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Dimercaptosuccinic acid

 

 
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Dimercaptosuccinic acid
 
 
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Dimercaptosuccinic acid, or DMSA, is the chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
 with the formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 HO2CCH(SH)CH(SH)CO2H. This colourless solid contains two carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
 and two thiol
Thiol

In organic chemistry, a thiol is a compound that contains the functional group composed of a sulfur atom and a hydrogen atom . Being the sulfur analogue of an alcohol group , this functional group is referred to either as a thiol group or a sulfhydryl group....
 groups, the latter being responsible for its mildly unpleasant odour. It occurs in two diastereomeric forms, meso and the chiral dl forms. The meso isomer is used as a chelating
Chelation

Chelation is the binding or complex of a bi- or multidentate ligand. These ligands, which are often organic compounds, are called chelants, chelators, chelating agents, or sequestration....
 agent.

may be prepared by reacting maleic
Maleic acid

Maleic acid or -butenedioic acid or cis-butenedioic acid or malenic acid or maleinic acid or toxilic acid is an organic compound that is a dicarboxylic acid ....
 or fumaric
Fumaric acid

Fumaric acid is the chemical compound with the formula HO2CCH=CHCO2H. This white crystalline compound is one of two isomeric unsaturated dicarboxylic acids, the other being maleic acid wherein the carboxylic acid groups are cis....
 acid with sodium thiosulfate
Sodium thiosulfate

Sodium thiosulfate , also spelled Sodium thiosulphate, is a colorless crystalline compound that is more familiar as the pentahydrate, Sodium2Sulfur2Oxygen3?5Hydrogen2Oxygen, an efflorescent, monoclinic crystalline substance also called sodium hyposulfite or ?hypo.?...
 followed by hydrolysis.

2,3-dimercaptosuccinic acid is used to sequester heavy metals such as mercury
Mercury (element)

Mercury , also called quicksilver or hydrargyrum , is a chemical element with the symbol Hg and atomic number 80. A heavy, silvery d-block metal, mercury is one of six elements that are liquid at or near room temperature and pressure....
 and lead
Lead

Lead is a main-group Chemical element with symbol Pb and atomic number 82. Lead is a soft, malleable poor metal, also considered to be one of the heavy metal ....
 for excretion.






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Encyclopedia


Dimercaptosuccinic acid, or DMSA, is the chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
 with the formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 HO2CCH(SH)CH(SH)CO2H. This colourless solid contains two carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
 and two thiol
Thiol

In organic chemistry, a thiol is a compound that contains the functional group composed of a sulfur atom and a hydrogen atom . Being the sulfur analogue of an alcohol group , this functional group is referred to either as a thiol group or a sulfhydryl group....
 groups, the latter being responsible for its mildly unpleasant odour. It occurs in two diastereomeric forms, meso and the chiral dl forms. The meso isomer is used as a chelating
Chelation

Chelation is the binding or complex of a bi- or multidentate ligand. These ligands, which are often organic compounds, are called chelants, chelators, chelating agents, or sequestration....
 agent.

Preparation

DMSA may be prepared by reacting maleic
Maleic acid

Maleic acid or -butenedioic acid or cis-butenedioic acid or malenic acid or maleinic acid or toxilic acid is an organic compound that is a dicarboxylic acid ....
 or fumaric
Fumaric acid

Fumaric acid is the chemical compound with the formula HO2CCH=CHCO2H. This white crystalline compound is one of two isomeric unsaturated dicarboxylic acids, the other being maleic acid wherein the carboxylic acid groups are cis....
 acid with sodium thiosulfate
Sodium thiosulfate

Sodium thiosulfate , also spelled Sodium thiosulphate, is a colorless crystalline compound that is more familiar as the pentahydrate, Sodium2Sulfur2Oxygen3?5Hydrogen2Oxygen, an efflorescent, monoclinic crystalline substance also called sodium hyposulfite or ?hypo.?...
 followed by hydrolysis.

Chelating agent

Meso 2,3-dimercaptosuccinic acid is used to sequester heavy metals such as mercury
Mercury (element)

Mercury , also called quicksilver or hydrargyrum , is a chemical element with the symbol Hg and atomic number 80. A heavy, silvery d-block metal, mercury is one of six elements that are liquid at or near room temperature and pressure....
 and lead
Lead

Lead is a main-group Chemical element with symbol Pb and atomic number 82. Lead is a soft, malleable poor metal, also considered to be one of the heavy metal ....
 for excretion. DMSA can cross the blood-brain barrier
Blood-brain barrier

The blood-brain barrier is a metabolic or cellular structure in the central nervous system that restricts the passage of various chemical substances and microscopic objects between the bloodstream and the neural tissue itself, while still allowing the passage of substances essential to metabolism function ....
 of mice, but not that of humans, limiting its use to extracting heavy metals from parts of the body other than the central nervous system.

DMSA is also called succimer and is sold under the brand name Chemet. The dimethyl ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
 is also known.

See also

  • Chelation therapy
    Chelation therapy

    Chelation therapy is the administration of chelations to remove heavy metals from the body. For the most common forms of heavy metal intoxication?those involving lead, arsenic or Mercury ?the standard of care in the USA dictates the use of dimercaptosuccinic acid ....
  • 2,3-Dimercapto-1-propanesulfonic_acid
    2,3-Dimercapto-1-propanesulfonic acid

    2,3-Dimercapto-1-propanesulfonic acid and its sodium salt are chelating agents that form complexes with various heavy metals. They are related to dimercaprol, which is another chelating agent....
  • EDTA
    EDTA

    EDTA is a widely used acronym for the chemical compound ethylenediaminetetraacetic acid . EDTA is a polyamino carboxylic acid with the chemical formula [CH2N2]2....
  • Heavy metal poisoning
  • Mercury poisoning
    Mercury poisoning

    Mercury poisoning is a disease caused by exposure to mercury or its compounds. Mercury is a Heavy metal which occurs in several forms, all of which can produce toxic effects in high enough doses....
  • Succinic acid
    Succinic acid

    Succinic acid is a dicarboxylic acid. Succinate plays a biochemical role in the citric acid cycle....
  • Tartaric acid
    Tartaric acid

    Tartaric acid is a white crystalline organic acid. It occurs naturally in many plants, particularly grapes, bananas, and tamarinds, and is one of the main acids found in wine....


Further reading