Arsanilic acid

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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

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treat dysentery in poultry and swine.[2][3][4] In 2013, its approval by US government as an animal drug was voluntarily withdrawn by its sponsors.[5] Still sometimes used in laboratories,[6] arsanilic acid's legacy is principally through its influence on Paul Ehrlich in launching the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]

Chemistry

Synthesis was first reported in 1863 by Antoine Béchamp and became the basis of the Bechamp reaction.[8][9] The process involves the reaction of aniline and arsenic acid via an electrophilic aromatic substitution reaction.

C6H5NH2 + H3AsO4 → H2O3AsC6H4NH2 + H2O

Arsanilic acid occurs as a zwitterion, H3N+C6H4AsO3H−,[10] yet is typically represented with the non-zwitterionic formula H2NC6H4AsO3H2.

History

Roots and synthesis

Since at least 2000 BC,

inorganic arsenical compounds were both medicine and poison.[11][12] In the 19th century, inorganic arsenicals became the preeminent medicines, for instance Fowler's solution, against diverse diseases.[11]

In 1859, in France, while developing

aniline dyes,[13] Antoine Béchamp synthesized a chemical that he identified, if incorrectly, as arsenic acid anilide.[14] Also biologist, physician, and pharmacist, Béchamp reported it 40 to 50 times less toxic as a drug than arsenic acid, and named it Atoxyl,[14] the first organic arsenical drug.[1]

Medical influence

In 1905, in Britain, H W Thomas and A Breinl reported successful treatment of

socioeconomically valuable was colonial medicine[15] that in 1922, German company Bayer offered to reveal the formula of Bayer 205—developed in 1917 and showing success on sleeping sickness in British and Belgian Africa—to the British government for return of German colonies lost via World War I.)[14][16]

Soon, however, Robert Koch found through an Atoxyl trial in German East Africa that some 2% of patients were blinded via atrophy of the optic nerve.[14] In Germany, Paul Ehrlich inferred Béchamp's report of Atoxyl's structure incorrect, and Ehrlich with his chief organic chemist Alfred Bertheim found its correct structure[13]—aminophenyl arsenic acid[17] or aminophenyl arsonic acid[14]—which suggested possible derivatives.[14][17] Ehrlich asked Bertheim to synthesize two types of Atoxyl derivatives: arsenoxides and arsenobenzenes.[14]

Ehrlich and Bertheim's 606th arsenobenzene, synthesized in 1907, was

magic bullet paradigm of treatment,[11] and Ehrlich won international fame while Salvarsan's success—the first particularly effective syphilis treatment—established the chemotherapy enterprise.[17][18] In the late 1940s, Salvarsan was replaced in most regions by penicillin, yet organic arsenicals remained in use for trypanosomiasis.[11]

Contemporary usage

Arsanilic acid gained use as a feed additive for poultry and swine to promote growth and prevent or treat

U.S. Food and Drug Administration (FDA).[19] In 2013, the FDA denied petitions by the Center for Food Safety and by the Institute for Agriculture and Trade Policy seeking revocation of approvals of the arsenical animal drugs, but the drugs' sponsors voluntarily requested the FDA to withdraw approvals of three, including arsanilic acid, leaving only nitarsone approved.[5] In 2015, the FDA withdrew nitarsone's approval.[20]

Arsanilic acid is still used in the laboratory, for instance in recent modification of nanoparticles.[6]

It is a reagent for the detection of

urinalysis dipsticks
.

Citations

  1. ^
    PMID 21772505
    .
  2. ^
    PMID 25101467
    .
  3. ^
    doi:10.2527/jas1955.142513x.[permanent dead link
    ]
  4. ^ a b "Arsanilic acid—MIB #4". Canadian Food Inspection Agency. Sep 2006. Archived from the original on 2012-12-13. Retrieved 3 Aug 2012.
  5. ^ a b U.S. Food and Drug Administration (1 Oct 2013). "FDA response to citizen petition on arsenic-based animal drugs".
  6. ^
    PMID 24246012
    .
  7. ^ Patrick J Collard, The Development of Microbiology (Cambridge, London, New York, Melbourne: Cambridge University Press, 1976), pp 53–4.
  8. Compt. Rend.
    56: 1172–1175.
  9. ISBN 978-0471264187. {{cite book}}: |journal= ignored (help); Missing or empty |title= (help
    )
  10. doi:10.1107/S010827019501657X
    .
  11. ^
    PMID 8505753
    .
  12. ISBN 978-3-642-13184-4
    .
  13. ^
    PMID 20763444
    .
  14. ^
    PMID 20219092
    .
  15. ^
  16. PMID 20771495
    .
  17. ^
    PMID 18679046
    .
  18. ^ "Paul Ehrlich, the Rockefeller Institute, and the first targeted chemotherapy". Rockefeller University. Retrieved 3 Aug 2012.
  19. ^ U.S. Food and Drug Administration (8 Jun 2011). "Questions and answers regarding 3-nitro (roxarsone)".
  20. ^ U.S. Food and Drug Administration (April 1, 2015). "FDA announces pending withdrawal of approval of nitarsone". Archived from the original on 2017-04-06.
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