Tmic
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Record Information
Version2.0
Creation Date2009-03-06 18:58:05 UTC
Update Date2014-12-24 20:21:06 UTC
Accession NumberT3D0102
Identification
Common Name4,6-Dinitro-o-cresol
ClassSmall Molecule
Description4,6-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. (4)
Compound Type
  • Aromatic Hydrocarbon
  • Nitrite
  • Organic Compound
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
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
Chemical FormulaC7H6N2O5
Average Molecular Mass198.133 g/mol
Monoisotopic Mass198.028 g/mol
CAS Registry Number534-52-1
IUPAC Name2-methyl-4,6-dinitrophenol
Traditional Namedinitro
SMILESCC1=CC(=CC(=C1O)[N+]([O-])=O)[N+]([O-])=O
InChI IdentifierInChI=1S/C7H6N2O5/c1-4-2-5(8(11)12)3-6(7(4)10)9(13)14/h2-3,10H,1H3
InChI KeyInChIKey=ZXVONLUNISGICL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dinitrophenols. These are organic aromatic compounds containing a benzene that carries a single phenol group and exactly two nitro groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassNitrophenols
Direct ParentDinitrophenols
Alternative Parents
Substituents
  • Dinitrophenol
  • Dinitrotoluene
  • Nitrobenzene
  • Nitrotoluene
  • Nitroaromatic compound
  • O-cresol
  • Toluene
  • Monocyclic benzene moiety
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceYellow solid.
Experimental Properties
PropertyValue
Melting Point86.6°C
Boiling PointNot Available
Solubility0.198 mg/mL at 20 °C [SCHWARZENBACH,RP et al.(1988)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP2.09ALOGPS
logP2.06ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)4.45ChemAxon
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area111.87 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.73 m³·mol⁻¹ChemAxon
Polarizability16.56 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-d59ff0bd014c543ab4e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0900000000-db05405efe84b782857aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007p-1900000000-3dabca56b7217ac455e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-8cc0e9707a165de70cdeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-ebd2c5a73e30a5a6253dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002s-0900000000-23028b68fd69670c19c3View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0udj-9500000000-93be374bf50b7c0c8646View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
Mechanism of Toxicity4,6-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. (4)
Metabolism4,6-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. (4)
Toxicity ValuesLD50: 200 mg/kg (Dermal, Rat) (2) LD50: 21 mg/kg (Oral, Mouse) (2) LD50: 19 mg/kg (Intraperitoneal, Mouse) (2) LD50: 25 600 ug/kg (Subcutaneous, Rat) (1)
Lethal Dose29 mg/kg (oral) or 1 mg/m3 (inhaled) for an adult human. (3)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources4,6-Dinitro-o-cresol is used primarily for insect control and crop protection. (4)
Minimum Risk LevelNot Available
Health EffectsExposure to DNOC may cause mild damage to the stomach, kidneys, and liver. Ingesting DNOC for long periods may cause cataracts and skin rashes. (4)
SymptomsExposure 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. (4)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID10800
ChEMBL IDCHEMBL419564
ChemSpider ID10343
KEGG IDC18653
UniProt IDNot Available
OMIM ID
ChEBI ID39349
BioCyc IDCPD-10489
CTD IDC024132
Stitch ID4,6-Dinitro-o-cresol
PDB IDNot Available
ACToR ID1947
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D0102.pdf
General References
  1. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  2. ITII (1988). Toxic and Hazardous Industrial Chemicals Safety Manual. Tokyo, Japan: The International Technical Information Institute.
  3. National Institute for Occupational Safety and Health (2002). RTECS: Registry of Toxic Effects of Chemical Substances.
  4. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for dinitrocresols. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Ubiquinone binding
Specific Function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:
SDHD
Uniprot ID:
O14521
Molecular Weight:
17042.82 Da
References
  1. Castilho RF, Vicente JA, Kowaltowski AJ, Vercesi AE: 4,6-Dinitro-o-cresol uncouples oxidative phosphorylation and induces membrane permeability transition in rat liver mitochondria. Int J Biochem Cell Biol. 1997 Jul;29(7):1005-11. [9375380 ]
General Function:
Succinate dehydrogenase activity
Specific Function:
Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). Can act as a tumor suppressor.
Gene Name:
SDHA
Uniprot ID:
P31040
Molecular Weight:
72690.975 Da
References
  1. Castilho RF, Vicente JA, Kowaltowski AJ, Vercesi AE: 4,6-Dinitro-o-cresol uncouples oxidative phosphorylation and induces membrane permeability transition in rat liver mitochondria. Int J Biochem Cell Biol. 1997 Jul;29(7):1005-11. [9375380 ]
General Function:
Ubiquinone binding
Specific Function:
Iron-sulfur protein (IP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:
SDHB
Uniprot ID:
P21912
Molecular Weight:
31629.365 Da
References
  1. Castilho RF, Vicente JA, Kowaltowski AJ, Vercesi AE: 4,6-Dinitro-o-cresol uncouples oxidative phosphorylation and induces membrane permeability transition in rat liver mitochondria. Int J Biochem Cell Biol. 1997 Jul;29(7):1005-11. [9375380 ]
General Function:
Succinate dehydrogenase activity
Specific Function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:
SDHC
Uniprot ID:
Q99643
Molecular Weight:
18610.03 Da
References
  1. Castilho RF, Vicente JA, Kowaltowski AJ, Vercesi AE: 4,6-Dinitro-o-cresol uncouples oxidative phosphorylation and induces membrane permeability transition in rat liver mitochondria. Int J Biochem Cell Biol. 1997 Jul;29(7):1005-11. [9375380 ]