(±)11(12)-EET Ethanolamide

Arachidonoyl ethanolamide (AEA, anandamide) is an endogenous lipid neurotransmitter with cannibingeric 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. (±)11(12)-EET ethanolamide is a potential cytochrome P450 (CYP450) metabolite of 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 FAAH inhibition. Evidence for the formation of (±)11(12)-EET ethanolamide in vivo has not been documented.Formal Name: N-(2-hydroxyethyl)-(±)11(12)-epoxy-5Z,8Z,14Z-eicosatrienamide. Synonyms: (±)11,12-EpETrE Ethanolamide. Molecular Formula: C22H37NO3. Formula Weight: 363.5. Purity: >98%. 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) (1:1): 0.5 mg/ml. SMILES: CCCCC/C=C\C[C@H]1O[C@H]1C/C=C\C/C=C\CCCC(=O)NCCO. InChi Code: InChI=1S/C22H37NO3/c1-2-3-4-5-9-12-15-20-21(26-20)16-13-10-7-6-8-11-14-17-22(25)23-18-19-24/h6,8-10,12-13,20-21,24H,2-5,7,11,14-19H2,1H3,(H,23,25)/b8-6-,12-9-,13-10-/t20-,21+/m1/s1. InChi Key: TYRRSRADDAROSO-ABRALVTRSA-N.