| Revision as of 15:36, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{chembox}} taken from revid 442094156 of page Sodium_diethyldithiocarbamate for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 07:07, 19 October 2024 edit GünniX (talk | contribs)Extended confirmed users312,730 edits Category |
| Line 1: |
Line 1: |
|
|
{{short description|Chemical compound}} |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
|
{{cs1 config|name-list-style=vanc}} |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
| ⚫ |
| verifiedrevid = 442092403 |
|
|
|
| Watchedfields = changed |
| ⚫ |
| ImageFile = Sodium diethyldithiocarbamate 2.png |
|
|
⚫ |
| verifiedrevid = 464401078 |
|
| ImageSize = |
|
|
|
| ImageFile = Et2dtcNa.svg |
|
| IUPACName = sodium (diethylcarbamothioyl)sulfanide |
|
|
| OtherNames = |
|
| ImageSize = 190 |
|
|
| PIN = Sodium diethylcarbamodithioate |
| ⚫ |
| Section1 = {{Chembox Identifiers |
|
|
|
| OtherNames = |
| ⚫ |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
⚫ |
| Section1 = {{Chembox Identifiers |
|
⚫ |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 8642 |
|
| ChemSpiderID = 8642 |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
| Line 20: |
Line 23: |
|
| StdInChIKey = IOEJYZSZYUROLN-UHFFFAOYSA-M |
|
| StdInChIKey = IOEJYZSZYUROLN-UHFFFAOYSA-M |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo = 148-18-5 |
|
| CASNo = 148-18-5 |
|
| PubChem = |
|
| CASNo1 = 20624-25-3 |
|
|
| CASNo1_Comment = trihydrate |
| ⚫ |
| SMILES = .C(=S)N(CC)CC |
|
|
|
| PubChem = 533728 |
|
⚫ |
| SMILES = .C(=S)N(CC)CC |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
| Section2 = {{Chembox Properties |
|
| Formula = C<sub>5</sub>H<sub>10</sub>NS<sub>2</sub>Na |
|
| Formula = C<sub>5</sub>H<sub>10</sub>NS<sub>2</sub>Na |
|
| MolarMass = 171.259 g/mol (anhydrous) |
|
| MolarMass = 171.259 g/mol (anhydrous) |
|
| Appearance = White, slightly brown, or slightly pink crystalline solid |
|
| Appearance = White, slightly brown, or slightly pink crystalline solid |
|
| Density = 1.1 g/cm<sup>3</sup> |
|
| Density = 1.1 g/cm<sup>3</sup> |
|
| MeltingPt = 95 °C |
|
| MeltingPtC = 95 |
|
| BoilingPt = |
|
| BoilingPt = |
|
| Solubility = Soluble |
|
| Solubility = Soluble |
|
|
| SolubleOther = soluble in ], ] <br> insoluble in ], ] |
|
}} |
|
}} |
|
| Section3 = {{Chembox Hazards |
|
| Section3 = {{Chembox Hazards |
|
| MainHazards = Harmful |
|
| MainHazards = Harmful |
|
| FlashPt = |
|
| FlashPt = |
|
| Autoignition = |
|
| AutoignitionPt = |
|
}} |
|
}} |
|
|
| Section5 = {{Chembox Related |
|
|
| OtherAnions = |
|
⚫ |
| OtherCations = ] |
|
|
}} |
|
}} |
|
}} |
|
|
'''Sodium diethyldithiocarbamate''' is the ] with the formula NaS<sub>2</sub>CN(C<sub>2</sub>H<sub>5</sub>)<sub>2</sub>. It is a pale yellow, water soluble salt. |
|
|
|
|
|
==Preparation== |
|
|
Sodium diethyldithiocarbamate typically crystallizes from water as the trihydrate NaS<sub>2</sub>CN(C<sub>2</sub>H<sub>5</sub>)<sub>2</sub><sup>'''.'''</sup>3H<sub>2</sub>O. The anhydrous salt and the trihydrate are often used interchangeably.<ref>{{cite journal |doi=10.1016/s0020-1693(00)84914-2 |title=Hydrogen bonds in sodium dialkylthiocarbamate hydrates. X-ray diffraction and vibrational spectroscopic study |date=1985 |last1=Mereiter |first1=K. |last2=Preisinger |first2=A. |last3=Mikenda |first3=W. |last4=Steidl |first4=H. |journal=Inorganica Chimica Acta |volume=98 |issue=2 |pages=71–78 }}</ref> |
|
|
|
|
|
