Structure via PubChem · Public domain (PubChem)
phenazocine
Sign in to saveAlso known as phenazocine, (-)-
Phenazocine (brand names Prinadol, Narphen) is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects.
Chemical data
- Formula
- C22H27NO
- Molecular weight
- 321.5 g/mol
- IUPAC name
- (1R,9R,13R)-1,13-dimethyl-10-(2-phenylethyl)-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- pain
via ChEMBL · EBI
Research
536 papers- (+)-and (-)-Phenazocine enantiomers: Evaluation of their dual opioid agonist/σ(1) antagonist properties and antinociceptive effects.European journal of medicinal chemistry · 2017
- Phenazocine analgesia.The Practitioner · 1962
- Effects of ketazocine, ethylketazocine and phenazocine on schedule-controlled behavior: antagonism by naloxone.Neuropharmacology · 1982
- Geometrical correspondence between phenazocine and the enkephalins.Journal of medicinal chemistry · 1986
- Oral pentazocine and phenazocine: a comparison in postoperative pain.British journal of anaesthesia · 1971
via PubMed
Wikidata facts
- Mass
- 321.209264
Show 5 more facts
- chemical formula
- C₂₂H₂₇NO
- canonical SMILES
- CC1C2CC3=C(C1(CCN2CCC4=CC=CC=C4)C)C=C(C=C3)O
- isomeric SMILES
- C[C@H]1[C@H]2CC3=C([C@@]1(CCN2CCC4=CC=CC=C4)C)C=C(C=C3)O
- Commons category
- Phenazocine
- defined daily dose
- 3
Sources (2)
via Wikidata · CC0
~2 min read
Article
3 sectionsContents
- History
- See also
- References
Phenazocine (brand names Prinadol, Narphen) is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects.
Effects of phenazocine include analgesia and euphoria, also may include dysphoria and hallucinations at high doses, most likely due to action at κ-opioid and σ receptors. Phenazocine appears to be a much stronger analgesic with fewer side effects than pentazocine, probably due to a more favorable μ/κ binding ratio. Phenazocine is a much more potent analgesic than pentazocine and other drugs in the benzomorphan series, most probably due to the presence of an N-phenethyl substitution, which is known to boost μ-opioid activity in many classes of opioid analgesics. Also, it does not cause spasm of the sphincter of Oddi, making it more suitable than morphine for the treatment of biliary or pancreatic pain.