Synthesis and characterization of the potent cannabinoid agonist [naphthyl‐³H] WIN 55212‐2 at high specific activity

Abstract

Summary [Naphthyl-3 H] WIN 55212-2 was prepared at high specific activity by the catalytic tritiation of dibromo precursor 3. Product 4 was characterized by chromatography as well as tritium NMR and proven to be a useful radioligand. Copyright # 2002 John Wiley & Sons, Ltd.Key Words: tritium; WIN 55212-2; cannabinoid; tritium NMR DiscussionAs a compound class the cannabinoids have demonstrated beneficial medicinal properties including analgesia, anti-emesis and the reduction of intraocular pressure. 1 However, the many untoward side effects of these substances has prompted the search for newer and safer alternative chemotherapeutic agents. During the last decade, the discovery and characterization of two distinct cannabinoid receptors, termed CB1 and CB2, has heightened interest in this area 2,3 and several diverse structures have been identified as potent agonists at these receptors.One such lead structure is the indole pravadoline 1, an analgesic and cyclooxygenase inhibitor. 4 To learn how the geometry of the morpho-