6-Keto Nalbuphine is a morphinan-derived opioid impurity arising from oxidative modification of the parent compound Nalbuphine. It features a ketone functional group at the C6 position, replacing the native hydroxyl moiety, and retains the core piperidine ring, phenolic hydroxyl, and tertiary amine characteristic of the nalbuphine scaffold. This structural alteration disrupts the stereochemical configuration critical for opioid receptor binding, rendering it pharmacologically inert. The compound serves as an HPLC reference standard for quantifying oxidative degradation pathways in nalbuphine formulations.
On RequestC1CC(C1)CN2CC[C@]34[C@@H]5C(=O)CC[C@]3([C@H]2CC6=C4C(=C(C=C6)O)O5)O
InChI=1S/C21H25NO4/c23-14-5-4-13-10-16-21(25)7-6-15(24)19-20(21,17(13)18(14)26-19)8-9-22(16)11-12-2-1-3-12/h4-5,12,16,19,23,25H,1-3,6-11H2/t16-,19+,20+,21-/m1/s1
VANAVLBJMFLURS-MBPVOVBZSA-N