2,3-Dimercapto-1-propanesulfonic acid

changed changed 477198497 2,3-Dimercapto-1-propanesulfonic acid.png skin-invert-image DMPS-3D-balls.png bg-transparent 230px 2,3-Bis(sulfanyl)propane-1-sulfonic acid Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) The Royal Society of Chemistry 2014 Cambridge 697 10.1039/9781849733069-FP001 978-0-85404-182-4 The prefixes 'mercapto' (–SH), and 'hydroseleno' or selenyl (–SeH), etc. are no longer recommended. 2,3-Dimercaptopropane-1-sulfonic acid correct chemspider correct EBI 888 6081 correct kegg C10922 1/C3H8O3S3/c4-9(5,6)2-3(8)1-7/h3,7-8H,1-2H2,(H,4,5,6) JLVSRWOIZZXQAD-UHFFFAOYAD O=S(=O)(O)CC(S)CS correct chemspider 1S/C3H8O3S3/c4-9(5,6)2-3(8)1-7/h3,7-8H,1-2H2,(H,4,5,6) correct chemspider JLVSRWOIZZXQAD-UHFFFAOYSA-N correct CAS 74-61-3 correct FDA 086L82361J 6321 Unithiol OS(=O)(=O)CC(S)CS 3 8 3 3 2,3-Dimercapto-1-propanesulfonic acid (abbreviated DMPS) and its sodium salt (known as Unithiol) are chelating agents that form complexes with various heavy metals. They are related to dimercaprol, which is another chelating agent. The synthesis of DMPS was first reported in 1956 by V. E. Petrunkin. Petrunkin V. E. 1956 Synthesis and properties of dimercapto derivatives of alkylsulfonic acids Ukrainsky Khemichisky Zhurnal 22 603–607 The effects of DMPS on heavy metal poisoning, including with polonium-210, were investigated in the following years. DMPS was found to have some protective effect, prolonging the survival time. Aposhian, H.V. Aposhian, M.M. 1990 Meso-2,3-dimercaptosuccinic acid: Chemical, pharmacological and toxicological properties of an orally effective metal chelating agent. Annual Review of Pharmacology and Toxicology 30 1 279–306 10.1146/annurev.pa.30.040190.001431 2160791 A study was undertaken of DMPS use by workers involved in the production of a calomel skin bleaching lotion and in direct contact with mercurous chloride 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. D. Gonzalez-Ramirez M. Zuniga-Charles A. Narro-Juarez Y. Molina-Recio K. M. Hurlbut R. C. Dart H. V. Aposhian DMPS (2,3-Dimercaptopropane-1-sulfonate, Dimaval) Decreases the Body Burden of Mercury in Humans Exposed to Mercurous Chloride 1 October 1998 Journal of Pharmacology and Experimental Therapeutics 287 1 8–12 http://jpet.aspetjournals.org/cgi/content/abstract/287/1/8 free full text 9765315 18 April 2009 3 July 2007 https://web.archive.org/web/20090418071214/http://jpet.aspetjournals.org/cgi/content/abstract/287/1/8 dead 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. James Rooney 2007 The role of thiols, dithiols, nutritional factors and interacting ligands in the toxicology of mercury Toxicology 234 145–156 10.1016/j.tox.2007.02.016 17408840 3 GianPaolo Guzzi Caterina A.M. La Porta 2008 Molecular mechanisms triggered by mercury Toxicology 244 1–12 10.1016/j.tox.2007.11.002 18077077 1 A 2008 study reported a case of Stevens–Johnson syndrome (SJS), a potentially serious disease, in a child undergoing chelation therapy with DMPS; the SJS resolved gradually after the chelation therapy was stopped. Clin Toxicol 2008 46 5 479–81 Stevens–Johnson syndrome in a child with chronic mercury exposure and 2,3-dimercaptopropane-1-sulfonate (DMPS) therapy Van der Linde AA, Pillen S, Gerrits GP, Bouwes Bavinck JN 18568806 10.1080/15563650701779687 free A 2020 study found DMPS to provide some benefits taken orally in mitigating effects from hemotoxic snakebites (using venom from saw-scaled vipers Echis) in mouse models when given soon after exposure, suggesting its potential for repurposing as a prehospital treatment.Albulescu Laura-Oana Hale Melissa S. Ainsworth Stuart Alsolaiss Jaffer Crittenden Edouard Calvete Juan J. Evans Chloe Wilkinson Mark C. Harrison Robert A. Kool Jeroen Casewell Nicholas R. 2020-05-06 Preclinical validation of a repurposed metal chelator as an early-intervention therapeutic for hemotoxic snakebite https://pmc.ncbi.nlm.nih.gov/articles/PMC7116364/ Science Translational Medicine 12 542 eaay8314 10.1126/scitranslmed.aay8314 1946-6242 7116364 32376771 See also Chelation therapy Dimercaptosuccinic acid EDTA Heavy metal poisoning Mercury poisoning References 2 Category:Chelating agents Category:Sulfonic acids Category:Thiols Category:Antidotes