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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:42:02 UTC
HMDB IDHMDB0015677
Secondary Accession Numbers
  • HMDB15677
Metabolite Identification
Common NameDimercaprol
DescriptionDimercaprol, also known as BAL or dithioglycerine, belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain. Dimercaprol is a drug. Dimercaprol is an extremely weak basic (essentially neutral) compound (based on its pKa). Administration is by (painful) intramuscular injection of a suspension of dimercaprol in peanut oil, typically every 4 hours for 2-10 days depending on the toxicity. Dimercaprol exists in all living organisms, ranging from bacteria to humans. a chelating agent originally developed during World War II as an experimental antidote against the arsenic-based poison gas Lewisite, it has been used clinically since 1949 for the treatment of poisoning by arsenic, mercury and gold. In the past, dimercaprol was also used for the treatment of Wilson's disease, a severely debilitating genetic disorder in which the body tends to retain copper, with resultant liver and brain injury. A dithiol that is propane-1,2-dithiol in which one of the methyl hydrogens is replaced by a hydroxy group. It can also be used for treatment of poisoning by antimony, bismuth and possibly thallium, and (with sodium calcium edetate) in cases of acute leaad poisoning.
Structure
Data?1582753322
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 O1HMDB
2,3-Dimercaptopropanol, cadmiumHMDB
Cadmium 2,3-dimercaptopropanolHMDB
Taylor brand OF dimercaprolHMDB
2,3 DimercaptopropanolHMDB
Anti-lewisite agent, britishHMDB
British anti lewisite agentHMDB
British anti-lewisite agentHMDB
Knoll brand OF dimercaprolHMDB
BAL in oilHMDB
British anti lewisiteHMDB
Cadmium 2,3 dimercaptopropanolHMDB
DicaptolHMDB
2,3-Dithiopropan-1-O1HMDB
Anti-lewisite, britishHMDB
B.A.L.HMDB
In oil, balMeSH
Oil, bal inMeSH
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
Description 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-02d345f6932e4df7ae4cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ds-9600000000-5c06a4ce37d095db5a1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-2900000000-5e1d01085e00977775acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6u-7900000000-2010199887988b9b1f5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9100000000-e15a808f41fdd35de8feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-008i-9300000000-b6482fcdaeab876341d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0acc-9200000000-f38fb9fba80629c643ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5c-9000000000-975b939359caaed4e935Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06782 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 ]