Naloxol: Difference between revisions
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{{Chembox |
{{Chembox |
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| verifiedrevid = 452697223 |
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| ImageFileL1 = alpha-Naloxol.svg |
| ImageFileL1 = alpha-Naloxol.svg |
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| ImageAltL1 = α-naloxol |
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| ImageSizeL1 = 120px |
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| ImageCaptionL1 = α-naloxol |
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| ImageCaptionL1 = α-Naloxol |
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| ImageFileR1 = beta-Naloxol.svg |
| ImageFileR1 = beta-Naloxol.svg |
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| ImageAltR1 = β-naloxol |
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| ImageSizeR1 = 120px |
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| ImageCaptionR1 = β-naloxol |
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⚫ | | 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 |
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| ImageCaptionR1 = β-Naloxol |
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⚫ | | IUPACName = α- |
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| IUPACName_hidden = yes |
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| OtherNames = |
| OtherNames = |
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|Section1={{Chembox Identifiers |
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| CASNo = 20410-95-1 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Comment = (α) |
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| CASNo1 = 53154-12-4 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| CASNo1_Comment = (β) |
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| CASNo2 = 58691-01-3 |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| CASNo2_Comment = (α/β) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = FLW43Q2H9L |
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| UNII_Comment = (α) |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = QY92ZV4EHS |
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| UNII1_Comment = (β) |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = K2SIX47W55 |
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| UNII2_Comment = (α/β) |
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| PubChem1 = 5492293 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 4590928 |
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| ChemSpiderID_Comment = (α) |
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| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID1 = 9177198 |
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| ChemSpiderID1_Comment = (β) |
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| SMILES_Comment = (α) |
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| 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 |
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| InChI_Comment = (α) |
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| InChIKey = HMWHERQFMBEHNG-AQQQZIQIBS |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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 |
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| StdInChI_Comment = (α) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = HMWHERQFMBEHNG-AQQQZIQISA-N |
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| 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 |
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| InChI1_Comment = (β) |
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| InChIKey1 = HMWHERQFMBEHNG-CSJNCLCHBP |
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| 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 |
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| InChI3_Comment = (β) |
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| InChIKey3 = HMWHERQFMBEHNG-CSJNCLCHSA-N |
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|Section2={{Chembox Properties |
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| C=19 | H=23 | N=1 | O=4 |
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| Appearance = |
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| Density = |
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| MeltingPt = |
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| Solubility = }} |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = }} |
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'''Naloxol''' is an [[opioid antagonist]] closely related to [[naloxone]]. |
'''Naloxol''' is an [[opioid antagonist]] closely related to [[naloxone]]. It exists in two [[isomer]]ic forms, α-naloxol and β-naloxol. |
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α- |
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> |
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Naloxol can be said to be the [[oxymorphol]] analogue of naloxone. |
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==See also== |
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* [[Naloxegol]] |
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==References== |
==References== |
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{{Reflist}} |
{{Reflist|2}} |
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{{Opioid receptor modulators}} |
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[[Category:Human drug metabolites]] |
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[[Category:Mu-opioid receptor antagonists]] |
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{{Analgesic-stub}} |
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[[Category:Morphinans]] |