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Overview of CAS 99-57-0

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4Nitro-o-aminophenol
PharmaCompass
  • Chemistry
4Nitro-o-aminophenol
Also known as: 99-57-0, 2-hydroxy-5-nitroaniline, Phenol, 2-amino-4-nitro-, 4-nitro-2-aminophenol, P-nitro-o-aminophenol, 4-nitro-2-aminofenol
Molecular Formula
C6H6N2O3
Molecular Weight
154.125  g/mol
InChI Key
VLZVIIYRNMWPSN-UHFFFAOYSA-N
FDA UNII
G501UCI6T9

1 2D Structure

4Nitro-o-aminophenol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-amino-4-nitrophenol
2.1.2 InChI
InChI=1S/C6H6N2O3/c7-5-3-4(8(10)11)1-2-6(5)9/h1-3,9H,7H2
2.1.3 InChI Key
VLZVIIYRNMWPSN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=C(C=C1[N+](=O)[O-])N)O
2.2 Other Identifiers
2.2.1 UNII
G501UCI6T9
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 99-57-0

2. 2-hydroxy-5-nitroaniline

3. Phenol, 2-amino-4-nitro-

4. 4-nitro-2-aminophenol

5. P-nitro-o-aminophenol

6. 4-nitro-2-aminofenol

7. P-nitroaminofenol

8. 3-amino-4-hydroxynitrobenzene

9. 1-nitro-3-amino-4-hydroxybenzene

10. Nci-c55958

11. Rodol 42

12. 2-amino-4-nitrofenol

13. 2-amino-4-nitro-phenol

14. 1-amino-2-hydroxy-5-nitrobenzene

15. 1-hydroxy-2-amino-4-nitrobenzene

16. Nsc 4664

17. P-nitroaminofenol [polish]

18. C.i. 76530

19. Ccris 890

20. 2-amino-4-nitrofenol [czech]

21. 4-nitro-2-aminofenol [czech]

22. Ci 76530

23. 2-amino-4-nitro Phenol

24. Hsdb 4165

25. Einecs 202-767-9

26. Brn 0776533

27. Ai3-08864

28. Chebi:82383

29. Vlzviiyrnmwpsn-uhfffaoysa-n

30. Mfcd00007695

31. Dsstox_cid_62

32. Dsstox_rid_75341

33. Dsstox_gsid_20062

34. Cas-99-57-0

35. Smr000221023

36. Unii-g501uci6t9

37. Ursol 4gl

38. 4nitro-o-aminophenol

39. 2-amino4-nitrophenol

40. 4-nitro-o-aminophenol

41. Pubchem14489

42. 5-nitro-2-hydroxyaniline

43. Wln: Zr Bq Enw

44. Acmc-209sd6

45. 2-amino-4-nitro-phenolate

46. 5-nitro 2-hydroxy Aniline

47. Schembl22943

48. Ksc486m5l

49. Mls000331524

50. Mls002152867

51. Ac1mu695

52. Ac1q516k

53. Chembl316992

54. G501uci6t9

55. 2-amino-4-nitrophenol, 96%

56. Dtxsid6020062

57. Schembl10232244

58. Ctk3i6655

59. Nsc4664

60. Molport-000-146-050

61. 1-hydroxy-2 Amino-4-nitrobenzene

62. 4-nitro-2-amino-1-hydroxybenzene

63. Bb_sc-1352

64. Hms2549h14

65. Act07277

66. Nsc-4664

67. Tox21_201351

68. Tox21_302788

69. Anw-41032

70. Bbl011594

71. Ca0059

72. Fc0777

73. Sbb058872

74. Stk802465

75. Zinc35051195

76. Akos000121534

77. Ls-2066

78. Mcule-7519476697

79. Ps-4603

80. Rp21815

81. Rtr-030456

82. Tra0001607

83. Ks-0000021v

84. Ncgc00091626-01

85. Ncgc00091626-02

86. Ncgc00091626-03

87. Ncgc00256395-01

88. Ncgc00258903-01

89. Ac-11277

90. Aj-90621

91. Ak-26492

92. Cj-18627

93. Kb-19957

94. Tl806261

95. 2-amino-4-nitrophenol, >=99.0% (nt)

96. Db-020444

97. Tr-030456

98. A0378

99. Bg01499742

100. Ft-0082758

101. Ft-0619188

102. St24032375

103. St51039935

104. Az0001-0118

105. A11337

106. C19321

107. M-5091

108. W-100031

109. F0001-2336

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 154.125 g/mol
Molecular Formula C6H6N2O3
XLogP31.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Exact Mass154.038 g/mol
Monoisotopic Mass154.038 g/mol
Topological Polar Surface Area92.1 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 Absorption, Distribution and Excretion

