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Palmitoylethanolamide

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Palmitoylethanolamide
Names
IUPAC name N-(2-hydroxyethyl)hexadecanamide
Other names Palmidrol; N-Palmitoylethanolamine; Palmitamide MEA; Palmitylethanolamide; Hydroxyethylpalmitamide
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.008.062 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
SMILES
  • CCCCCCCCCCCCCCCC(=O)NCCO
Properties
Chemical formula C18H37NO2
Molar mass 299.49
Appearance White solid
Density 0.91g/cm3
Melting point 59-60 °C
Boiling point 461.5°C @ 760mmHg
Solubility in other solvents soluble in ethanol,chloroform,THF and DMSO
Hazards
Flash point 323.9°C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

Palmitoylethanolamide (PEA) is an endogenous fatty acid amide that has been demonstrated to bind to peroxisome proliferator-activated receptor alpha (PPAR-α), GPR55 and GPR119. PEA has been shown to have anti-inflammatory, anti-nociceptive and anticonvulsant properties Palmitoylethanolamide is marketed by the Italian company Epitech under the trade name Normast.

PEA is has physico-chemical properties comparable to anandamide and belongs to the class of endogenous cannabinoids. Lipids like PEA can act as signaling molecules, activating intracellular and membrane-associated receptors to regulate a variety of physiological functions. The signaling lipid PEA is known to activate intracellular, nuclear and membrane-associated receptors and regulate many physiological functions related to the inflammatory cascade and chronic pain states. These lipids are widely distributed in nature, in a variety of plant, invertebrate, and mammalian tissues.

IN 1968 the first paper on PEA was indexed in Pubmed and since than more than 200 entries can be found, using the keyword 'palmitoylethanolamide'. In the 90s the relation between anandamide and PEA was described, and the expression on mastcells of receptors sensitive for those two molecules was first demonstrated. In animal models it seems promising, and demonstrated relevant clinical activity in a variety of disorders, such as multiple sclerosis and neuropathic pain.

PEA has been explored in man in various clinical trials in a variety of pain states, as well as in pet animals, for inflammatory and painsyndromes. The compound is available for human use as food for medical purposes in Italy and Spain and as a diet supplement in the Netherlands.

PEA is metabolized by fatty acid amide hydrolase (FAAH) and N-acylethanolamine-hydrolyzing acid amidase (NAAA), the latter of which has more specificity toward PEA over other fatty acid amides.


See also

References

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  5. Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 11442148, please use {{cite journal}} with |pmid=11442148 instead.
  6. Normast®, palmitoylethanolamide in neuropathic sciatic pain: clinical results. Behandelcentrum Neuropathische Pijn . Accessed 23 September 2011.
  7. Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 5699335, please use {{cite journal}} with |pmid=5699335 instead.
  8. Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 7724569, please use {{cite journal}} with |pmid=7724569 instead.
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  12. Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 21483401, please use {{cite journal}} with |pmid=21483401 instead.
  13. Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 20176435, please use {{cite journal}} with |pmid=20176435 instead.
  14. Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 19744255, please use {{cite journal}} with |pmid=19744255 instead.
  15. Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 17712833, please use {{cite journal}} with |pmid=17712833 instead.


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