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Merck
CN

N165

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
NACRES:
NA.77
PubChem Substance ID:
24278048
UNSPSC Code:
12352200
MDL number:
MFCD05662358

Key Documents

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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

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 key

AKXCFAYOTIEFOH-XTNAHFASSA-N

form

solid

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

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
050K4621

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D Paul et al.
The Journal of pharmacology and experimental therapeutics, 255(2), 769-774 (1990-11-01)
Naloxone benzoylhydrazone (NalBzoH) is a novel mixed agonist/antagonist. Against mu agonists, NalBzoH is a potent antagonist with a prolonged duration of action corresponding to its extremely slow rate of dissociation from mu receptors in binding assays. In the present studies
Thomas M Tzschentke
Psychopharmacology, 172(1), 58-67 (2003-11-15)
Buprenorphine is widely used as an analgesic drug and it is also increasingly considered for maintenance and detoxification of heroin addicts. It is a potent micro -receptor partial agonist with a long duration of action. An inverted U-shaped dose-effect curve
M A Gistrak et al.
The Journal of pharmacology and experimental therapeutics, 251(2), 469-476 (1989-11-01)
NalBzoH (6-desoxy-6-benzoylhydrazido-N-allyl-14-hydroxydihydronomorphin one) is a novel opiate with potent actions at both mu and kappa receptors. Analgesic studies in mice examining increasing doses of NalBzoH with a fixed dose of morphine revealed a biphasic curve. NalBzoH at doses as low
R Bigoni et al.
Canadian journal of physiology and pharmacology, 80(5), 407-412 (2002-06-12)
We have studied the effects of naloxone benzoylhydrazone (NalBzoH) at recombinant human OP4 receptors expressed in Chinese hamster ovary (CHO) cells (CHOhOP4) and native OP4 sites in isolated tissues from various species. In CHOhOP4 membranes, nociceptin (NC) and NalBzoH displaced
S Liu et al.
American journal of physiology. Gastrointestinal and liver physiology, 281(1), G237-G246 (2001-06-16)
Actions of nociceptin on electrical and synaptic behavior of morphologically and neurochemically identified neurons in the guinea pig duodenal myenteric plexus were studied with conventional techniques. Nociceptin hyperpolarized the membrane potential in 104 of 121 AH-type and 28 of 51
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