The relationship between analgesic activity, acute toxicity and chemical structure in esters of 14-hydroxycodeinone

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Abstract
Acylation of 14-hydroxycodeinone with long chain unbranched fatty acids produced compounds of varying analgesic potency, maximal activity being in 14-n-heptoyl-oxycodeinone. In 14-phenylalkyloxy derivatives maximal analgesic potency was found in 14-cinnamoyloxycodeinone. All codeinone derivatives studied had approximately one-third the duration of morphine in mice. Intravenous and subcutaneous toxicities in mice were generally similar in compounds causing death by convulsions, but differed widely in those causing death by respiratory depression.

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