Palmitoylethanolamide

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Cat.No. 0879 - Palmitoylethanolamide | C18H37NO2 | CAS No. 544-31-0
Description: Selective GPR55 agonist. FAAH and PAA substrate
Alternative Names: PEA
Chemical Name: N-(2-Hydroxyethyl)hexadecanamide
Datasheet
Citations (10)
Reviews
Literature

Biological Activity

Endogenous lipid that acts as a selective GPR55 agonist (EC50 values are 4, 19 800 and > 30 000 nM at GPR55, CB2 and CB1 receptors respectively). Substrate for fatty acid amide hydrolase (FAAH) and PEA-preferring acid amidase (PAA) and exhibits antinociceptive and anticonvulsant in vivo. Directly activates PPARα (EC50 = 3 μM) producing robust anti-inflammatory actions.

Technical Data

M. Wt 299.5
Formula C18H37NO2
Storage Store at RT
CAS Number 544-31-0
PubChem ID 4671
InChI Key HXYVTAGFYLMHSO-UHFFFAOYSA-N
Smiles O=C(CCCCCCCCCCCCCCC)NCCO

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 5.99 20
ethanol 7.49 25

Preparing Stock Solutions

The following data is based on the product molecular weight 299.5. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.25 mM 13.36 mL 66.78 mL 133.56 mL
1.25 mM 2.67 mL 13.36 mL 26.71 mL
2.5 mM 1.34 mL 6.68 mL 13.36 mL
12.5 mM 0.27 mL 1.34 mL 2.67 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

Lambert et al (2001) Anticonvulsant activity of N-palmitoylethanolamide, a putative endocannabinoid, in mice. Epilepsia 42 321 PMID: 11442148

Lambert et al (2002) The palmitoylethanolamide family: a new class of anti-inflammatory agents? Curr.Med.Chem. 9 663 PMID: 11945130

Lo Verme et al (2005) The search for the palmitoylethanolamide receptor. Life Sci. 77 1685 PMID: 15963531

Re et al (2005) Palmitoylethanolamide, endocannabinoids and related cannabimimetic compounds in protection against tissue inflammation and pain: potential use in companion animals. Vet.J. 173 21 PMID: 16324856

Ryberg et al (2007) The orphan receptor GPR55 is a novel cannabinoid receptor. Br.J.Pharmacol. 152 1092 PMID: 17876302


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Keywords: Palmitoylethanolamide, Palmitoylethanolamide supplier, Endogenous, lipid, PPARα, PPARalpha, agonists, activity, Selective, GPR55, FAAH, PAA, PEA-preferring, acid, amidase, Peroxisome, Proliferator-activating, Receptors, PPAR, Cannabinoid, Anandamide, Fatty, Acid, Amide, Hydrolases, PEA, Hydrolase, (FAAH), Other, Cannabinoids, 0879, Tocris Bioscience

10 Citations for Palmitoylethanolamide

Citations are publications that use Tocris products. Selected citations for Palmitoylethanolamide include:

Scuderi et al (2012) Palmitoylethanolamide exerts neuroprotective effects in mixed neuroglial cultures and organotypic hippocampal slices via peroxisome proliferator-activated receptor-α. Br J Pharmacol 9 49 PMID: 22405189

Nieri et al (2006) Modulation of P-glycoprotein activity by cannabinoid molecules in HK-2 renal cells. Br J Pharmacol 148 682 PMID: 16715117

Raso et al (2015) Palmitoylethanolamide treatment reduces blood pressure in spontaneously hypertensive rats: involvement of cytochrome p450-derived eicosanoids and renin angiotensin system. Int J Mol Sci 10 e0123602 PMID: 25951330

Lin et al (2015) Palmitoylethanolamide inhibits glutamate release in rat cerebrocortical nerve terminals. J Neuroinflammation 16 5555 PMID: 25768340

Maingret et al (2001) The endocannabinoid anandamide is a direct and selective blocker of the background K(+) channel TASK-1. EMBO J 20 47 PMID: 11226154

Musella (2017) A novel crosstalk within the endocannabinoid system controls GABA transmission in the striatum. Sci Rep 7 7363 PMID: 28779174

Redlich et al (2014) Palmitoylethanolamide stimulates phagocytosis of Escherichia coli K1 by macrophages and increases the resistance of mice against infections. PLoS One 11 108 PMID: 24927796

Chataigneau et al (1998) Cannabinoid CB1 receptor and endothelium-dependent hyperpolarization in guinea-pig carotid, rat mesenteric and porcine coronary arteries. Proc Natl Acad Sci U S A 123 968 PMID: 9535027

Ho et al (2008) 'Entourage' effects of N-palmitoylethanolamide and N-oleoylethanolamide on vasorelaxation to anandamide occur through TRPV1 receptors. Br J Pharmacol 155 837 PMID: 18695637

Melis et al (2008) Endogenous fatty acid ethanolamides suppress nicotine-induced activation of mesolimbic DA neurons through nuclear receptors. J Neurosci 28 13985 PMID: 19091987


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Literature in this Area

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