3871
T3D3816
Cyanamide
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.
420-04-2
9864
CH2N2
White powder.
44°C
260°C (decomposes)
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. (L97)
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)
No indication of carcinogenicity to humans (not listed by IARC).
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).
2013-04-25T07:56:50Z
2014-12-24T20:26:32Z
C01566
16698
DB02679
true
NC#N
CH2N2
InChI=1S/CH2N2/c2-1-3/h2H2
InChIKey=XZMCDFZZKTWFGF-UHFFFAOYSA-N
42.04
42.021798074
Exogenous
Solid
CHEMBL56279
9480
<p>Joachim Ebeling, “Process for the preparation of calcium cyanamide.” U.S. Patent US4849197, issued July, 1931.</p>