(±)-2-Methyl Arachidonoyl-2'-Fluoroethylamide

(±)-2-Methyl arachidonoyl-2'-fluoroethylamide (2-Methyl-2'-fluoro AEA) is an analog of anandamide (AEA) in which the alcohol of the ethanolamide group has been removed and replaced with a fluorine atom. This substitution confers considerably increased binding affinity for the CB1 receptor (Ki = 5.7 nM in rat brain). It also confers additional selectivity, in that binding to CB2 is decreased relative to AEA. However, the in vivo activity of 2-fluoro AEA is enhanced much less than the binding affinity, because the analog remains a good substrate for FAAH and is rapidly hydrolyzed by this enzyme. 2-Methyl-2'-fluoro AEA is further modified by the addition of an alpha-methyl group at the C-2 position of arachidonic acid. This substitution confers enhanced metabolic stability. 2-Methyl-2'-fluoro AEA can fully substitute for Delta9-THC in animal self-administration tests, whereas AEA and 2-fluoro AEA cannot.Formal Name: (±)-N-(2-fluoroethyl)-2-methyl-5Z,8Z,11Z,14Z-eicosatetraenamide. CAS Number: 166100-39-6. Synonyms: 2-methyl-2'-fluoro AEA, 2-Methyl-2'-fluoro Anandamide, O-689. Molecular Formula: C23H38FNO. Formula Weight: 363.6. Purity: >95%. Formulation: (Request formulation change), A solution in ethanol. Solubility: DMF: >10 mg/ml, DMSO: >30 mg/ml, Ethanol: >100 mg/ml, Ethanol:PBS (1:2): 8.5 mg/ml, PBS (pH 7.2): <100 µg/ml. SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCC(C)C(=O)NCCF. InChi Code: InChI=1S/C23H38FNO/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(2)23(26)25-21-20-24/h7-8,10-11,13-14,16-17,22H,3-6,9,12,15,18-21H2,1-2H3,(H,25,26)/b8-7-,11-10-,14-13-,17-16-. InChi Key: HMMNZALKMVCHHZ-ZKWNWVNESA-N.