipid Mediators. 89 (3–4): 105–11. doi:10.1016/j.prostaglandins.2009.07.001. PMC 2751869. PMID 19615459.
  6. ^ O'Sullivan SE, Kendall DA (August 2010). "Cannabinoid activation of peroxisome proliferator-activated receptors: potential for modulation of inflammatory disease". Immunobiology. 215 (8): 611–6. doi:10.1016/j.imbio.2009.09.007. PMID 19833407.