2,6-Methano-3-benzazocine-11-propanols. Lack of antagonism between optical antipodes and observation of potent narcotic antagonism by two N-methyl derivatives

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Abstract
Resolution of a 2,6-methano-3-benzazocine-11-propanol analog of buprenorphine showed that the biological activity resides in the levo antipode. An attempt to enhance agonist activity by preparation of N-methyl derivatives resulted in 2 compounds 3 and 5 times as potent as nalorphine as antagonists of phenazocine. These compounds are the most potent N-methyl narcotic antagonists [in rats and mice] reported to date.