3-Benzazocine amidinium nitronates. An unusual type of opiate antagonist

An interesting type of 3-benzazocine ring system which contains amidine functionality has been found to have significant narcotic antagonist activity. The isomeric 2-benzazocine, which incorporates similar structural features, except for the position of the ring nitrogen and adjacent phenyl substituent, is inactive. These 2- and 3-benzazocines can be synthesized in a single step from appropriately structured amidines and naphthalenes, and such syntheses may provide useful routes to new and interesting types of narcotic antagonists.