ContaminantDB: 1,1'-Azobis(cyclohexanecarbonitrile)

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (39)XML

Record Information

Version

1.0

Creation Date

2009-06-22 16:08:27 UTC

Update Date

2026-04-03 07:43:37 UTC

Accession Number

CHEM001443

Identification

Common Name

1,1'-Azobis(cyclohexanecarbonitrile)

Class

Small Molecule

Description

1,1'-Azobis(cyclohexanecarbonitrile) is a chemical compound of cyanide.

Contaminant Sources

HPV EPA Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Cyanide Compound
Industrial/Workplace Toxin
Nitrile
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₄H₂₀N₄

Average Molecular Mass

244.342 g/mol

Monoisotopic Mass

244.169 g/mol

CAS Registry Number

2094-98-6

IUPAC Name

1-[(E)-2-(1-cyanocyclohexyl)diazen-1-yl]cyclohexane-1-carbonitrile

Traditional Name

1-[(E)-2-(1-cyanocyclohexyl)diazen-1-yl]cyclohexane-1-carbonitrile

SMILES

N#CC1(CCCCC1)\N=N\C1(CCCCC1)C#N

InChI Identifier

InChI=1S/C14H20N4/c15-11-13(7-3-1-4-8-13)17-18-14(12-16)9-5-2-6-10-14/h1-10H2/b18-17+

InChI Key

KYIKRXIYLAGAKQ-ISLYRVAYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as azo compounds. These are derivatives of diazene(diimide), HN=NH, wherein both hydrogens are substituted by hydrocarbyl groups, e.g. PhN=NPh azobenzene or diphenyldiazene.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Azo compounds

Direct Parent

Azo compounds

Alternative Parents

Substituents

Azo compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Nitrile
Carbonitrile
Organopnictogen compound
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	116°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.061 g/L	ALOGPS
logP	3.69	ALOGPS
logP	3.32	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	72.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.03 m³·mol⁻¹	ChemAxon
Polarizability	27.18 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0490000000-5a4e6b26562eef7a1978	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bta-6690000000-5fc2bd6bf002944648a0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9400000000-50e857ce451756beb436	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00dl-0940000000-7767c1a438fcb52c138c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-0960000000-71232285818d25392632	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-4900000000-69b095bd71af712f2200	Spectrum

Toxicity Profile

Route of Exposure

Oral (1) ; inhalation (1) ; dermal (1)

Mechanism of Toxicity

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (2)

Metabolism

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. (1)

Toxicity Values

Not Available

Lethal Dose

203 to 300 milligrams for an adult human (cyanide salts). (3)

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

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. (1, 2)

Symptoms

Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (1, 2)

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. (2)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

1,1'-Azobis(cyclohexanecarbonitrile) (CHEM001443)

Structure for CHEM001443: 1,1'-Azobis(cyclohexanecarbonitrile)