3209. Dimercaprol

Nomenclature

CAS number: 59-52-9
2,3-Dimercapto-1-propanol; 1,2-dithioglycerol; British anti-lewisite; BAL; Dicaptol (Chinoin); Sulfactin (Viatris).
C3H8OS2; mol wt 124.23.
C 29.00%, H 6.49%, O 12.88%, S 51.62%.

Description and references

Developed as an antidote to the vesicant warfare agent, dichloro(2-chlorovinyl)arsine, q.v., also known as Lewisite. Inhibits the toxic action of arsenic on pyruvate dehydrogenase. Discovery and development: R. A. Peters et al., Nature 156, 616 (1945); L. L. Waters, C. Stock, Science 102, 601 (1945). Prepn by hydrogenation of hydroxypropylene trisulfide: W. J. Peppel, F. K. Signaigo, US 2402665 (1946 to DuPont). Stereospecific synthesis: A. K. M. Anisuzzaman, L. N. Owen, J. Chem. Soc. C 1967, 1021. GC/MS determn in plasma: C. E. Byers et al., J. Anal. Toxicol. 28, 384 (2004). Toxicity study: P. Zvirblis, R. I. Ellin, Toxicol. Appl. Pharmacol. 36, 297 (1976). Review of discovery, biochemistry and clinical applications: J. A. Vilensky, K. Redman, Ann. Emerg. Med. 41, 378-383 (2003).

Chemical structure

Properties

Viscous oily liq. Pungent offensive odor of mercaptans. d425 1.2385. nD25 1.5720. bp0.0001 68-69°. Vapor pressure at 80°: 1.9 mm Hg; at 140°: 40 mm Hg. Soly in water: 8.7 g/100 g. Sol in vegetable oils. LD50 i.m. in rats: 86.7 mg/kg (Zvirblis, Ellin).

Therapeutic Category

Antidote (heavy metal poisoning).

Therapeutic Category (Veterinary)

Antidote (heavy metal poisoning).

Keywords

Antidote (Heavy Metal Poisoning)