Oleoyl ethanolamide (OEA) is an analog of the endocannabinoid AEA found in brain tissue and in chocolate.1 It is one of the long chain fatty acid ethanolamides that accumulates rapidly in infarcted tissue,2 but its biosynthesis is reduced in the intestine of rats following food deprivation.3 OEA is an endogenous, potent agonist for PPARα, exhibiting an EC50 value of 120 nM in a transactivation assay.4 Systemic administration of OEA suppresses food intake and reduces weight gain in rats (10 mg/kg intraperitoneally) and PPARα wild-type mice, but not in PPARα knockout mice.3,4 These data indicate that OEA regulates food intake by a PPARα-mediated mechanism.
1
di Tomaso, E., Beltramo, M., and Piomelli, D. Brain cannabinoids in chocolate. Nature382677-678(1996).
2
Epps, D.E., Palmer, J.W., Schmid, H.H.O., et al. Inhibition of permeability-dependent Ca2+ release from mitochondria by N-acelethanolamines, a class of lipids synthesized in ischemic heart tissue. J Biol Chem2571383-1392(1982).
3
de Fonseca, F.R., Navarro, M., Gómez, R., et al. An anorexic lipid mediator regulated by feeding. Nature414209-212(2001).
4
Fu, J., Gaetani, S., Oveisi, F., et al. Oleylethanolamide regulates feeding and body weight through activation of the nuclear receptor PPAR-α. Nature42590-93(2003).
Synonyms
Oleic Acid Ethanolamide
OEA
Formal Name
N-(2-hydroxyethyl)-9Z-octadecenamide
CAS Number
111-58-0
Molecular Formula
C20H39NO2
Formula Weight
325.5
Formulation
A crystalline solid
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)NCCO
Background Reading
de Fonseca, F.R., Navarro, M., Gómez, R., et al. An anorexic lipid mediator regulated by feeding. Nature414209-212(2001).
Fu, J., Gaetani, S., Oveisi, F., et al. Oleylethanolamide regulates feeding and body weight through activation of the nuclear receptor PPAR-α. Nature42590-93(2003).
Epps, D.E., Palmer, J.W., Schmid, H.H.O., et al. Inhibition of permeability-dependent Ca2+ release from mitochondria by N-acelethanolamines, a class of lipids synthesized in ischemic heart tissue. J Biol Chem2571383-1392(1982).
di Tomaso, E., Beltramo, M., and Piomelli, D. Brain cannabinoids in chocolate. Nature382677-678(1996).