C2920

Sigma-Aldrich

Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone

≥98% (TLC), powder

Synonym(s):
Mesoxalonitrile 4-trifluoromethoxyphenylhydrazone, FCCP
Linear Formula:
CF3OC6H4NHN=C(CN)2
CAS Number:
Molecular Weight:
254.17
Beilstein/REAXYS Number:
664446
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (TLC)

form

powder

color

yellow

mp

174-175 °C (dec.) (lit.)

solubility

95% ethanol: soluble

storage temp.

2-8°C

SMILES string

FC(F)(F)Oc1ccc(N\N=C(/C#N)C#N)cc1

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

InChI key

BMZRVOVNUMQTIN-UHFFFAOYSA-N

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Packaging

10 mg in poly bottle
50 mg in glass bottle

Biochem/physiol Actions

FCCP is a protonophore (H+ ionophore) and uncoupler of oxidative phosphorylation in mitochondria. It is capable of depolarizing plasma and mitochondrial membranes. FCCP has been shown to have a number of effects on cellular calcium. It also is reported to inhibit a background K+ current and induce a small inward current, reduce pH by 0.1 unit, and induce a rise of intracellular [Na+]. FCCP stimulates Mg2+-ATPase activity, inhibits β-amyloid production, and mimics the effect of selective glutamate agonist N-methyl-D-aspartate (NMDA) on mitochondrial superoxide production.

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2811 6.1 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Sheng-Po Chiu et al.
Sensors (Basel, Switzerland), 19(14) (2019-07-25)
Electric cell-substrate impedance sensing (ECIS) is an emerging technique for sensitively monitoring morphological changes of adherent cells in tissue culture. In this study, human mesenchymal stem cells (hMSCs) were exposed to different concentrations of carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone (FCCP) for 20...
Aleksandar Rakovic et al.
Cell death and differentiation, 26(8), 1428-1441 (2018-10-31)
The Parkinson's disease (PD)-related ubiquitin ligase Parkin and mitochondrial kinase PINK1 function together in the clearance of damaged mitochondria. Upon mitochondrial depolarization, Parkin translocates to mitochondria in a PINK1-dependent manner to ubiquitinate outer mitochondrial membrane proteins. According to the current...
Isa Mambetsariev et al.
Journal of clinical medicine, 8(7) (2019-07-19)
Small cell lung cancer (SCLC) is an aggressive neuroendocrine disease with an overall 5 year survival rate of ~7%. Although patients tend to respond initially to therapy, therapy-resistant disease inevitably emerges. Unfortunately, there are no validated biomarkers for early-stage SCLC...
Yuki Kunisada et al.
EBioMedicine, 25, 154-164 (2017-10-27)
CD4
Sunjin Lee et al.
Ecotoxicology and environmental safety, 182, 109377-109377 (2019-06-30)
The measurement of oxygen consumption rate (OCR) provides a comprehensive understanding of mitochondrial metabolism. However, no study has been conducted to investigate the mitochondrial dysfunction caused by organophosphate flame retardants (OPFRs). The objectives of this study were to optimize the...
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