Arsanilic acid

Arsanilic acid
Names
	Preferred IUPAC name (4-Aminophenyl)arsonic acid
	Other names 4-Aminobenzenearsonic acid, 4-Aminophenylarsonic acid, 4-Arsanilic acid, Atoxyl
Identifiers
CAS Number	98-50-0 [ECHA];
3D model (JSmol)	Interactive image; zwitterion: Interactive image;
Beilstein Reference	1102334
ChEBI	CHEBI:49477 ;
ChEMBL	ChEMBL351769 ;
ChemSpider	7111 ;
DrugBank	DB03006 ;
ECHA InfoCard	100.002.432
EC Number	202-674-3;
Gmelin Reference	406354
PubChem CID	7389;
UNII	UDX9AKS7GM ;
CompTox Dashboard (EPA)	DTXSID8035138 ;
	InChI InChI=1S/C6H8AsNO3/c8-6-3-1-5(2-4-6)7(9,10)11/h1-4H,8H2,(H2,9,10,11) Key: XKNKHVGWJDPIRJ-UHFFFAOYSA-N ; 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;
	SMILES O=[As](O)(O)c1ccc(N)cc1; zwitterion: O=[As]([O-])(O)c1ccc([NH3+])cc1;
Properties
Chemical formula	C6H8AsNO3
Molar mass	217.054 g/mol
Appearance	white solid
Density	1.957 g/cm3
Melting point	232 °C (450 °F; 505 K)
Solubility in water	modest
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Toxic
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H331, H410
NFPA 704 (fire diamond)	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). verify (what is ?) Infobox references

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.

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 In 2013, its approval by US government as an animal drug was voluntarily withdrawn by its sponsors.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

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