2,3-disulfanylpropan-1-ol

• ChemBase ID: 4478
• Molecular Formular: C3H8OS2
• Molecular Mass: 124.22502
• Monoisotopic Mass: 124.00165688
• SMILES: C(C(CS)S)O
• Canonical SMILES: OCC(CS)S
• InChI: InChI=1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2
• InChIKey: WQABCVAJNWAXTE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-disulfanylpropan-1-ol
• IUPAC Traditional name: BAL; dimercaprol
• Brand Name: Dimercaprol; Bal In Oil Injection
• Synonyms: 2,3-Dimercaptopropanol; British Anti-Lewisite; BAL; 2,3-Dimercapro; Dimercaprol; 2,3-DIMERCAPTOPROPANOL; 2,3-Dimercaptopropanol; Dimercaprol; Dithioglycerol; DMP; 2,3-Dimercapto-1-propanol; 2,3-二巯基丙醇; 二巯丙醇; 二硫代甘油; 英国抗路易气剂; 2,3-二巯基-1-丙醇

Database IDs

• CAS Number: 59-52-9
• EC Number: 200-433-7
• MDL Number: MFCD00004864
• Beilstein Number: 1732058
• Merck Index: 143209
• PubChem SID: 99443293; 160967910; 24893357; 24864016; 24883093
• PubChem CID: 3080
• ATC CODE: V03AB09
• CHEMBL: 1597
• Chemspider ID: 2971
• DrugBank ID: DB06782
• KEGG ID: D00167
• MeSH Name: Dimercaprol
• Unique Ingredient Identifier: 0CPP32S55X
• Wikipedia Title: Dimercaprol

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.578214
• H Acceptors: 1
• H Donor: 3
• LogD (pH = 5.5): 0.21170121
• LogD (pH = 7.4): 0.20906766
• Log P: 0.21173488
• Molar Refractivity: 32.9087 cm^3
• Polarizability: 12.995918 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.58
• LOG S: -1.65
• Solubility (Water): 2.76e+00 g/l

PROPERTIES

Physical Property

• Boiling Point: 119.85°C (393K) (at 2.0 kPa); 120 °C/15 mmHg(lit.); 120°C/15mm
• Flash Point: >110°C(230°F); 112 °C; 233.6 °F
• Density: 1.239 g cm^-3; 1.239 g/mL at 25 °C(lit.); 1.244
• Refractive Index: 1.573; 1.5740; n20/D 1.572-1.574; n20/D 1.573(lit.); n20/D 1.574
• Partition Coefficient: 0.627
• pKa: 8.999
• pKb: 4.998

Safety Information

• Storage Warning: Air Sensitive
• RTECS: UB2625000
• European Hazard Symbols: X; Irritant (Xi); Harmful (Xn)
• UN Number: 2810; UN2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 22-36/37/38; 22-36/38-43; R:36/37/38; R22, R36/37/38
• Safety Statements: 24-26-36/37; 26-36; S:20-25-26-37/39; S26, S36
• TSCA Listed: 是
• GHS Pictograms: GHS skull and crossbones; GHS06; GHS07
• GHS Signal Word: DANGER; Danger
• NFPA704:
  

  1

  2

  0
• GHS Hazard statements: 301, 315, 319, 335; H301-H315-H319-H335; H302-H315-H319-H317
• GHS Precautionary statements: 261, 301+310, 305+351+338; P261-P280-P305+P351+P338-P302+P352-P321-P501A; P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (iodometric); ≥98.0%; ≥98.0% (GC); 95%; 97%
• Grade: for complexometry
• Quality: for spectrophotometric det. of Cu
• Linear Formula: HOCH2CH(SH)CH2SH

DETAILS

MP Biomedicals - 05202073

MP Biomedicals Rare Chemical collection

DrugBank - DB06782

• Drug Groups: approved
• Description: Dimercaprol 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.
• Indication: For the treatment of arsenic, gold and mercury poisoning. Indicated in acute lead poisoning when used concomitantly with edetate calcium disodium (DB00974).
• Pharmacology: Due to its oily nature, dimercaprol is not absorbed orally and its administration requires deep intra-muscular injection that is extremely painful and allergenic. It was found to mobilize and relocate lead to the brain, increasing its neurotoxic effects. Although treatment with dimercaprol increases the excretion of cadmium, there is a concomitant increase in renal cadmium concentration, so its use should be avoided in cases of cadmium toxicity.
• Toxicity: The intramuscular LD50 in rats is approximately 105 mg/kg; intraperitoneally 140 mg/kg. The intraperitoneal LD80 in mice is approximately 125 mg/kg. Dimercaprol has been shown in animal experiments to increase brain deposition of arsenite, organic mercury compounds and increase the toxicity of cadmium and lead. Dimercaprol has been shown to induce seizure in animal studies and also is nephrotoxic.
• Absorption: After intra-muscular injection.
• Half Life: The drug has a short half life.
• Elimination: Urine.
• References: Walshe JM: The conquest of Wilson's disease. Brain. 2009 Aug;132(Pt 8):2289-95. Epub 2009 Jul 13. [Pubmed] ; 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] ; Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. Epub 2010 Jun 28. [Pubmed] ; 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]
• External Links: Wikipedia

Sigma Aldrich - 38520

General description
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Other Notes
Chelator for heavy metals; used as antidote to heavy metal poisoning (arsenic, gold, mercury, etc)1,2; Reagent for extracting Cu(II)3; Semi-quantitative det. of Cu(II)4

REFERENCES

• Walshe JM: The conquest of Wilson's disease. Brain. 2009 Aug;132(Pt 8):2289-95. Epub 2009 Jul 13. Pubmed
• 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
• Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. Epub 2010 Jun 28. Pubmed
• 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