Numerous analogs of fatty acyl ethanolamides potentiate the intrinsic biological activity of arachidonoyl ethanolamide (anandamide; AEA).1 This potentiation is ascribed either to inhibition of AEA reuptake into neurons, or inhibition of fatty amide acyl hydrolase (FAAH) within the neurons.2 Oleoyl ethyl amide (OEtA) has potent FAAH inhibitory activity (IC50 5.25 nM in rat brain homogenates) but does not inhibit acidic PEAase or bind to CB1 or CB2 receptors. OEtA is therefore a selective FAAH inhibitor with potential analgesic and anxiolytic activity.3
1
Khanolkar, A.D., and Makriyannis, A. Structure-activity relationships of anandamide, an endogenous cannabinoid ligand. Life Sci65607-616(1999).
2
Deutsch, D.G., Glaser, S.T., Howell, J.M., et al. The cellular uptake of anandamide is coupled to its breakdown by fatty-acid amide hydrolase. J Biol Chem276(10)6967-6973(2001).
3
Vandevoorde, S., Lavand'homme, P., Fowler, C.J., et al. Oleoylethylamide, an analgesic FAAH inhibitor which modulates endogenous anandamide, oleoylethanolamide, and 2-arachidonoylglycerol levels in the brain. 14th Annual Symposium on the Cannabinoids15(2004).
Synonyms
N-Ethyloleamide
OEtA
Formal Name
N-ethyl-9Z-octadecenamide
CAS Number
85075-82-7
Molecular Formula
C20H39NO
Formula Weight
309.5
Formulation
A solution in methyl acetate
Purity
>98%
Stability
1 year
Storage
-20°C
Shipping
Room temperature
in continental US; may vary elsewhere
SMILES
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CCCCCCCC/C=C\CCCCCCCC(=O)NCC
Background Reading
Deutsch, D.G., Glaser, S.T., Howell, J.M., et al. The cellular uptake of anandamide is coupled to its breakdown by fatty-acid amide hydrolase. J Biol Chem276(10)6967-6973(2001).
Vandevoorde, S., Lavand'homme, P., Fowler, C.J., et al. Oleoylethylamide, an analgesic FAAH inhibitor which modulates endogenous anandamide, oleoylethanolamide, and 2-arachidonoylglycerol levels in the brain. 14th Annual Symposium on the Cannabinoids15(2004).
Khanolkar, A.D., and Makriyannis, A. Structure-activity relationships of anandamide, an endogenous cannabinoid ligand. Life Sci65607-616(1999).
Oleoyl Ethyl Amide is available in the following screening
library: