nalbuphine Struktur

Nalbuphin

Bezeichnung:Nalbuphin

CAS-Nr20594-83-6

Englisch Name:nalbuphine

CBNumberCB4918699

SummenformelC21H27NO4

Molgewicht357.45

MOL-Datei20594-83-6.mol

Synonyma

Nalbuphin

Nalbuphin physikalisch-chemischer Eigenschaften

Schmelzpunkt	230.5°
Siedepunkt	566.6±50.0 °C(Predicted)
Dichte	1.44±0.1 g/cm3(Predicted)
Löslichkeit	soluble in Methanol
Aggregatzustand	Solid
pka	9.39±0.60(Predicted)
Farbe	White

Gefahreninformationscode (GHS)

nalbuphine Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
Pale Yellow Solid
Originator
Nubain,Du Pont,US,1979
Verwenden
Mixed opioid agonist-antagonist. Analgesic (narcotic).
Verwenden
Nalbuphine is a mixed opioid agonist-antagonist. Nalbuphine is an analgesic (narcotic).
Definition
ChEBI: Nalbuphine is an organic heteropentacyclic compound. It has a role as a mu-opioid receptor antagonist and an opioid analgesic. It derives from a hydride of a morphinan.
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.
Trademarks
Nubain (Endo).
Therapeutic Function
Analgesic

nalbuphine Upstream-Materialien And Downstream Produkte

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