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N165

Sigma-Aldrich

Naloxone benzoylhydrazone

solid

Synonym(s):

[(5α)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)morphinan-6-ylidene]hydrazide benzoic acid

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About This Item

Empirical Formula (Hill Notation):
C26H27N3O4
CAS Number:
119630-94-3
Molecular Weight:
445.51
MDL number:
MFCD05662358
UNSPSC Code:
12352200
PubChem Substance ID:
24278048
NACRES:
NA.77

form

solid

Quality Level

100

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

color

yellow

solubility

DMSO: soluble
H2O: soluble (with the addition of 0.1 N HCl)
ethanol: soluble

storage temp.

−20°C

SMILES string

[H][C@@]12Oc3c(O)ccc4C[C@H]5N(CC[C@@]1(c34)[C@@]5(O)CC\C2=N/NC(=O)c6ccccc6)CC=C

InChI

1S/C26H27N3O4/c1-2-13-29-14-12-25-21-17-8-9-19(30)22(21)33-23(25)18(10-11-26(25,32)20(29)15-17)27-28-24(31)16-6-4-3-5-7-16/h2-9,20,23,30,32H,1,10-15H2,(H,28,31)/b27-18+/t20-,23+,25+,26-/m1/s1

InChI key

AKXCFAYOTIEFOH-XTNAHFASSA-N

Gene Information

human ... OPRK1(4986) , OPRL1(4987) , OPRM1(4988)

Biochem/physiol Actions

Agonist for κ3 opioid receptors; antagonist for ORL1 and μ opioid receptors.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D Ichikawa et al.
Neuroreport, 12(8), 1757-1761 (2001-06-21)
J-113397 (1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one) is a recently developed antagonist of the opioid receptor-like 1 (ORL1) receptor. We compared the in vitro functional profile J-113397 on [35S]guanosine 5'-O-(gamma-thio)triphosphate (GTPgammaS) binding to mouse brain with that of [Phe1psi(CH2-NH)Gly2]nociceptin(1-13)NH2 and naloxone benzoylhydrazone (NalBzoH). J-113397 antagonized
Eve Salonius et al.
Journal of cellular physiology, 235(4), 3497-3507 (2019-09-26)
Cell therapy combined with biomaterial scaffolds is used to treat cartilage defects. We hypothesized that chondrogenic differentiation bone marrow-derived mesenchymal stem cells (BM-MSCs) in three-dimensional biomaterial scaffolds would initiate cartilaginous matrix deposition and prepare the construct for cartilage regeneration in
Maria C Olianas et al.
British journal of pharmacology, 147(4), 360-370 (2006-01-13)
1. In the present study, we examined the pharmacological activity of the putative kappa3-opioid receptor agonist naloxone benzoylhydrazone (NalBzoH) at recombinant human opioid receptors individually expressed in Chinese hamster ovary (CHO) cells and native opioid receptors present in rat striatum.
T Mamiya et al.
Journal of neural transmission (Vienna, Austria : 1996), 108(12), 1349-1361 (2002-01-26)
Here we report the involvement of nociceptin receptor in tolerance to morphine-induced antinociception and in morphine dependence. There was no different nociceptive perception and antinociceptive effects of morphine between wild-type and the nociceptin receptor knockout mice. Tolerance to morphine (10
Veronica Cox et al.
Neuropharmacology, 48(2), 228-235 (2005-02-08)
Naloxone benzoylhydrazone (NalBzoH) is a ligand used to study opioid receptors. It has been suggested to act at a novel kappa3 receptor but also appears to bind to classical opioid receptors, and possibly the ORL1 receptor. We have used opioid
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