Mersalyl

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Structural formula
Mersalyl acid.svg
General
Surname Mersalyl
other names
  • Salyrgan
  • Mercusal
  • Mersalylic acid (rare)
  • Mersalin
  • Salurine
Molecular formula C 13 H 17 HgNO 6
Brief description

White dust

External identifiers / databases
CAS number
EC number 207-637-5
ECHA InfoCard 100.006.943
PubChem 443130
ChemSpider 11337655
Wikidata Q424871
Drug information
ATC code

C03 BC01

Drug class

Diuretic

properties
Molar mass 483.87 g · mol -1
Physical state

firmly

density

1.043

Melting point

192–193 ° C (decomposition)

solubility

soluble in ammonia,
immiscible with water

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
06 - Toxic or very toxic 08 - Dangerous to health 09 - Dangerous for the environment

danger

H and P phrases H: 300-310-330-373-410
P: 260-264-273-280-284-301 + 310
Toxicological data
  • 72.6 mg kg −1 ( LD 50 ,  mouse ,  iv , sodium salt)
  • 17.7 mg kg −1 ( LD 50 ,  rat ,  iv , sodium salt)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mersalyl (actually Mersalylic Acid ) is an organomercury compound with a diuretic effect. Mersalyl is no longer used as a drug today as it has been supplanted by other diuretics that do not contain mercury and are therefore less toxic .

Mersalyl has been used in biochemical experiments since the 1960s as a water-soluble, non-membrane-permeable inhibitor for the reversible blocking of sulfhydryl groups in proteins .

synthesis

The first synthesis of mersalyl (sodium salt, 505.87 g / mol) was published by Otto Diels and Erich Beccard . The taste is described as bitter . When Mersalyl is exposed to daylight or is in solution, the compound slowly decomposes and releases mercury; For this reason, small amounts of theophylline are often added to the substance , which slow down this process.

Bockmühl and Schwarz applied for a patent on Mersalyl for Hoechst in 1925 .

Individual evidence

  1. ↑ a b c Mersalyl acid data sheet (PDF; 274 kB) from Santa Cruz Biotechnology, accessed on April 13, 2012.
  2. ↑ a b c d data sheet Mersalyl acid, analytical standard at Sigma-Aldrich , accessed on October 22, 2016 ( PDF ).
  3. ↑ a b E. Brown Robbins, K. K Chen: A new mercurial diuretic . In: Journal of the American Pharmaceutical Association . tape 40 , no. 5 , May 1951, p. 249-251 , doi : 10.1002 / jps.3030400509 .
  4. ↑ Otto Diels, Erich Beccard: On the knowledge of acylated allylamines . In: Reports of the German Chemical Society . tape 39 , no. 4 , 1906, pp. 4125-4132 , doi : 10.1002 / cber.190603904108 .
  5. ↑ Patent DE423031 : Published January 6, 1926 . ‌

literature

  • The Merck Index (1983), No. 5750 (p. 843)