Dimercaptosuccinic acid
| Dimercaptosuccinic acid[1] | |
|---|---|
| File:Dimercaptosuccinic-acid-2D-skeletal.png | |
| File:DMSA-3D-balls.png | |
| meso-2,3-dimercaptosuccinic acid | |
| Other names succimer, APRD01236 (Drugbank), Chemet | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 304-55-2 
|
| ChemSpider | 8988 |
| EC number | 259-952-2 |
| SMILES | Script error: No such module "collapsible list". |
| InChI | Script error: No such module "collapsible list". |
| InChI key | ACTRVOBWPAIOHC-UHFFFAOYAF |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C4H6O4S2 |
| Molar mass | 182.22 g/mol |
| Melting point |
125 °C, 398 K, 257 °F |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Dimercaptosuccinic acid (DMSA), is the organosulfur 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 its mildly unpleasant odour. It occurs in two diastereomers, meso and the chiral dl forms. The meso isomer is used as a chelating agent.
Preparation and reactivity
DMSA may be prepared by reacting maleic or fumaric acid with sodium thiosulfate followed by hydrolysis.[2] The dimethyl ester is also known.[3]
Meso 2,3-dimercaptosuccinic acid binds to "soft" heavy metals such as Hg2+ and Pb2+, mobilizing these ions for excretion. It binds to metal cations through the thiol groups, which ionize upon complexation.
Medical use
Dimercaptosuccinic acid (CHEMET) is indicated for the treatment of lead poisoning in children with blood level measured above 45 µg/dL. The use of DMSA is not approved for prophylactic/prevention of lead poisoning in anticipation of exposure in known lead contaminated environments. Its elimination half-life is 2.5-3.5 h. DMSA can cross the blood-brain barrier of mice,[4] but not that of humans, limiting its use to extracting heavy metals from parts of the body other than the central nervous system.[5][6]
Another application for DMSA is for provocation of tissue heavy metals in anticipation of a urine test. This is sometimes called a "challenge" or "provoked" heavy metals test. The ability of DMSA to mobilize heavy metals stored in body tissues (and therefore not typically present in the circulation) increases the excretion of heavy metals in the urine, leading to more accurate identification of total heavy metal toxicology than blood tests alone.
See also
- Chelation therapy
- 2,3-Dimercapto-1-propanesulfonic acid
- EDTA
- Heavy metal poisoning
- Mercury poisoning
- Succinic acid
References
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es:Ácido dimercaptosuccínico it:DMSA pl:Kwas dimerkaptobursztynowy
pt:Ácido dimercaptosuccínico- ↑ Merck Index, 11th Edition, 8854.
- ↑ US 4550193, Lindemann, Martin K. O. & Lukenbach, Elvin R., "Process for the preparation of 2,3-dimercaptosuccinic acid and its lower alkyl esters", assigned to Johnson & Johnson Baby Products
- ↑ 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.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ 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.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
