Basic information Safety Supplier Related

nalbuphine

Basic information Safety Supplier Related

nalbuphine Basic information

Product Name:
nalbuphine
Synonyms:
  • NETZHAKZCGBWSS-CEDHKZHLSA-N
  • Nalbuphinebase
  • 17-[Cyclobutylmethyl]-4,5α-epoxymorphinan-3,6α,14-triol
  • NALBUPNINE
  • Nalbuphine (base and/or unspecified salts)
  • C07251
  • Morphinan-3,6,14-triol, 17-(cyclobutylmethyl)-4,5-epoxy-, (5α,6α)- (9CI)
  • Nalbuphine (1.0mg/ml in Acetonitrile)
CAS:
20594-83-6
MF:
C21H27NO4
MW:
357.45
EINECS:
243-901-6
Product Categories:
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
20594-83-6.mol
More
Less

nalbuphine Chemical Properties

Melting point:
230.5°
Boiling point:
566.6±50.0 °C(Predicted)
Density 
1.44±0.1 g/cm3(Predicted)
pka
9.39±0.60(Predicted)
More
Less

nalbuphine Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Originator

Nubain,Du Pont,US,1979

Uses

Nalbuphine is a mixed opioid agonist-antagonist. Nalbuphine is an analgesic (narcotic).

Uses

Mixed opioid agonist-antagonist. Analgesic (narcotic).

Manufacturing Process

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.

brand name

Nubain (Endo).

Therapeutic Function

Analgesic

nalbuphine Supplier