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Norbinaltorphimine

Chemical compound

Field	Value
Verifiedfields	changed
Watchedfields	changed
verifiedrevid	430510891
IUPAC_name	17,17'-(Dicyclopropylmethyl)-6,6',7,7'-6,6'-imino-7,7'-bimorphinan-3,4',14,14'-tetrol
image	Norbinaltorphimine structural formula.png
image_class	skin-invert-image
width	280
legal_US	Schedule II (derivative of noroxymorphone)
excretion
CAS_number_Ref
CAS_number	105618-26-6
UNII_Ref
PDB_ligand	A1AD6
UNII	36OOQ86QM1
ATC_prefix	none
PubChem	3034416
IUPHAR_ligand	1642
ChemSpiderID_Ref
ChemSpiderID	21248347
<!--Chemical data-->	C	40
H	43
N	3
O	6
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@@HCC1=C2C(=C(C=C1)O)O9)CC1CC1
StdInChI_Ref
StdInChI	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
StdInChIKey_Ref
StdInChIKey	APSUXPSYBJVPPS-YAUKWVCOSA-N

| elimination_half-life =

Norbinaltorphimine (nor-BNI or nBNI) is an opioid receptor antagonist used in scientific research. It is a highly selective inverse agonist for the κ-opioid receptor. In animals, nor-BNI blocks the effects of κ-opioids with a slow onset and an exceptionally long duration of action (up to several months). It produces antidepressant-like and anxiolytic-like effects in animal models.

Legality

In the United States, a letter from Terrence L. Boos, Ph.D., Chief Drug & Chemical Evaluation Section Diversion Control Division at the DEA shows they consider nor-BNI a Schedule II substance as a derivative of noroxymorphone due to its broad definition in the CSA covering "derivatives". However, no court cases are known to exist for its prosecution and it is possible this could be challenged in court.

References

(2013-08-14). "Selective κ opioid antagonists nor-BNI, GNTI and JDTic have low affinities for non-opioid receptors and transporters". PLOS ONE.
(January 2025). "Molecular mechanisms of inverse agonism via κ-opioid receptor-G protein complexes". Nature Chemical Biology.
(July 1988). "Nor-binaltorphimine, a highly selective kappa-opioid antagonist in analgesic and receptor binding assays". The Journal of Pharmacology and Experimental Therapeutics.
(December 1988). "Suppression by nor-binaltorphimine of kappa opioid-mediated diuresis in rats". The Journal of Pharmacology and Experimental Therapeutics.
(October 2005). "Kappa opioid antagonists: past successes and future prospects". The AAPS Journal.
(October 2011). "Repeated exposure to the κ-opioid receptor agonist salvinorin A modulates extracellular signal-regulated kinase and reward sensitivity". Biological Psychiatry.
(September 2004). "Stress increases dynorphin immunoreactivity in limbic brain regions and dynorphin antagonism produces antidepressant-like effects". Journal of Neurochemistry.
(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.
US Drug Enforcement Administration. (2024). "Letter to Vice Media Group".

Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

4,5-epoxymorphinans irreversible-antagonists hydroxyarenes tertiary-alcohols kappa-opioid-receptor-antagonists heterocyclic-compounds-with-7-or-more-rings cyclopropyl-compounds

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