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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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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
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
Pierluigi Onali et al.
British journal of pharmacology, 143(5), 638-648 (2004-09-29)
1 Naloxone benzoylhydrazone (NalBzoH) has initially been developed as an agonist of the pharmacologically defined kappa3-opioid receptor and has recently been employed as an antagonist at the opioid receptor-like (ORL1) receptor. In the present study, we investigated the ability of
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
J P Mathis et al.
Synapse (New York, N.Y.), 34(3), 181-186 (1999-10-19)
The presence of pairs of basic amino acids within the orphanin FQ/Nociceptin (OFQ/N) sequence has raised the possibility that truncated versions of the peptide might be physiologically important. OFQ/N(1-11) is pharmacologically active in mice, despite its poor affinity in binding
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