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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2019-01-11 19:36:17 UTC
HMDB IDHMDB0015677
Secondary Accession Numbers
  • HMDB15677
Metabolite Identification
Common NameDimercaprol
DescriptionDimercaprol is a traditional chelating agent developed by British biochemists at Oxford University during World War II. It was developed as an experimental antidote against the arsenic-based poison gas Lewisite. It has been used clinically since 1949 in arsenic, cadmium and mercury poisoning. In addition, it has in the past been used for the treatment of Wilson's disease, a genetic disorder in which the body tends to retain copper. Dimercaprol is a potentially toxic drug, and its use may be accompanied by multiple side effects.
Structure
Data?1547235377
Synonyms
ValueSource
1,2-dimercapto-3-PropanolChEBI
1,2-DithioglycerolChEBI
2,3-dimercapto-1-PropanolChEBI
2,3-Dimercaptol-1-propanolChEBI
2,3-DimercaptopropanolChEBI
2,3-DithiopropanolChEBI
2,3-Mercaptopropan-1-olChEBI
2,3-MercaptopropanolChEBI
3-Hydroxy-1,2-propanedithiolChEBI
alpha,beta-DithioglycerolChEBI
BALChEBI
British anti-lewisiteChEBI
British antilewisiteChEBI
DimercaprolumChEBI
DimercaptopropanolChEBI
DithioglycerineChEBI
DithioglycerolChEBI
SulfactinChEBI
a,b-DithioglycerolGenerator
α,β-dithioglycerolGenerator
SulphactinGenerator
2,3-DimercaproHMDB
2,3 Dithiopropan 1 O1MeSH
2,3-Dimercaptopropanol, cadmiumMeSH
Cadmium 2,3-dimercaptopropanolMeSH
Taylor brand OF dimercaprolMeSH
2,3 DimercaptopropanolMeSH
Anti-lewisite agent, britishMeSH
British anti lewisite agentMeSH
British anti-lewisite agentMeSH
Knoll brand OF dimercaprolMeSH
BAL in oilMeSH
British anti lewisiteMeSH
Cadmium 2,3 dimercaptopropanolMeSH
DicaptolMeSH
2,3-Dithiopropan-1-O1MeSH
Anti-lewisite, britishMeSH
B.A.L.MeSH
Chemical FormulaC3H8OS2
Average Molecular Weight124.225
Monoisotopic Molecular Weight124.001656258
IUPAC Name2,3-disulfanylpropan-1-ol
Traditional Namedimercaprol
CAS Registry Number59-52-9
SMILES
OCC(S)CS
InChI Identifier
InChI=1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2
InChI KeyWQABCVAJNWAXTE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThiols
Sub ClassAlkylthiols
Direct ParentAlkylthiols
Alternative Parents
Substituents
  • Alkylthiol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.76 g/LALOGPS
logP0.58ALOGPS
logP0.21ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.58ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.91 m³·mol⁻¹ChemAxon
Polarizability12.88 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-02d345f6932e4df7ae4cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ds-9600000000-5c06a4ce37d095db5a1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-2900000000-5e1d01085e00977775acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6u-7900000000-2010199887988b9b1f5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9100000000-e15a808f41fdd35de8feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-008i-9300000000-b6482fcdaeab876341d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0acc-9200000000-f38fb9fba80629c643ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5c-9000000000-975b939359caaed4e935View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06782 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06782 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06782
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2971
KEGG Compound IDC02924
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDimercaprol
METLIN IDNot Available
PubChem Compound3080
PDB IDNot Available
ChEBI ID64198
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Andersen O: Chemical and biological considerations in the treatment of metal intoxications by chelating agents. Mini Rev Med Chem. 2004 Jan;4(1):11-21. [PubMed:14754439 ]
  2. Walshe JM: The conquest of Wilson's disease. Brain. 2009 Aug;132(Pt 8):2289-95. doi: 10.1093/brain/awp149. Epub 2009 Jul 13. [PubMed:19596747 ]
  3. Boscolo M, Antonucci S, Volpe AR, Carmignani M, Di Gioacchino M: Acute mercury intoxication and use of chelating agents. J Biol Regul Homeost Agents. 2009 Oct-Dec;23(4):217-23. [PubMed:20003760 ]
  4. Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. doi: 10.3390/ijerph7072745. Epub 2010 Jun 28. [PubMed:20717537 ]