Structure via PubChem · Public domain (PubChem)
nalbuphine
Sign in to saveAlso known as N-cyclobutylmethyl-4,5alpha-epoxy-3,6alpha,14-morphinantriol
Nalbuphine, sold under the brand names Nubain among others, is an opioid analgesic which is used in the treatment of pain. It is given by injection into a vein, muscle, or fat.
Key facts
- Drug.Verifiedfields
- verified
- Drug.Watchedfields
- verified
- Drug.verifiedrevid
- 459830736
- Drug.IUPAC_name
- (4R,4aS,7S,7aR,12bS)-3-(cyclobutylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol
- Drug.image
- Nalbuphine.svg
- Drug.image_class
- skin-invert-image
- Drug.alt
- Skeletal formula
- Drug.width
- 225px
- Drug.image2
- Nalbuphine molecule ball.png
- Drug.image_class2
- bg-transparent
- Drug.alt2
- Ball-and-stick model of nalbuphine
- Drug.width2
- 250px
- Drug.tradename
- Nubain, Nalpain, Nalbuphin, others
- Drug.MedlinePlus
- a682668
- Drug.pregnancy_category
- B
- Drug.legal_BR
- A2
- Drug.legal_CA
- Schedule IV
- Drug.legal_US
- Rx only (unscheduled) Schedule IV in some states
via Wikipedia infobox
Chemical data
- Formula
- C21H27NO4
- Molecular weight
- 357.4 g/mol
- IUPAC name
- (4R,4aS,7S,7aR,12bS)-3-(cyclobutylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol
- SMILES
- C1CC(C1)CN2CC[C@]34[C@@H]5[C@H](CC[C@]3([C@H]2CC6=C4C(=C(C=C6)O)O5)O)O
- InChIKey
- NETZHAKZCGBWSS-CEDHKZHLSA-N
- XLogP
- 0.2
- Polar surface area
- 73.2 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
1,379 papersvia PubMed
~7 min read
Encyclopedic overview
14 sectionsContents
- Medical uses
- Available forms
- Side effects
- Overdose
- Pharmacology
- Pharmacodynamics
- Chemistry
- History
- Society and culture
- Brand names
- Legal status
- Veterinary use
- See also
- Notes
Nalbuphine, sold under the brand names Nubain among others, is an opioid analgesic which is used in the treatment of pain. It is given by injection into a vein, muscle, or fat.
Side effects of nalbuphine include sedation, sweatiness, clamminess, nausea, vomiting, dizziness, vertigo, dry mouth, and headache. Unlike other opioids, it has little to no capacity to cause euphoria or respiratory depression. There is also little to no incidence of dysphoria, dissociation, hallucinations, and related side effects at typical therapeutic doses. Nalbuphine is a mixed agonist/antagonist opioid modulator. Specifically, it acts as a moderate-efficacy partial agonist or antagonist of the μ-opioid receptor (MOR) and as a high-efficacy partial agonist of the κ-opioid receptor (KOR), whereas it has relatively low affinity for the δ-opioid receptor (DOR) and sigma receptors.
Excerpted from Wikipedia’s “nalbuphine” article, available under the CC BY-SA 4.0 licence.