Cerebrodiene, arachidonylethanolamide, and hybrid structures: potential for interaction with brain cannabinoid receptors

• Published in: Prostaglandins, leukotrienes and essential fatty acids leukotrienes and essential fatty acids, 1996-09, Vol.55 (3), p.207-210
• Main Authors: Boring, D.L., Berglund, B.A., Howlett, A.C.
• Format: Article
• Language: English
• ISSN: 0952-3278; 1532-2823
• DOI: 10.1016/S0952-3278(96)90100-3

Cerebrodiene ( cis-9, 10-octadecanoamide) was recently isolated from cerebral fluid of sleep-deprived cats and shown to induce sleep in rats. Because this lipid amide is related to arachidonylethanolamide (AEA), and because AEA binds to the cannabinoid receptor with high affinity, we investigated the binding affinity of cerebrodiene and some analogs to the cannabinoid receptor. In addition, we tested the ability of these compounds to act as cannabinoid receptor agonists by determining GTPγS binding. Each of the analogs competed for [ 3H] CP55940 binding, but with relatively low affinity ( K i = 26–44 μM). These analogs were not able to stimulate binding of GTPγS at concentrations of 100 μM or 1 mM. We conclude that the sleep-inducing actions of cerebrodiene are not mediated via activation of the cannabinoid receptor.