Arsanilic acid

Arsanilic acid
Chemical structure of arsanilic acid
Ball-and-stick model of the solid-state zwitterionic structure of arsanilic acid
Names
Preferred IUPAC name
(4-Aminophenyl)arsonic acid
Other names
4-Aminobenzenearsonic acid, 4-Aminophenylarsonic acid, 4-Arsanilic acid, Atoxyl
Identifiers
3D model (JSmol)
1102334
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.002.432 Edit this at Wikidata
EC Number
  • 202-674-3
406354
UNII
  • InChI=1S/C6H8AsNO3/c8-6-3-1-5(2-4-6)7(9,10)11/h1-4H,8H2,(H2,9,10,11) checkY
    Key: XKNKHVGWJDPIRJ-UHFFFAOYSA-N checkY
  • InChI=1/C6H8AsNO3/c8-6-3-1-5(2-4-6)7(9,10)11/h1-4H,8H2,(H2,9,10,11)
    Key: XKNKHVGWJDPIRJ-UHFFFAOYAQ
  • O=[As](O)(O)c1ccc(N)cc1
  • zwitterion: O=[As]([O-])(O)c1ccc([NH3+])cc1
Properties
C6H8AsNO3
Molar mass 217.054 g/mol
Appearance white solid
Density 1.957 g/cm3
Melting point 232 °C (450 °F; 505 K)
modest
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
GHS labelling:
GHS06: ToxicGHS09: Environmental hazard
Danger
H301, H331, H410
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Related compounds
Related compounds
 phenylarsonic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Arsanilic acid, also known as aminophenyl arsenic acid or aminophenyl arsonic acid, is an organoarsenic compound, an amino derivative of phenylarsonic acid whose amine group is in the 4-position. A crystalline powder introduced medically in the late 19th century as Atoxyl, its sodium salt was used by injection in the early 20th century as the first organic arsenical drug, but it was soon found prohibitively toxic for human use.[1]

Arsanilic acid saw long use as a veterinary feed additive promoting growth and to prevent or treat dysentery in poultry and swine.[2][3][4] In 2013, its approval by US government as an animal drug was voluntarily withdrawn by its sponsors.[5] Still sometimes used in laboratories,[6] arsanilic acid's legacy is principally through its influence on Paul Ehrlich in launching the antimicrobial chemotherapy approach to treating infectious diseases of humans.[7]

  1. ^ Burke ET (1925). "The arseno-therapy of syphilis; stovarsol, and tryparsamide". British Journal of Venereal Diseases. 1 (4): 321–38. doi:10.1136/sti.1.4.321. PMC 1046841. PMID 21772505.
  2. ^ National Research Council (US) Committee on Medical Biological Effects of Environmental Pollutants (1977). "Biological effects of arsenic on plants and animals: Domestic animals: Phenylarsonic feed additives". In Levander OA (ed.). Arsenic: Medical and Biological Effects of Environmental Pollutants. Washington DC: National Academies Press. pp. 149–51. doi:10.17226/9003. ISBN 978-0-309-02604-8. PMID 25101467.
  3. ^ Hanson LE, Carpenter LE, Aunan WJ, Ferrin EF (1955). "The use of arsanilic acid in the production of market pigs". Journal of Animal Science. 14 (2): 513–24. doi:10.2527/jas1955.142513x.[permanent dead link‍]
  4. ^ "Arsanilic acid—MIB #4". Canadian Food Inspection Agency. Sep 2006. Archived from the original on 2012-12-13. Retrieved 3 Aug 2012.
  5. ^ Cite error: The named reference FDA2013 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Ahn-etal was invoked but never defined (see the help page).
  7. ^ Patrick J Collard, The Development of Microbiology (Cambridge, London, New York, Melbourne: Cambridge University Press, 1976), pp 53–4.