3653 4-Aminophenol 4-Aminophenol is an amphoteric molecule and a reducing agent. Aminophenols are intermediates in the synthesis of dyes and can thus be found in numerous cosmetics products, particularly hair dyes. 4-aminophenol is considered a minor nephrotoxic metabolite of phenacetin and acetaminophen (paracetamol) in man. 4-Aminophenol can undergo autoxidations and metal-catalyzed and enzymatic oxidations in man to produce reactive oxygen species. (A7848) (L1882) 123-30-8 403 C6H7NO White powder. (L1883) 187.5°C 187.5°C 16 mg/mL at 20°C Oral (L138) ; inhalation (L138) 4-Aminobiphenyl requires metabolic activation in order to exert its toxicity. This is catalyzed by N-hydroxylation via cytochrome P450 1A2, then followed by O-sulfation and O-acetylation by sulfotransferase 1A1 and arylamine N-acetyltransferase 2. The metabolites of 4-aminobiphenyl then form adducts with DNA, inducing mutations. 4-Aminobiphenyl and its metabolites may also cross the placenta and have fetal effects. (1, 2, 3, 4). It is also though that the mode of action involves metabolic activation by N-hydroxylation, followed by N-esterification leading to the formation of a reactive electrophile, which binds covalently to DNA, principally to deoxyguanosine, leading to an increased rate of DNA mutations and ultimately to the development of cancer. In humans and dogs, the urinary bladder urothelium is the target organ, whereas in mice it is the bladder and liver; in other species, other tissues can be involved. Differences in organ specificity are thought to be due to differences in metabolic activation versus inactivation (A15085). LD50: 375 mg/kg (Oral, Rat) (T14) Not listed by IARC. 4-Aminophenol is commonly used as a developer in black and white film, marketed under the name Rodinal. Aminophenols are also intermediates in the synthesis of dyes and can thus be found in numerous cosmetics products, particularly hair dyes. (L1882, L1883) 4-Aminophenol may act as a skin sensitizer and cause contact dermatitis. In addition, inhalation of large amounts can cause methemoglobinemia and bronchial asthma. (T21) 4-Aminophenol may cause contact dermatitis. Signs and symptoms of methemoglobinemia may include shortness of breath, cyanosis, mental status changes, headache, fatigue, exercise intolerance, dizziness and loss of consciousness. Severe methemoglobinemia can result in dysrhythmias, seizures, coma, and death. (T21, L1613) Methemoglobinemia can be treated with supplemental oxygen and methylene blue 1% solution administered intravenously slowly over five minutes followed by IV flush with normal saline. Methylene blue restores the iron in hemoglobin to its normal (reduced) oxygen-carrying state. (L1613) 2009-11-11T22:18:18Z 2026-03-27T01:00:36Z http://en.wikipedia.org/wiki/4-Aminophenol C02372 237900 17602 CPD-259 C026729 p-aminophenol 4NL 27285 true NC1=CC=C(O)C=C1 C6H7NO InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 PLIKAWJENQZMHA-UHFFFAOYSA-N 109.1259 109.052763851 Exogenous Liquid 0.04 HMDB01169 CHEMBL1142 392 Zhu, Jianliang; Yang, Ying; Xu, Jinlai; Gu, Zhiqiang; Zhang, Xiaowei; Zheng, Zhigang; Li, Jianlin; Hao, Xiangyang. Method for preparation of p-aminophenol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 6 pp. CHEM002576 DTXSID3024499 NS00006730 4-aminophenol