P-Phenetidine
{{DISPLAYTITLE:p-Phenetidine}}
{{Chembox
| Name = p-Phenetidine
| ImageFile = 4-ethoxyaniline.svg
| ImageSize =180px
| PIN = 4-Ethoxyaniline
| OtherNames = para-Phenetidine; 4-Aminophenetole
| Section1 = {{Chembox Identifiers
| CASNo = 156-43-4
| PubChem = 9076
| UNII = 9TSL224ZSE
| EC_number = 205-855-5
| RTECS = SI6465500
| SMILES = CCOC1=CC=C(C=C1)N
| 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{{cite book | title = Merck Index | edition = 12th | id = 7373. p-Phenetidine | page = 1244}}
| Density = 1.07 g/mL{{GESTIS|ZVG=14490}}
| MeltingPtC = 3
| BoilingPtC = 254
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPtC = 116
| AutoignitionPt =
}}
}}
p-Phenetidine (4-ethoxyaniline) is a chemical compound with the molecular formula C8H11NO. 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.
p-Phenetidine is a metabolite of the pharmaceutical drugs bucetin and phenacetin{{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 }} and of the preservative ethoxyquin.{{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 }} It is also used as a chemical intermediate in the manufacture of bucetin, phenacetin, ethoxyquin, and phenacaine.
p-Phenetidine has high renal toxicity 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.