| Revision as of 15:40, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 462988265 of page 2,3-Dimercapto-1-propanesulfonic_acid for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 20:57, 26 August 2023 edit Wprlh (talk | contribs)Extended confirmed users21,401 edits Fixed typoTags: Mobile edit Mobile web edit |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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| ImageFile = 2,3-Dimercapto-1-propanesulfonic acid.png |
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| verifiedrevid = 477198497 |
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| ImageFile1 = DMPS-3D-balls.png |
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| ImageFile = 2,3-Dimercapto-1-propanesulfonic acid.png |
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| ImageFile1 = DMPS-3D-balls.png |
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| PIN = 2,3-Bis(sulfanyl)propane-1-sulfonic acid<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 697 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = The prefixes ‘mercapto’ (–SH), and ‘hydroseleno’ or selenyl (–SeH), etc. are no longer recommended.}}</ref> |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = 2,3-Dimercaptopropane-1-sulfonic acid |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI = 888 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = JLVSRWOIZZXQAD-UHFFFAOYSA-N |
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| StdInChIKey = JLVSRWOIZZXQAD-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 74-61-3 --> |
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| PubChem = 6321 |
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| CASNo = 74-61-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| MeSHName = Unithiol |
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| UNII = 086L82361J |
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| SMILES = OS(=O)(=O)CC(S)CS |
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| PubChem = 6321 |
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| MeSHName = Unithiol |
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| SMILES = OS(=O)(=O)CC(S)CS |
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| C=3 | H=8 | O=3 | S=3 |
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| Formula = C<sub>3</sub>H<sub>8</sub>O<sub>3</sub>S<sub>3</sub> |
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| MolarMass = 188.289 g/mol |
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'''2,3-Dimercapto-1-propanesulfonic acid''' (abbreviated '''DMPS''') and its sodium salt (known as '''Unithiol''') are ]s that form complexes with various heavy metals. They are related to ], which is another chelating agent. |
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The synthesis of DMPS was first reported in 1956 by V. E. Petrunkin.<ref>{{cite journal |last= Petrunkin |first= V. E. |year=1956 |title= Synthesis and properties of dimercapto derivatives of alkylsulfonic acids |journal= Ukrainsky Khemichisky Zhurnal |volume=22 |pages=603–607 }}</ref> The effects of DMPS on ] poisoning, including with ]-210, were investigated in the following years. DMPS was found to have some protective effect, prolonging the survival time.<ref>{{cite journal| author = Aposhian, H.V.|author2= Aposhian, M.M.| year = 1990| title = Meso-2,3-dimercaptosuccinic acid: Chemical, pharmacological and toxicological properties of an orally effective metal chelating agent.| journal = Annual Review of Pharmacology and Toxicology| volume = 30| issue = 1| pages = 279–306| doi = 10.1146/annurev.pa.30.040190.001431| pmid = 2160791 }}</ref> |
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A study was undertaken of DMPS use by workers involved in the production of a calomel ] lotion and in direct contact with ] and that already showed elevated urine mercury levels. The sodium salt of DMPS was found to be effective in lowering the body burden of mercury and in decreasing the urinary mercury concentration to normal levels.<ref>{{cite journal |author1=D. Gonzalez-Ramirez |author2=M. Zuniga-Charles |author3=A. Narro-Juarez |author4=Y. Molina-Recio |author5=K. M. Hurlbut |author6=R. C. Dart |author7=H. V. Aposhian | title = DMPS (2,3-Dimercaptopropane-1-sulfonate, Dimaval) Decreases the Body Burden of Mercury in Humans Exposed to Mercurous Chloride | date=1 October 1998| journal = Journal of Pharmacology and Experimental Therapeutics | volume = 287 | issue = 1 | pages = 8–12 | url = http://jpet.aspetjournals.org/cgi/content/abstract/287/1/8 | format = free full text | pmid = 9765315 }}</ref> |
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DMPS administered to a mercury poisoned animal model failed to remove the mercury from tissues and reduce the inorganic mercury burden in the brain, indicating it is not a useful intra-cellular chelation agent. <ref>{{cite journal| first = James| last = Rooney| year = 2007| title = The role of thiols, dithiols, nutritional factors and interacting ligands in the toxicology of mercury| journal = Toxicology| volume = 234| pages = 145–156| doi = 10.1016/j.tox.2007.02.016| pmid = 17408840| issue = 3 }}</ref><ref>{{cite journal| first = GianPaolo| last = Guzzi| author2= Caterina A.M. La Porta| year = 2008| title = Molecular mechanisms triggered by mercury| journal = Toxicology| volume = 244| pages = 1–12| doi = 10.1016/j.tox.2007.11.002| pmid = 18077077| issue = 1 }}</ref> |
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A 2008 study reported a case of ] (SJS), a potentially serious disease, in a child undergoing ] with DMPS; the SJS resolved gradually after the chelation therapy was stopped.<ref>{{cite journal |journal= Clin Toxicol |year=2008 |volume=46 |issue=5 |pages=479–81 |title= Stevens–Johnson syndrome in a child with chronic mercury exposure and 2,3-dimercaptopropane-1-sulfonate (DMPS) therapy |vauthors=Van der Linde AA, Pillen S, Gerrits GP, Bouwes Bavinck JN |pmid=18568806 |doi= 10.1080/15563650701779687|doi-access=free }}</ref> |
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A 2020 study found DMPS to provide some benefits taken orally in mitigating effects from ] snakebites (using venom from ] ''Viperidae Echis'') in mouse models when given soon after exposure, suggesting its potential for repurposing as a prehospital treatment. |
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==See also== |
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==References== |
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{{Reflist|2}} |
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{{Chelating agents}} |
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{{DEFAULTSORT:Dimercapto-1-Propanesulfonic Acid, 2,3-}} |
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