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| Formula | C18H25NO2 |
| Molar mass | 287.403 g·mol−1 |
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Moxazocine (BL-4566) is anopioidanalgesic of thebenzomorphan family which was never marketed.[1] It acts as apartial agonist or mixedagonist/antagonist of theopioid receptors and binds preferentially to theκ-opioid receptor.[2] Despite its failure to reach the market,clinical studies demonstrated moxazocine to be approximately 10x aspotent by weight asmorphine as an analgesic.[3]
Reduction of the carbonyl group in oxygenatedbenzomorphan1 affords the corresponding alcohol (2). This intermediate is then N-demethylated by means ofBrCN. Acylation withcyclopropylcarbonyl chloride[6][7] gives the amide (3). The alcohol is then converted to the ether by treatment withMeI and base (4). Treatment withLiAlH4 serves to reduce the amide function. Cleavage of the phenolic ether by one of the standard schemes affords moxazocine (6).
