Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone

Carbonyl cyanide-4-(trifluoromethoxy)phenylhydrazone (FCCP) is an ionophore that is a mobile ion carrier. It is referred to as an uncoupling agent because it disrupts ATP synthesis by transporting hydrogen ions through the mitochondrial membrane before they can be used to provide the energy for oxidative phosphorylation.[2] It is a nitrile and hydrazone. FCCP was first described in 1962 by Heytler.[3]

Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone[1]

Names
IUPAC name 2-[[4-(trifluoromethoxy)phenyl]hydrazinylidene]propanedinitrile
Identifiers
CAS Number	370-86-5
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:75458
ChEMBL	ChEMBL457504
ChemSpider	3213
ECHA InfoCard	100.006.119
MeSH	FCCP
PubChem CID	3330
CompTox Dashboard (EPA)	DTXSID40190494
InChI InChI=1S/C10H5F3N4O/c11-10(12,13)18-9-3-1-7(2-4-9)16-17-8(5-14)6-15/h1-4,16H Key: BMZRVOVNUMQTIN-UHFFFAOYSA-N InChI=1/C10H5F3N4O/c11-10(12,13)18-9-3-1-7(2-4-9)16-17-8(5-14)6-15/h1-4,16H Key: BMZRVOVNUMQTIN-UHFFFAOYAT
SMILES C1=CC(=CC=C1NN=C(C#N)C#N)OC(F)(F)F FC(F)(F)Oc1ccc(cc1)N/N=C(\C#N)C#N
Properties
Chemical formula	C10H5F3N4O
Molar mass	254.16811 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 m-chlorophenyl hydrazone (CCCP)

References

1. FCCP - Compound Summary, PubChem.
2. MeSH Descriptor Data, MeSH.
3. Heytler, P G (1962). "A new class of uncoupling agents — Carbonyl cyanide phenylhydrazones". Biochemical and Biophysical Research Communications. 7 (4): 272–275. doi:10.1016/0006-291X(62)90189-4.