Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H37NO2 |
| Molecular Weight | 299.4919 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCCCC(=O)NCCO
InChI
InChIKey=HXYVTAGFYLMHSO-UHFFFAOYSA-N
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)
Palmidrol (palmitoylethanolamide, PEA) is a natural fatty acid amide found in a variety of foods, which was initially identified in egg yolk. It is an endogenous compound, locally synthesized in animal and human tissues and body fluids, to protect against perturbing inflammation. In addition to its anti-inflammatory activity, palmidrol (palmitoylethanolamide, PEA) also produces analgesia, neuroprotection, and possesses anti-epileptic properties. It also reduces gastrointestinal motility and cancer cell proliferation, as well as protecting the vascular endothelium in the ischemic heart. The physiological stimuli that regulate palmidrol (palmitoylethanolamide, PEA) levels in mammalian tissues are largely unknown, however, multiple studies indicate that this lipid accumulates during cellular stress, particularly following tissue injury. Palmidrol (palmitoylethanolamide, PEA) is a potent and selective agonist of orphan receptor GPR55.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| The psychedelic haze of inflammation. | 2007-01 |
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| Palmitoylethanolamide, endocannabinoids and related cannabimimetic compounds in protection against tissue inflammation and pain: potential use in companion animals. | 2007-01 |
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| [Topical cannabinoid agonists. An effective new possibility for treating chronic pruritus]. | 2006-09 |
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| Structure-based design of a FAAH variant that discriminates between the N-acyl ethanolamine and taurine families of signaling lipids. | 2006-08-01 |
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| A FAAH-regulated class of N-acyl taurines that activates TRP ion channels. | 2006-08-01 |
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| High-throughput screening for the discovery of inhibitors of fatty acid amide hydrolase using a microsome-based fluorescent assay. | 2006-08 |
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| Modulation of P-glycoprotein activity by cannabinoid molecules in HK-2 renal cells. | 2006-07 |
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| Molecular packing and intermolecular interactions in two structural polymorphs of N-palmitoylethanolamine, a type 2 cannabinoid receptor agonist. | 2006-07 |
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| Diurnal variation of arachidonoylethanolamine, palmitoylethanolamide and oleoylethanolamide in the brain of the rat. | 2006-05-30 |
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| Cannabinoid receptors and endocannabinoids: evidence for new players. | 2006-04-28 |
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| Oxyhomologues of anandamide and related endolipids: chemoselective synthesis and biological activity. | 2006-04-06 |
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| MimyX cream. | 2006-03-09 |
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| Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents. | 2006-03 |
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| The cannabinoid CB2 receptor selective agonist JWH133 reduces mast cell oedema in response to compound 48/80 in vivo but not the release of beta-hexosaminidase from skin slices in vitro. | 2006-01-02 |
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| Cannabinoid receptor agonists inhibit Ca(2+) influx to synaptosomes from rat brain. | 2006 |
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| Identification of an unusual naturally occurring apolar fatty acid amide in mammalian brain and a method for its quantitative determination. | 2006 |
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| Molecular biology of the enzymes that degrade endocannabinoids. | 2005-12 |
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| Involvement of N-acylethanolamine-hydrolyzing acid amidase in the degradation of anandamide and other N-acylethanolamines in macrophages. | 2005-10-01 |
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| Fatty acid amide hydrolase controls mouse intestinal motility in vivo. | 2005-09 |
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| Increased plasma concentrations of palmitoylethanolamide, an endogenous fatty acid amide, affect oxidative damage of human low-density lipoproteins: an in vitro study. | 2005-09 |
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| Endogenous cannabinoid receptor agonists inhibit neurogenic inflammations in guinea pig airways. | 2005-09 |
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| Effects of N-acylethanolamines on the respiratory chain and production of reactive oxygen species in heart mitochondria. | 2005-08-29 |
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| The search for the palmitoylethanolamide receptor. | 2005-08-19 |
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| Anandamide induced PPARgamma transcriptional activation and 3T3-L1 preadipocyte differentiation. | 2005-07-11 |
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| Emollients with endocannabinoids in the treatment of uremic pruritus: discussion of the therapeutic options. | 2005-06 |
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| Involvement of the cannabimimetic compound, N-palmitoyl-ethanolamine, in inflammatory and neuropathic conditions: review of the available pre-clinical data, and first human studies. | 2005-06 |
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| A second N-acylethanolamine hydrolase in mammalian tissues. | 2005-06 |
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| Accumulation of anandamide: evidence for cellular diversity. | 2005-06 |
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| Finding of endocannabinoids in human eye tissues: implications for glaucoma. | 2005-05-20 |
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| Idiopathic infertility: effect of palmitoylethanolamide (a homologue of anandamide) on hyperactivated sperm cell motility and Ca2+ influx. | 2005-05-04 |
