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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 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

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Certificates of Analysis (COA)

Lot/Batch Number
050K4621

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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
Mark Connor et al.
British journal of pharmacology, 147(4), 349-350 (2006-01-13)
Mu-opioid receptor agonists are a mainstay of clinical analgesia, despite the significant unwanted effects and dependence liability associated with drugs like morphine. The quest for opioids that produce analgesia with fewer undesirable effects has lead to the putative identification of
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
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
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
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