Carbonyl cyanide m-chlorophenyl hydrazone

Carbonyl cyanide m-chlorophenyl hydrazone (CCCP) ([(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.[1][2] CCCP affects the protein synthesis reactions in seedling mitochondria.[3] 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.

Carbonyl cyanide m-chlorophenyl hydrazone

Names
IUPAC name [(3-chlorophenyl)hydrazono]malononitrile
Systematic IUPAC name [(3-chlorophenyl)hydrazono]propanedinitrile
Identifiers
CAS Number	555-60-2^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:3259^Y
ChEMBL	ChEMBL224214^Y
ChemSpider	2504^Y
ECHA InfoCard	100.008.277
KEGG	C11164^Y
MeSH	CCCP
PubChem CID	2603
CompTox Dashboard (EPA)	DTXSID7040990
InChI 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
SMILES Clc1cc(N\N=C(/C#N)C#N)ccc1
Properties
Chemical formula	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).
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Infobox references

See also

• Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone (FCCP)

References

1. J.W. Park; S.Y. Lee; J.Y. Yang; H.W. Rho; B.H. Park; S.N. Lim; J.S. Kim; H.R. Kim (1997). "Effect of carbonyl cyanide m-chlorophenylhydrazone (CCmCP) on the dimerization of lipoprotein lipase". Biochimica et Biophysica Acta. 1344 (2): 132–8. doi:10.1016/s0005-2760(96)00146-4. PMID 9030190.
2. D. Gášková; B. Brodská; A. Holoubek; K. Sigler (1999). "Factors and processes involved in membrane potential build-up in yeast: diS-C3(3) assay". The International Journal of Biochemistry & Cell Biology. 31 (5): 575–584. doi:10.1016/S1357-2725(99)00002-3. PMID 10399318.
3. Y.M. Konstantinov; I.V. Subota; A.S. Arziev. "Protein synthesis in mitochondria under different redox conditions". Preprint of the Irkutsk Institute of Plant Physiology and Biochemistry. Archived from the original on 2011-07-17. Retrieved 2009-02-04.