ContaminantDB: Dimercaprol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 04:27:17 UTC

Update Date

2016-11-09 01:15:37 UTC

Accession Number

CHEM017545

Identification

Common Name

Dimercaprol

Class

Small Molecule

Description

A dithiol that is propane-1,2-dithiol in which one of the methyl hydrogens is replaced by a hydroxy group. 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. 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. 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. 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.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Dimercapto-3-propanol	ChEBI
1,2-Dithioglycerol	ChEBI
2,3-Dimercapto-1-propanol	ChEBI
2,3-Dimercaptol-1-propanol	ChEBI
2,3-Dimercaptopropanol	ChEBI
2,3-Dithiopropanol	ChEBI
2,3-Mercaptopropan-1-ol	ChEBI
2,3-Mercaptopropanol	ChEBI
3-Hydroxy-1,2-propanedithiol	ChEBI
alpha,beta-Dithioglycerol	ChEBI
BAL	ChEBI
British anti-lewisite	ChEBI
British antilewisite	ChEBI
Dimercaprolum	ChEBI
Dimercaptopropanol	ChEBI
Dithioglycerine	ChEBI
Dithioglycerol	ChEBI
Sulfactin	ChEBI
a,b-Dithioglycerol	Generator
Α,β-dithioglycerol	Generator
Sulphactin	Generator
2,3-Dimercapro	HMDB
2,3 Dithiopropan 1 O1	HMDB
2,3-Dimercaptopropanol, cadmium	HMDB
Cadmium 2,3-dimercaptopropanol	HMDB
Taylor brand OF dimercaprol	HMDB
2,3 Dimercaptopropanol	HMDB
Anti-lewisite agent, british	HMDB
British anti lewisite agent	HMDB
British anti-lewisite agent	HMDB
Knoll brand OF dimercaprol	HMDB
BAL in oil	HMDB
British anti lewisite	HMDB
Cadmium 2,3 dimercaptopropanol	HMDB
Dicaptol	HMDB
2,3-Dithiopropan-1-O1	HMDB
Anti-lewisite, british	HMDB
B.A.L.	HMDB
In oil, bal	HMDB
Oil, bal in	HMDB

Chemical Formula

C₃H₈OS₂

Average Molecular Mass

124.225 g/mol

Monoisotopic Mass

124.002 g/mol

CAS Registry Number

59-52-9

IUPAC Name

2,3-disulfanylpropan-1-ol

Traditional Name

dimercaprol

SMILES

OCC(S)CS

InChI Identifier

InChI=1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2

InChI Key

WQABCVAJNWAXTE-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.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thiols

Sub Class

Alkylthiols

Direct Parent

Alkylthiols

Alternative Parents

Substituents

Alkylthiol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:64198 )
dithiol (CHEBI:64198 )
a small molecule (23-DIMERCAPTOPROPAN-1-OL )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.76 g/L	ALOGPS
logP	0.58	ALOGPS
logP	0.21	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.58	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	32.91 m³·mol⁻¹	ChemAxon
Polarizability	12.88 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-02d345f6932e4df7ae4c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00ds-9600000000-5c06a4ce37d095db5a1c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-2900000000-5e1d01085e00977775ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6u-7900000000-2010199887988b9b1f5e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-9100000000-e15a808f41fdd35de8fe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-008i-9300000000-b6482fcdaeab876341d3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0acc-9200000000-f38fb9fba80629c643ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a5c-9000000000-975b939359caaed4e935	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0adl-7900000000-9b2eced4f80479d4220b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0596-9000000000-dfbf45f840944602d259	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-9000000000-f9a12c59d4f73bb8e6e3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-b6d4cfef7736df5ca9d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001l-9000000000-12de67a14d053353befb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000x-9000000000-72344935882f89d86e04	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum