Naloxonazine

Naloxonazine
Names
Other names
NIH 10894; NSC 612113, Bis-[5-α-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)-morphinan-6-ylidene] hydrazine dihydrochloride
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=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 ☒N
    Key: AJPSBXJNFJCCBI-YOHUGVJRSA-N ☒N
  • 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
    Key: AJPSBXJNFJCCBI-YOHUGVJRBH
  • 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
Properties
C38H42N4O6
Molar mass 650.776 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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Naloxonazine is a potent, irreversible μ-opioid receptor antagonist.[1] 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.[2]

  1. ^ Naloxonazine dihydrochloride
  2. ^ Hahn, E. F.; Pasternak, G. W. (September 1982). "Naloxonazine, a potent, long-lasting inhibitor of opiate binding sites". Life Sciences. 31 (12–13): 1385–1388. doi:10.1016/0024-3205(82)90387-3. PMID 6292633.