Sodium diethyldithiocarbamate
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| Names | |
|---|---|
| Preferred IUPAC name Sodium diethylcarbamodithioate | |
| Identifiers | |
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3D model (JSmol) | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.005.192 |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| 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 | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | Harmful |
| Related compounds | |
Other cations | Silver diethyldithiocarbamate |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Sodium diethyldithiocarbamate is the organosulfur compound with the formula NaS2CN(C2H5)2. It is a pale yellow, water soluble salt.
Preparation
[edit]Sodium diethyldithiocarbamate typically crystallizes from water as the trihydrate NaS2CN(C2H5)2.3H2O. The anhydrous salt and the trihydrate are often used interchangeably.[1]
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
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Oxidation of sodium diethyldithiocarbamate gives the disulfide, also called a thiuram disulfide (Et = ethyl):
- 2 NaS2CNEt2 + I2 → (S2CNEt2)2 + 2 NaI
Dithiocarbamates are nucleophiles and thus can be alkylated. Even dichloromethane suffices:[2]
- 2 NaS2CNEt2 + CH2Cl2 → CH2(S2CNEt2)2 + 2 NaCl
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.[3]
Laboratory and practical use
[edit]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.[4][5][6]
The zinc chelation of diethyldithiocarbamate inhibits metalloproteinases, which in turn prevents the degradation of extracellular matrix, an initial step in cancer metastasis and angiogenesis.[7]
Diethyldithiocarbamate inhibits superoxide dismutase, which can both have antioxidant and oxidant effects on cells, depending on the time of administration.[7]
References
[edit]- ^ Mereiter K, Preisinger A, Mikenda W, Steidl H (1985). "Hydrogen bonds in sodium dialkylthiocarbamate hydrates. X-ray diffraction and vibrational spectroscopic study". Inorganica Chimica Acta. 98 (2): 71–78. doi:10.1016/s0020-1693(00)84914-2.
- ^ Heckley PR, Holah DG, Hughes AN, Leh F (1970). "Reactions of Sodium N,N-Diethyldithiocarbamate with Some Organic Solvents". Canadian Journal of Chemistry. 48 (24): 3827–3830. doi:10.1139/v70-645.
- ^ 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
- ^ Henry Y.; Guissani A.; Ducastel B. (eds); "Nitric oxide research from chemistry to biology: EPR spectroscopy of nitrosylated compounds." Landes, Austin 1997.
- ^ Vanin A, Huisman A, van Faassen E (2002). "Iron dithiocarbamate as spin trap for nitric oxide detection: Pitfalls and successes". Nitric Oxide, Part D: Oxide Detection, Mitochondria and Cell Functions, and Peroxynitrite Reactions. Methods in Enzymology. Vol. 359. pp. 27–42. doi:10.1016/s0076-6879(02)59169-2. ISBN 978-0-12-182262-0. PMID 12481557.
- ^ van Faassen E.E.; Vanin A.F. (eds); "Radicals for life: The various forms of nitric oxide." Elsevier, Amsterdam 2007.
- ^ a b diethyldithiocarbamate National Cancer Institute - Drug Dictionary
Further reading
[edit]- Cvek B, Dvorak Z (2007). "Targeting of nuclear factor-kappaB and proteasome by dithiocarbamate complexes with metals". Curr. Pharm. Des. 13 (30): 3155–67. doi:10.2174/138161207782110390. PMID 17979756. Archived from the original on February 18, 2009.
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