1.02011-09-21 00:15:08 UTC2018-05-28 18:32:56 UTCFDB022512N-AcetylarylamineAcetanilide 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 As such, acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen, which is a metabolite of acetanilide and whose use Axelrod and Brodie suggested in the same study.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]AcetamidobenzeneAcetanilAcetanilidAcetanilideAcetate anilideAcetic acid anilideAntifebrinN-AcetylaminobenzeneN-AcetylarylamineN-PhenylacetamideC8H9NO135.1632135.068413915N-phenylacetamideacetanilide55576-55-1CC(=O)NC1=CC=CC=C1InChI=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 derivativesOrganic compoundsBenzenoidsBenzene and substituted derivativesAromatic homomonocyclic compoundsCarboximidic acidsHydrocarbon derivativesOrganonitrogen compoundsOrganooxygen compoundsOrganopnictogen compoundsPropargyl-type 1,3-dipolar organic compoundsAromatic homomonocyclic compoundCarboximidic acidCarboximidic acid derivativeHydrocarbon derivativeMonocyclic benzene moietyOrganic 1,3-dipolar compoundOrganic nitrogen compoundOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPropargyl-type 1,3-dipolar organic compounda small moleculeacetamidesanilideSolidlogp1.05logs-1.53solubility4.03e+00 g/llogp1.21pka_strongest_acidic14.38pka_strongest_basic-4.4iupacN-phenylacetamideaverage_mass135.1632mono_mass135.068413915smilesCC(=O)NC1=CC=CC=C1formulaC8H9NOinchiInChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)inchikeyFZERHIULMFGESH-UHFFFAOYSA-Npolar_surface_area29.1refractivity40.92polarizability14.52rotatable_bond_count1acceptor_count1donor_count1physiological_charge0formal_charge0Specdb::CMs21589Specdb::CMs29717Specdb::CMs31744Specdb::CMs31745Specdb::CMs31746Specdb::CMs99675Specdb::CMs99676Specdb::CMs99677Specdb::CMs99678Specdb::CMs147250Specdb::MsIr1153Specdb::MsIr1154Specdb::MsIr1155Specdb::MsMs77049Specdb::MsMs77050Specdb::MsMs77051Specdb::MsMs137055Specdb::MsMs137056Specdb::MsMs137057Specdb::MsMs437226Specdb::MsMs437227Specdb::MsMs437228Specdb::MsMs437229Specdb::MsMs437230Specdb::MsMs445696Specdb::MsMs445697Specdb::MsMs445698Specdb::MsMs445699Specdb::MsMs445700Specdb::MsMs2248646Specdb::MsMs3034886Specdb::MsMs3034887Specdb::MsMs3034888Specdb::MsMs3104672Specdb::MsMs3104673Specdb::MsMs3104674HMDB01250#<Reference:0x0000555673723890>#<Reference:0x00005556737232a0>#<Reference:0x0000555673722c60>#<Reference:0x0000555673722670>#<Reference:0x00005556737223c8>#<Reference:0x0000555673722148>#<Reference:0x0000555673721e50>#<Reference:0x0000555673721a90>#<Reference:0x00005556737217c0>#<Reference:0x0000555673721428>#<Reference:0x0000555673721090>#<Reference:0x0000555673720d20>#<Reference:0x0000555673720898>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Arylamine N-acetyltransferase 1P18440NAT1