Percutaneous absorption through the skin of Sprague-Dawley rats of each sex was examined following application of two hair dye formulations: formulation 1 contained 1.54% 14C-2-amino-4-nitrophenol; formulation 2 contained 0.77% 14C-2-amino-4-nitrophenol, 1,4-diaminobenzene (1,4-phenylenediamine), 2,4-diaminoanisole, oleic acid and isopropanol and was mixed with equal amt of a 6% hydrogen peroxide soln. After 1 and 5 days, 0.21 and 0.36% of the radiolabel administered in formulation 1 and 1.12 and 1.67% of that administered in formulation 2 had been absorbed (calculated as combined radiolabel in urine, feces, expired air and carcass, without treated skin area). Absorbed material was excreted predominantly in the urine within 24 hr after the initial application ... .

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: http://monographs.iarc.fr/ENG/Classification/index.php, p. V57 170 (1993)


Five days after oral administration by gavage of 2 mL (14)C-2-amino-4-nitrophenol (0.2% in saline), 68.3% + 9.4 (SD) of the radiolabel had been excreted in the urine and 25.4% + 6.9% in the feces. Within 3 hr, about 4% of the radiolabel was eliminated in the bile. Following subcutaneous injection of the same dose, 89% of the dose was eliminated after 1 day, predominantly in the urine ... (/It was/ noted that metabolites were not identified in the urine, bile or feces in either study.)

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: http://monographs.iarc.fr/ENG/Classification/index.php, p. V57 170 (1993)


Percutaneous absorption of (14)C-2-amino-4-nitrophenol (specific radioactivity 10 mCi/mmol (65 uCi/mg); purity, 98%) was studied in vitro by partitioning between excised human abdominal skin preparations and water. 2-Amino-4-nitrophenol appeared to bind to skin components ... .

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: http://monographs.iarc.fr/ENG/Classification/index.php, p. V57 170 (1993)


4.2 Metabolism/Metabolites

A liquid chromatography-tandem mass spectrometry (LC-MS-MS) analysis of biological fluids (blood, urine, gastric content, and bile) collected at autopsy in a case of suspected 2,4-dinitrophenol (DNP) fatal poisoning allowed the determination of DNP and its known metabolites (2-amino-4-nitrophenol and nitro-4-aminophenol). The tentative identification of three conjugated metabolites (DNP glucuronide, DNP sulfate, and 2-amino-4-nitrophenol glucuronide) could be made on the basis of their pseudomolecular ion, isotopic and fragmentation patterns, and retention characteristics. Another DNP metabolite reported in the literature, 2,4-diaminophenol, was not detected in the samples. Postmortem blood concentrations were 48.4 mg/L for DNP and 1.2 mg/L for 2-amino-4-nitrophenol. ...

Politi L et al; J Anal Toxicol 31 (1): 55-61 (2007)


YIELDS 2,4-DIAMINOPHENOL PROBABLY IN RATS. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. A-46


2-Amino-4-nitrophenol was the predominant metabolite formed enzymatically by nitroreduction following oral administration of 2,4-dinitrophenol (22.5 mg/kg bw) to ICR mice.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: http://monographs.iarc.fr/ENG/Classification/index.php, p. V57 170 (1993)


4.3 Biological Half-Life

It had an elimination half-time from the plasma /of ICR mice/ of 46 hr ... .

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: http://monographs.iarc.fr/ENG/Classification/index.php, p. V57 170 (1993)


4.4 Mechanism of Action

Two hair dye components, carcinogenic 4-nitro-2-aminophenol and 5-nitro-2-aminophenol, induced Cu(II)-dependent DNA cleavage frequently at thymine and guanine residues in DNA fragments obtained from the c-Ha-ras-1 protooncogene. When the p53 tumor suppressor gene was used, 4-nitro-2-aminophenol caused Cu(II)-dependent piperidine-labile sites at poly G sequences. In the presence of Cu(II), both components increased 8-oxo-7,8-dihydro-2'-deoxyguanosine formation in DNA. The inhibitory effects of catalase and bathocuproine on DNA damage suggest the involvement of H2O2 and Cu(I). It is speculated that nitro-2-aminophenols undergo Cu(II)-mediated autoxidation to generate active oxygen species causing DNA damage which leads to their carcinogenesis.

Chen F et al; Cancer Lett 126 (1): 67-74 (1998)


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