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6-Methylenedihydrodesoxymorphine is a potent μ-opioid agonist, reportedly up to 80x stronger than morphine. Compared to morphine it has a faster onset of action and similar duration of effects. It produces around the same degree of respiratory depression as morphine, but less inhibition of gastrointestinal motility. Animal studies show it to be a potent analgesic which produces significant analgesic effects even at low doses which produce comparatively few side effects, however it has never been developed for medical use in humans.
6-Methylenedihydrodesoxymorphine is synthesised in two steps; first a Wittig reaction is used, reacting hydrocodone with methylenetriphenylphosphorane and an alkyl lithium reagent in diethyl ether to form 6-Methylenedihydrodesoxycodeine. The 3-methoxy group is then cleaved to hydroxy, by reaction with pyridine. The second step tends to be incomplete and often gives fairly low yields, but these can be improved by changing the reaction conditions.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "6-Methylenedihydrodesoxymorphine". A list of authors is available in Wikipedia.|