6357. Nalbuphine

Nomenclature

CAS number: 20594-83-6
(5α,6α)-17-(Cyclobutylmethyl)-4,5-epoxymorphinan-3,6,14-triol; N-cyclobutylmethyl-14-hydroxydihydronormorphine.
C21H27NO4; mol wt 357.44.
C 70.56%, H 7.61%, N 3.92%, O 17.90%.

Description and references

Mixed opioid agonist-antagonist. Prepn: GB 1119270; I. J. Pachter, Z. Matossian, US 3393197 (both 1968 to Endo). HPLC determn in plasma: F. de Cazanove et al., J. Chromatogr. B 690, 203 (1997). Opioid receptor binding profile: J.-C. Chen et al., Life Sci. 52, 389 (1993). Review of pharmacology and abuse potential: W. K. Schmidt et al., Drug Alcohol Depend. 14, 339-362 (1985); of analgesic efficacy and clinical experience: M. W. Gunion et al., Acute Pain 6, 29-39 (2004).

Chemical structure

Properties

Cryst from methanol-acetone, mp 230.5°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 23277-43-2
EN-2234A; Nubain (Endo).
C21H27NO4.HCl; mol wt 393.90.
C 64.03%, H 7.16%, N 3.56%, O 16.25%, Cl 9.00%.

Properties

pKa1 8.71; pKa2 9.96. Soly in water at 25°: 35.5 mg/ml. Sol in ethanol (0.8%). Insol in chloroform, ether.

Therapeutic Category

Analgesic.

Keywords

Analgesic; Opioids; Phenanthrenes