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Desnitro-imidacloprid

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Desnitro-imidacloprid
Names
IUPAC name 1-(6-Chloro-pyridin-3-yl)methyl-2-iminoimidazolidine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H11ClN4/c10-8-2-1-7(5-13-8)6-14-4-3-12-9(14)11/h1-2,5H,3-4,6H2,(H2,11,12)Key: UEQZFAGVRGWPDK-UHFFFAOYSA-N
SMILES
  • C1CN(C(=N1)N)CC2=CN=C(C=C2)Cl
Properties
Chemical formula C9H11ClN4
Molar mass 210.67 g·mol
Appearance Colorless crystals
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Desnitro-imidacloprid is a metabolite of the insecticide imidacloprid, a very common insecticide and the most important member of the class of insecticides called neonicotinoids, the only significant new class of insecticides to be developed between 1970 and 2000. While imidacloprid has proved highly selective against insects, the desnitro- version is highly toxic to mammals, due to its agonist action at the alpha4beta2 nicotinic acetylcholine receptor (nAChR) in the mammalian brain, at least as demonstrated in experiments involving mice.

References

  1. ^ M. Towizawa; J.E. Casida (1 November 2002). "Desnitro-imidacloprid activates the extracellular signal-regulated kinase cascade via the nicotinic receptor and intracellular calcium mobilization in N1E-115 cells". Toxicol Appl Pharmacol. 184 (3): 180–186. doi:10.1006/taap.2002.9503. PMID 12460746.


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