Sodium diethyldithiocarbamate

Sodium diethyldithiocarbamate is the organosulfur compound with the formula NaS2CN(C2H5)2.

Sodium diethyldithiocarbamate
Names
IUPAC name
sodium (diethylcarbamothioyl)sulfanide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.192
UNII
Properties
C5H10NS2Na
Molar mass 171.259 g/mol (anhydrous)
Appearance White, slightly brown, or slightly pink crystalline solid
Density 1.1 g/cm3
Melting point 95 °C (203 °F; 368 K)
Soluble
Solubility soluble in alcohol, acetone
insoluble in ether, benzene
Hazards
Main hazards Harmful
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation

This salt 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.

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 as an anti-alcoholism drug under the labels Antabuse and Disulfiram. Chlorination of the above-mentioned thiuram disulfide affords the thiocarbamoyl chloride.[1]

Ligand bonding

The diethyldithiocarbamate ion chelates to many "softer" 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.[2]

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.[3][4][5]

In cancer

The zinc chelation of diethyldithiocarbamate inhibits metalloproteinases, which in turn prevents the degradation of extracellular matrix, an initial step in cancer metastasis and angiogenesis.[6]

Antioxidant

Diethyldithiocarbamate inhibits superoxide dismutase, which can both have antioxidant and oxidant effects on cells, depending on the time of administration.[6]

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References
  1. Goshorn, R. H.; Levis, Jr., W. W. ;Jaul, E.; Ritter, E. J. (1963). "Diethylthiocarbamyl Chloride". Organic Syntheses.CS1 maint: multiple names: authors list (link); Collective Volume, 4, p. 307
  2. Cotton, F. Albert; Wilkinson, Geoffrey; Murillo, Carlos A.; Bochmann, Manfred (1999), Advanced Inorganic Chemistry (6th ed.), New York: Wiley-Interscience, ISBN 0-471-19957-5
  3. Henry Y.; Guissani A.; Ducastel B. (eds); "Nitric oxide research from chemistry to biology: EPR spectroscopy of nitrosylated compounds." Landes, Austin 1997.
  4. Vanin, A.F.; Huisman, A.; van Faassen, E.E. (2002). "Iron dithiocarbamates as spin trap for nitric oxide: Pitfalls and successes". Methods in Enzymology. 359: 27–42. doi:10.1016/s0076-6879(02)59169-2. PMID 12481557.
  5. van Faassen E.E.; Vanin A.F. (eds); "Radicals for life: The various forms of nitric oxide." Elsevier, Amsterdam 2007.
  6. diethyldithiocarbamate National Cancer Institute - Drug Dictionary

Further reading
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