2,3-Dimercapto-1-propanesulfonic acid

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.

2,3-Dimercapto-1-propanesulfonic acid
Names
Preferred IUPAC name
2,3-Bis(sulfanyl)propane-1-sulfonic acid[1]
Other names
2,3-Dimercaptopropane-1-sulfonic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
MeSH Unithiol
UNII
  • InChI=1S/C3H8O3S3/c4-9(5,6)2-3(8)1-7/h3,7-8H,1-2H2,(H,4,5,6) checkY
    Key: JLVSRWOIZZXQAD-UHFFFAOYSA-N checkY
  • InChI=1/C3H8O3S3/c4-9(5,6)2-3(8)1-7/h3,7-8H,1-2H2,(H,4,5,6)
    Key: JLVSRWOIZZXQAD-UHFFFAOYAD
  • OS(=O)(=O)CC(S)CS
  • O=S(=O)(O)CC(S)CS
Properties
C3H8O3S3
Molar mass 188.27 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The synthesis of DMPS was first reported in 1956 by V. E. Petrunkin.[2] 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.[3]

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.[4]

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. [5][6]

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.[7]

A 2020 study found DMPS to provide some benefits taken orally in mitigating effects from hemotoxic snakebites (using venom from saw-scaled vipers Viperidae Echis) in mouse models when given soon after exposure, suggesting its potential for repurposing as a prehospital treatment. [Albulescu, L.; Hale, M.S.;Ainsworth, S.; Alsolaiss, J.; Crittenden, E.; Calvete, J.J.; Evans, C.; Wilkinson, M.C.; Harrison, R.A.; Kool, J.; Casewell, N.R. (2020). "Preclinical validation of a repurposed metal chelator as an early-intervention therapeutic for hemotoxic snakebite". Science Translational Medicine, Vol 12, Issue 542, 8314 DOI: 10.1126/scitranslmed.aay8314]

See also

References
  1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 697. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The prefixes 'mercapto' (–SH), and 'hydroseleno' or selenyl (–SeH), etc. are no longer recommended.
  2. Petrunkin, V. E. (1956). "Synthesis and properties of dimercapto derivatives of alkylsulfonic acids". Ukrainsky Khemichisky Zhurnal. 22: 603–607.
  3. 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. doi:10.1146/annurev.pa.30.040190.001431. PMID 2160791.
  4. D. Gonzalez-Ramirez; M. Zuniga-Charles; A. Narro-Juarez; Y. Molina-Recio; K. M. Hurlbut; R. C. Dart; H. V. Aposhian (1 October 1998). "DMPS (2,3-Dimercaptopropane-1-sulfonate, Dimaval) Decreases the Body Burden of Mercury in Humans Exposed to Mercurous Chloride" (free full text). Journal of Pharmacology and Experimental Therapeutics. 287 (1): 8–12. PMID 9765315.
  5. Rooney, James (2007). "The role of thiols, dithiols, nutritional factors and interacting ligands in the toxicology of mercury". Toxicology. 234 (3): 145–156. doi:10.1016/j.tox.2007.02.016. PMID 17408840.
  6. Guzzi, GianPaolo; Caterina A.M. La Porta (2008). "Molecular mechanisms triggered by mercury". Toxicology. 244 (1): 1–12. doi:10.1016/j.tox.2007.11.002. PMID 18077077.
  7. Van der Linde AA, Pillen S, Gerrits GP, Bouwes Bavinck JN (2008). "Stevens–Johnson syndrome in a child with chronic mercury exposure and 2,3-dimercaptopropane-1-sulfonate (DMPS) therapy". Clin Toxicol. 46 (5): 479–81. doi:10.1080/15563650701779687. PMID 18568806.
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