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Tox21_300418

Tox21_300418

Synopsis, Chemistry

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1 Analytical Solutions

1 Analytical Solutions

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Also known as: 528-29-0, O-dinitrobenzene, 1,2-dinitrobenzol, Benzene, o-dinitro-, Ortho-dinitrobenzene, Benzene, 1,2-dinitro-

Molecular Formula

C₆H₄N₂O₄

Molecular Weight

168.11 g/mol

InChI Key

IZUKQUVSCNEFMJ-UHFFFAOYSA-N

FDA UNII

35XUO924Y0

1 2D Structure

Tox21_300418

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,2-dinitrobenzene

2.1.2 InChI

InChI=1S/C6H4N2O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H

2.1.3 InChI Key

IZUKQUVSCNEFMJ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C(C(=C1)[N+](=O)[O-])[N+](=O)[O-]

2.2 Other Identifiers

2.2.1 UNII

35XUO924Y0

2.3 Synonyms

2.3.1 MeSH Synonyms

1. O-dinitrobenzene

2. Ortho-dinitrobenzene

2.3.2 Depositor-Supplied Synonyms

1. 528-29-0

2. O-dinitrobenzene

3. 1,2-dinitrobenzol

4. Benzene, O-dinitro-

5. Ortho-dinitrobenzene

6. Benzene, 1,2-dinitro-

7. 1,2-dinitro-benzene

8. 25154-54-5

9. Chebi:34053

10. 35xuo924y0

11. Nsc-60682

12. Dsstox_cid_4066

13. Dsstox_rid_77278

14. Dsstox_gsid_24066

15. Dinitrobenzene, O-

16. O-dintrobenzene

17. Cas-528-29-0

18. Ccris 3091

19. Hsdb 4486

20. Einecs 208-431-8

21. Nsc 60682

22. Unii-35xuo924y0

23. Ai3-15338

24. Wln: Wnr Bnw

25. Schembl22566

26. 1,2-dinitrobenzene, 97%

27. Ghl.pd_mitscher_leg0.923

28. Bidd:er0518

29. O-dinitrobenzene [mi]

30. Chembl168075

31. 1,2-dinitrobenzene, >=99%

32. Dtxsid4024066

33. Act12765

34. Nsc60682

35. Zinc4261808

36. Tox21_201580

37. Tox21_300418

38. Mfcd00007093

39. Stl453602

40. Td1044

41. Akos000120631

42. Gs-3201

43. 1,2-dinitrobenzene, Analytical Standard

44. Ncgc00164050-01

45. Ncgc00164050-02

46. Ncgc00164050-03

47. Ncgc00254393-01

48. Ncgc00259129-01

49. O-dinitrobenzene [un1597] [poison]

50. Ac-26090

51. D0818

52. Ft-0632304

53. En300-17305

54. A20874

55. J-200033

56. Q2238767

57. Z56914842

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₆H₄N₂O₄
Molecular Weight	168.11 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	0
Exact Mass	168.01710661 g/mol
Monoisotopic Mass	168.01710661 g/mol
Topological Polar Surface Area	91.6 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	173
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Absorption, Distribution and Excretion

Readily absorbed through the skin, either as solid, liquid, or vapor. /Dinitrobenzene/

Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981., p. 1

4.2 Metabolism/Metabolites

Nitroreductase activity was previously known to occur under nitrogen atmosphere in the cytosolic and microsomal fractions of liver homogenates. This study describes a subcellular nitroreductase activity which occurs in liver mitochondria under aerobic conditions. Mitochondria were isolated from rat liver and assayed for their capacity to reduce certain nitro compounds by measuring spectrophotometrically both the appearance of amino compounds and the consumption of nicotinamide adenine dinucleotide. Intact mitochondria were found to possess a p-dinitrobenzene reductase activity. The activity was destroyed by heat, and was present at only 20% in the microsomal fraction. It was strictly nicotinamide adenine dinucleotide-dependent, while only little or no activity occurred with reduced nicotinamide adenine dinucleotide or other oxidative substrates. Nitro reduction was inhibited by thiol reagents. Rat liver mitochondria showed about 15% activity with o-dinitrobenzene and m-dinitrobenzene, while there was less than 5% activity with a series of p-nitro compounds including chloramphenicol.

Abou-Khalil S et al; Pharmacology (Basal) 31 (6): 301-8 (1985)

The metabolism of radiolabeled dinitrobenzene isomers was compared in hepatocytes and hepatic subcellular fractions isolated from male Fischer-344 rats. Under aerobic conditions, reduction was the major metabolic pathway for m- and p-dinitrobenzene in hepatocytes with m- and p-nitroaniline accounting for 74.0 + or - 1.2 and 81.0 + or - 0.6% (mean + or - SE, n= 4), respectively, of the radioactivity present after a 30 min incubation. The major metabolite of o-dinitrobenzene in similar incubations was S-(2-nitrophenyl)glutathione which represented 48.1 + or - 5.5% of the total radioactivity; o-nitroaniline accounted for 29.5 + or - 2.1% of the radioactivity. Incubation of dinitrobenzene with microsomes produced nitroanilines as well as nitrosonitrobenzenes and nitrophenylhydroxylamines. Reduction of o- and m-dinitrobenzene by microsomes was reduced nicotinamide adenine dinucleotide-dependent. Reduction of p-dinitrobenzene could be supported by nicotinamide adenine dinucleotide as well as reduced nicotinamide adenine dinucleotide, although the rate of reduction was slower with NADH. Conjugation of o- and p-dinitrobenzene, but not m-dinitrobenzene, with glutathione occurred in cytosol incubations although only o-dinitrobenzene formed the glutathione conjugate in intact hepatocytes.

PMID:2867868 Cossum PA, Rickert DE; Drug Metab Dispos 13 (6): 664-8 (1985)