ContaminantDB: Cyanamide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2013-04-25 07:56:50 UTC

Update Date

2016-11-09 01:08:58 UTC

Accession Number

CHEM002777

Identification

Common Name

Cyanamide

Class

Small Molecule

Description

Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol deterrent drug in Canada, Europe and Japan. The molecule features a nitrile group attached to an amino group. Although it is similar in structure to hydrogen cyanide, it is not as toxic. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2). Calcium cyanamide or CaCN2 is a calcium compound used as fertilizer, first synthesized in 1898 by Adolph Frank and Nikodem Caro (Frank-Caro process). It is formed when calcium carbide reacts with nitrogen. It is commercially known as Nitrolime. In enzymology, a cyanamide hydratase is an enzyme that catalyzes the chemical reaction.

Contaminant Sources

HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Fertilizer
Industrial/Workplace Toxin
Nitrile
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Amidocyanogen	ChEBI
Carbamonitrile	ChEBI
Carbodiimide	ChEBI
Cyanoamine	ChEBI
H2N-C#N	ChEBI
NH2CN	ChEBI
Abstem	MeSH
Calcium carbimide	MeSH
Calcium cyanamide	MeSH
Calcium cyanamide, citrated	MeSH
Calcium salt cyanamide	MeSH
Carbimide	MeSH
Carbimide, calcium	MeSH
Citrated calcium cyanamide	MeSH
Colme	MeSH
Cyanamide, calcium	MeSH
Cyanamide, calcium (1:1) salt	MeSH
Cyanamide, calcium (2:1) salt	MeSH
Cyanamide, calcium salt	MeSH
Cyanamide, citrated calcium	MeSH
Temposil	MeSH
Ipsen brand OF calcium carbimide	MeSH

Chemical Formula

CH₂N₂

Average Molecular Mass

42.040 g/mol

Monoisotopic Mass

42.022 g/mol

CAS Registry Number

420-04-2

IUPAC Name

aminoformonitrile

Traditional Name

cyanamide

SMILES

NC#N

InChI Identifier

InChI=1S/CH2N2/c2-1-3/h2H2

InChI Key

XZMCDFZZKTWFGF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Monoalkylamines

Alternative Parents

Substituents

Organopnictogen compound
Hydrocarbon derivative
Primary aliphatic amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:16698 )
nitrile (CHEBI:16698 )
Pesticides (C01566 )
a small molecule (CPD-657 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor

Chemical Roles

EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	44°C
Boiling Point	260°C (decomposes)
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	27.4 g/L	ALOGPS
logP	-0.86	ALOGPS
logP	-0.64	ChemAxon
logS	-0.19	ALOGPS
pKa (Strongest Acidic)	10.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.81 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	10.88 m³·mol⁻¹	ChemAxon
Polarizability	3.68 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-42d670fed59f7b545794	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-c4250dd42f35aa652456	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-c4250dd42f35aa652456	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-c4250dd42f35aa652456	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-2a6fb71961852fe89d18	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-2a6fb71961852fe89d18	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-2a6fb71961852fe89d18	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-36e3aa30c6cc4afb2049	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-36e3aa30c6cc4afb2049	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-36e3aa30c6cc4afb2049	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-1c8520c5f7efb1187e43	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-1c8520c5f7efb1187e43	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-1c8520c5f7efb1187e43	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-817e18f9f536d9b71cdb	Spectrum

Toxicity Profile

Route of Exposure

Not Available

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

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol deterrent drug in Canada, Europe and Japan. Calcium cyanamide or CaCN2 is a calcium compound used as fertilizer, first synthesized in 1898 by Adolph Frank and Nikodem Caro (Frank-Caro process).

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID