Crimidine

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Crimidine
Names
Preferred IUPAC name
2-Chloro-N,N,6-trimethylpyrimidin-4-amine
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.007.840 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C7H10ClN3/c1-5-4-6(11(2)3)10-7(8)9-5/h4H,1-3H3
    Key: HJIUPFPIEBPYIE-UHFFFAOYSA-N
  • Cc1cc(N(C)C)nc(Cl)n1
Properties
C7H10ClN3
Molar mass 171.627
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).
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Crimidine is a

extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[2]
It is also no longer used in the United States as a rodenticide, but is still used to this day in other countries.

Mechanism of action

Crimidine is a highly reactive compound. The main mechanism of toxicity with crimidine is that it inhibits

amino acids. This is due to the pyrimidine ring that both compounds contain. Although, the exact mechanism of how crimidine antagonizes vitamin B6 is unknown. Another mechanism of toxicity with crimidine is due to its deactivating effect on acetylcholinesterase[3]

The serine residue, which is part of the acetylcholinesterase, acts a nucleophile and eventually replaces the C-Cl bond that is present in crimidine. Unlike with acetylcholine, the resulting serine-crimidine bond does not hydrolyze, permanently deactivating the enzyme

Toxicity

Crimidine is a fast acting convulsant, with an LD50 of 5 mg/kg. Earliest symptoms can develop within 20–40 minutes. These symptoms can include burning, irritation, and itching at the site of exposure or intake. Following these initial symptoms, convulsions follow and can be fatal. Low dose, long-term exposure can lead to damage in the

secreted
and can pass through the system in less than 24 hours..

intravenous vitamin B6 should be given as soon as poisoning is suspected

References

  1. ^ Reigart JR, Roberts JR (2013). "Rodenticides". Recognition and Management of Pesticide Poisoning: 173–187.
  2. ^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Retrieved October 29, 2011. {{cite journal}}: Cite journal requires |journal= (help)
  3. PMID 4405126
    .
  4. ^ "Crimidine". U.S. National Library of Medicine, National Institutes of Health. 2016. {{cite journal}}: Cite journal requires |journal= (help)

External links

  • Media related to Crimidine at Wikimedia Commons
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