Cayman Chemical | Linoleoyl Ethanolamide-d4

9000553 Linoleoyl Ethanolamide-d4

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Linoleoyl ethanolamide is an endocannabinoid detected in porcine brain and murine peritoneal macrophages which contains linoleate in place of the arachidonate moiety of arachidonyl ethanolamide (AEA).^1,2 It has weak affinity for the cannabinoid 1 (CB₁) and CB₂ receptors, exhibiting K_i 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 K_i 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 tissue. Prostaglandins 22(1) 105-115 (1981).

2 Schmid, P.C., Kuwae, T., Krebsbach, R.J., et al. Anandanide and other N-acylethanolamines in mouse peritoneal macrophages. Chem Phys Lipids 87 103-110 (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 stability. J Med Chem 41 5353-5361 (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 fluoride. Biol Pharm Bull 22(4) 366-370 (1999).

5 Berdyshev, E.V., Schmid, P.C., Krebsbach, R.J., et al. Cannabinoid-receptor-independent cell signalling by N-acylethanolamines. Biochem J 360 67-75 (2001).

6 Maccarrone, M., van der Stelt, M., Rossi, A., et al. Anandamide hydrolysis by human cells in culture and brain. J Biol Chem 273 32332-32339 (1998).

7 Bisogno, T., Maurelli, S., Melck, D., et al. Biosynthesis, uptake, and degradation of anandamide and palmitoylethanolamide in leukocytes. J Biol Chem 272 3315-3323 (1997).

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Pricing updated 2010-03-18.
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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.