103 4,6-Dinitro-o-cresol 4,6-Dinitro-o-cresol is the most commercially important of the 18 different dinitrocresols, a class of manufactured chemicals. 4,6-Dinitro-o-cresol (DNOC) is used primarily for insect control and crop protection. It may be sold under different trade names, including Antinonnin, Detal, and Dinitrol. DNOC was used in diet pills in the 1930s, but has since been banned for this use. (L198) 534-52-1 10800 C7H6N2O5 198.027670 Yellow solid. 86.6°C 0.198 mg/mL at 20 °C [SCHWARZENBACH,RP et al.(1988)] Oral (L198) ; inhalation (L198) ; dermal (L198) 4,6-Dinitro-o-cresol is an uncoupler of oxidative phosphorylation. It is believed to cause an acceleration of metabolic processes that are part of the tricarboxylic acid (TCA) cycle. DNOC produces its accelerative effect by increasing the permeability of the inner mitochondrial membrane to Ca+, altering the proton electrochemical gradient and thus interrupting the phosphate transfer to adenosine diphosphate (ADP) to form ATP. Uncoupling allows electron transport to proceed unchecked even when ATP synthesis is inhibited. As a consequence, more ADP and inorganic phosphate are available to drive the TCA cycle, and most of the energy produced from catabolism of glucose is not stored in high energy phosphate bonds as ATP but is given off as heat. This results in the elevated body temperature and related effects characteristic of DNOC toxicity. (L198) 4,6-Dinitro-o-cresol is absorbed via oral, inhalation, and dermal routes, then binds to albumin and is distributed to most tissues, including the lungs, heart, liver, kidney, brain, spleen, and muscle. Although small quantities of DNOC may be conjugated, most of it appears to be reduced to less toxic mono amino derivatives, such as 6-amino-4-nitro-o-cresol and 6-acetamido-4-nitro-o-cresol, and then subsequently conjugated. DNOC and its metabolites are eliminated primarily via the urine. (L198) LD50: 200 mg/kg (Dermal, Rat) (T22) LD50: 21 mg/kg (Oral, Mouse) (T22) LD50: 19 mg/kg (Intraperitoneal, Mouse) (T22) LD50: 25 600 ug/kg (Subcutaneous, Rat) (T14) 29 mg/kg (oral) or 1 mg/m3 (inhaled) for an adult human. (T26) No indication of carcinogenicity to humans (not listed by IARC). 4,6-Dinitro-o-cresol is used primarily for insect control and crop protection. (L198) Exposure to DNOC may cause mild damage to the stomach, kidneys, and liver. Ingesting DNOC for long periods may cause cataracts and skin rashes. (L198) Exposure to high levels of DNOC for short periods may cause convulsions, unconsciousness, and death. Exposure to low levels of DNOC may result in an increased basal metabolic rate, increased sweating, weight loss, and increased heart rate, breathing rate, and body temperature. Other effects from DNOC exposure may include difficulty in breathing, headache, drowsiness, dizziness, and a yellowing of skin and the whites of the eyes. (L198) 2009-03-06T18:58:05Z 2016-11-09T01:08:09Z Serum albumin (P02768) (L198) C18653 39349 CPD-10489 C024132 4,6-Dinitro-o-cresol 1947 true CC1=CC(=CC(=C1O)[N+]([O-])=O)[N+]([O-])=O C7H6N2O5 InChI=1S/C7H6N2O5/c1-4-2-5(8(11)12)3-6(7(4)10)9(13)14/h2-3,10H,1H3 ZXVONLUNISGICL-UHFFFAOYSA-N 198.1329 198.027671312 Exogenous Solid CHEMBL419564 10343 CHEM000093 2-methyl-4,6-dinitrophenol