Sodium diethyldithiocarbamate

Preparation

Sodium diethyldithiocarbamate typically crystallizes from water as the trihydrate . The anhydrous salt and the trihydrate are often used interchangeably.

Sodium diethyldithiocarbamate is obtained by treating carbon disulfide with diethylamine in the presence of sodium hydroxide: :CS2 + HN(C2H5)2 + NaOH → NaS2CN(C2H5)2 + H2O Other dithiocarbamates can be prepared similarly from secondary amines and carbon disulfide. They are used as chelating agents for transition metal ions and as precursors to herbicides and vulcanization reagents.

Reactions

Oxidation of sodium diethyldithiocarbamate gives the disulfide, also called a thiuram disulfide (Et = ethyl): :

Dithiocarbamates are nucleophiles and thus can be alkylated. Even dichloromethane suffices: :

Diethyldithiocarbamate reacts with many metal salts to give transition metal dithiocarbamate complexes. The ligands coordinate 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.

Laboratory and practical use

By the technique of 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.

The zinc chelation of diethyldithiocarbamate inhibits metalloproteinases, which in turn prevents the degradation of extracellular matrix, an initial step in cancer metastasis and angiogenesis.

Diethyldithiocarbamate inhibits superoxide dismutase, which can both have antioxidant and oxidant effects on cells, depending on the time of administration.

References

References

1. (1985). "Hydrogen bonds in sodium dialkylthiocarbamate hydrates. X-ray diffraction and vibrational spectroscopic study". Inorganica Chimica Acta.
2. (1970). "Reactions of Sodium ''N,N''-Diethyldithiocarbamate with Some Organic Solvents". Canadian Journal of Chemistry.
3. {{Cotton&Wilkinson6th
4. Henry Y.; Guissani A.; Ducastel B. (eds); "Nitric oxide research from chemistry to biology: EPR spectroscopy of nitrosylated compounds." Landes, Austin 1997.
5. (2002). "Nitric Oxide, Part D: Oxide Detection, Mitochondria and Cell Functions, and Peroxynitrite Reactions".
6. van Faassen E.E.; Vanin A.F. (eds); "Radicals for life: The various forms of nitric oxide." Elsevier, Amsterdam 2007.
7. [http://www.cancer.gov/Templates/drugdictionary.aspx?CdrID=40247 diethyldithiocarbamate] National Cancer Institute - Drug Dictionary