|Jmol-3D images||Image 1|
|Molar mass||217.054 g/mol|
|Solubility in water||modest|
|Related compounds||phenylarsonic acid|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 for human patients, but was soon found prohibitively toxic. Eventually it became, and is still used as, a veterinary feed additive to promote growth and prevent or treat dysentery in poultry and swine. Arsanilic acid is one of four arsenical animal drugs approved by the U.S. Food and Drug Administration for use in poultry and/or swine, along with roxarsone, nitarsone, and carbarsone.
- C6H5NH2 + H3AsO4 → H2O3AsC6H4NH2 + H2O
Since at least 2000 BC, arsenic and inorganic arsenical compounds were both medicine and poison. In the 19th century, inorganic arsenicals became the preeminent medicines, for instance Fowler's solution, against diverse diseases.
In 1859, in France, while developing aniline dyes, Antoine Béchamp synthesized a chemical that he identified, if incorrectly, as arsenic acid anilide. Also biologist, physician, and pharmacist, Béchamp reported it 40 to 50 times less toxic as a drug than arsenic acid, and named it Atoxyl, the first organic arsenical drug.
In 1905, in Britain, H W Thomas and A Breinl reported successful treatment of trypanosomiasis in animals by Atoxyl, and recommended high doses, given continuously, for human trypanomiasis (sleeping sickness). By 1907, more successful and less toxic than inorganic arsenicals, Atoxyl was expected to greatly aid expansion of British colonization of Africa and stem loss of cattle in Africa and India. (So valuable was the interest, in 1922 Bayer offered to reveal the formula of Bayer 205—developed in 1917 and showing success on sleeping sickness in British and Belgian Africa—to British government for return of German colonies lost via World War I.)
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. 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, aminophenyl arsenic acid or aminophenyl arsonic acid, which suggested possible derivatives. Ehrlich asked Bertheim to synthesize two types of Atoxyl derivatives: arsenoxides and arsenobenzenes.
Synthesized in 1907, arsphenamine—their 606th arsenobenzene—was ineffective against trypanosomes, but found in 1909 by Ehrlich and bacteriologist Sahachiro Hata effective against the microorganism involved in syphilis, a disease roughly equivalent then to today's AIDS. The company Farbwerke Hoechst marketed arsphenamine as the drug Salvarsan, "the arsenic that saves". Its specificity of action fit Ehrlich's silver bullet or magic bullet paradigm of treatment, and Ehrlich won international fame while Salvarsan's success—the first particularly effective syphilis treatment—established the chemotherapy enterprise.
In the late 1940s, Salvarsan was replaced in most regions by penicillin, yet organic arsenicals remained in use for trypanosomiasis. At about the same time, arsanilic acid gained use as a feed additive for poultry and swine to promote growth and prevent or treat dysentery.
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