Naloxol

Naloxol
α-Naloxol	β-Naloxol
IUPAC name 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
CAS number	20410-95-1 (α) Y, 53154-12-4 (β) Y, 58691-01-3 (α/β) Y
PubChem	5492271 (α), 5492293 (β)
Jmol-3D images	Image 1 Image 2
SMILES OC1=C2C3=C(C=C1)C[C@@H]4[C@]5(O)CC[C@H](O)[C@H](O2)[C@@]53CCN4CC=C (α) OC1=C2C3=C(C=C1)C[C@@H]4[C@]5(O)CC[C@@H](O)[C@H](O2)[C@@]53CCN4CC=C (β)
Properties
Molecular formula	C19H23NO4
Molar mass	329.39 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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]

References

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.