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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/20 04:46:11」(JST)
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Sodium diethyldithiocarbamate
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| Names |
| IUPAC name
sodium (diethylcarbamothioyl)sulfanide
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| Identifiers |
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CAS Registry Number
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148-18-5 Y |
| ChEMBL |
ChEMBL107217 Y |
| ChemSpider |
8642 Y |
InChI
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InChI=1S/C5H11NS2.Na/c1-3-6(4-2)5(7)8;/h3-4H2,1-2H3,(H,7,8);/q;+1/p-1 Y
Key: IOEJYZSZYUROLN-UHFFFAOYSA-M Y
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InChI=1/C5H11NS2.Na/c1-3-6(4-2)5(7)8;/h3-4H2,1-2H3,(H,7,8);/q;+1/p-1
Key: IOEJYZSZYUROLN-REWHXWOFAF
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| Jmol-3D images |
Image |
| PubChem |
533728 |
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| UNII |
A5304YEB5E Y |
| Properties |
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Chemical formula
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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) |
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Solubility in water
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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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| N verify (what is: Y/N?) |
| Infobox references |
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Sodium diethyldithiocarbamate is the organosulfur compound with the formula NaS2CN(C2H5)2.
Contents
- 1 Preparation
- 2 Oxidation to thiuram disulfide
- 3 Ligand bonding
- 3.1 Spin trapping of nitric oxide radicals
- 3.2 In cancer
- 3.3 Antioxidant
- 3.4 In metabolism
- 4 References
- 5 Further reading
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 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.[6]
Antioxidant
Diethyldithiocarbamate inhibits superoxide dismutase, which can both have antioxidant and oxidant effects on cells, depending on the time of administration.[6]
In metabolism
Diethyldithiocarbamate has been described to interfere with glucocorticoid metabolism, by inhibiting the activity of the enzyme 11beta-hydroxysteroid dehydrogenase type 2, which converts cortisol to cortisone.[7]
References
- ^ Goshorn, R. H.; Levis, Jr., W. W. ;Jaul, E.; Ritter, E. J. (1963). "Diethylthiocarbamyl Chloride". Org. Synth. ; Coll. Vol. 4, p. 307
- ^ 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.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.
- ^ 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
- ^ Atanasov, AG; Tam, S; Röcken, JM; Baker, ME; Odermatt, A (Aug 2003). "Inhibition of 11beta-hydroxysteroid dehydrogenase type 2 bydithiocarbamates". Biochem Biophys ResCommun 308 (2): 257–62. PMID 12901862.
Further reading
- 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.
UpToDate Contents
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English Journal
- Surface enhanced Raman scattering, electronic spectrum, natural bond orbital, and Mulliken charge distribution in the normal modes of diethyldithiocarbamate copper (II) complex, [Cu(DDTC)2].
- Téllez Soto CA, Costa AC Jr, Ramos JM, Vieira LS, Rost NC, Versiane O, Rangel JL, Mondragón MA, Raniero L, Martin AA.SourceLaboratory of Biomedical Vibrational Spectroscopy, IP&D, Research and Development Institute - UNIVAP, Av. Shishima Hifumi, 2911, Urbanova, 12.224-000 São José dos Campos, SP, Brazil. Electronic address: cayotellez@gmail.com.
- Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2013 Dec;116:546-55. doi: 10.1016/j.saa.2013.07.083. Epub 2013 Aug 6.
- Surface-enhanced Raman scattering (SERS) was used to study the interactions of the normal modes of the diethyldithiocarbamate copper (II) complex, [Cu(DDTC)2] on nano-structured mixture silver-gold surfaces and on silver surfaces. The electronic spectrum of this complex was measured and the charge t
- PMID 23978740
- Mitochondrial dysfunction in the hippocampus of rats caused by chronic oxidative stress.
- Rodríguez-Martínez E, Martínez F, Espinosa-García MT, Maldonado P, Rivas-Arancibia S.SourceDepartamento de Fisiología, Facultad de Medicina, Universidad Nacional Autónoma de México, AP 70-250, CP 04510 México D.F., Mexico.
- Neuroscience.Neuroscience.2013 Nov 12;252:384-95. doi: 10.1016/j.neuroscience.2013.08.018. Epub 2013 Aug 27.
- The aim of this study was to analyze the effects of chronic oxidative stress on mitochondrial function and its relationship to progressive neurodegeneration in the hippocampus of rats chronically exposed to ozone. Animals were exposed to 0.25ppm ozone for 7, 15, 30, or 60days. Each group was tested
- PMID 23988432
- CYP1A1 and Cnr nitroreductase bioactivated niclosamide in vitro.
- Beristain-Castillo E, Martínez-Vázquez M, Camacho-Carranza R, Espinosa-Aguirre JJ.SourceDepartamento de Medicina Genómica y Toxicología Ambiental, Instituto de Investigaciones Biomédicas and.
- Mutagenesis.Mutagenesis.2013 Nov;28(6):645-51. doi: 10.1093/mutage/get043. Epub 2013 Aug 16.
- Niclosamide produces genotoxic effects, such as point mutations in Salmonella sp., sperm-head abnormalities in mice and clastogenic effects in human lymphocytes in vitro and in vivo. As cytochrome P450 could be involved in the bioactivation of niclosamide, we investigated which subfamily was involve
- PMID 23956140
Japanese Journal
- Diethyldithiocarbamate, a superoxide dismutase inhibitor, inhibits axonal transport in cultured mouse dorsal root ganglion neurons
- Isonaka Risa
- The Kitasato medical journal 44(2), 183-188, 2014-09
- NAID 40020211075
- 有機-無機ハイブリッド分子による生体防御系の活性化
- 藤江 智也,中 寛史,山本 千夏,新開 泰弘,熊谷 嘉人,鍜冶 利幸
- 薬学雑誌. 乙号 134(7), 813-815, 2014
- … In this review, we introduce copper diethyldithiocarbamate (Cu10), a copper complex, as a compound that activates nuclear factor erythroid 2-related factor 2 (Nrf2) and induces metallothionein, which are the key cellular defense factors against toxic metals and oxidative stress in vascular endothelial cells. …
- NAID 130004756450
- Rotating Disk Sorptive Extraction of Cu-Bisdiethyldithiocarbamate Complex from Water and Its Application to Solid Phase Spectrophotometric Quantification
- MUÑOZ Carlos,TORAL M. Inés,AHUMADA Inés,RICHTER Pablo
- Analytical Sciences 30(5), 613-617, 2014
- … To accomplish the solid-phase extraction and the direct solvent-free spectrophotometric measurement, sodium diethyldithiocarbamate (NaDDTC) was used as an analytical reagent to form the uncharged chromophore complex Cu(DDTC)2, which absorbs at 432 nm. …
- NAID 130004442296
Related Links
- 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.
- Sigma-Aldrich offers Sigma-Aldrich-Sodium diethyldithiocarbamate trihydrate for your research needs. Find product specific information, including CAS, MSDS, protocols and references.
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