| Identification | Back Directory | [Name]
O-689 | [CAS]
166100-39-6 | [Synonyms]
O-689
F-2-ME-AN
FLUOROMETHANANDAMIDE
2-METHYL-2'-FLUORO AEA
(±)-2-Methyl Arachidonoyl-2&rsquo
(+/-)-2-METHYLARACHIDONYL-2'-FLUOROETHYLAMIDE
(+/-)-2-METHYLARACHIDONOYL-2'-FLUOROETHYLAMIDE
(+/-)-2-METHYLARACHIDONOLY-2'*-FLUOROETHYLAMIDE
2-Methyl-2μ-fluoro AEA, Fluoromethanandamide, O-689
(+/-)-N-(2-FLUOROETHYL)-2-METHYL-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE
(5Z,8Z,11Z,14Z)-N-(2-fluoroethyl)-2-methylicosa-5,8,11,14-tetraenamide
(+/-)-2-Methylarachidonoyl-2'-fluoroethylamide >=95%, ethanol solution
5,8,11,14-Eicosatetraenamide, N-(2-fluoroethyl)-2-methyl-, (5Z,8Z,11Z,14Z)- | [EINECS(EC#)]
200-578-6 | [Molecular Formula]
C23H38FNO | [MDL Number]
MFCD01862615 | [MOL File]
166100-39-6.mol | [Molecular Weight]
363.55 |
| Chemical Properties | Back Directory | [Boiling point ]
503.6±50.0 °C(Predicted) | [density ]
0.921±0.06 g/cm3(Predicted) | [Fp ]
14 °C | [storage temp. ]
−20°C | [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 | [form ]
ethanol solution | [pka]
14.98±0.46(Predicted) |
| Hazard Information | Back Directory | [Description]
(±)-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 α-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 Δ9-THC in animal self-administration tests, whereas AEA and 2-fluoro AEA cannot. |
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