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Record Information
Version2.0
Creation Date2009-05-25 21:11:21 UTC
Update Date2014-12-24 20:22:49 UTC
Accession NumberT3D0782
Identification
Common Name1,3-Dinitrobenzene
ClassSmall Molecule
Description1,3-Dinitrobenzene (1,3-DNB) is a synthetic substance that is used in explosives. Nitrite is a toxic compound known to cause methemoglobinemia. (8, 7)
Compound Type
  • Amine
  • Aromatic Hydrocarbon
  • Explosive Agent
  • Industrial/Workplace Toxin
  • Nitrate
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1,3-Dinitro-benzen
1,3-Dinitrobenzol
2,4-Dinitrobenzene
4,6-dinitro-1,3-benzenediamine
Binitrobenzene
m-Dinitro-benzene
m-Dinitrobenzene
NIN
Chemical FormulaC6H6N4O4
Average Molecular Mass198.136 g/mol
Monoisotopic Mass198.039 g/mol
CAS Registry Number99-65-0
IUPAC Name4,6-dinitrobenzene-1,3-diamine
Traditional Name4,6-dinitrobenzene-1,3-diamine
SMILESNC1=CC(N)=C(C=C1[N+]([O-])=O)[N+]([O-])=O
InChI IdentifierInChI=1S/C6H6N4O4/c7-3-1-4(8)6(10(13)14)2-5(3)9(11)12/h1-2H,7-8H2
InChI KeyInChIKey=DFBUFGZWPXQRJV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dinitroanilines. These are organic compounds containing an aniline moiety, which is substituted at 2 positions by a nitro group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAniline and substituted anilines
Direct ParentDinitroanilines
Alternative Parents
Substituents
  • Dinitroaniline
  • Nitrobenzene
  • Nitroaromatic compound
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic nitrogen compound
  • Organic zwitterion
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceYellow solid.
Experimental Properties
PropertyValue
Melting Point90°C
Boiling PointNot Available
Solubility0.533 mg/mL at 25°C [SPANGGORD,RJ et al. (1980)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP1.18ALOGPS
logP1.5ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area143.68 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.11 m³·mol⁻¹ChemAxon
Polarizability16.31 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-d0da97c87af62b76ad50JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006y-0900000000-7cd28fa04d83f5ef3930JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ry-0900000000-e04318ea9f6067a3305eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-47416b6028f6eee611f1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-58a12a85abaa30bee99cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000e-1900000000-9432f54780cfbfa8ffbfJSpectraViewer
Toxicity Profile
Route of ExposureOral (7) ; inhalation (7) ; dermal (7)
Mechanism of ToxicityIn the red blood cell, 1,3-DNB induces formation of methemoglobin, leading to cyanosis. Reduction of the nitrogroup(s) of 1,3-DNB produces reactive nitroaromatic radical anions which redox cycle to produce other reactive, toxic species such as superoxide anion. Redox cycling of these intermediates probably causes the methemoglobinemia. In the male reproductive system, 1,3-DNB causes disruption of spermatogenesis resulting in hypospermia, poor sperm quality, and infertility. Reduction of 1,3-DNB to reactive species such as nitrosonitrobenzene is believed to damage Sertoli cells. (7)
Metabolism1,3-Dinitrobenzene is absorbed via oral, inhalation, and dermal routes and is believed to be able to penetrate the red blood cell membrane. The metabolism of 1,3-DNB includes both oxidative and reductive biotransformations, followed by conjugation. The main metabolites are 3-aminoacetanilide, 4-acetamidophenylsulfate, 1,3-diacetamidobenzene, and 3-nitroaniline-N-glucuronide. The main route of excretion of 1,3-DNB metabolites is the urine. (7)
Toxicity ValuesLD50: 59 mg/kg (Oral, Rat) (7) LD50: 1990 mg/kg (Dermal, Rabbit) (7) LD50: 10 mg/kg (Intravenous, Dog) (2) LD50: 28 mg/kg (Intraperitoneal, Rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (5)
Uses/Sources1,3-Dinitrobenzene is used in explosives. Waste discharges from army ammunitions plants or other chemical manufacturers are the primary sources for release into the air, water, and soil. (7)
Minimum Risk LevelAcute Oral: 0.008 mg/kg/day (4) Intermediate Oral: 0.0005 mg/kg/day (4)
Health EffectsChronic exposure to 1,3-dinitrobenzene can cause a reduction (or loss) in the number of red blood cells (anemia). It may also cause behavioral changes and male reproductive system damage. (7)
SymptomsExposure to high concentrations of 1,3-dinitrobenzene can reduce the ability of blood to carry oxygen and can cause your skin to become bluish in color. Other symptoms of 1,3-dinitrobenzene exposure include headache, nausea, and dizziness.(7)
TreatmentTreatment is mainly symptomatic and may include gastric lavage and/or the administration of activated charcoal. Benzodiazepine may be administered if seizures occur. If methemoglobinemia is evident, 1 to 2 mg/kg of 1% methylene blue should be administered via IV. (3)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID291796
ChEMBL IDNot Available
ChemSpider ID257460
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDC017906
Stitch ID1,3-Dinitrobenzene
PDB IDNot Available
ACToR ID6434
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D0782.pdf
General References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  3. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  4. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  5. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  6. ATSDR - Agency for Toxic Substances and Disease Registry (2008). Toxicological profile for diazinon. U.S. Public Health Service in collaboration with U.S. [Link]
  7. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for 1,3-dinitrobenzene and 1,3,5-trinitrobenzene (1,3-DNB and 1,3,5-TNB). U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  8. ATSDR - Agency for Toxic Substances and Disease Registry (2007). Case Studies in Environmental Medicine. Nitrate/Nitrite Toxicity. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  9. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBA1
Uniprot ID:
P69905
Molecular Weight:
15257.405 Da
References
  1. Zwirner-Baier I, Kordowich FJ, Neumann HG: Hydrolyzable hemoglobin adducts of polyfunctional monocyclic N-substituted arenes as dosimeters of exposure and markers of metabolism. Environ Health Perspect. 1994 Oct;102 Suppl 6:43-5. [7889857 ]
  2. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  3. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.LVV-hemorphin-7 potentiates the activity of bradykinin, causing a decrease in blood pressure.Spinorphin: functions as an endogenous inhibitor of enkephalin-degrading enzymes such as DPP3, and as a selective antagonist of the P2RX3 receptor which is involved in pain signaling, these properties implicate it as a regulator of pain and inflammation.
