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CAS 193-39-5
  • Chemistry
CAS 193-39-5
Also known as: Indeno[1,2,3-cd]pyrene, 193-39-5, O-phenylenepyrene, 1,10-(1,2-phenylene)pyrene, 2,3-phenylenepyrene, 1,10-(o-phenylene)pyrene
Molecular Formula
Molecular Weight
276.338  g/mol
InChI Key

1 2D Structure

CAS 193-39-5

2 Identification
2.1 Computed Descriptors
2.1.1 InChI
2.1.2 InChI Key
2.1.3 Canonical SMILES
2.2 Other Identifiers
2.2.1 UNII
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. Indeno[1,2,3-cd]pyrene

2. 193-39-5

3. O-phenylenepyrene

4. 1,10-(1,2-phenylene)pyrene

5. 2,3-phenylenepyrene

6. 1,10-(o-phenylene)pyrene

7. Rcra Waste Number U137

8. 1,10-(ortho-phenylene)pyrene

9. 2,3-o-phenylenepyrene

10. Unii-t4swx8i0u2

11. Ccris 345

12. Hsdb 5101

13. Indeno(1,2,3-c,d)pyrene

14. Einecs 205-893-2

15. Rcra Waste No. U137

16. Brn 1879312

17. T4swx8i0u2

18. Sxqbharymnfbps-uhfffaoysa-n

19. Indeno(1,2,3-cd)pyrene In Methanol

20. Indeno[1,2,3-c,d]pyrene

21. Indeno(1,2,3-cd)pyrene [polycyclic Aromatic Compounds]

22. Indeno(1,2,3-cd)pyrene [polycyclic Aromatic Hydrocarbons]

23. Hexacyclo[,?.0?,(2)(1).0(1)(1),(2)?.0(1)?,(1)?]docosa-1(22),2,4,6,8(21),9,11(20),12,14(19),15,17-undecaene

24. Ac1l1sdy

25. Dsstox_cid_4153

26. 2,3-(o-phenylene)pyrene

27. Dsstox_gsid_24153

28. Chembl3561582

29. Dtxsid8024153

30. Chebi:82335

31. Ctk0i3412

32. Molport-006-111-111

33. Zinc2516903

34. Indeno[1,2,3-c,d]pyrene Solution

35. Tox21_304020

36. Mfcd00152577

37. Akos015902991

38. Mcule-3222035827

39. Ncgc00357288-01

40. Ak307004

41. Cas-193-39-5

42. Ls-81874

43. Sc-50901

44. Tr-008973

45. Ft-0670326

46. St45022191

47. St51047576

48. Indeno[1,2,3-cd]pyrene, Analytical Standard

49. C19251

50. J-012519

51. I14-18502

52. Indeno(1,2,3-c,d)pyrene 10 Microg/ml In Acetonitrile

53. Indeno(1,2,3-c,d)pyrene 10 Microg/ml In Cyclohexane

54. Indeno(1,2,3-c,d)pyrene 100 Microg/ml In Acetonitrile

55. Indeno(1,2,3-c,d)pyrene 100 Microg/ml In Cyclohexane

56. Indeno[1,2,3-cd]pyrene, Vial Of 1 G, Analytical Standard

57. Indeno[1,2,3-cd]pyrene, Vial Of 25 Mg, Analytical Standard

58. Indeno[1,2,3-cd]pyrene, Certified Reference Material, Tracecert(r)

59. Indeno[1,2,3-c,d]pyrene Solution, 100 Mug/ml In Cyclohexane, Analytical Standard

60. Indeno[1,2,3-c,d]pyrene Solution, Certified Reference Material, 200 Mug/ml In Methanol

61. 348085-46-1

62. Inchi=1/c22h12/c1-2-7-17-16(6-1)18-11-10-14-9-8-13-4-3-5-15-12-19(17)22(18)21(14)20(13)15/h1-12

2.4 Create Date
3 Chemical and Physical Properties
Molecular Weight 276.338 g/mol
Molecular Formula C22H12
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count0
Exact Mass276.094 g/mol
Monoisotopic Mass276.094 g/mol
Topological Polar Surface Area0 A^2
Heavy Atom Count22
Formal Charge0
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 Pharmacology

