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90055 (±)-2-Methyl Arachidonoyl-2'-Fluoroethylamide
O-689; 2-Methyl-2'-fluoro Anandamide; 2-methyl-2'-fluoro AEA
(CAS 166100-39-6)
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(±)-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. It also confers additional selectivity, in that binding to CB2 is decreased relative to AEA.1 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.2
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1
Lin, S., Khanolkar, A.D., Fan, P., et al. Novel analogues of arachidonylethanolamide (anandamide): Affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability. J Med Chem 41 5353-5361 (1998).
2
Ryan, W.J., Banner, K., Crocker, P.J., et al. Synthesis of (+)- and (−)-2-methylarachidonyl-2'-fluoroethylamide (O-689). Bioorg Medicinal Chem Letters 7 2669-2672 (1997).
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Pricing updated 2010-03-17.
Prices are subject to change without notice.
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Stability of this item is suitable for room temperature overnight shipping. If shipment on ice is desired, it must be requested when the order is placed.
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