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Overview of CAS 99-56-9

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4NDB
PharmaCompass
4NDB
Also known as: 99-56-9, 4-nitrobenzene-1,2-diamine, 1,2-diamino-4-nitrobenzene, 4-nitro-1,2-phenylenediamine, 2-amino-4-nitroaniline, 3,4-diaminonitrobenzene
Molecular Formula
C6H7N3O2
Molecular Weight
153.141  g/mol
InChI Key
RAUWPNXIALNKQM-UHFFFAOYSA-N
FDA UNII
5A9AX7Y0TT

1 2D Structure

4NDB

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-nitrobenzene-1,2-diamine
2.1.2 InChI
InChI=1S/C6H7N3O2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H,7-8H2
2.1.3 InChI Key
RAUWPNXIALNKQM-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=C(C=C1[N+](=O)[O-])N)N
2.2 Other Identifiers
2.2.1 UNII
5A9AX7Y0TT
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 99-56-9

2. 4-nitrobenzene-1,2-diamine

3. 1,2-diamino-4-nitrobenzene

4. 4-nitro-1,2-phenylenediamine

5. 2-amino-4-nitroaniline

6. 3,4-diaminonitrobenzene

7. P-nitro-o-phenylenediamine

8. 1,2-benzenediamine, 4-nitro-

9. 4-nitro-1,2-benzenediamine

10. 4-nitro-1,2-diaminobenzene

11. 4-nitrophenylenediamine

12. 4-nopd

13. 4-nop

14. 4-n-o-pda

15. 4-no

16. 4ndb

17. Nci-c03941

18. O-phenylenediamine, 4-nitro-

19. Nitro-o-phenylenediamine

20. Nsc 5378

21. C.i. 76020

22. 4-nitro-1,2-fenylendiamin

23. 4-nitro-o-phenylene-diamine

24. 4-nitro-para-phenylenediamine

25. Ccris 451

26. Hsdb 2895

27. P-nitro-o-phenylendiamine

28. Einecs 202-766-3

29. 4-nitro-1,2-fenylendiamin [czech]

30. Brn 0608106

31. Ci 76020

32. 1,2-diamino-4-nitrobenezene

33. Ai3-52605

34. Chebi:67116

35. Rauwpnxialnkqm-uhfffaoysa-n

36. Mfcd00007724

37. Dsstox_cid_958

38. Dsstox_rid_75886

39. Dsstox_gsid_20958

40. Cas-99-56-9

41. Unii-5a9ax7y0tt

42. Ac1noefy

43. Pubchem21027

44. 2-amino-5-nitroaniline

45. 4-nitrophenylene Diamine

46. 3,4-diamino-nitrobenzene

47. Wln: Zr Bz Dnw

48. Acmc-209sd5

49. 4-nitro-o-phenylene Diamine

50. 4-ndb

51. 5a9ax7y0tt

52. Schembl78293

53. 4-13-00-00075 (beilstein Handbook Reference)

54. Ksc490g3p

55. 4-nitro-orto-phenylenediamine

56. 1,2-benzenediamine,4-nitro-

57. 4-nitro 1,2-phenylenediamine

58. 4-nitro-ortho-phenylenediamine

59. 4-nitro-benzene-1,2-diamine

60. Chembl433721

61. 4-nitro 1,2-phenylene Diamine

62. 4-nitro-1,2-phenylene Diamine

63. Dtxsid9020958

64. Ctk3j0337

65. (2-amino-5-nitro-phenyl)-amine

66. Nsc5378

67. Molport-001-641-008

68. 4-nitro-o-phenylenediamine, 98%

69. Bb_sc-5347

70. Acn-s002619

71. Act07448

72. Albb-021305

73. Ks-000009rn

74. Nsc-5378

75. Zinc3860878

76. Tox21_202313

77. Tox21_302811

78. Anw-41031

79. Bbl016368

80. Sbb007571

81. Stk317795

82. Akos000119818

83. Ac-2759

84. Cs-w007627

85. Gs-3013

86. Ls-2065

87. Mcule-1032714780

88. Rp21713

89. Rtr-030455

90. Tra0083868

91. Ncgc00091593-01

92. Ncgc00091593-02

93. Ncgc00091593-03

94. Ncgc00256320-01

95. Ncgc00259862-01

96. Aj-46073

97. Ak-29652

98. An-13639

99. Br-29652

100. Cj-10896

101. Kb-40110

102. Or019959

103. Or174231

104. Sc-25715

105. Ab1002234

106. Db-028981

107. Kb-148739

108. Kb-204533

109. St2411571

110. Tr-030455

111. D0103

112. Ft-0614201

113. St45061383

114. A11336

115. C19384

116. M-6457

117. S01-0299

118. W-100032

119. F0001-2335

120. Z1245635744

121. Inchi=1/c6h7n3o2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3h,7-8h

122. 58833-52-6

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 153.141 g/mol
Molecular Formula C6H7N3O2
XLogP30.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Exact Mass153.054 g/mol
Monoisotopic Mass153.054 g/mol
Topological Polar Surface Area97.9 A^2
Heavy Atom Count11
Formal Charge0
Complexity156
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Carcinogens

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.


Indicators and Reagents

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499)


4.2 Mechanism of Action

4-Nitro-o-phenylenediamine (NOP) is a powerful direct-acting mutagen which demonstrates significant enhancement in mutagenicity when exposed to plant enzymatic systems. Evidence implicating the involvement of peroxidactic oxidation in NOP activation has been obtained from plant-cell suspension and isolated enzyme experiments. Using selected cytochrome P450 and peroxidase enzyme inhibitors in conjunction with Salmonella typhimurium strain TA98 and intact plant-cell activating systems as well as isolated horseradish peroxidase enzyme /the authors/ have further investigated NOP activation by plant systems. The activation of NOP by both plant cells and by horseradish peroxidase was suppressed by the P450 inhibitors methimazole and (+)-catechin and by the peroxidase inhibitors diethyldithiocarbamate and potassium cyanide, but was not suppressed by the P450 inhibitors metyrapone and 7,8-benzoflavone. In addition, peroxidase enzymatic activity was measured and found to be inhibited by methimazole, diethyldithiocarbamate and potassium cyanide but not by (+)-catechin. The data strongly support the involvement of exogenous peroxidase in the plant activation of NOP, but point to a complex metabolic system that requires multistep processing before full mutagenic potential of the plant-activated component of NOP is expressed.

Wilson L et al; Mutat Res 307 (1): 185-92 (1994)


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