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{{chembox
{{Chembox
|ImageFile=Norbormide.png
| ImageFile = Norbormide.png
| PIN = 5-(α-Hydroxy-α-2-pyridylbenzyl)-7-(α-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximide
|ImageSize=
| SystematicName = (10''E'')-8-[hydroxy(phenyl)pyridin-2-ylmethyl]-10-[phenyl(pyridin-2-yl)methylidene]-4-azatricyclo[5.2.1.0<sup>2,6</sup>]dec-8-ene-3,5-dione
|IUPACName= 5-(α-hydroxy- α-2-pyridylbenzyl)- 7-(α-2- pyridylbenzylidene)- 5-norbornene- 2,3-dicarboximide
| Section1 = {{Chembox Identifiers
|OtherNames=
| CASNo = 991-42-4
|Section1={{Chembox Identifiers
| PubChem = 24744067
| CASNo=991-42-4
| PubChem_Comment = (1''R'',7''S'')
| PubChem=13814
| PubChem_Ref = {{pubchemcite}}
| SMILES=C1=CC=C(C=C1)C(=C2C3C=C(C2C4C3C(=O)NC4=O)C(C5=CC=CC=C5)(C6=CC=CC=N6)O)C7=CC=CC=N7
| PubChem1 = 24840617
}}
| PubChem1_Comment = (6''R'',7''R'')
| PubChem1_Ref = {{pubchemcite}}
| PubChem2 = 12399560
| PubChem2_Ref = {{pubchemcite}}
| ChemSpiderID = 10468605
| ChemSpiderID_Ref = {{chemspidercite}}
| EINECS = 213-589-6
| 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 = 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+
| InChIKey = DNTHHIVFNQZZRD-CYYJNZCTSA-N}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| Formula=C<sub>33</sub>H<sub>25</sub>N<sub>3</sub>O<sub>3</sub>
| Formula=C<sub>33</sub>H<sub>25</sub>N<sub>3</sub>O<sub>3</sub>

Revision as of 22:26, 15 July 2010

Norbormide
Names
Preferred IUPAC name
5-(α-Hydroxy-α-2-pyridylbenzyl)-7-(α-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximide
Systematic IUPAC name
(10E)-8-[hydroxy(phenyl)pyridin-2-ylmethyl]-10-[phenyl(pyridin-2-yl)methylidene]-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.354 Edit this at Wikidata
EC Number
  • 213-589-6
  • 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
  • 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
Properties
C33H25N3O3
Molar mass 511.570
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

  1. ^ 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
  2. ^ 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