Naloxonazine
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 412250774
| ImageFile=Naloxonazine.png
| ImageClass = skin-invert-image
| ImageSize=200px
| IUPACName=
| OtherNames=NIH 10894; NSC 612113, Bis-[5-α-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)-morphinan-6-ylidene] hydrazine dihydrochloride
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=82824-01-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = BW5W4K4S7Z
| PubChem=9576413
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1618376
| IUPHAR_ligand = 1677
| SMILES=C=CCN1[C@H]2[C@]3([C@]4(C5=C(C2)C=CC(=C5O[C@H]4/C(=N/N=C\6/[C@@H]7OC8=C(C=CC9=C8[C@]72[C@]([C@@H](C9)N(CC2)CC=C)(CC6)O)O)/CC3)O)CC1)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 7850858
| InChI = 1/C38H42N4O6/c1-3-15-41-17-13-35-29-21-5-7-25(43)31(29)47-33(35)23(9-11-37(35,45)27(41)19-21)39-40-24-10-12-38(46)28-20-22-6-8-26(44)32-30(22)36(38,34(24)48-32)14-18-42(28)16-4-2/h3-8,27-28,33-34,43-46H,1-2,9-20H2/b39-23+,40-24+/t27-,28-,33+,34+,35+,36+,37-,38-/m1/s1
| InChIKey = AJPSBXJNFJCCBI-YOHUGVJRBH
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C38H42N4O6/c1-3-15-41-17-13-35-29-21-5-7-25(43)31(29)47-33(35)23(9-11-37(35,45)27(41)19-21)39-40-24-10-12-38(46)28-20-22-6-8-26(44)32-30(22)36(38,34(24)48-32)14-18-42(28)16-4-2/h3-8,27-28,33-34,43-46H,1-2,9-20H2/b39-23+,40-24+/t27-,28-,33+,34+,35+,36+,37-,38-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = AJPSBXJNFJCCBI-YOHUGVJRSA-N
}}
|Section2={{Chembox Properties
| C=38 | H=42 | N=4 | O=6
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
}}
Naloxonazine is a potent, irreversible μ-opioid receptor antagonist.[http://www.tocris.com/dispprod.php?ItemId=1677 Naloxonazine dihydrochloride] Naloxonazine forms spontaneously in acidic solutions of naloxazone, and may be responsible for much or all of the irreversible μ opioid receptor binding displayed by the latter.{{cite journal
| last = Hahn | first = E. F. |author2=Pasternak, G. W.
| title = Naloxonazine, a potent, long-lasting inhibitor of opiate binding sites
| journal = Life Sciences | volume = 31 | issue = 12–13 | pages = 1385–1388
| date = September 1982
| doi = 10.1016/0024-3205(82)90387-3 | pmid = 6292633
}}
See also
- Oxymorphone-3-methoxynaltrexonazine, a similar opioid also having two complete and mirrored morphinan carbon skeletons
References
{{Reflist|2}}
{{Opioid receptor modulators}}
Category:Mu-opioid receptor antagonists
Category:Semisynthetic opioids
Category:Irreversible antagonists
{{analgesic-stub}}