Dimercaprol

Dimercaprol
IUPAC name 2,3-Disulfanylpropan-1-ol[citation needed]
Other names 2,3-Dimercaptopropanol[citation needed]
Identifiers
CAS number	59-52-9 Y, 16495-08-2 (2R)-2-sulfanyl Y, 16495-16-2 (2S)-2-sulfanyl Y
PubChem	3080, 6971262 (2R)-2-sulfanyl, 3246063 (2S)-2-sulfanyl
ChemSpider	2971 Y, 5342114 (2R)-2-sulfanyl Y, 2496803 (2S)-2-sulfanyl Y
UNII	0CPP32S55X Y
EC number	200-433-7
UN number	2810
DrugBank	DB06782
KEGG	D00167 Y
MeSH	Dimercaprol
ChEMBL	CHEMBL1597 Y
RTECS number	UB2625000
ATC code	V03AB09
Beilstein Reference	1732058
Jmol-3D images	Image 1
SMILES OCC(S)CS
InChI InChI=1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2 Y Key: WQABCVAJNWAXTE-UHFFFAOYSA-N Y
Properties
Molecular formula	C3H8S2O
Molar mass	124.225 g mol-1
Exact mass	124.001656258 g mol-1
Density	1.239 g cm-3
Boiling point	120 °C, 393 K, 248 °F (at 2.0 kPa)
log P	0.627
Acidity (pKa)	8.999
Basicity (pKb)	4.998
Refractive index (nD)	1.573
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H301, H315, H319, H335
GHS precautionary statements	P261, P301+310, P305+351+338
EU classification	Xn
R-phrases	R22, R36/37/38
S-phrases	S26, S36
NFPA 704	1 2 0
Flash point	112 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Dimercaprol (INN) or British anti-Lewisite (abbreviated BAL), is a compound developed by British biochemists at Oxford University during World War II.^[1][2] It was developed secretly as an antidote for lewisite, the now-obsolete arsenic-based chemical warfare agent.^[3] Today, it is used medically in treatment of arsenic, mercury, gold and lead, and other toxic metal poisoning.^[4] 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.^[5]

Biochemical function

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.^[6] Dimercaprol competes with the thiol groups for binding the metal ion, which is then excreted in the urine.^{[citation needed]}

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.^[7] 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 metals from the body.^{[citation needed]}

See also

• Chelation therapy
• Chemical warfare agent
• Toxic metal poisoning

References

1. ^ Domingo Tabangcura, Jr., G. Patrick Daubert. "British anti-Lewisite". http://www.chm.bris.ac.uk/motm/bal/development.html. 
2. ^ Peters, R; Stocken, L; Thompson, R. (1945). "British Anti-Lewisite (BAL)". Nature 156 (3969): 616–619. doi:10.1038/156616a0. PMID 21006485. 
3. ^ Domingo Tabangcura, Jr., G. Patrick Daubert. "British anti-Lewisite". http://www.chm.bris.ac.uk/motm/bal/development.html. 
4. ^ "Dimercaprol". http://www.drugs.com/dict/dimercaprol.html. 
5. ^ Denny-Brown D, PORTER H (December 1951). "The effect of BAL (2,3-dimercaptopropanol) on hepatolenticular degeneration (Wilson's disease)". N. Engl. J. Med. 245 (24): 917–25. doi:10.1056/NEJM195112132452401. PMID 14882450. 
6. ^ Goldman M, Dacre JC. (1989) Lewisite: its chemistry, toxicology, and biological effects. Rev Environ Contam Toxicol 110: 75-115
7. ^ Mückter H, Liebl B, Reichl FX et al. (1997) Are we ready to replace dimercaprol (BAL) as an arsenic antidote? Human and Experimental Toxicology 16: 460-465