Sodium diethyldithiocarbamate

Sodium diethyldithiocarbamate is the chemical compound with the formula NaS₂CN(C₂H₅)₂. This salt is obtained by treating carbon disulfide with diethylamine in the presence of sodium hydroxide. Many dithiocarbamates can be prepared similarly from secondary amines and carbon disulfide. They are used as chelating agents for transition metal ions and as building blocks in the organic synthesis of herbicides and vulcanization reagents.

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Oxidation to thiuram disulfide

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

2 NaS₂CNEt₂ + I₂ → Et₂NC(S)S-SC(S)NEt₂ + 2 NaI

This disulfide is marketed under the labels Antabuse and Disulfiram, as anti-alcoholism drug.

Other reactions

Chlorination of the above-mentioned thiuram disulfide affords the thiocarbamoyl chloride.^[1]

Uses

Diethyldithiocarbamate is used in spin trapping of nitric oxide radicals, in cancer and as an antioxidant.

Spin trapping of nitric oxide radicals

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.^{[2] [3] [4]}

In cancer

The effect of diethyldithiocarbamate of chelating zinc inhibits metalloproteinases, which in turn prevents the degradation of extracellular matrix, which is an initial step in cancer metastasis and angiogenesis. ^[5]

Antioxidant

Diethyldithiocarbamate inhibits superoxide dismutase, which can both have antioxidant and oxidant effects on cells, depending on the time of administration.^[5]

References

1. ^ Goshorn, R. H.; Levis, Jr., W. W. ;Jaul, E.; Ritter, E. J. (1963). "Diethylthiocarbamyl Chloride". Org. Synth.; Coll. Vol. 4: 307. 
2. ^ Henry Y.; Guissani A.; Ducastel B. (eds); "Nitric oxide research from chemistry to biology: EPR spectroscopy of nitrosylated compounds." Landes, Austin 1997.
3. ^ Vanin A.F.; Huisman A.; van Faassen E.E.; "Iron dithiocarbamates as spin trap for nitric oxide: Pitfalls and successes." Methods in Enzymology vol 359 (2002) 27 - 42.
4. ^ van Faassen E.E.; Vanin A.F. (eds); "Radicals for life: The various forms of nitric oxide." Elsevier, Amsterdam 2007.
5. ^ ^{a b} diethyldithiocarbamate National Cancer Institute - Drug Dictionary