1.0 2011-09-21 00:15:08 UTC 2025-11-19 02:41:51 UTC FDB022512 N-Acetylarylamine Acetanilide has analgesic and fever-reducing properties; it is in the same class of drugs as acetaminophen (paracetamol). Under the name acetanilid it formerly figured in the formula of a number of patent medicines and over the counter drugs. In 1948, Julius Axelrod and Bernard Brodie discovered that acetanilide is much more toxic in these applications than other drugs, causing methemoglobinemia and ultimately doing damage to the liver and kidneys. As such, acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen, which is a metabolite of acetanilide and whose use Axelrod and Brodie suggested in the same study. Acetanilide is an odourless solid chemical of leaf or flake-like appearance. It is also known as N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name antifebrin. Compounds based on N-phenylacetamide, that are similar in structure to 2-phenylacetamides. They are precursors of many other compounds. They were formerly used as analgesics and antipyretics, but often caused lethal methemoglobinemia. In the 19th century it was one of a large number of compounds used as experimental photographic developers. [HMDB] Acetamidobenzene Acetanil Acetanilid Acetanilide Acetate anilide Acetic acid anilide Antifebrin N-Acetylaminobenzene N-Acetylarylamine N-Phenylacetamide C8H9NO 135.1632 135.068413915 N-phenylacetamide acetanilide 55576-55-1 CC(=O)NC1=CC=CC=C1 InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10) FZERHIULMFGESH-UHFFFAOYSA-N belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Benzene and substituted derivatives Organic compounds Benzenoids Benzene and substituted derivatives Aromatic homomonocyclic compounds Carboximidic acids Hydrocarbon derivatives Organonitrogen compounds Organooxygen compounds Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Aromatic homomonocyclic compound Carboximidic acid Carboximidic acid derivative Hydrocarbon derivative Monocyclic benzene moiety Organic 1,3-dipolar compound Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Propargyl-type 1,3-dipolar organic compound a small molecule acetamides anilide Solid logp 1.05 ALOGPS logs -1.53 ALOGPS solubility 4.03e+00 g/l ALOGPS logp 1.21 ChemAxon pka_strongest_acidic 14.38 ChemAxon pka_strongest_basic -4.4 ChemAxon iupac N-phenylacetamide ChemAxon average_mass 135.1632 ChemAxon mono_mass 135.068413915 ChemAxon smiles CC(=O)NC1=CC=CC=C1 ChemAxon formula C8H9NO ChemAxon inchi InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10) ChemAxon inchikey FZERHIULMFGESH-UHFFFAOYSA-N ChemAxon polar_surface_area 29.1 ChemAxon refractivity 40.92 ChemAxon polarizability 14.52 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 21589 Specdb::CMs 29717 Specdb::CMs 31744 Specdb::CMs 31745 Specdb::CMs 31746 Specdb::CMs 99675 Specdb::CMs 99676 Specdb::CMs 99677 Specdb::CMs 99678 Specdb::CMs 147250 Specdb::MsIr 1153 Specdb::MsIr 1154 Specdb::MsIr 1155 Specdb::MsMs 77049 Specdb::MsMs 77050 Specdb::MsMs 77051 Specdb::MsMs 137055 Specdb::MsMs 137056 Specdb::MsMs 137057 Specdb::MsMs 437226 Specdb::MsMs 437227 Specdb::MsMs 437228 Specdb::MsMs 437229 Specdb::MsMs 437230 Specdb::MsMs 445696 Specdb::MsMs 445697 Specdb::MsMs 445698 Specdb::MsMs 445699 Specdb::MsMs 445700 Specdb::MsMs 2248646 Specdb::MsMs 3034886 Specdb::MsMs 3034887 Specdb::MsMs 3034888 Specdb::MsMs 3104672 Specdb::MsMs 3104673 Specdb::MsMs 3104674 HMDB01250 #<Reference:0x000055ce326d55c8> #<Reference:0x000055ce326d5410> #<Reference:0x000055ce326d51e0> #<Reference:0x000055ce326d4bf0> #<Reference:0x000055ce326d48f8> #<Reference:0x000055ce326d4718> #<Reference:0x000055ce326d4510> #<Reference:0x000055ce326d41f0> #<Reference:0x000055ce326d3cf0> #<Reference:0x000055ce326d38e0> #<Reference:0x000055ce326d34a8> #<Reference:0x000055ce326d3098> #<Reference:0x000055ce326d2e90> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Arylamine N-acetyltransferase 1 P18440 NAT1