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Name Description
id 89
T3DB ID T3D0102
Name 4,6-Dinitro-o-cresol
Class SmallMolecule
Description 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)
Categories "Pesticide", "Pollutant", "Airborne Pollutant", "Synthetic Toxin"
Types "Organic Compound", "Aromatic Hydrocarbon", "Pesticide", "Nitrite", "Pollutant", "Synthetic Compound"
Synonyms "2, 4-Dinitro-o-cresol", "2,4-bis(hydroxy(oxido)amino)-6-methylphenol", "2,4-Dinitro-6-methylphenol", "2,4-Dinitro-o-cresol", "2-Methyl-4,6-dinitrophenol", "3, 5-Dinitro-2-hydroxytoluene", "3,5-Dinitro-2-hydroxytoluene", "4,6-Dinitro-2-methylphenol", "4,6-Dinitro-O-cresol", "4,6-DNOC", "6-Methyl-2,4-dinitrophenol", "Antinonin", "Antinonnin", "Arborol", "Capsine", "Degrassan", "Dekryll", "Dekrysil", "Detal", "Detol", "Dillex", "Dinitro", "Dinitro-o-cresol", "Dinitrocresol", "Dinitrodendtroxal", "Dinitrol", "Dinitromethyl cyclohexyltrienol", "Dinitrosol", "Dinoc", "Dinok", "Dinurania", "Ditrosol", "DNOC", "Effusan", "Elgetol", "Elgetol 30", "Elgetox", "Elipol", "Extrar", "Flavin-samdoz", "Hedolit", "Hedolite", "Krenite", "Kreozan", "Kresamone", "Kresonite-e", "Krezotol 50", "Lipan", "Neudorff DN 50", "Nitrador", "Nitrofan", "Prokarbol", "Rafex", "Rafex 35", "Raphatox", "Sandolin", "Selinon", "Sinox", "Trifocide", "Trifrina", "Winterwash"
CAS Number 534-52-1
Chemical Formula C7H6N2O5
Average Molecular Mass 198.13
Monoisotopic Mass 198.03
IUPAC Name 2-methyl-4,6-dinitrophenol
Traditional Name dinitro
SMILES CC1=CC(=CC(=C1O)[N+]([O-])=O)[N+]([O-])=O
InChI Identifier InChI=1S/C7H6N2O5/c1-4-2-5(8(11)12)3-6(7(4)10)9(13)14/h2-3,10H,1H3
InChI Key InChIKey=ZXVONLUNISGICL-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Benzenoids
Class Benzene and Substituted Derivatives
Sub Class Toluenes
Direct Parent Nitrophenols and Derivatives
Alternate Parents "Nitrophenols and Derivatives", "Nitrobenzenes", "Aminophenols", "Ortho Cresols", "Nitronic Acids", "Nitro Compounds", "Organic Oxoazanium Compounds", "Propargyl-Type 1,3-Dipolar Organic Compounds", "Organonitrogen Compounds", "Organic Salts", "Aromatic Alcohols", "Organic Zwitterions"
Geometric Description Aromatic Homomonocyclic Compounds
Substituents "organonitrogen compound", "nitronic acid", "nitro compound", "organic oxoazanium", "o-cresol", "nitrobenzene", "nitrophenol derivative", "Phenol", "Aromatic Alcohol", "Aromatic Homomonocyclic Compound", "Propargyl-Type 1,3-Dipolar Organic Compound", "Organic 1,3-Dipolar Compound", "Allyl-Type 1,3-Dipolar Organic Compound", "Organic Salt", "Organic Zwitterion", "Aminophenol", "Dinitrotoluene"
Descriptors "hydroxytoluene (ChEBI)", "dinitrophenol acaricide (ChEBI)", "nitrotoluene (ChEBI)", "Nitrophenol herbicides (KEGG)"
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Membrane"
Biofluids
Tissues
Pathways
State Solid
Appearance Yellow solid.
Melting Point 86.6°C
Boiling Point
Solubility 0.198 mg/mL at 20 °C [SCHWARZENBACH,RP et al.(1988)]
LogP
Route of Exposure Oral (L198) ; inhalation (L198) ; dermal (L198)
Mechanism of Toxicity 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)
Metabolism 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)
Toxicity 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)
Lethal Dose 29 mg/kg (oral) or 1 mg/m3 (inhaled) for an adult human. (T26)
Carcinogenicity No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources 4,6-Dinitro-o-cresol is used primarily for insect control and crop protection. (L198)
Minimum Risk Level
Health Effects 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)
Symptoms 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)
Treatment
DrugBank ID
HMDB ID
PubChem Compound ID 10800
ChEMBL ID CHEMBL419564
ChemSpider ID 10343
KEGG Compound ID C18653
UniProt ID 0
OMIM ID 0
ChEBI ID 39349
BioCyc ID CPD-10489
CTD ID C024132
Stitch ID 4,6-Dinitro-o-cresol
PDB ID
ACToR ID 1947
Wikipedia Link
Creation Date 2009-03-06 18:58:05
Update Date 2014-12-24 20:21:06