Desnitro-imidacloprid

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.[1] 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.[1]

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
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−1
Appearance Colorless crystals
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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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