Virodhamine-endogenous cannabinoid

ViRODHAMINE----ENDOGENOUS CANNABINOID WITH ANTAGONIST PROPERTIES... 

FIGURE 8.1 The principal endogenous cannabinoids. Anandamide and 2-arachidonyl glycerol (2-AG) are the most well-studied endocannabinoids however, conjugates with other fatty acids such as palmitic and eicosapenteneoic acid are well known. Novel structures such as virodhamine and noladin ether have also been reported. Arachidonic acid derivatives with other molecules such as dopamine (NADA) and glycine (NAGly) are also known. 

The best studied of the endocarmabinoids are anandamide (A -arachidonyl-ethanolamine, AEA)(1) and 2-arachidonylglycerol (2-AG)(2). Anandamide was first identified from porcine brain extracts by Devane and co-workers in 1992 [13], while 2-AG was first reported in 1995 to have been isolated from canine gut [14] and rat brain [15]. More recently, noladin ether (2-arachidonyl-glyceryl ether, 2-AGE)(3) [16], virodhamine (D-arachidonyl-ethanolamine)(4) [17] and A-arachidonyl-dopamine (NADA)(5) [18] were proposed as endogenous ligands for the cannabinoid receptors. In a subsequent publication, the authors failed to detect noladin ether in mammalian brains and questioned the relevance of this compound as an endocarmabinoid [19]. Anandamide, noladin ether and NADA have functional selectivity for CBi receptors, virodhamine is CB2 selective and 2-AG is essentially non-selective. 

FIGURE 14.1 Four endogenous substances suggested as being endocannabinoids anandamide (N-arachi-donoylethanolamine), 2-AG (2-arachidonoylglycerol), noladin ether (2-arachidonylglyceryl ether), and virodhamine (O-arachidonoylethanolamine). The stracture of the principal cannabinoid of plant origin, A -THC (A -tetrahydrocannabinol), is inserted. 

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