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2D Structure
Also known as: P-nitroaniline, 100-01-6, 4-nitrobenzenamine, P-aminonitrobenzene, P-nitraniline, P-nitrophenylamine
Molecular Formula
C6H6N2O2
Molecular Weight
138.12  g/mol
InChI Key
TYMLOMAKGOJONV-UHFFFAOYSA-N
FDA UNII
1MRQ0QZG7G

1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-nitroaniline
2.1.2 InChI
InChI=1S/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2
2.1.3 InChI Key
TYMLOMAKGOJONV-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=CC=C1N)[N+](=O)[O-]
2.2 Other Identifiers
2.2.1 UNII
1MRQ0QZG7G
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-nitroaniline Monohydrochloride

2. 4-nitroaniline Sulfate (2:1)

3. 4-nitroaniline, Mercury (2+) Salt (2:1)

4. P-nitroaniline

5. Para-nitroaniline

6. Paranitronaniline

2.3.2 Depositor-Supplied Synonyms

1. P-nitroaniline

2. 100-01-6

3. 4-nitrobenzenamine

4. P-aminonitrobenzene

5. P-nitraniline

6. P-nitrophenylamine

7. 4-nitraniline

8. 1-amino-4-nitrobenzene

9. Benzenamine, 4-nitro-

10. Aniline, P-nitro-

11. Developer P

12. Aniline, 4-nitro-

13. Para-nitroaniline

14. Azoamine Red Zh

15. Nitrazol Cf Extra

16. Devol Red Gg

17. Fast Red P Base

18. Fast Red P Salt

19. Fast Red Base Gg

20. Fast Red Gg Base

21. Fast Red Gg Salt

22. Fast Red Mp Base

23. Fast Red Salt Gg

24. Diazo Fast Red Gg

25. Red 2g Base

26. Fast Red 2g Base

27. Fast Red 2g Salt

28. Fast Red Base 2j

29. Fast Red Salt 2j

30. Azofix Red Gg Salt

31. C.i. Developer 17

32. Naphtoelan Red Gg Base

33. Azoic Diazo Component 37

34. Paranitroaniline

35. P-nitroanilina

36. Shinnippon Fast Red Gg Base

37. Rcra Waste Number P077

38. C.i. Azoic Diazo Component 37

39. P-nitro Aniline

40. Nci-c60786

41. Nsc 9797

42. C.i. 37035

43. 4-nitro-aniline

44. 1mrq0qzg7g

45. Dtxsid8020961

46. Chebi:17064

47. Nsc-9797

48. Ncgc00091426-02

49. 4-nitrobenzeneamine

50. 4-aminonitrobenzene

51. Ci Developer 17

52. Para-aminonitrobenzene

53. P-nitroanilina [polish]

54. Pna (van)

55. 4-nitro-phenylamine

56. 4-nitrophenylamine

57. Nitroaniline, P-

58. Azoamine Red 2h

59. Ci Azoic Diazo Component 37

60. Ccris 1184

61. Hsdb 1156

62. Benzen-2,3,5,6-d4-amine-d2, 4-nitro-

63. Einecs 202-810-1

64. Para Nitro Aniline

65. Unii-1mrq0qzg7g

66. Mfcd00007858

67. Rcra Waste No. P077

68. Ci 37035

69. P-nitro-aniline

70. Para-nitroanilin

71. Ai3-08926

72. 4-nitro Aniline

73. P-nitroaniline, Solid

74. (4-nitrophenyl)-amine

75. 4-nitroaniline, 99%

76. 4-nitrobenzeneamine Anion

77. Dsstox_cid_961

78. Wln: Zr Dnw

79. Ec 202-810-1

80. 4-nitroaniline, Crystalline

81. 4-nitroaniline, >=99%

82. Dsstox_rid_75889

83. Nciopen2_002864

84. P-nitroaniline [mi]

85. Dsstox_gsid_20961

86. Schembl16451

87. Mls002454441

88. Chembl14282

89. 4-nitroaniline [hsdb]

90. 4-nitro-3-chloro Benzoic Acid

91. Schembl10163408

92. Nsc9797

93. Hms3039b17

94. 4-nitroaniline, Analytical Standard

95. Str00350

96. Zinc3860644

97. Tox21_400031

98. Stk301653

99. Akos000119131

100. Akos025293369

101. P-nitroaniline [un1661] [poison]

102. Ncgc00091426-01

103. Ncgc00091426-03

104. Cas-100-01-6

105. Smr001372024

106. Ft-0650287

107. N0119

108. 00n016

109. C02126

110. Ae-641/01643038

111. Q419842

112. Q-200503

113. Z275127984

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 138.12 g/mol
Molecular Formula C6H6N2O2
XLogP31.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass138.042927438 g/mol
Monoisotopic Mass138.042927438 g/mol
Topological Polar Surface Area71.8 Ų
Heavy Atom Count10
Formal Charge0
Complexity124
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

MEDICATION (VET): IN VET MEDICINE FOR POULTRY

SRI


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

It is absorbed through the skin.

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2468


... Absorbed ... by inhalation of dust or vapor.

