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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

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

Cayman Chemical Item Number 90055

O-689; 2-Methyl-2'-fluoro Anandamide; 2-methyl-2'-fluoro AEA (CAS 166100-39-6)

(±)-2-Methyl Arachidonoyl-2'-Fluoroethylamide (CAS 166100-39-6)

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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. 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

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 Med Chem Lett 7 2669-2672 (1997).

Synonyms
  • O-689
  • 2-Methyl-2'-fluoro Anandamide
  • 2-methyl-2'-fluoro AEA
Formal Name (±)-​N-​(2-​fluoroethyl)-​2-​methyl-​5Z,​8Z,​11Z,​14Z-​eicosatetraenamide
CAS Number 166100-39-6
Molecular Formula C23H38FNO
Formula Weight 363.6
Formulation A solution in ethanol
Purity >95%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCC(C)​C(=O)​NCCF

Background Reading

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).

Ryan, W.J., Banner, K., Crocker, P.J., et al. Synthesis of (+)- and (−)-2-methylarachidonyl-2'-fluoroethylamide (O-689). Bioorg Med Chem Lett 7 2669-2672 (1997).

(±)-2-Methyl Arachidonoyl-2'-Fluoroethylamide is available in the following screening library:

Size Price Quantity Subtotal
1 mg $19.00 $0.00
5 mg $86.00 $0.00
10 mg $152.00 $0.00
50 mg $665.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-02-09. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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