Norbormide

Norbormide: Norbormide

Preferred IUPAC name

5-(α-Hydroxy-α-2-pyridylbenzyl)-7-(α-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximide

Systematic name

(10E)-8-[hydroxy(phenyl)pyridin-2-ylmethyl]-10-[phenyl(pyridin-2-yl)methylidene]-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

Identifiers

CAS number 991-42-4

PubChem 24744067 (1R,7S) ^Y, 24840617 (6R,7R) ^Y, 12399560 ^Y

ChemSpider 10468605 ^Y

EC number 213-589-6

KEGG C19139^Y

Jmol-3D images Image 1

SMILES

OC(C1=CC2C3C(C1\C2=C(/C1=CC=CC=C1)C1=CC=CC=N1)C(=O)NC3=O)(C1=CC=CC=C1)C1=NC=CC=C1

InChI

InChI=1S/C33H25N3O3/c37-31-28-22-19-23(33(39,21-13-5-2-6-14-21)25-16-8-10-18-35-25)29(30(28)32(38)36-31)27(22)26(20-11-3-1-4-12-20)24-15-7-9-17-34-24/h1-19,22,28-30,39H,(H,36,37,38)/b27-26+
Key: DNTHHIVFNQZZRD-CYYJNZCTSA-N

Properties

Molecular formula C₃₃H₂₅N₃O₃

Molar mass 511.570

Hazards

Main hazards Toxic

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Norbormide (Raticate, Shoxin) is a toxic compound used as a rodenticide. It has several mechanisms of action, acting as a vasoconstrictor and calcium channel blocker,^[1] but is selectively toxic to rats and has relatively low toxicity to other species, due to a species specific action of opening the permeability transition pores in rat mitochondria.^[2]

References

^ Rennison D, Bova S, Cavalli M, Ricchelli F, Zulian A, Hopkins B, Brimble MA. Synthesis and activity studies of analogues of the rat selective toxicant norbormide. Bioorganic and Medicinal Chemistry. 2007 Apr 15;15(8):2963-74. PMID 17321141

^ Zulian A, Petronilli V, Bova S, Dabbeni-Sala F, Cargnelli G, Cavalli M, Rennison D, Stäb J, Laita O, Lee DJ, Brimble MA, Hopkins B, Bernardi P, Ricchelli F. Assessing the molecular basis for rat-selective induction of the mitochondrial permeability transition by norbormide. Biochimica et Biophysica Acta. 2007 Jul;1767(7):980-8. PMID 17509521

v · d · ePest control: rodenticides

Anticoagulants/
vitamin K antagonists

coumarins/4-Hydroxycoumarins: 1st generation (Warfarin, Coumatetralyl) • 2nd generation (Brodifacoum, Difenacoum, Flocoumafen)

1,3-Indandiones: Chlorophacinone • Pindone • Diphacinone
other: Difethialone

Convulsants
Crimidine • Phenylsilatrane • Strychnine • Tetramethylenedisulfotetramine

Calciferols
Cholecalciferol • Ergocalciferol

Inorganic compounds
Aluminium phosphide • Arsenic • Barium carbonate • Calcium phosphide • Cyanide • Thallium • Zinc phosphide

Organochlorine
Chloralose • Endrin

Organophosphorus
Phosacetim

Metabolic poisons
Bromethalin • Fluoroacetamide • 1,3-Difluoro-2-propanol (Gliftor) • Sodium fluoroacetate

Other
α-Naphthylthiourea • Norbormide • Pyrinuron • Scilliroside

This article about an organic compound is a stub. You can help Wikipedia by expanding it.

Academic Dictionaries and Encyclopedias

Norbormide

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Norbormide

Preferred IUPAC name 5-(α-Hydroxy-α-2-pyridylbenzyl)-7-(α-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximide
Systematic name (10E)-8-[hydroxy(phenyl)pyridin-2-ylmethyl]-10-[phenyl(pyridin-2-yl)methylidene]-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione
Identifiers
CAS number	991-42-4
PubChem	24744067 (1R,7S) ^Y, 24840617 (6R,7R) ^Y, 12399560 ^Y
ChemSpider	10468605 ^Y
EC number	213-589-6
KEGG	C19139^Y
Jmol-3D images	Image 1
SMILES OC(C1=CC2C3C(C1\C2=C(/C1=CC=CC=C1)C1=CC=CC=N1)C(=O)NC3=O)(C1=CC=CC=C1)C1=NC=CC=C1
InChI InChI=1S/C33H25N3O3/c37-31-28-22-19-23(33(39,21-13-5-2-6-14-21)25-16-8-10-18-35-25)29(30(28)32(38)36-31)27(22)26(20-11-3-1-4-12-20)24-15-7-9-17-34-24/h1-19,22,28-30,39H,(H,36,37,38)/b27-26+ Key: DNTHHIVFNQZZRD-CYYJNZCTSA-N
Properties
Molecular formula	C₃₃H₂₅N₃O₃
Molar mass	511.570
Hazards
Main hazards	Toxic
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Wikipedia

Norbormide

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