International Labour Office. Encyclopedia of Occupational Health and Safety. Vols. I&II. Geneva, Switzerland: International Labour Office, 1983., p. 145


The disposition of 14(C)-labeled p-nitroaniline was studied in male rats following oral or iv admin. The clearance of 14(C) p-nitroaniline-derived radioactivity from various tissues was rapid and followed a 2-component decay curve. The whole-body half-life of p-nitroaniline was approximately 1 hr. Within 3 days, clearance of p-nitroaniline-derived radioactivity from the body was almost complete. 14(C) p-nitroaniline was rapidly cleared by metabolism to 9 metabolites which were excreted primarily in the urine and to a lesser extent in the feces. Most (56%) of the urinary radioactivity was in the form of sulfate conjugates of 2 metabolites of p-nitroaniline.

PMID:6745538 Chopade HM, Matthews HB; Fundam Appl Toxicol 4 (3): 485-93 (1984)


The percutaneous absorption of nitrobenzene, p-nitroaniline, 2,4-dinitrochlorobenzene, 2-nitro-p-phenylenediamine, and 4-amino-2-nitrophenol was studied in vivo and in vitro. The compounds were applied to shaved abdominal skins of Rhesus-monkeys at a concentration of 4 ug/sq cm. Five day urine samples were collected and analyzed for the compounds. Radiolabeled nitrobenzene, p-nitroaniline, 2-4-dinitrochlorobenzene, 2-nitro-p-phenylenediamine, or 4-amino-2-nitrophenol were applied to excised human skin at a dose of 4 ug/sq cm using a diffusion cell technique. Penetration of radioactivity through the skin was monitored for the next 24 hours. The compounds rapidly penetrated excised human skin, the greatest penetration occurring in the first 2 hours after exposure. The ability of the compounds to penetrate human skin ranked in decreasing order of permeability and corrected for evaporation was 4-amino-2-nitrophenol, nitrobenzene, p-nitroaniline, 2,4-dinitrochlorobenzene, and 2-nitro-p-phenylenediamine. The corresponding rank for penetration of monkey skin was 4-amino-2-nitrophenol, p-nitroaniline, 2,4-dinitrochlorobenzene, 2-nitro-p-phenylenediamine, and nitrobenzene.

Bronaugh RL, Maibach HI; Toxicity of Nitroaromatic Compounds 141-8 (1985)


5.2 Metabolism/Metabolites

Given orally or ip in doses of 20-40 mg/kg in rats, analysis of 24-hr urine samples showed that 4-nitroaniline was excreted partly unchanged & also as 4-phenylenediamine & 2-amino-5-nitrophenol...

PMID:4868295 MATE C ET AL; FOOD COSMET TOXICOL 5 (5): 657-63 (1967)


The principal rat liver microsomal metabolite of 4-nitroaniline was isolated by high performance liquid chromatography and characterized as 2-amino-5-nitrophenol. Pretreatment of rats with phenobarbital and 3-methylcholanthrene increased the rate of conversion of 4-nitroaniline to 2-amino-5-nitrophenol by 2- and 4-fold, respectively.

PMID:6144483 Anderson MM et al; Drug Metab Dispos 12 (2): 179-85 (1984)


The metabolism of radiolabeled dinitrobenzene isomers was compared in hepatocytes and hepatic subcellular fractions isolated from male rats. Under aerobic conditions, reduction was the major metabolic pathway for m-dinitrobenzene and p-dinitrobenzene in hepatocytes with m-nitroaniline and p-nitroaniline accounting for 74.0 and 81.0% respectively, of the radioactivity present after a 30-minute incubation. The major metabolite of o-nitrobenzene in similar incubations was S-(2-nitrophenyl)glutathione which represented 48.1% of the total radioactivity. o-Nitroaniline accounted for 29.5% of the radioactivity.

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


14(C) p-nitroaniline was rapidly cleared by metabolism to 9 metabolites which were excreted primarily in the urine and to a lesser extent in the feces. Most (56%) of the urinary radioactivity was in the form of sulfate conjugates of 2 metabolites of p-nitroaniline.

PMID:6745538 Chopade HM, Matthews HB; Fundam Appl Toxicol 4 (3): 485-93 (1984)


5.3 Biological Half-Life

The whole-body half-life of p-nitroaniline was approximately 1 hr.

PMID:6745538 Chopade HM, Matthews HB; Fundam Appl Toxicol 4 (3): 485-93 (1984)


5.4 Mechanism of Action

... To assess further the role of the 4-substituent in methaemoglobinaemia, the toxicity of a series of 4-substituted aniline derivatives was also studied. Of the anilines studied, 4-nitroaniline caused the most methemoglobin (36.5 +/- 8.0%), while aniline caused the least (0.3 +/- 0.5%). Overall, there was a significant correlation (r2 = 0.83) between the hemotoxicity and the Hammett constant, sigma(p), suggesting that it is the electron-withdrawing properties of the substituent that influence the methemoglobin formation. ...

PMID:9020194 Mahmud R et al; Toxicology 117 (1): 1-11 (1997)


The relative mutagenic activities of aminoanilines have been attempted to be related to parameters reflecting potential for n-hydroxylation and stability of the arylnitrenium ions. Both chloro and the nitro groups deactivate the amine group to n-hydroxylation and the ring to epoxidation, & no active products from cytochrome p450 would be predicted. The activity of the nitro derivatives is presumed to be due to transformation of the nitro group itself to an active mutagenic species by other enzyme systems. /Aminoanilines/

PMID:448254 LOEW GH ET AL; J ENVIRON PATHOL TOXICOL 2 (4): 1069-78 (1979)