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Dimercaptosuccinic acid

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Dimercaptosuccinic acid
Dimercaptosuccinic acid
General
Systematic name  ?
Other names  ?
Molecular formula  ?
SMILES  ?
Molar mass  ?.?? g/mol
Appearance  ?
CAS number [?-?-?]
Properties
Density and phase  ? g/cm³, ?
Solubility in water  ? g/100 ml (?°C)
Melting point  ?°C (? K)
Boiling point  ?°C (? K)
Acidity (pKa)  ?
Basicity (pKb)  ?
Chiral rotation [α]D  ?°
Viscosity  ? cP at ?°C
Structure
Molecular shape  ?
Coordination
geometry
 ?
Crystal structure  ?
Dipole moment  ? D
Hazards
MSDS External MSDS
Main hazards  ?
NFPA 704
Flash point  ?°C
R/S statement R: ?
S: ?
RTECS number  ?
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Other anions  ?
Other cations  ?
Related ?  ?
Related compounds  ?
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and 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 reactivityEdit

DMSA may be prepared by reacting maleic or fumaric acid with sodium thiosulfate followed by hydrolysis.[1] The dimethyl ester is also known.[2]

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 useEdit

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,[3] but not that of humans, limiting its use to extracting heavy metals from parts of the body other than the central nervous system.[4][5]

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 alsoEdit

ReferencesEdit

  1. Template:Ref patent
  2. M. Gerecke, E. A. H. Friedheim, A. Brossi (1961). Zur Kenntnis der 2,3-Dimercapto-bernsteinsäuren. Helvetica Chimca Acta 44: 955–960.
  3. 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.
  4. Rooney, James (2007). The role of thiols, dithiols, nutritional factors and interacting ligands in the toxicology of mercury. Toxicology 234: 145–156.
  5. Guzzi, GianPaolo, Caterina A.M. La Porta (2008). Molecular mechanisms triggered by mercury. Toxicology 244: 1–12.

Further readingEdit

  • 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.

Template:Chelating agents

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