258 4-Nitrophenol 4-Nitrophenol is a phenolic compound that is used mainly to make fungicides and dyes, and to darken leather. It is also used in the synthesis of drugs such as paracetamol, phenetidine, and acetophenetidine. 4-Nitrophenol measurement in urine is used in biological monitoring for establishing the presence and magnitude of exposures to pesticides. (A7736) (Methods in Biotechnology, 2006,61-78) (L1661, L1662) 100-02-7 980 C6H5NO3 139.026940 Colorless to light yellow solid. 113.8°C 11.6 mg/mL at 20°C [SCHWARZENBACH,RP et al.(1988)] Oral (L1661) ; inhalation (L1661) ; dermal (L1661) The nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen. (A2450, L1613) Nitrophenol may be absorbed following ingestion, inhalation, or dermal exposure. The major metabolic route for nitrophenols is conjugation, with the resultant formation of either glucuronide or sulfate conjugates. Conjugates are more polar than the parent compounds and therefore are easier to excrete in the urine. (L1661) LD50: 380 mg/kg (Oral, Mouse) (T14) LD50: 75 mg/kg (Intraperitoneal, Mouse) (T14) No indication of carcinogenicity to humans (not listed by IARC). 4-Nitrophenol is used mainly to make fungicides and dyes, and to darken leather. It is also used in the synthesis of drugs such as paracetamol, phenetidine, and acetophenetidine. (L1661, L1662) Nitrophenols may cause methemoglobinemia. This is a disorder in which there is an abnormally high level of methemoglobin in the blood, resulting in a decrease in the amount of oxygen that can be carried to the tissues and organs. (L1661, L1613) Symptoms of methemoglobinemia include shortness of breath, cyanosis, mental status changes, headache, fatigue, exercise intolerance, dizziness and loss of consciousness. Severe methemoglobinemia may cause dysrhythmias, seizures, coma and death. (L1613) Methemoglobinemia can be treated with supplemental oxygen and methylene blue 1% solution at 1-2mg/kg administered intravenously slowly over five minutes followed by an IV flush with normal saline. Methylene blue restores the iron in hemoglobin to its normal (reduced) oxygen-carrying state. (L1613) 2009-03-06T18:58:23Z 2026-03-31T19:11:21Z Cytochrome P450 2E1 (P05181) (A2462) http://en.wikipedia.org/wiki/4-Nitrophenol C00870 168820 16836 P-NITROPHENOL 4-Nitrophenol DB04417 NPO 1778 true Cytochrome P450 2E1 (P05181) (A2462) OC1=CC=C(C=C1)[N+]([O-])=O C6H5NO3 InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H BTJIUGUIPKRLHP-UHFFFAOYSA-N 139.1088 139.026943031 Exogenous Solid 1.91 HMDB01232 CHEMBL14130 955 CHEM000222 DTXSID0021834 NS00010495 4-nitrophenol