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  • 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, Rodol 42
Molecular Formula
C6H6N2O3
Molecular Weight
154.12  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 MeSH Synonyms

1. 2-amino-p-nitrophenol

2.3.2 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. Rodol 42

7. 4-nitro-2-aminofenol

8. P-nitroaminofenol

9. 3-amino-4-hydroxynitrobenzene

10. 1-amino-2-hydroxy-5-nitrobenzene

11. 1-hydroxy-2-amino-4-nitrobenzene

12. 1-nitro-3-amino-4-hydroxybenzene

13. Nci-c55958

14. C.i. 76530

15. 2-amino-4-nitrofenol

16. 2-amino-4-nitro-phenol

17. Nsc 4664

18. Mfcd00007695

19. 2-amino-4-nitro Phenol

20. 5-nitro-2-hydroxyaniline

21. G501uci6t9

22. Chebi:82383

23. 4-nitro-2-amino-1-hydroxybenzene

24. Nsc-4664

25. Dsstox_cid_62

26. Dsstox_rid_75341

27. Dsstox_gsid_20062

28. P-nitroaminofenol [polish]

29. Cas-99-57-0

30. Smr000221023

31. Ccris 890

32. 2-amino-4-nitrofenol [czech]

33. 4-nitro-2-aminofenol [czech]

34. Ci 76530

35. Hsdb 4165

36. Einecs 202-767-9

37. Brn 0776533

38. Unii-g501uci6t9

39. Ai3-08864

40. 4nitro-o-aminophenol

41. 2-amino4-nitrophenol

42. 4-nitro-o-aminophenol

43. Wln: Zr Bq Enw

44. 2-amino-4-nitro-phenolate

45. 5-nitro 2-hydroxy Aniline

46. Ec 202-767-9

47. Schembl22943

48. Mls000331524

49. Mls002152867

50. Chembl316992

51. 2-amino-4-nitrophenol, 96%

52. Dtxsid6020062

53. Schembl10232244

54. Nsc4664

55. 1-hydroxy-2 Amino-4-nitrobenzene

56. Amino-4-nitrophenol, 2-

57. Hms2549h14

58. Act07277

59. Tox21_201351

60. Tox21_302788

61. Bbl011594

62. Stk802465

63. Zinc35051195

64. Akos000121534

65. 2-amino-4-nitrophenol [hsdb]

66. 2-amino-4-nitrophenol [iarc]

67. 2-amino-4-nitrophenol [inci]

68. Am10716

69. Ps-4603

70. Ncgc00091626-01

71. Ncgc00091626-02

72. Ncgc00091626-03

73. Ncgc00256395-01

74. Ncgc00258903-01

75. Ac-11277

76. 2-amino-4-nitrophenol, >=99.0% (nt)

77. Db-020444

78. A0378

79. Ft-0619188

80. C19321

81. W-100031

82. Q27155912

83. F0001-2336

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 154.12 g/mol
Molecular Formula C6H6N2O3
XLogP31.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Exact Mass154.03784206 g/mol
Monoisotopic Mass154.03784206 g/mol
Topological Polar Surface Area92.1 Ų
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: https://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: https://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: https://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. ...

PMID:17389084 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: https://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: https://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.

PMID:9563650 Chen F et al; Cancer Lett 126 (1): 67-74 (1998)


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