Carbonyl cyanide m-chlorophenyl hydrazone

Carbonyl cyanide m-chlorophenyl hydrazone
Names
Preferred IUPAC name
N-(4-Chlorophenyl)carbonohydrazonoyl dicyanide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.277
KEGG
MeSH CCCP
UNII
  • InChI=1S/C9H5ClN4/c10-7-2-1-3-8(4-7)13-14-9(5-11)6-12/h1-4,13H Y
    Key: UGTJLJZQQFGTJD-UHFFFAOYSA-N Y
  • InChI=1/C9H5ClN4/c10-7-2-1-3-8(4-7)13-14-9(5-11)6-12/h1-4,13H
    Key: UGTJLJZQQFGTJD-UHFFFAOYAQ
  • Clc1cc(N\N=C(/C#N)C#N)ccc1
Properties
C9H5ClN4
Molar mass 204.616 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Carbonyl cyanide m-chlorophenyl hydrazone (CCCP; also known as [(3-chlorophenyl)hydrazono]malononitrile) is a chemical inhibitor of oxidative phosphorylation. It is a nitrile, hydrazone and protonophore. In general, CCCP causes the gradual destruction of living cells and death of the organism, although mild doses inducing partial decoupling have been shown to increase median and maximum lifespan in C. elegans models, suggesting a degree of hormesis. CCCP causes an uncoupling of the proton gradient that is established during the normal activity of electron carriers in the electron transport chain. The chemical acts essentially as an ionophore and reduces the ability of ATP synthase to function optimally. It is routinely used as an experimental uncoupling agent in cell and molecular biology, particularly in the study of mitophagy, where it was integral in discovering the role of the Parkinson's disease-associated ubiquitin ligase Parkin. Outside of its effects on mitochondria, CCCP may also disrupt lysosomal degradation during autophagy.