Dimercaptosuccinic acid

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Dimercaptosuccinic acid
Systematic (IUPAC) name
2,3-bis-sulfanylbutanedioic acid
Identifiers
CAS number	304-55-2
ATC code	?
PubChem	9354
DrugBank	APRD01236
Chemical data
Formula	C4H6O4S2
Mol. mass	182.22 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	2.5-3.5 hours
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Dimercaptosuccinic_acid
Routes	?

Dimercaptosuccinic acid, or DMSA, is the chemical compound with the formula HO₂CCH(SH)CH(SH)CO₂H. This colourless solid contains two carboxylic acid and two thiol groups, the latter being responsible for the mildly unpleasant odour of this dicarboxylic acid. It occurs in two diastereomeric forms, meso and the chiral dl forms. The meso isomer is used as a chelating agent.

Contents 1 Preparation 2 Chelating agent 3 See also 4 References 5 Further reading

[edit] Preparation

DMSA may be prepared by reacting maleic or fumaric acid with sodium thiosulfate followed by hydrolysis.^[1]

[edit] Chelating agent

Meso 2,3-dimercaptosuccinic acid is used to sequester heavy metals such as mercury and lead for excretion. DMSA can cross the blood-brain barrier of mice,^[2] but not that of humans, limiting its use to extracting heavy metals parts of the body other than the central nervous system.^[3][4]

DMSA is also called succimer and is sold under the brand name Chemet. The dimethyl ester is also known.^[5]

[edit] See also

• Chelation therapy
• 2,3-Dimercapto-1-propanesulfonic_acid
• EDTA
• Heavy metal poisoning
• Mercury poisoning
• Succinic acid
• Tartaric acid

[edit] References

1. ^ US patent 4550193, "Process for the preparation of 2,3-dimercaptosuccinic acid and its lower alkyl esters", granted [[{{{gdate}}}]], assigned to Johnson & Johnson Baby Products 
2. ^ Aasath, Jan; Dag Jacobsen, Ole Andersen, Elsa Wickstrøm (March 1995). "Treatment of Mercury and Lead Poisonings with Dimercaptosuccinic Acid (DMSA) and Sodium Dimercaptopropanesulfonate (DMPS)". Analyst 120: 853ff. 
3. ^ Rooney, James (2007). "The role of thiols, dithiols, nutritional factors and interacting ligands in the toxicology of mercury". Toxicology 234: 145-156. doi:10.1016/j.tox.2007.02.016. 
4. ^ Guzzi, GianPaolo; Caterina A.M. La Porta (2008). "Molecular mechanisms triggered by mercury". Toxicology 244: 1-12. doi:10.1016/j.tox.2007.11.002. 
5. ^ M. Gerecke, E. A. H. Friedheim, A. Brossi (1961). "Zur Kenntnis der 2,3-Dimercapto-bernsteinsäuren". Helvetica Chimca Acta 44: 955-960. doi:10.1002/hlca.19610440410. 

[edit] Further reading

• 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.