Dimercaprol

Base Information

• Chemical Name: Dimercaprol
• CAS No.: 59-52-9
• Deprecated CAS: 31855-41-1,81600-56-8,98923-19-4,81600-56-8,98923-19-4
• Molecular Formula: C3H8OS2
• Molecular Weight: 124.228
• Hs Code.: 29309070
• European Community (EC) Number: 200-433-7
• NSC Number: 760094,39515,4646
• UN Number: 2810
• UNII: 0CPP32S55X
• DSSTox Substance ID: DTXSID5040461
• Nikkaji Number: J2.808H
• Wikipedia: Dimercaprol
• Wikidata: Q413968
• NCI Thesaurus Code: C47494
• RXCUI: 3445
• Metabolomics Workbench ID: 43705
• ChEMBL ID: CHEMBL1597
• Mol file: 59-52-9.mol

Synonyms:2,3 Dimercaptopropanol;2,3 Dithiopropan 1 o1;2,3-Dimercaptopropanol;2,3-Dimercaptopropanol, Cadmium;2,3-Dithiopropan-1-o1;Anti-Lewisite Agent, British;Anti-Lewisite, British;B.A.L.;BAL in Oil;British Anti Lewisite;British Anti Lewisite Agent;British Anti-Lewisite;British Anti-Lewisite Agent;Cadmium 2,3 Dimercaptopropanol;Cadmium 2,3-Dimercaptopropanol;Dicaptol;Dimercaprol;in Oil, BAL;Oil, BAL in

Chemical Property of Dimercaprol

Chemical Property:

• Appearance/Colour: colourless oily liquid with a typically offensive mercaptan smell
• Vapor Pressure: 0.0196mmHg at 25°C
• Melting Point: 77 °C
• Refractive Index: n20/D 1.573(lit.)
• Boiling Point: 223.4 °C at 760 mmHg
• PKA: 9.00±0.25(Predicted)
• Flash Point: 89.1 °C
• PSA: 97.83000
• Density: 1.194 g/cm³
• LogP: 0.20690
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: 87g/l (slow decomposition)
• Water Solubility.: 87 g/L (25 ºC)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 124.00165722
• Heavy Atom Count: 6
• Complexity: 32
• Transport DOT Label: Poison

Purity/Quality:

97%min ^*data from raw suppliers

2,3-Dimercapto-1-propanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-36/38
• Safety Statements: 26-36-24/25-23

