Skip to content
(E)-nitenpyram
EntityQ3817186· pop 10· linked from 211 articles

(E)-nitenpyram

Sign in to save

Also known as nitenpyram, (1E)-N-((6-chloro-3-pyridinyl)methyl)-N-ethyl-N'-methyl-2-nitro-1,1-ethenediamine, TI 304, NIT

Nitenpyram is a chemical frequently used as an insecticide in agriculture and veterinary medicine. The compound is an insect neurotoxin belonging to the class of neonicotinoids which works by blocking neural signaling of the central nervous system. It does so by binding irreversibly to the nicotinic acetylcholine receptor (nACHr) causing a stop of the flow of ions in the postsynaptic membrane of neurons leading to paralysis and death. Nitenpyram is highly selective towards the variation of the nACHr which insects possess, and has seen extensive use in targeted, insecticide applications.

Wikidata facts

Mass
270.088
Show 6 more facts
chemical formula
C₁₁H₁₅ClN₄O₂
canonical SMILES
CCN(CC1=CN=C(C=C1)Cl)C(=C[N+](=O)[O-])NC
NCI Thesaurus ID
C80604
Commons category
Nitenpyram
short name
NIT
isomeric SMILES
CCN(Cc1ccc(Cl)nc1)/C(=C/[N+](=O)[O-])NC
Sources (2)

via Wikidata · CC0

~15 min read

Encyclopedic overview

17 sections
Contents
  • Structure
  • Mechanism of action
  • Metabolism
  • Synthesis
  • Derivatives
  • Toxicology
  • Invertebrates
  • Vertebrates
  • Aquatic animals
  • Mammals
  • Degradation
  • Veterinary applications
  • Side effects
  • Agricultural applications
  • Side effects
  • References
  • External links

Nitenpyram is a chemical frequently used as an insecticide in agriculture and veterinary medicine. The compound is an insect neurotoxin belonging to the class of neonicotinoids which works by blocking neural signaling of the central nervous system. It does so by binding irreversibly to the nicotinic acetylcholine receptor (nACHr) causing a stop of the flow of ions in the postsynaptic membrane of neurons leading to paralysis and death. Nitenpyram is highly selective towards the variation of the nACHr which insects possess, and has seen extensive use in targeted, insecticide applications.

Known under the codename TI 304 during field testing starting in 1989, the compound's first documented commercial use was in 1995 under the name "Bestguard" as an agricultural insecticide. Later, nitenpyram was expanded for use as a flea treatment by the Novartis company under the trade name "Capstar", with a subsequent FDA approval for non-food producing animals in October 2000. The current producer of nitenpyram itself is the Sumitomo chemical company. Nitenpyram continues to be used commercially, though data from market surveys indicate a significant decrease in the global usage compared to other insecticides or neonicotinoids.

Excerpted from Wikipedia’s “(E)-nitenpyram” article, available under the CC BY-SA 4.0 licence.

Gallery (3)

Available in 9 languages

via Wikidata sitelinks · CC0