Nalbuphine: Nalbuphine, 17-(cyclobutylmethyl)-4,5-a-epoximorphinan-3,6a,14-triol (3.1.85), is synthesized from oxymorphone (3.1.26), which after protecting the hydroxyl group by acetylation undergoes a reaction with cyanogen bromide, giving an N-cyano derivative, and further hydrolysis of which using hydrochloric acid gives 14-hydroxydihy-dronormorphone (3.1.82). Transformation of the resulting product into the desired nalbuphine (3.1.85) is accomplished either by reduction of the carbonyl group of the resulting 14-hydroxydihydronormaphone by sodium borohydride into (3.1.83) and the subsequent alkylation of the product by cyclobutylmethylbromide, or by the acylation (3.1.82) with cyclobutancarboxylic acid chloride into (3.1.84) and the subsequent simultaneous reduction of two carbonyl groups in the resulting compound using lithium aluminum hydride, giving the desired product [51,52].
Nalbuphine is a strong analgesic with activity equal to that of morphine. It is structurally similar to oxymorphone and the opioid antagonist naloxone. It exhibits fewer side effects than nalorphine. Nalbuphine is prescribed as a drug for alleviating moderate to severe pain. It is used as a supplementary drug for balanced anesthesia, for pre- and post-operational analgesia, and in gynecological interventions. The most common synonym for nalbuphine is nubaine.
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