Norbinaltorphimine

Norbinaltorphimine (nor-BNI or nBNI) is an opioid antagonist used in scientific research. It is one of the few opioid antagonists available that is highly selective for the κ-opioid receptor, and blocks this receptor without affecting the μ- or δ-opioid receptors,[1][2] although it has less selectivity in vivo than when used in isolated tissues.[3] nor-BNI blocks the effects of κ-opioid agonists in animal models,[4][5] and produces antidepressant[6] and antipanic-like effects.[2]

Norbinaltorphimine
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 17,17'-(Dicyclopropylmethyl)-6,6',7,7'-6,6'-imino- 7,7'-bimorphinan-3,4',14,14'-tetrol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC40H43N3O6
Molar mass661.799 g·mol−1
3D model (JSmol)
SMILES
  • C1CC1CN2CC[C@]34[C@@H]5C6=C(C[C@]3([C@H]2CC7=C4C(=C(C=C7)O)O5)O)C8=C(N6)[C@H]9[C@@]12CCN([C@@H]([C@@]1(C8)O)CC1=C2C(=C(C=C1)O)O9)CC1CC1
InChI
  • InChI=1S/C40H43N3O6/c44-25-7-5-21-13-27-39(46)15-23-24-16-40(47)28-14-22-6-8-26(45)34-30(22)38(40,10-12-43(28)18-20-3-4-20)36(49-34)32(24)41-31(23)35-37(39,29(21)33(25)48-35)9-11-42(27)17-19-1-2-19/h5-8,19-20,27-28,35-36,41,44-47H,1-4,9-18H2/t27-,28-,35+,36+,37+,38+,39-,40-/m1/s1 N
  • Key:APSUXPSYBJVPPS-YAUKWVCOSA-N N
 NY (what is this?)  (verify)

See also

References
  1. Portoghese PS, Lipkowski AW, Takemori AE (March 1987). "Binaltorphimine and nor-binaltorphimine, potent and selective kappa-opioid receptor antagonists". Life Sciences. 40 (13): 1287–92. doi:10.1016/0024-3205(87)90585-6. PMID 2882399.
  2. Maraschin JC, Almeida CB, Rangel MP, Roncon CM, Sestile CC, Zangrossi H, et al. (June 2017). "Participation of dorsal periaqueductal gray 5-HT1A receptors in the panicolytic-like effect of the κ-opioid receptor antagonist Nor-BNI". Behavioural Brain Research. 327: 75–82. doi:10.1016/j.bbr.2017.03.033. PMID 28347824. S2CID 22465963.
  3. Birch PJ, Hayes AG, Sheehan MJ, Tyers MB (December 1987). "Norbinaltorphimine: antagonist profile at kappa opioid receptors". European Journal of Pharmacology. 144 (3): 405–8. doi:10.1016/0014-2999(87)90397-9. PMID 2831070.
  4. Takemori AE, Ho BY, Naeseth JS, Portoghese PS (July 1988). "Nor-binaltorphimine, a highly selective kappa-opioid antagonist in analgesic and receptor binding assays". The Journal of Pharmacology and Experimental Therapeutics. 246 (1): 255–8. PMID 2839664.
  5. Takemori AE, Schwartz MM, Portoghese PS (December 1988). "Suppression by nor-binaltorphimine of kappa opioid-mediated diuresis in rats". The Journal of Pharmacology and Experimental Therapeutics. 247 (3): 971–4. PMID 2849679.
  6. Shirayama Y, Ishida H, Iwata M, Hazama GI, Kawahara R, Duman RS (September 2004). "Stress increases dynorphin immunoreactivity in limbic brain regions and dynorphin antagonism produces antidepressant-like effects". Journal of Neurochemistry. 90 (5): 1258–68. doi:10.1111/j.1471-4159.2004.02589.x. PMID 15312181.


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