Sodium diethyldithiocarbamate
Encyclopedia
Sodium diethyldithiocarbamate is the organosulfur compound with the formula NaS2CN(C2H5)2.
with diethylamine
in the presence of sodium hydroxide:
Other dithiocarbamate
s can be prepared similarly from secondary amines and carbon disulfide. They are used as chelating agents for transition metal ions and as precursors to herbicide
s and vulcanization
reagents.
, also called a thiuram disulfide
(Et = ethyl
):
This disulfide is marketed as an anti-alcoholism drug under the labels Antabuse and Disulfiram
. Chlorination of the above-mentioned thiuram disulfide affords the thiocarbamoyl chloride.
" metals via the two sulfur atoms. Other more complicated bonding modes are known including binding as unidentate ligand and a bridging ligand
using one or
both sulfur atoms.
Spin trapping
Complexes of Dithiocarbamates with iron provide one of the very few methods to study the formation of nitric oxide
(NO) radicals in biological materials. Although the lifetime of NO in tissues is too short to allow detection of this radical itself, NO readily binds to iron-dithiocarbamate complexes. The resulting mono-nitrosyl-iron complex (MNIC) is stable, and may be detected with Electron Paramagnetic Resonance
(EPR) spectroscopy.
inhibits metalloproteinase
s, which in turn prevents the degradation of extracellular matrix
, which is an initial step in cancer metastasis
and angiogenesis
.
, which can both have antioxidant
and oxidant effects on cells, depending on the time of administration.
Preparation
This salt is obtained by treating carbon disulfideCarbon disulfide
Carbon disulfide is a colorless volatile liquid with the formula CS2. The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical non-polar solvent...
with diethylamine
Diethylamine
Diethylamine is a secondary amine with the molecular structure CH3CH2NHCH2CH3. It is a flammable, strongly alkaline liquid. It is miscible with water and ethanol. It is a colorless liquid which often appears brown due to impurities...
in the presence of sodium hydroxide:
- CS2 + HN(C2H5)2 + NaOH → NaS2CN(C2H5)2 + H2O
Other dithiocarbamate
Dithiocarbamate
A dithiocarbamate is a functional group in organic chemistry. It is the analog of a carbamate in which both oxygen atoms are replaced by sulfur atoms. Sodium diethyldithiocarbamate is a common ligand in inorganic chemistry....
s can be prepared similarly from secondary amines and carbon disulfide. They are used as chelating agents for transition metal ions and as precursors to herbicide
Herbicide
Herbicides, also commonly known as weedkillers, are pesticides used to kill unwanted plants. Selective herbicides kill specific targets while leaving the desired crop relatively unharmed. Some of these act by interfering with the growth of the weed and are often synthetic "imitations" of plant...
s and vulcanization
Vulcanization
Vulcanization or vulcanisation is a chemical process for converting rubber or related polymers into more durable materials via the addition of sulfur or other equivalent "curatives." These additives modify the polymer by forming crosslinks between individual polymer chains. Vulcanized material is...
reagents.
Oxidation to thiuram disulfide
Oxidation of sodium diethyldithiocarbamate gives the disulfideDisulfide
In chemistry, a disulfide usually refers to the structural unit composed of a linked pair of sulfur atoms. Disulfide usually refer to a chemical compound that contains a disulfide bond, such as diphenyl disulfide, C6H5S-SC6H5....
, also called a thiuram disulfide
Thiuram disulfide
Thiuram disulfides are a class of organic disulfides that have the general structural formula shown to the right.-Preparation:They are prepared from the oxidation of their corresponding sodium salts of thiocarbamates with iodine:-Example:...
(Et = ethyl
Ethyl group
In chemistry, an ethyl group is an alkyl substituent derived from ethane . It has the formula -C2H5 and is very often abbreviated -Et.Ethylation is the formation of a compound by introduction of the ethyl functional group, C2H5....
):
- 2 NaS2CNEt2 + I2 → Et2NC(S)S-SC(S)NEt2 + 2 NaI
This disulfide is marketed as an anti-alcoholism drug under the labels Antabuse and Disulfiram
Disulfiram
Disulfiram is a drug discovered in the 1920s and used to support the treatment of chronic alcoholism by producing an acute sensitivity to alcohol. Trade names for disulfiram in different countries are Antabuse and Antabus manufactured by Odyssey Pharmaceuticals...
