Basic information
- CAS
555-60-2- Standard SMILES
N#CC(C#N)=NNc1cccc(Cl)c1- InChIKey
UGTJLJZQQFGTJD-UHFFFAOYSA-N- Molecular formula
- C9H5ClN4
- Average molar mass
- 204.61 g/mol
- Monoisotopic mass
- 204.0202739
Overview
CCCP is a member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death. It has a role as a geroprotector, an ionophore and an antibacterial agent. It is a nitrile, a hydrazone and a member of monochlorobenzenes. It is functionally related to a hydrazonomalononitrile.
Names & identifiers
- Preferred name
- Carbonyl cyanide (m-chlorophenyl)hydrazone
- IUPAC
- 2-[(3-chlorophenyl)hydrazinylidene]propanedinitrile
- English name
- CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE
- Molecular formula
- C9H5ClN4
- Molecular weight
- 204.62
Names & synonyms
cccp555-60-2Carbonyl cyanide m-chlorophenylhydrazoneCarbonylcyanide-3-chlorophenylhydrazonem-Chlorophenyl carbonylcyanide hydrazoneCarbonyl cyanide m-chlorophenyl hydrazonePropanedinitrile, [(3-chlorophenyl)hydrazono]-[(3-chlorophenyl)hydrazono]malononitrileMesoxalonitrile, (m-chlorophenyl)hydrazone((3-Chlorophenyl)hydrazono)propanedinitrileCarbonylcyanide-m-chlorophenylhydrazone((3-Chlorophenyl)hydrazono)malononitrile
Show more names
Carbonyl Cyanide(3-CHLOROPHENYL)HYDRAZONOMALONONITRILEMESOXALONITRILE 3-CHLOROPHENYLHYDRAZONECCCPHM-CL-CCPm-Cl-CCP (CCCP)BUTTPARK 91\04-41TIMTEC-BB SBB003506CCCP, 10 mM in DMSOCCCP apoptosis inducer
Carbonyl cyanide, (3-chlorophenyl)hydrazoneCarbonylcyanide m-chlorophenylhydrazonePropanedinitrile, ((3-chlorophenyl)hydrazono)-Carbonyl cyanide-m-chlorophenylhydrazone4D4NW27CG5CHEBI:3259Carbonyl cyanide (m-chlorophenyl)hydrazoneN-(3-chlorophenyl)-1-cyanomethanecarbohydrazonoyl cyanide
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 72 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 300
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
LogP3.13
Vapor Pressure0.00000567 [mmHg]
Physical DescriptionFine crystals; [MSDSonline]
Collision Cross Section142.8 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID7040990]
Physicochemical properties
- Melting point
- 170 · 170-175 °C (dec.)
- Boiling point
- 333.84 °C · 333.84°C (rough estimate)
- Density
- 1.3807 · 1.3807 (rough estimate)
- refractive index
- 1.611 · 1.6110 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- 10 mg/mL, · methanol: 10 mg/mL, clear, very deep yellow
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301+H311+H331 (39.2%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 74 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazards SummaryAn irritant; May cause skin sensitization; [MSDSonline] See NITRILES.
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Toxicology
Treatment
Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)
Health Effects
Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)
MeSH Pharmacological ClassificationChemical agents that increase the permeability of CELL MEMBRANES to PROTONS.
Uses & manufacturing
UsesA proton ionophore. It is commonly used as an uncoupling agent and inhibitor of photosynthesis because of its effects on mitochondrial and chloroplast membranes. [ChemIDplus]
General Manufacturing InformationPropanedinitrile, 2-[2-(3-chlorophenyl)hydrazinylidene]-: ACTIVE
Applications
DescriptionCCCP is a protonophore mitochondrial uncoupler that increases membrane permeability to protons, leading to a disruption in the mitochondrial membrane potential. It inhibits mitochondrial respiration and ATPase activity when used at concentrations of 110 and 35 nM, respectively. CCCP inhibits activation of stimulation of interferon genes (STING), decreasing the expression of downstream STING targets, including IFN-β, TBK1, and IRF3 when used at a concentration of 50 μM in RAW 264.7 cells. It induces mitochondrial fission in a manner dependent on the GTPase Drp1. CCCP (4 mg/kg) increases body temperature as well as left ventricular systolic and diastolic dimensions and decreases fractional shortening in rats. It also increases myocardial glucose and fatty acid uptake in rats.
UsesCarbonyl cyanide 3-chlorophenylhydrazone is a widely used uncoupler of oxidative phosphorylation.
Carbonyl cyanide 3-chlorophenylhydrazone (CCCP) has been used:in the inhibition of efflux pump in clinical Pseudomonas aeruginosato inhibit oxidative phosphorylation activity of mitochondria in human Beas-2B bronchial epithelial cellsto prepare carbonyl cyanide m-chlorophenylhydrazone solution for oxidative and mitochondrial stress assay and mitophagy induction in Caenorhabditis elegans
Related reactions
4 records
Compound notes
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