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{{Chembox
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 452697223
| ImageFileL1 = alpha-Naloxol.svg
| ImageFileL1 = alpha-Naloxol.svg
| ImageAltL1 = α-naloxol
| ImageSizeL1 = 120px
| ImageAltL1 = α-Naloxol
| ImageCaptionL1 = α-naloxol
| ImageCaptionL1 = α-Naloxol
| ImageFileR1 = beta-Naloxol.svg
| ImageFileR1 = beta-Naloxol.svg
| ImageAltR1 = β-naloxol
| ImageSizeR1 = 120px
| ImageAltR1 = β-Naloxol
| ImageCaptionR1 = β-naloxol
⚫
| IUPACName = α-naloxol: (4''R'',4a''S'',7''S'',7a''R'',12b''S'')-3-allyl-2,3,4,4a,5,6,7,7a-octahydro-1''H''-4,12-methanobenzofuro[3,2-''e'']isoquinoline-4a,7,9-triol<br>β-naloxol: (4''R'',4a''S'',7''R'',7a''R'',12b''S'')-3-allyl-2,3,4,4a,5,6,7,7a-octahydro-1''H''-4,12-methanobenzofuro[3,2-''e'']isoquinoline-4a,7,9-triol
| ImageCaptionR1 = β-Naloxol
⚫
| IUPACName = α-Naloxol: (4''R'',4a''S'',7''S'',7a''R'',12b''S'')-3-allyl-2,3,4,4a,5,6,7,7a-octahydro-1''H''-4,12-methanobenzofuro[3,2-''e'']isoquinoline-4a,7,9-triol<br>β-Naloxol: (4''R'',4a''S'',7''R'',7a''R'',12b''S'')-3-allyl-2,3,4,4a,5,6,7,7a-octahydro-1''H''-4,12-methanobenzofuro[3,2-''e'']isoquinoline-4a,7,9-triol
| IUPACName_hidden = yes
| OtherNames =
| OtherNames =
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo = 20410-95-1
| CASNo = 20410-95-1
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Comment = (α)
| CASNo_Comment = (α)
| CASNo1 = 53154-12-4
| CASNo1 = 53154-12-4
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1_Comment = (β)
| CASNo1_Comment = (β)
| CASNo2 = 58691-01-3
| CASNo2 = 58691-01-3
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2_Comment = (α/β)
| CASNo2_Comment = (α/β)
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| PubChem = 5492271
| UNII = FLW43Q2H9L
⚫
| PubChem_Comment = (α)
| PubChem1 = 5492293
| UNII_Comment = (α)
| UNII1_Ref = {{fdacite|correct|FDA}}
⚫
| PubChem1_Comment = (β)
| UNII1 = QY92ZV4EHS
⚫
| SMILES = OC1=C2C3=C(C=C1)C[C@@H]4[C@]5(O)CC[C@H](O)[C@H](O2)[C@@]53CCN4CC=C
| SMILES_Comment = (α)
| UNII1_Comment = (β)
| UNII2_Ref = {{fdacite|correct|FDA}}
⚫
| SMILES1 = OC1=C2C3=C(C=C1)C[C@@H]4[C@]5(O)CC[C@@H](O)[C@H](O2)[C@@]53CCN4CC=C
| UNII2 = K2SIX47W55
⚫
| SMILES1_Comment = (β)
| UNII2_Comment = (α/β)
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| PubChem = 5492271
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| PubChem_Comment = (α)
| PubChem1 = 5492293
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| PubChem1_Comment = (β)
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4590928
| ChemSpiderID_Comment = (α)
| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID1 = 9177198
| ChemSpiderID1_Comment = (β)
⚫
| SMILES = OC1=C2C3=C(C=C1)C[C@@H]4[C@]5(O)CC[C@H](O)[C@H](O2)[C@@]53CCN4CC=C
| SMILES_Comment = (α)
⚫
| SMILES1 = OC1=C2C3=C(C=C1)C[C@@H]4[C@]5(O)CC[C@@H](O)[C@H](O2)[C@@]53CCN4CC=C
⚫
| SMILES1_Comment = (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+/m0/s1
| InChI_Comment = (α)
| InChIKey = HMWHERQFMBEHNG-AQQQZIQIBS
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChI_Comment = (α)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = HMWHERQFMBEHNG-AQQQZIQISA-N
| InChI1 = 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
| InChI1_Comment = (β)
| InChIKey1 = HMWHERQFMBEHNG-CSJNCLCHBP
| InChI3 = 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
| InChI3_Comment = (β)
| InChIKey3 = HMWHERQFMBEHNG-CSJNCLCHSA-N
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=19|H=23|N=1|O=4
| C=19 | H=23 | N=1 | O=4
| Appearance =
| Appearance =
| Density =
| Density =
| MeltingPt =
| MeltingPt =
| BoilingPt =
| BoilingPt =
| Solubility = }}
| Solubility = }}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition = }}
| AutoignitionPt = }}
}}
}}


