Dimercaprol Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R36/38:Reizt die Augen und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
Beschreibung
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.
Chemische Eigenschaften
colourless oily liquid with a typically offensive mercaptan smell
Verwenden
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.
Definition
ChEBI: 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 use
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. Administrati
n 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 g
netic disorder in which the body tends to retain copper, with resultant liver and brain injury.
Biologische Funktion
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.
Allgemeine Beschreibung
Clear colorless viscous liquid with a pungent offensive odor of mercaptans. Used as a medicine and an antidote to the chemical warfare agent LEWISITE.
Air & Water Reaktionen
Moderately soluble in water with decomposition [Hawley].
Reaktivität anzeigen
2,3-Dimercapto-1-propanol forms highly stable chelates with a variety of metal ions. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid.
Brandgefahr
2,3-Dimercapto-1-propanol is probably combustible.
Pharmazeutische Anwendungen
Dimercaprol (BAL) is a chelating agent used as an antidote for arsenic, antimony, bismuth, gold and mercury poisoning. It has the chemical name 2,3-dimercapto-1-propanol and is a clear, colourless or slightly yellow liquid.
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.
Sicherheitsprofil
Poison via ingestion,
intramuscular, parenteral, intraperitoneal,
and intravenous routes. Experimental
teratogenic effects. Human systemic effects
by intramuscular route: hemorrhage and dermatitis. Human blood and systemic skin
effects by intramuscular route. It causes
redness and swelling when applied locally to
the skin, but does not produce blisters or
ulcers. Intensely irritating to eyes and
mucous membranes. Systemic symptoms are
caused by injection. When heated to
decomposition, it emits toxic fumes of SO,.
Used as an antidote to arsenic, gold, and
mercury poisoning.
Environmental Fate
BAL is believed to compete with tissue sulfhydryl groups and
interferes with cellular respiration. It also competes with
metallic cofactors of metabolic enzyme systems and increases
capillary permeability. Metabolic degradation and excretion are
essentially complete within 4 h. BAL not excreted as dimercaprol–
metal complex is quickly metabolized by the liver and
excreted as an inactive product in the urine. Because it is
a lipophilic drug, it penetrates rapidly the intracellular spaces.
The highest concentrations are found in the liver, kidneys,
brain, and small intestine. Due to its lipophilic characteristic,
the complexes formed with mercury and other metals may be
redistributed into sensitive cells in the brain following dimercaprol
treatment.
läuterung methode
Precipitate BAL as the Hg mercaptide [see Bj.berg Chem Ber 75 13 1942], regenerate with H2S, and distil it under a vacuum [Rosenblatt & Jean Anal Chem 951 1955]. It is an antidote for heavy metal (As, Hg, Au etc) poisoning. [Beilstein 1 IV 2770.]
Dimercaprol Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
