Structure via PubChem · Public domain (PubChem)
nalmexone
Sign in to saveNalmexone (INN; also known as nalmexone hydrochloride (USAN) or by the development codes EN-1620A and UM-592) is a semisynthetic, opioid partial agonist or mixed agonist-antagonist with both analgesic and narcotic antagonist properties that was never marketed. In clinical studies it was found to have comparable analgesic efficacy to morphine, though with several-fold reduced potency. In addition, nalmexone's side effects, the most common of which were sleepiness and sweating, were reported to be similar to those of morphine, albeit with a noticeably higher degree of incidence.
Chemical data
- Formula
- C21H25NO4
- Molecular weight
- 355.4 g/mol
- IUPAC name
- (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-(3-methylbut-2-enyl)-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 355.178
Show 4 more facts
- chemical formula
- C₂₁H₂₅NO₄
- canonical SMILES
- CC(=CCN1CCC23C4C(=O)CCC2(C1CC5=C3C(=C(C=C5)O)O4)O)C
- isomeric SMILES
- CC(=CCN1CC[C@]23[C@@H]4C(=O)CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O)C
- different from
- naltrexone
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Synthesis
- See also
- References
Nalmexone (INN; also known as nalmexone hydrochloride (USAN) or by the development codes EN-1620A and UM-592) is a semisynthetic, opioid partial agonist or mixed agonist-antagonist with both analgesic and narcotic antagonist properties that was never marketed. In clinical studies it was found to have comparable analgesic efficacy to morphine, though with several-fold reduced potency. In addition, nalmexone's side effects, the most common of which were sleepiness and sweating, were reported to be similar to those of morphine, albeit with a noticeably higher degree of incidence.
==Synthesis== Nalmexone can be synthesized from oxymorphone: 700px|left|class=skin-invert-image|Nalmexone synthesis
Excerpted from Wikipedia’s “nalmexone” article, available under the CC BY-SA 4.0 licence.