Sodium diethyldithiocarbamate is obtained by treating ] with ] in the presence of ]: |
|
|
:CS<sub>2</sub> + HN(C<sub>2</sub>H<sub>5</sub>)<sub>2</sub> + NaOH → NaS<sub>2</sub>CN(C<sub>2</sub>H<sub>5</sub>)<sub>2</sub> + H<sub>2</sub>O |
|
|
Other ]s can be prepared similarly from secondary amines and carbon disulfide. They are used as ] for transition metal ions and as precursors to ]s and ] reagents. |
|
|
|
|
|
==Reactions== |
|
|
], a black solid that is soluble in organic solvents, is a representative complex of diethyldithiocarbamate.]] |
|
|
|
|
|
Oxidation of sodium diethyldithiocarbamate gives the ], also called a ] (Et = ]): |
|
|
:{{chem2|2 NaS2CNEt2 + I2 -> (S2CNEt2)2 + 2 NaI}} |
|
|
|
|
|
Dithiocarbamates are nucleophiles and thus can be alkylated. Even ] suffices:<ref>{{cite journal |doi=10.1139/v70-645|title=Reactions of Sodium ''N,N''-Diethyldithiocarbamate with Some Organic Solvents |year=1970 |last1=Heckley |first1=P. R. |last2=Holah |first2=D. G. |last3=Hughes |first3=A. N. |last4=Leh |first4=F. |journal=Canadian Journal of Chemistry |volume=48 |issue=24 |pages=3827–3830 }}</ref> |
|
|
:{{chem2|2 NaS2CNEt2 + CH2Cl2 -> CH2(S2CNEt2)2 + 2 NaCl}} |
|
|
|
|
|
Diethyldithiocarbamate reacts with many metal salts to give ]. The ligands coordinate via the two sulfur atoms. Other more complicated bonding modes are known including binding as unidentate ligand and a ] using one or both sulfur atoms.<ref>{{Cotton&Wilkinson6th}}</ref> |
|
|
|
|
|
==Laboratory and practical use== |
|
|
By the technique of ], complexes of dithiocarbamates with iron provide one of the very few methods to study the formation of ] (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 ] (EPR) spectroscopy.<ref>Henry Y.; Guissani A.; Ducastel B. (eds); "Nitric oxide research from chemistry to biology: EPR spectroscopy of nitrosylated compounds." Landes, Austin 1997.</ref><ref>{{cite book | last1 = Vanin | first1 = A.F. | last2 = Huisman | first2 = A. | last3 = van Faassen | first3 = E.E. | chapter = Iron dithiocarbamate as spin trap for nitric oxide detection: Pitfalls and successes | year = 2002 | title = Nitric Oxide, Part D: Oxide Detection, Mitochondria and Cell Functions, and Peroxynitrite Reactions | series = Methods in Enzymology | volume = 359 | pages = 27–42 | doi=10.1016/s0076-6879(02)59169-2 | pmid=12481557| isbn = 978-0-12-182262-0 }}</ref><ref>van Faassen E.E.; Vanin A.F. (eds); "Radicals for life: The various forms of nitric oxide." Elsevier, Amsterdam 2007.</ref> |
|
|
|
|
|
The ] chelation of diethyldithiocarbamate inhibits ]s, which in turn prevents the degradation of ], an initial step in cancer ] and ].<ref name=NCI> National Cancer Institute - Drug Dictionary</ref> |
|
|
|
|
|
Diethyldithiocarbamate inhibits ], which can both have ] and oxidant effects on cells, depending on the time of administration.<ref name=NCI/> |
|
|
|
|
|
==References== |
|
|
{{reflist}} |
|
|
|
|
|
==Further reading== |
|
|
* {{cite journal |vauthors=Cvek B, Dvorak Z |title=Targeting of nuclear factor-kappaB and proteasome by dithiocarbamate complexes with metals |journal=Curr. Pharm. Des. |volume=13 |issue=30 |pages=3155–67 |year=2007 |pmid=17979756 |doi= 10.2174/138161207782110390|url=http://www.bentham-direct.org/pages/content.php?CPD/2007/00000013/00000030/0010B.SGM|archive-url=https://web.archive.org/web/20090218044048/http://www.bentham-direct.org/pages/content.php?CPD/2007/00000013/00000030/0010B.SGM|url-status=usurped|archive-date=February 18, 2009}} |
|
|
|
|
|
] |
|
|
] |
|
|
] |
|
|
] |