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| Molecular characterization of N-acylethanolamine-hydrolyzing acid amidase, a novel member of the choloylglycine hydrolase family with structural and functional similarity to acid ceramidase. | 2005-03-25 |
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| Effects of saturated long-chain N-acylethanolamines on voltage-dependent Ca2+ fluxes in rabbit T-tubule membranes. | 2005-02-15 |
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| The postmortal accumulation of brain N-arachidonylethanolamine (anandamide) is dependent upon fatty acid amide hydrolase activity. | 2005-02 |
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| The nuclear receptor peroxisome proliferator-activated receptor-alpha mediates the anti-inflammatory actions of palmitoylethanolamide. | 2005-01 |
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| Efficacy and tolerance of the cream containing structured physiological lipids with endocannabinoids in the treatment of uremic pruritus: a preliminary study. | 2005 |
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| Focus on the three key enzymes hydrolysing endocannabinoids as new drug targets. | 2005 |
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| Lipopolysaccharide-induced pulmonary inflammation is not accompanied by a release of anandamide into the lavage fluid or a down-regulation of the activity of fatty acid amide hydrolase. | 2004-12-10 |
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| Selective antiepileptic effects of N-palmitoylethanolamide, a putative endocannabinoid. | 2004-10 |
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| Anandamide transport inhibitor AM404 and structurally related compounds inhibit synaptic transmission between rat hippocampal neurons in culture independent of cannabinoid CB1 receptors. | 2004-08-02 |
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| Effects of N-acylethanolamines on mitochondrial energetics and permeability transition. | 2004-07-09 |
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| Biosynthesis of anandamide and N-palmitoylethanolamine by sequential actions of phospholipase A2 and lysophospholipase D. | 2004-06-15 |
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| N-cyclohexanecarbonylpentadecylamine: a selective inhibitor of the acid amidase hydrolysing N-acylethanolamines, as a tool to distinguish acid amidase from fatty acid amide hydrolase. | 2004-04-01 |
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| Analyses of anandamide and endocannabinoid-like compounds using collision-induced dissociation in fast atom bombardment ionization-mass spectrometry and gas chromatography/chemical ionization-mass spectrometry. | 2003-12 |
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| A novel neuroimmune mechanism in cannabinoid-mediated attenuation of nerve growth factor-induced hyperalgesia. | 2003-12 |
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| Cannabinoid CB1 receptor activation does not prevent the toxicity of glutamate towards embryonic chick telencephalon primary cultures. | 2003-11 |
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| Effects of water-soluble cigarette smoke extracts upon the release of beta-hexosaminidase from RBL-2H3 basophilic leukaemia cells in response to substance P, compound 48/80, concanavalin A and antigen stimulation. | 2003-11 |
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| Miscibility and phase behaviour of binary mixtures of N-palmitoylethanolamine and dipalmitoylphosphatidylcholine. | 2003-10-13 |
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| Esters, retroesters, and a retroamide of palmitic acid: pool for the first selective inhibitors of N-palmitoylethanolamine-selective acid amidase. | 2003-10-09 |
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| An endogenous cannabinoid tone attenuates cholera toxin-induced fluid accumulation in mice. | 2003-09 |
|
| Palmitoylethanolamide increases after focal cerebral ischemia and potentiates microglial cell motility. | 2003-08-27 |
Patents
Sample Use Guides
Ultra-micronized palmitoylethanolamide 600 mg twice daily.
Route of Administration:
Oral
Palmitoylethanolamide (PEA) potently enhances the anti-proliferative effects of arachidonoylethanolamide (AEA) on human breast cancer cells (HBCCs), in part by inhibiting the expression of fatty acid amide hydrolase (FAAH), the major enzyme catalyzing AEA degradation. PEA (1-10 microM) enhanced in a dose-related manner the inhibitory effect of AEA on both basal and nerve growth factor (NGF)-induced HBCC proliferation, without inducing any cytostatic effect by itself. PEA (5 microM) decreased the IC50 values for AEA inhibitory effects by 3-6-fold. The effect of PEA was due in part to inhibition of AEA degradation, since treatment of MCF-7 breast cancer cells with 5 microM PEA caused an approximately 30-40% down-regulation of FAAH expression and activity.
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NCI_THESAURUS |
C2198
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DSLD |
4007 (Number of products:10)
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2045
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871
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DTXSID4042254
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SUB09590MIG
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4671
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C66294
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208-867-9
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m8366
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CHEMBL417675
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23320
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6R8T1UDM3V
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PALMITOYLETHANOLAMIDE
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100000082761
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544-31-0
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DB14043
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2001986
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71464
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ACTIVE MOIETY
