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NALBUPHINE HYDROCHLORIDE

NALBUPHINE HYDROCHLORIDE Basic information
Product Name:NALBUPHINE HYDROCHLORIDE
Synonyms:NalbuphineHCl;17-(Cyclobutylmethyl)-4,5-epoxymorphinan-3,6,14-triol hydrate hydrochloride;Nalbuphine hydrate hydrochloride;Nalbuphine hydrochloride hydrate,17-(Cyclobutylmethyl)-4,5-epoxymorphinan-3,6,14-triol hydrochloride hydrate;17-(Cyclobutylmethyl)-4,5-epoxymorphinan-3,6,14-triol hydrochloride hydrate;Nalbuphine hydrochloride solution;NALBUPHINE HYDROCHLORIDE;N-CYCLOBUTYLMETHYL-14-HYDROXY-DIHYDROMORPHINE HYDROCHLORIDE
CAS:23277-43-2
MF:C21H28ClNO4
MW:393.91
EINECS:245-549-9
Product Categories:
Mol File:23277-43-2.mol
NALBUPHINE HYDROCHLORIDE Structure
NALBUPHINE HYDROCHLORIDE Chemical Properties
Fp 9℃
storage temp. -20°C
solubility H2O: soluble
Safety Information
Hazard Codes T+,T,F
Risk Statements 26/27/28-39/23/24/25-23/24/25-11
Safety Statements 22-36/37/39-45-36/37-16
RIDADR 1544
WGK Germany 3
RTECS QD3181000
HazardClass 6.1(a)
PackingGroup II
MSDS Information
NALBUPHINE HYDROCHLORIDE Usage And Synthesis
OriginatorNubain,Du Pont,US,1979
UsesAnalgesic;Opioid ligand
UsesNalbuphine is the free base form of Nalbuphine Hydrochloride. Nalbuphine is a mixed opioid agonist-antagonist. Nalbuphine is an analgesic (narcotic).
Manufacturing ProcessTo 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 nameNubain (Endo).
Therapeutic FunctionAnalgesic
Acquired resistanceNalbuphine is an antagonist at μ receptors and an agonist at κ receptors. As an antagonist, it has approximately one-fourth the potency of naloxone, and it produces withdrawal when given to addicts. On a weight basis, the analgesic potency of nalbuphine approaches that of morphine. An intramuscular injection of 10 mg will give about the same degree and duration of analgesia as an equivalent dose of morphine.
Clinical UseNalbuphine is only available for parenteral dosage. Its elimination half-life is 2 to 3 hours. Metabolism of nalbuphine is by conjugation of the 3-OH group, and greater than 90% of the drug is excreted as conjugates in the feces.
Side effectsSide effects of nalbuphine are like those of other κ. Dysphoria is not as common as with pentazocine. Sedation is the most common side effect. Nalbuphine does not have the adverse cardiovascular properties found with pentazocine and butorphanol. Nalbuphine has low abuse potential and is not listed under the Controlled Substances Act.
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