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds (Alcohols)
• Drug Classes: Chelating Agents
• Canonical SMILES: C(C(CS)S)O
• Description: Dimercaprol (INN) or British anti - Lewisite (abbreviated BAL), is a compound developed by British biochemists at Oxford University during World War II . It was developed secretly as an antidote for lewisite, the now - obsolete arsenic - based chemical warfare agent . Today, it is used medically in treatment of arsenic, mercury , gold, lead, antimony, and other toxic metal 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.
• Uses: chelating agent (As, Au, Hg antidote) BAL is a chelating agent used as an antidote for the treatment of metal poisoning, especially arsenic (organic and inorganic), gold salts, and inorganic mercury. BAL is more effective when given soon after toxic exposure because it is more effective in preventing inhibition of sulfhydryl enzymes than in reactivating them. BAL is also used in the treatment of Wilson’s disease. The drug cannot be used in poisonings due to iron, cadmium, tellurium, selenium, vanadium, and uranium. It is contraindicated in poisonings due to elemental mercury vapor, because it can further increase the metal in the brain. British Anti-Lewisite. A chelator that inhibits sugar nucleotide degradation.2,3-Dimercaptopropanol is used as a chelating agent involved in the treatment of arsenic, antimony, lead, gold and mercury poisoning. It is also used as an antidote to the warfare agent Lewisite. Further, it is used for the treatment of Wilson's disease. In addition to this, it is used as an adjunct in the treatment of the acute encephalopathy of lead toxicity. 2,3-Dimercapto-1-propanol has been used in synthesizing novel (2-substituted phenyl-1,3-dithiolan-4-yl) methanol (PDTM) derivatives, which are potent tyrosinase inhibitors. It can also be considered for developing new drugs against AIDS due to its ability to inhibit HIV-1 tat activity.
• Biological Functions: Arsenic and some other heavy metals act by chemically reacting with adjacent thiol residues on metabolic enzymes, creating a chelate complex that inhibits the affected enzyme's activity. Dimercaprol competes with the thiol groups for binding the metal ion, which is then excreted in the urine . Dimercaprol is itself toxic, with a narrow therapeutic range and a tendency to concentrate arsenic in some organs. Other drawbacks include the need to administer it by painful intramuscular injection. Serious side effects include nephrotoxicity and hypertension. Dimercaprol has been found to form stable chelates in vivo with many other toxic metals including inorganic mercury, antimony, bismuth, cadmium, chromium, cobalt, gold, and nickel. However, it is not necessarily the treatment of choice for toxicity to these metals. Dimercaprol has been used as an adjunct in the treatment of the acute encephalopathy of lead toxicity. It is a potentially toxic drug, and its use may be accompanied by multiple side effects. Although treatment with dimercaprol will increase the excretion of cadmium, there is a concomitant increase in renal cadmium concentration, so that its use in case of cadmium toxicity is to be avoided. It does, however, remove inorganic mercury from the kidneys; but is not useful in the treatment of alkylmercury or phenyl mercury toxicity. Dimercaprol also enhances the toxicity of selenium and tellurium, so it is not to be used to remove these elements from the body.
• Clinical Use: 2,3-Dimercapto-1-propanol, BAL, or dithioglycerol is afoul-smelling, colorless liquid. It is soluble in water (1:20)and alcohol. It was developed by the British during WorldWar II as an antidote for “Lewisite,” hence the name Britishanti-Lewisite or BAL. Dimercaprol is effective topicallyand systematically as an antidote for poisoning caused byarsenic, antimony, mercury, gold, and lead. It can, therefore,also be used to treat arsenic and antimony toxicity associatedwith overdose or accidental ingestion of organoarsenicalsor organoantimonials.The antidotal properties of BAL are associated with theproperty of heavy metals to react with sulfhydryl (SH)groups in proteins (e.g., the enzyme pyruvate oxidase) andinterfere with their normal function. 1,2-Dithiol compoundssuch as BAL compete effectively with such proteins for themetal by reversibly forming metal ring compounds.These are relatively nontoxic, metabolically conjugated(as glucuronides), and rapidly excreted.BAL may be applied topically as an ointment or injectedintramuscularly as a 5% or 10% solution in peanut oil.

Technology Process of Dimercaprol

There total 19 articles about Dimercaprol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 64.0%

poly(1-hydroxymethylethylenedisulfide) → 1,3-dimercapto-2-propanol (584-04-3) + 2,3-dimercaptopropanol (59-52-9)

Guidance literature:

poly(1-hydroxymethylethylenedisulfide); With sodium hydroxide; hydrazine hydrate; In water; at 75 ℃; for 2h;

lead acetate; In water;

With hydrogen sulfide; In diethyl ether;

Reference yield: 62.0%

poly(2-hydroxypropylenedisulfide) → 1,3-dimercapto-2-propanol (584-04-3) + 2,3-dimercaptopropanol (59-52-9)

Guidance literature:

poly(2-hydroxypropylenedisulfide); With sodium hydroxide; hydrazine hydrate; In water; at 75 ℃; for 2h;

lead acetate; In water;

With hydrogen sulfide; In diethyl ether;

Reference yield: 58.0%

2,3-Dibromopropan-1-ol (96-13-9) → 2,3-dimercaptopropanol (59-52-9)

Guidance literature:

With sulfur; ethanolamine; hydrazine; In water; at 70 - 73 ℃; for 2.5h;

2,3-Dibromopropan-1-ol; With ethanolamine; hydrazine; In water; at 45 - 50 ℃; for 2h;

With potassium hydroxide; hydrazine; In water; at 80 ℃; for 2h; Inert atmosphere;

DOI:10.1134/S1070428008100059

upstream raw materials:

tetrachloromethane

1-acetoxy-2,3-bis-acetylsulfanyl-propane

2,3-Dibromopropan-1-ol

2,3-Dichloro-1-propanol

Downstream raw materials:

thiiranemethanethiol

2,3-Dibutyryl-thiopropyl-butyrat

5-[2-[(3-hydroxy-2-mercaptopropyl)thio]-2-(thien-3-yl)ethyl]-2-methyl-2-phenylfuran-3(2H)-one

(2,2-dimethyl-1,3-dithiolan-4-yl)methanol

Refernces

• 1、 Alekminskaya,Russavskaya,Korchevin,Deryagina,Trofimov. "Reduction of thiokols in the system hydrazine hydrate-base as a new route to alkanedithiols". . p. 732 - 737. Retrieved 2007/10/03.