'''Naloxol''' is an [[opioid antagonist]] closely related to [[naloxone]]. It exists in two [[isomer]]ic forms, α-naloxol and β-naloxol.
'''Naloxol''' is an [[opioid antagonist]] closely related to [[naloxone]]. It exists in two [[isomer]]ic forms, α-naloxol and β-naloxol.


α-Naloxol is a human [[metabolite]] of naloxone.<ref>{{cite journal | title = Metabolites of naloxone in human urine | author = Weinstein, S. H.; Pfeffer, M.; Schor, J. M.; Indindoli, L.; Mintz, M. | journal = Journal of Pharmaceutical Sciences | year = 1971 | volume = 60 | issue = 10 | pages = 1567–1568 | doi = 10.1002/jps.2600601030 | pmid = 5129377}}</ref> Synthetically, α-naloxol can be prepared from naloxone by [[Organic redox reaction|reduction]] of the [[ketone]] group, and β-naloxol can be prepared from α-naloxol by a [[Mitsunobu reaction]].<ref>{{cite journal | doi = 10.1016/S0040-4020(01)85541-1 | title = Stereoselective synthesis of β-naltrexol, β-naloxol β-naloxamine, β-naltrexamine and related compounds by the application of the mitsunobu reac | year = 1994 | last1 = Simon | first1 = C | journal = Tetrahedron | volume = 50 | issue = 32 | pages = 9757}}</ref>
α-naloxol is a human [[metabolite]] of naloxone.<ref>{{cite journal | title = Metabolites of naloxone in human urine |author1=Weinstein, S. H. |author2=Pfeffer, M. |author3=Schor, J. M. |author4=Indindoli, L. |author5=Mintz, M. | journal = Journal of Pharmaceutical Sciences | year = 1971 | volume = 60 | issue = 10 | pages = 1567–1568 | doi = 10.1002/jps.2600601030 | pmid = 5129377}}</ref> Synthetically, α-naloxol can be prepared from naloxone by [[Organic redox reaction|reduction]] of the [[ketone]] group, and β-naloxol can be prepared from α-naloxol by a [[Mitsunobu reaction]].<ref>{{cite journal | doi = 10.1016/S0040-4020(01)85541-1 | title = Stereoselective synthesis of β-naltrexol, β-naloxol β-naloxamine, β-naltrexamine and related compounds by the application of the mitsunobu reac | year = 1994 | last1 = Simon | first1 = C | journal = Tetrahedron | volume = 50 | issue = 32 | pages = 9757–9768}}</ref>

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

==See also==
* [[Naloxegol]]


==References==
==References==
{{Reflist}}
{{Reflist|2}}

{{Opioid receptor modulators}}

⚫
[[Category:4,5-Epoxymorphinans]]
[[Category:Human drug metabolites]]
[[Category:Mu-opioid receptor antagonists]]
⚫
[[Category:Allyl compounds]]



{{Analgesic-stub}}
⚫
[[Category:Metabolism]]
⚫
[[Category:Opioids]]
[[Category:Morphinans]]
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