Linoleoyl Ethanolamide-d4

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 (Item No. 90155) 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).{11172,11151} It has weak affinity for the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors, exhibiting Ki values of 10 µM and 25 µM, respectively.{7422} However, it is only approximately 4-fold less potent than AEA at causing catalepsy in mice (ED50 of 26.5 mg/kg).{11177} 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.{11152} 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.{7251,3922}