(±)8(9)-EET Ethanolamide

Arachidonoyl ethanolamide (AEA, anandamide) 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 COX-2, lipoxygenases, and cytochrome P450 (CYP450) enzymes has also been documented. (±)8(9)-EET ethanolamide is a CYP450 metabolite of AEA, although specific stereochemistry rather than a racemic mixture would likely ensue from enzymatic metabolism. Human liver microsomes metabolize AEA to 5,6-, 8,9-, 11,12-, and 14,15-EET ethanolamides in a time and protein concentration dependent manner. (±)8(9)-EET reduces glomerular filtration rate through cyclooxygenase dependent preglomerular vasoconstriction. The physiological actions of (±)8(9)-EET ethanolamide have not been examined.Formal Name: N-(2-hydroxyethyl)-(±)8(9)-epoxy-5Z,11Z,14Z-eicosatrienoic amide. Synonyms: (±)8,9-EET Ethanolamide. Molecular Formula: C22H37NO3. Formula Weight: 363.5. Purity: >98%. Formulation: (Request formulation change), A solution in ethanol. Solubility: DMF: 50 mg/ml, DMSO: 50 mg/ml, Ethanol: 50 mg/ml, PBS (pH 7.2): 1 mg/ml. SMILES: CCCCC/C=C\C/C=C\C[C@H]1O[C@H]1C/C=C\CCCC(=O)NCCO. InChi Code: InChI=1S/C22H37NO3/c1-2-3-4-5-6-7-8-9-12-15-20-21(26-20)16-13-10-11-14-17-22(25)23-18-19-24/h6-7,9-10,12-13,20-21,24H,2-5,8,11,14-19H2,1H3,(H,23,25)/b7-6-,12-9-,13-10-/t20-,21+/m1/s1. InChi Key: BXHPMUQFGGSDAK-PDFUHZMOSA-N.