Indeno[1,2,3-cd]pyrene is a yellowish, aromatic hydrocarbon consisting of six fused rings and produced by the incomplete combustion of organic matter. Indene[1,2,3-cd]pyrene is primarily found in certain foods, gasoline and diesel exhaust, cigarette smoke, coal tar and coal tar pitch, soot and petroleum asphalt. This substance is used only for research purposes. Indene[1,2,3-cd]pyrene is reasonably anticipated to be a human carcinogen. (NCI05)

4.2 Metabolism/Metabolites

A porphyrin/peroxynitrite biomimetic system was used to study the metabolism of indeno[1,2,3-cd]pyrene (IND) induced by peroxynitrite. The metabolites were identified using high-performance liquid chromatography coupled with electro-spray ionization tandem mass spectrometry as OH-IND, IND-quinone and 2NO2-IND. By stopping the reaction at different stages, we discovered that IND was first transformed to IND-quinone and 2NO2-IND, which were then transformed to OH-IND. Mutation assays including Ames tests and cell transformation experiments showed enhancement of the mutagenicity after the activation by the peroxynitrite/Fe(III)porphyrin system. The results also showed that 2NO2-IND and IND-quinone played key roles in the mutagenicity of PAHs after metabolic activation.

Luo Y et al; Bull Environ Contam Toxicol 94 (1): 112-7 (2015)

... The major metabolites of indeno[1,2,3-cd]pyrene as formed in vivo in mouse skin have been identified. 8-Hydroxyindeno[1,2,3-cd]pyrene is the most abundant metabolite identified. 9-Hydroxyindeno[1,2,3-cd]pyrene and trans-1,2-dihydro-1,2-dihydroxyindeno[1,2,3-cd]pyrene are also major in vivo metabolites in mouse skin. Several minor metabolites were also identified. Among these are trans-1,2-dihydro-1,2,8-trihydroxyindeno[1,2,3-cd]pyrene, trans-1,2-dihydro-1,2,9-trihydroxyindeno[1,2,3-cd]pyrene, indeno[1,2,3-cd]pyrene-1,2-dione, and 10-hydroxyindeno[1,2,3-cd]pyrene. The tumor-initiating activity of several of the major in vivo metabolites of indeno[1,2,3-cd]pyrene has been investigated on mouse skin. Trans-1,2-dihydro-1,2-dihydroxyindeno[1,2,3-cd]pyrene and 1,2-dihydro-1,2-epoxyindeno[1,2,3-cd]pyrene both produced an 80% incidence of tumor-bearing mice at a total initiating dose of 1.0 mg. The activity of this K-region dihydrodiol and K-region oxide was, however, less than that of the parent hydrocarbon. These data suggest that 1,2-dihydro-1,2-epoxyindeno[1,2,3-cd]pyrene, which is an ultimate mutagenic metabolite of indeno[1,2,3-cd]pyrene, is not the ultimate tumorigenic metabolite on mouse skin. 8-Hydroxyindeno[1,2,3-cd]pyrene, which is mutagenic when assayed in the presence of a microsomal activation system, exhibited only weak tumor-initiating activity. These results indicate that the principal metabolic activation pathways associated with the mutagenic activity of indeno[1,2,3-cd]pyrene are not related to its tumor-initiating activity on mouse skin.

Rice JE et al; Carcinogenesis 7 (10): 1761-64 (1986)

Indeno[1,2,3-cd]pyrone (ip) ... is carcinogenic on mouse skin and in rat lung. Unlike benzo(a)pyrene, IP is a nonalternant polycyclic aromatic hydrocarbon which is devoid of a bay region. IP was mutagenic in Salmonella typhimurium TA100 in the presence of a 9000 x g supernatant from the livers of Aroclor-pretreated rats. With a similar activation system, the major metabolites of IP were ... identified ... . trans-1,2-Dihydro-1,2-dihydroxy-IP, 8-, 9-, and 10-hydroxy-IP, 8- and 9-hydroxy-trans-1,2-dihydro-1,2-dihydroxy-IP, and IP-1,2-quinone are among the metabolites formed in vitro. The 1,2-epoxide of indeno[1,2,3-cd]pyrene is a potent direct-acting mutagen. 8- and 9-hydroxy-IP and the trans-1,2-dihydrodiol had no significant mutagenic activity in S. typhimurium TA100 with metabolic activation. These data suggest that the K-region oxides of IP and of 8- and 9-hydroxy-IP are ultimately responsible for its mutagenic activity.

Rice J et al; Cancer Res 45 (11): 5421-25 (1985)

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