Analgesic narcotic antagonists. 9. 6-Methylene-8.beta.-alkyl-N-(cycloalkylmethyl)-3-hydroxy- or -methoxymorphinans

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Abstract
Series of N-(cyclopropylmethyl) or N-(cyclobutylmethyl) 3-methoxy or 3-hydroxy morphinan-6-ones with hydrogen, methyl or ethyl groups in the 8.beta. position were converted to the 6-methylene compounds 4-hydroxy-3-methoxy-7.alpha.,8.beta.,17-trimethylmorphinan-6-one or 4-hydroxy-3-methoxy-7.alpha.-methyl- or -7.alpha.,8.beta.-dimethyl morphinan-6-ones by reaction with methylene triphenylphosphorane. One member of this new series, N-(cyclobutylmethyl)-8.beta.-methyl-6-methylenemorphinan-3-ol, had potent mixed agonist-narcotic antagonist properties and, in contrast to the previously studied 6-oxo compound, did not substitute for morphine in dependent rats or monkeys.

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