Naloxol

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Naloxol
α-naloxol
α-naloxol
β-naloxol
β-naloxol
Names
IUPAC names
α-naloxol: (4R,4aS,7S,7aR,12bS)-3-allyl-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol
β-naloxol: (4R,4aS,7R,7aR,12bS)-3-allyl-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol
Identifiers
20410-95-1 (α) YesY
53154-12-4 (β) YesY
58691-01-3 (α/β) YesY
ChemSpider 4590928 (α) N
9177198 (β) N
Jmol 3D model (α): Interactive image
(β): Interactive image
PubChem 5492271 (α)
5492293 (β)
Properties
C19H23NO4
Molar mass 329.40 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Naloxol is an opioid antagonist closely related to naloxone. It exists in two isomeric forms, α-naloxol and β-naloxol.

α-naloxol is a human metabolite of naloxone.[1] Synthetically, α-naloxol can be prepared from naloxone by reduction of the ketone group, and β-naloxol can be prepared from α-naloxol by a Mitsunobu reaction.[2]

Naloxol can be said to be the oxymorphol analogue of naloxone.

See also[edit]

References[edit]

  1. ^ Weinstein, S. H.; Pfeffer, M.; Schor, J. M.; Indindoli, L.; Mintz, M. (1971). "Metabolites of naloxone in human urine". Journal of Pharmaceutical Sciences 60 (10): 1567–1568. doi:10.1002/jps.2600601030. PMID 5129377. 
  2. ^ Simon, C (1994). "Stereoselective synthesis of β-naltrexol, β-naloxol β-naloxamine, β-naltrexamine and related compounds by the application of the mitsunobu reac". Tetrahedron 50 (32): 9757. doi:10.1016/S0040-4020(01)85541-1.