Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone

Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone^[1]
Names
	Preferred IUPAC name N-[4-(Trifluoromethoxy)phenyl]carbonohydrazonoyl dicyanide
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;
UNII	SQR3W2FLV5 ;
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). verify (what is ?) Infobox references

Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone (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]

References

^ FCCP - Compound Summary, PubChem.
^ MeSH Descriptor Data, MeSH.
^ 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. PMID 13907155.