Naloxol

α-naloxol

β-naloxol

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

CAS Number

20410-95-1 (α)^Y
53154-12-4 (β)^Y
58691-01-3 (α/β)^Y

3D model (JSmol)

(α): Interactive image
(β): Interactive image

ChemSpider

4590928 (α)^N
9177198 (β)^N

ECHA InfoCard

100.236.696

PubChem CID

5492271 (α)
5492293 (β)

UNII

FLW43Q2H9L (α)^Y
QY92ZV4EHS (β)^Y
K2SIX47W55 (α/β)^Y

CompTox Dashboard (EPA)

DTXSID20942579

InChI

InChI=1S/C19H23NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,13-14,17,21-23H,1,5-10H2/t13-,14+,17-,18-,19+/m0/s1^N
Key: HMWHERQFMBEHNG-AQQQZIQISA-N^N
(α): InChI=1/C19H23NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,13-14,17,21-23H,1,5-10H2/t13-,14+,17-,18-,19+/m0/s1
Key: HMWHERQFMBEHNG-AQQQZIQIBS
(β): InChI=1/C19H23NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,13-14,17,21-23H,1,5-10H2/t13-,14-,17+,18+,19-/m1/s1
Key: HMWHERQFMBEHNG-CSJNCLCHBP
(β): InChI=1S/C19H23NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,13-14,17,21-23H,1,5-10H2/t13-,14-,17+,18+,19-/m1/s1
Key: HMWHERQFMBEHNG-CSJNCLCHSA-N

SMILES

(α): OC1=C2C3=C(C=C1)C[C@@H]4[C@]5(O)CC[C@H](O)[C@H](O2)[C@@]53CCN4CC=C
(β): OC1=C2C3=C(C=C1)C[C@@H]4[C@]5(O)CC[C@@H](O)[C@H](O2)[C@@]53CCN4CC=C

Properties

Chemical formula

C₁₉H₂₃NO₄

Molar mass

329.396 g·mol⁻¹

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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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.

References

^ 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.
^ 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): 9757–9768. doi:10.1016/S0040-4020(01)85541-1.