(±)14(15)-EET Ethanolamide

Arachidonyl ethanolamide (AEA) is an endogenous lipid neurotransmitter with cannabinergic activity, binding to both the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors. Fatty acid amide hydrolase (FAAH) is the enzyme responsible for the hydrolysis and inactivation of AEA. Metabolism of AEA by cyclooxygenase-2, leading to formation of prostaglandin ethanolamides, and by lipoxygenases has also been documented. (±)14(15)-EET ethanolamide is a potential cytochrome P450 (CYP450) metabolite of arachidonoyl ethanolamide (AEA), although specific stereochemistry rather than a racemic mixture would likely ensue from enzymatic metabolism. CYP450 metabolism of AEA may be particularly relevant under conditions of fatty acid amide hydrolase inhibition. Evidence for the formation of (±)14(15)-EET ethanolamide in vivo has not been documented.Formal Name: N-(2-hydroxyethyl)-(±)14(15)-epoxy-5Z,8Z,11Z-eicosatrienamide. Synonyms: (±)14,15-EpETrE Ethanolamide, (±)14(15)-Epoxy Eicosatrienoyl Ethanolamide. Molecular Formula: C22H37NO3. Formula Weight: 363.5. Purity: >95%. Formulation: (Request formulation change), A solution in ethanol. Solubility: DMF: 30 mg/ml, DMSO: 20 mg/ml, Ethanol: 30 mg/ml, Ethanol:PBS (pH 7.2) (1:6): 0.5 mg/ml. SMILES: CCCCC[C@H]1O[C@H]1C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO. InChi Code: InChI=1S/C22H37NO3/c1-2-3-12-15-20-21(26-20)16-13-10-8-6-4-5-7-9-11-14-17-22(25)23-18-19-24/h4,6-7,9-10,13,20-21,24H,2-3,5,8,11-12,14-19H2,1H3,(H,23,25)/b6-4-,9-7-,13-10-/t20-,21+/m1/s1. InChi Key: WYVHLKMCZZDTOU-XYFYYYGJSA-N.