Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone

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]

Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone[1]
Names
Preferred IUPAC name
N-[4-(Trifluoromethoxy)phenyl]carbonohydrazonoyl dicyanide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.119 Edit this at Wikidata
MeSH FCCP
UNII
  • 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 checkY
    Key: BMZRVOVNUMQTIN-UHFFFAOYSA-N checkY
  • 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
  • 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
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).
☒N verify (what is checkY☒N ?)

See also

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References

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  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. PMID 13907155.