- Product Name:
- Nalbuphine (base and/or unspecified salts)
- Morphinan-3,6,14-triol, 17-(cyclobutylmethyl)-4,5-epoxy-, (5α,6α)- (9CI)
- Nalbuphine (1.0mg/ml in Acetonitrile)
- Product Categories:
- Chiral Reagents
- Intermediates & Fine Chemicals
- Mol File:
nalbuphine Chemical Properties
- Melting point:
- Boiling point:
- 566.6±50.0 °C(Predicted)
- 1.44±0.1 g/cm3(Predicted)
nalbuphine Usage And Synthesis
Pale Yellow Solid
Nalbuphine is a mixed opioid agonist-antagonist. Nalbuphine is an analgesic (narcotic).
Mixed opioid agonist-antagonist. Analgesic (narcotic).
To a slurry of 110.5 g of 14-hydroxydihydronormorphinone in 2.5 liters of
methylene chloride and 280 ml of triethylamine was added a solution of 106 g
of cyclobutanecarboxylic acid chloride in 500 ml of methylene chloride. The
temperature of the reaction mixture was maintained at 20°C to 25°C during
the addition. After 5 minutes the reaction mixture was brought to reflux and
heated for 5 hours.
It was then cooled, washed with water, dried over sodium sulfate and evaporated to dryness. The residue was crystallized from benzene and pentane to give 138.5 g of the dicyclobutanecarbonyl derivative, melting point about 112°C (dec.).
The dicyclobutanecarbonyl derivative (136.7 g) was dissolved in 200 ml of tetrahydrofuran and added dropwise to a suspension of 34.2 g of lithium aluminum hydride in 1 liters of tetrahydrofuran. The temperature of the mixture rose to reflux during the addition. Reflux was maintained for 2 hours after the addition was completed. After cooling, 110 ml of ethyl acetate was added dropwise, followed by 30 ml of water, followed by a solution of 53 g of ammonium chloride in 125 ml of water. The resulting mixture was filtered and the inorganic precipitate was washed with methanol. Evaporation of the combined filtrates gave 66 g of N-cyclobutylmethyl-14-hydroxydihydronormorphinone, melting point 229°C to 231°C.