{{DISPLAYTITLE:''p''-Phenetidine}} {{Chembox | Name = ''p''-Phenetidine <!-- Images --> | ImageFile = 4-ethoxyaniline.svg | ImageSize =180px <!-- Names --> | PIN = 4-Ethoxyaniline | OtherNames = ''para''-Phenetidine; 4-Aminophenetole <!-- Sections --> | Section1 = {{Chembox Identifiers | CASNo = 156-43-4 | ChEBI = 85505 | ChEMBL = 250969 | ChemSpiderID = 21106155 | EC_number = 205-855-5 | PubChem = 9076 | UNII = 9TSL224ZSE | UNNumber = 2311 | RTECS = SI6465500 | SMILES = CCOc1ccc(N)cc1 | InChI = 1S/C8H11NO/c1-2-10-8-5-3-7(9)4-6-8/h3-6H,2,9H2,1H3 | InChIKey = IMPPGHMHELILKG-UHFFFAOYSA-N }} | Section2 = {{Chembox Properties | C=8|H=11|N=1|O=1 | Appearance = Colorless liquid; turns red to brown on exposure to air<ref name=Merck>{{cite book | title = Merck Index | edition = 12th | id = '''7373. ''p''-Phenetidine''' | page = 1244}}</ref> | Density = 1.07 g/mL<ref name=GESTIS>{{GESTIS|ZVG=14490}}</ref> | MeltingPtC = 3 | MeltingPt_ref = <ref name=GESTIS/> | BoilingPtC = 254 | BoilingPt_ref = <ref name=GESTIS/> | Solubility = 20 g/L (20 °C)<ref name=GESTIS/> }} | Section3 = {{Chembox Hazards | GHS_ref=[https://pubchem.ncbi.nlm.nih.gov/compound/9076#section=Safety-and-Hazards] | GHSPictograms = {{GHS07}}{{GHS08}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|302|312|317|319|332|341}} | PPhrases = {{P-phrases|203|261|264|264+265|270|271|272|280|301+317|302+352|304+340|305+351+338|317|318|321|330|333+317|337+317|362+364|405|501}} | MainHazards = | FlashPtC = 116 | FlashPt_ref = <ref name=GESTIS/> | AutoignitionPt = }} }} '''''p''-Phenetidine''' ('''4-ethoxyaniline''') is a chemical compound with the molecular formula C<sub>8</sub>H<sub>11</sub>NO. It is one of the three isomers of phenetidine. It is used as an intermediate in the synthesis of pharmaceutical drugs, dyes, and the sweetener dulcin.<ref name=Merck/>
''p''-Phenetidine is a metabolite of the pharmaceutical drugs bucetin and phenacetin<ref name=Kankuri>{{Cite journal | doi = 10.1016/S0049-3848(03)00416-X | pmid = 14592552 | title = Effects of phenacetin and its metabolite p-phenetidine on COX-1 and COX-2 activities and expression in vitro | journal = Thrombosis Research | volume = 110 | issue = 5–6 | pages = 299–303 | year = 2003 | last1 = Kankuri | first1 = Esko | last2 = Solatunturi | first2 = Erkka | last3 = Vapaatalo | first3 = Heikki }}</ref> and of the preservative ethoxyquin.<ref name=efsa>{{Cite web | url = http://www.efsa.europa.eu/en/press/news/151118 | title = Ethoxyquin: EFSA safety assessment inconclusive | publisher = European Food Safety Authority| date = 2015-11-18 }}</ref> It is also used as a chemical intermediate in the manufacture of bucetin, phenacetin, ethoxyquin, and phenacaine.
''p''-Phenetidine has high renal toxicity<ref name=Kankuri/> and it is believed to be responsible for the adverse effects that led to the withdrawal of phenacetin and bucetin from pharmaceutical use. ''p''-Phenetidine is also a possible mutagen.<ref name=efsa/>
==References== {{reflist}}
{{DEFAULTSORT:Phenetidine, p-}} Category:4-Aminophenyl compounds Category:Human drug metabolites Category:Ethoxy compounds