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Linoleoyl ethanolamide-d4 contains four deuterium atoms at the hydroxyethyl 1,1',2, and 2' positions. It is intended for use as an internal standard for the quantification of linoleoyl ethanolamide by GC- or LC-mass spectrometry. Linoleoyl ethanolamide is an endocannabinoid detected in porcine brain and murine peritoneal macrophages which contains linoleate in place of the arachidonate moiety of arachidonoyl ethanolamide (AEA).1,2 It has weak affinity for the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors, exhibiting Ki values of 10 µM and 25 µM, respectively.3 However, it is only approximately 4-fold less potent than AEA at causing catalepsy in mice (ED50 of 26.5 mg/kg).4 In addition, linoleoyl ethanolamide increases ERK phosphorylation and AP-1-dependent transcription approximately 1.5-fold at 15 µM in a CB-receptor-independent manner.5 However, cellular toxicity is readily apparent at concentrations of 10-20 µM. Linoleoyl ethanolamide inhibits human fatty acid amide hydrolase-dependent hydrolysis of AEA with a Ki value of 9.0 µM, but also is hydrolyzed effectively by the enzyme.6,7

1.Patrono, C., Rotella, C.M., Toccafondi, R.S., et al.Prostacyclin stimulates the adenylate cyclase system of human thyroid tissueProstaglandins22(1)105-115(1981) 2.Schmid, P.C., Kuwae, T., Krebsbach, R.J., et al.Anandanide and other N-acylethanolamines in mouse peritoneal macrophagesChemistry and Physics of Lipids87103-110(1997) 3.Lin, S., Khanolkar, A.D., Fan, P., et al.Novel analogues of arachidonylethanolamide (anandamide): Affinities for the CB1 and CB2 cannabinoid receptors and metabolic stabilityJournal of Medicinal Chemistry415353-5361(1998) 4.Watanabe, K., Matsunaga, T., Nakamura, S., et al.Pharmacological effects in mice of anandamide and its related fatty acid ethanolamides, and enhancement of cataleptogenic effect of anandamide by phenylmethylsulfonyl fluorideBiological and Pharmaceutical Bullentin22(4)366-370(1999) 5.Berdyshev, E.V., Schmid, P.C., Krebsbach, R.J., et al.Cannabinoid-receptor-independent cell signalling by N-acylethanolaminesBiochemistry Journal36067-75(2001) 6.Maccarrone, M., van der Stelt, M., Rossi, A., et al.Anandamide hydrolysis by human cells in culture and brainThe Journal of Biological Chemisty27332332-32339(1998) 7.Bisogno, T., Maurelli, S., Melck, D., et al.Biosynthesis, uptake, and degradation of anandamide and palmitoylethanolamide in leukocytesThe Journal of Biological Chemisty2723315-3323(1997)

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