((3-Chlorphenyl)hydrazono)-malanonitril
Carbonyl cyanide (m-chlorophenyl)hydrazone
Grundinformationen
- CAS
555-60-2- Standard-SMILES
N#CC(C#N)=NNc1cccc(Cl)c1- InChIKey
UGTJLJZQQFGTJD-UHFFFAOYSA-N- Summenformel
- C9H5ClN4
- Durchschnittliche Molmasse
- 204,61 g/mol
- Monoisotopische Masse
- 204,0202739
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Carbonyl cyanide (m-chlorophenyl)hydrazone
- IUPAC
- 2-[(3-chlorophenyl)hydrazinylidene]propanedinitrile
- Lokaler Name
- ((3-Chlorphenyl)hydrazono)-malanonitril
- Englischer Name
- CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE
- Summenformel
- C9H5ClN4
- Molmasse
- 204.62
Namen und Synonyme
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
Weitere Namen anzeigen
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
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,4
- Polarare Oberfläche (TPSA)
- 72 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 14
- Formalladung
- 0
- Komplexität
- 300
Experimentelle und physikochemische Eigenschaften
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]
Physikochemische Eigenschaften
- Schmelzpunkt
- 170 · 170-175 °C (dec.)
- Siedepunkt
- 333.84 °C · 333.84°C (rough estimate)
- Dichte
- 1.3807 · 1.3807 (rough estimate)
- Brechungsindex
- 1.611 · 1.6110 (estimate)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- 10 mg/mL, · methanol: 10 mg/mL, clear, very deep yellow
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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.
Gefahrenhinweise
Hazards SummaryAn irritant; May cause skin sensitization; [MSDSonline] See NITRILES.
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Toxikologische Informationen
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)
Chemie und Industrie
Pharmakologische Informationen
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.
Verwendung und Herstellung
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
Anwendungen
BeschreibungCCCP 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.
VerwendenCarbonyl cyanide 3-chlorophenylhydrazone is a widely used uncoupler of oxidative phosphorylation.
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