. Chlorination of the above-mentioned thiuram disulfide affords the thiocarbamoyl chloride.
Ligand bonding
The diethyldithiocarbamate ion chelates to many "softerHSAB theory
The HSAB concept is an acronym for 'hard and soft acids and bases. Also known as the Pearson acid base concept, HSAB is widely used in chemistry for explaining stability of compounds, reaction mechanisms and pathways....
" metals via the two sulfur atoms. Other more complicated bonding modes are known including binding as unidentate ligand and a bridging ligand
Bridging ligand
A bridging ligand is a ligand that connects two or more atoms, usually metal ions. The ligand may be atomic or polyatomic. Virtually all complex organic compounds can serve as bridging ligands, so the term is usually restricted to small ligands such as pseudohalides or to ligands that are...
using one or
both sulfur atoms.
Spin trappingSpin trappingSpin trapping in chemistry is an analytical technique employed in the detection and identification of short-lived free radicals. Spin trapping involves the addition of radical to a nitrone spin trap resulting in the formation of a spin adduct, a nitroxide-based persistent radical, that can be...
of nitric oxide radicals
Complexes of Dithiocarbamates with iron provide one of the very few methods to study the formation of nitric oxideNitric oxide
Nitric oxide, also known as nitrogen monoxide, is a diatomic molecule with chemical formula NO. It is a free radical and is an important intermediate in the chemical industry...
(NO) radicals in biological materials. Although the lifetime of NO in tissues is too short to allow detection of this radical itself, NO readily binds to iron-dithiocarbamate complexes. The resulting mono-nitrosyl-iron complex (MNIC) is stable, and may be detected with Electron Paramagnetic Resonance
Electron paramagnetic resonance
Electron paramagnetic resonance or electron spin resonance spectroscopyis a technique for studying chemical species that have one or more unpaired electrons, such as organic and inorganic free radicals or inorganic complexes possessing a transition metal ion...
(EPR) spectroscopy.
In cancer
The effect of diethyldithiocarbamate of chelating zincZinc
Zinc , or spelter , is a metallic chemical element; it has the symbol Zn and atomic number 30. It is the first element in group 12 of the periodic table. Zinc is, in some respects, chemically similar to magnesium, because its ion is of similar size and its only common oxidation state is +2...
inhibits metalloproteinase
Metalloproteinase
Metalloproteinases constitute a family of enzymes from the group of proteases, classified by the nature of the most prominent functional group in their active site. These are proteolytic enzymes whose catalytic mechanism involves a metal. Most metalloproteases are zinc-dependent, but some use...
s, which in turn prevents the degradation of extracellular matrix
Extracellular matrix
In biology, the extracellular matrix is the extracellular part of animal tissue that usually provides structural support to the animal cells in addition to performing various other important functions. The extracellular matrix is the defining feature of connective tissue in animals.Extracellular...
, which is an initial step in cancer metastasis
Metastasis
Metastasis, or metastatic disease , is the spread of a disease from one organ or part to another non-adjacent organ or part. It was previously thought that only malignant tumor cells and infections have the capacity to metastasize; however, this is being reconsidered due to new research...
and angiogenesis
Angiogenesis
Angiogenesis is the physiological process involving the growth of new blood vessels from pre-existing vessels. Though there has been some debate over terminology, vasculogenesis is the term used for spontaneous blood-vessel formation, and intussusception is the term for the formation of new blood...
.
Antioxidant
Diethyldithiocarbamate inhibits superoxide dismutaseSuperoxide dismutase
Superoxide dismutases are a class of enzymes that catalyze the dismutation of superoxide into oxygen and hydrogen peroxide. As such, they are an important antioxidant defense in nearly all cells exposed to oxygen...
, which can both have antioxidant
Antioxidant
An antioxidant is a molecule capable of inhibiting the oxidation of other molecules. Oxidation is a chemical reaction that transfers electrons or hydrogen from a substance to an oxidizing agent. Oxidation reactions can produce free radicals. In turn, these radicals can start chain reactions. When...
and oxidant effects on cells, depending on the time of administration.