Oleylethanolamide - CAS 111-58-0
Catalog number: B0084-081716
Category: Inhibitor
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Molecular Formula:
C20H39NO2
Molecular Weight:
325.53
COA:
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Targets:
PPAR
Description:
Oleylethanolamide is an endogenous agonist for PPARα with an EC50 value of 120 nM in a transactivation assay. Oleylethanolamide is also a selective GPR55 agonist with EC50 value of 120 μM. It is involved in peripheral regulation of feeding.
Nutritional supplement in health care products.
Purity:
≥99% by HPLC
Synonyms:
(9Z)-N-(2-Hydroxyethyl)-9-octadecenamide
MSDS:
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Application:
Ingredient of health care products.
InChIKey:
BOWVQLFMWHZBEF-KTKRTIGZSA-N
InChI:
InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-
Canonical SMILES:
CCCCCCCCC=CCCCCCCCC(=O)NCCO
1.Inhibition of FAAH confers increased stem cell migration via PPARα.
Wollank Y1, Ramer R2, Ivanov I2, Salamon A3, Peters K3, Hinz B2. J Lipid Res. 2015 Oct;56(10):1947-60. doi: 10.1194/jlr.M061473. Epub 2015 Aug 11.
Regenerative activity in tissues of mesenchymal origin depends on the migratory potential of mesenchymal stem cells (MSCs). The present study focused on inhibitors of the enzyme fatty acid amide hydrolase (FAAH), which catalyzes the degradation of endocannabinoids (anandamide, 2-arachidonoylglycerol) and endocannabinoid-like substances (N-oleoylethanolamine, N-palmitoylethanolamine). Boyden chamber assays, the FAAH inhibitors, URB597 and arachidonoyl serotonin (AA-5HT), were found to increase the migration of human adipose-derived MSCs. LC-MS analyses revealed increased levels of all four aforementioned FAAH substrates in MSCs incubated with either FAAH inhibitor. Following addition to MSCs, all FAAH substrates mimicked the promigratory action of FAAH inhibitors. Promigratory effects of FAAH inhibitors and substrates were causally linked to activation of p42/44 MAPKs, as well as to cytosol-to-nucleus translocation of the transcription factor, PPARα.
2.Alterations in Spinal Cord Metabolism during Treatment of Neuropathic Pain.
Johnson CH1, Patti GJ, Courade JP, Shriver LP, Hoang LT, Manchester M, Siuzdak G. J Neuroimmune Pharmacol. 2015 Sep;10(3):396-401. doi: 10.1007/s11481-015-9624-y. Epub 2015 Aug 2.
Therapeutic options for neuropathic pain have improved over the last 20 years yet still only provide partial relief with numerous side effects. Recently, metabolomics revealed that the concentration of the endogenous metabolite N,N-dimethylsphingosine (DMS) is increased in the spinal cord in a model of neuropathic pain. Additionally, it was shown that introduction of DMS to the central nervous system (CNS) resulted in mechanical allodynia. Here, we have examined two compounds; pregabalin (Lyrica®), a drug used to treat neuropathic pain, and N-oleoylethanolamine (NOE), an endogenous endocannabinoid-like compound that is known to affect multiple lipid pathways. We found that the concentration of DMS in the spinal cord was not significantly altered upon pregabalin treatment of rats suffering from neuropathic pain. We further explored whether modulating lipid metabolism may impact neuropathic pain by testing NOE as a potential novel therapeutic.
3.Comparative effects of parathion and chlorpyrifos on endocannabinoid and endocannabinoid-like lipid metabolites in rat striatum.
Liu J1, Parsons L2, Pope C3. Neurotoxicology. 2015 Sep;50:20-7. doi: 10.1016/j.neuro.2015.07.006. Epub 2015 Jul 26.
Parathion and chlorpyrifos are organophosphorus insecticides (OPs) that elicit acute toxicity by inhibiting acetylcholinesterase (AChE). The endocannabinoids (eCBs, N-arachidonoylethanolamine, AEA; 2-arachidonoylglycerol, 2AG) are endogenous neuromodulators that regulate presynaptic neurotransmitter release in neurons throughout the central and peripheral nervous systems. While substantial information is known about the eCBs, less is known about a number of endocannabinoid-like metabolites (eCBLs, e.g., N-palmitoylethanolamine, PEA; N-oleoylethanolamine, OEA). We report the comparative effects of parathion and chlorpyrifos on AChE and enzymes responsible for inactivation of the eCBs, fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL), and changes in the eCBs AEA and 2AG and eCBLs PEA and OEA, in rat striatum. Adult, male rats were treated with vehicle (peanut oil, 2 ml/kg, sc), parathion (27 mg/kg) or chlorpyrifos (280 mg/kg) 6-7 days after surgical implantation of microdialysis cannulae into the right striatum, followed by microdialysis two or four days later.
4.Simultaneous determination of endocannabinoids in murine plasma and brain substructures by surrogate-based LC-MS/MS: Application in tumor-bearing mice.
Gong Y1, Li X1, Kang L2, Xie Y1, Rong Z1, Wang H1, Qi H3, Chen H1. J Pharm Biomed Anal. 2015;111:57-63. doi: 10.1016/j.jpba.2015.03.017. Epub 2015 Mar 26.
The endocannabinoids (eCBs), N-arachidonoylethanolamine (anandamide, AEA) and 2-ararchidonylglycerol (2-AG) have been identified as main endogenous ligands for cannabinoid receptors. Developing a sensitive and robust method to determine AEA and 2-AG has been shown to be essential to understand their effects in stress regulation and the pathogenesis of affective disorders. Since eCBs are endogenous molecules, there is no true blank matrix available to construct calibration curves, thus, it has been a challenge to determine eCBs in plasma and brain matrix. A liquid chromatography tandem mass spectrometry (LC-MS/MS) method is developed to determine the concentrations of AEA and 2-AG in murine plasma and different brain substructures (prefrontal cortex, hippocampus and hypothalamus). To overcome the endogenous interference, a "surrogate analyte" approach was adopted using stable isotope-labeled standards as surrogates of authentic analytes to generate calibration curves in biological matrix.
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CAS 111-58-0 Oleylethanolamide

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