Gene Name:
HBB
Uniprot ID:
P68871
Molecular Weight:
15998.34 Da
References
  1. Zwirner-Baier I, Kordowich FJ, Neumann HG: Hydrolyzable hemoglobin adducts of polyfunctional monocyclic N-substituted arenes as dosimeters of exposure and markers of metabolism. Environ Health Perspect. 1994 Oct;102 Suppl 6:43-5. [7889857 ]
  2. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  3. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBD
Uniprot ID:
P02042
Molecular Weight:
16055.41 Da
References
  1. Zwirner-Baier I, Kordowich FJ, Neumann HG: Hydrolyzable hemoglobin adducts of polyfunctional monocyclic N-substituted arenes as dosimeters of exposure and markers of metabolism. Environ Health Perspect. 1994 Oct;102 Suppl 6:43-5. [7889857 ]
  2. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  3. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Oxygen transporter activity
Specific Function:
The epsilon chain is a beta-type chain of early mammalian embryonic hemoglobin.
Gene Name:
HBE1
Uniprot ID:
P02100
Molecular Weight:
16202.71 Da
References
  1. Zwirner-Baier I, Kordowich FJ, Neumann HG: Hydrolyzable hemoglobin adducts of polyfunctional monocyclic N-substituted arenes as dosimeters of exposure and markers of metabolism. Environ Health Perspect. 1994 Oct;102 Suppl 6:43-5. [7889857 ]
  2. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  3. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Oxygen transporter activity
Specific Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Gene Name:
HBG1
Uniprot ID:
P69891
Molecular Weight:
16140.37 Da
References
  1. Zwirner-Baier I, Kordowich FJ, Neumann HG: Hydrolyzable hemoglobin adducts of polyfunctional monocyclic N-substituted arenes as dosimeters of exposure and markers of metabolism. Environ Health Perspect. 1994 Oct;102 Suppl 6:43-5. [7889857 ]
  2. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  3. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Specific Function:
Heme binding
Gene Name:
HBG2
Uniprot ID:
P69892
Molecular Weight:
16126.35 Da
References
  1. Zwirner-Baier I, Kordowich FJ, Neumann HG: Hydrolyzable hemoglobin adducts of polyfunctional monocyclic N-substituted arenes as dosimeters of exposure and markers of metabolism. Environ Health Perspect. 1994 Oct;102 Suppl 6:43-5. [7889857 ]
  2. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  3. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Oxygen transporter activity
Specific Function:
Not Available
Gene Name:
HBM
Uniprot ID:
Q6B0K9
Molecular Weight:
15617.97 Da
References
  1. Zwirner-Baier I, Kordowich FJ, Neumann HG: Hydrolyzable hemoglobin adducts of polyfunctional monocyclic N-substituted arenes as dosimeters of exposure and markers of metabolism. Environ Health Perspect. 1994 Oct;102 Suppl 6:43-5. [7889857 ]
  2. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  3. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Oxygen transporter activity
Specific Function:
Not Available
Gene Name:
HBQ1
Uniprot ID:
P09105
Molecular Weight:
15507.575 Da
References
  1. Zwirner-Baier I, Kordowich FJ, Neumann HG: Hydrolyzable hemoglobin adducts of polyfunctional monocyclic N-substituted arenes as dosimeters of exposure and markers of metabolism. Environ Health Perspect. 1994 Oct;102 Suppl 6:43-5. [7889857 ]
  2. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  3. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Oxygen transporter activity
Specific Function:
The zeta chain is an alpha-type chain of mammalian embryonic hemoglobin.
Gene Name:
HBZ
Uniprot ID:
P02008
Molecular Weight:
15636.845 Da
References
  1. Zwirner-Baier I, Kordowich FJ, Neumann HG: Hydrolyzable hemoglobin adducts of polyfunctional monocyclic N-substituted arenes as dosimeters of exposure and markers of metabolism. Environ Health Perspect. 1994 Oct;102 Suppl 6:43-5. [7889857 ]
  2. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  3. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]