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Suanfarma Suanfarma

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Technical details about 1,2,3,4-Tetrahydronaphthalene, learn more about the structure, uses, toxicity, action, side effects and more

2D Structure
1. Also known as: Tetralin, 119-64-2, Benzocyclohexane, Tetrahydronaphthalene, Bacticin, Tetraline
Molecular Formula
C10H12
Molecular Weight
132.20  g/mol
InChI Key
CXWXQJXEFPUFDZ-UHFFFAOYSA-N
FDA UNII
FT6XMI58YQ

1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1,2,3,4-tetrahydronaphthalene
2.1.2 InChI
InChI=1S/C10H12/c1-2-6-10-8-4-3-7-9(10)5-1/h1-2,5-6H,3-4,7-8H2
2.1.3 InChI Key
CXWXQJXEFPUFDZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CCC2=CC=CC=C2C1
2.2 Other Identifiers
2.2.1 UNII
FT6XMI58YQ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Tetralin

2.3.2 Depositor-Supplied Synonyms

1. Tetralin

2. 119-64-2

3. Benzocyclohexane

4. Tetrahydronaphthalene

5. Bacticin

6. Tetraline

7. Tetranap

8. Naphthalene, 1,2,3,4-tetrahydro-

9. Tetralina

10. Naphthalene, Tetrahydro-

11. Naphthalene 1,2,3,4-tetrahydride

12. Tetralene

13. Nsc 77451

14. (c4-c5) Alkyltetrahydronaphthalenes

15. Ft6xmi58yq

16. Naphthalene, 1,2,3,4-tetrahydro-, C1-4-alkyl Derivs.

17. Chebi:35008

18. 1,2,3,4-tetrahydro-naphthalene

19. Nsc-77451

20. Dsstox_cid_6118

21. Dsstox_rid_78023

22. Dsstox_gsid_26118

23. 68412-24-8

24. Tetralina [polish]

25. Caswell No. 842a

26. Cas-119-64-2

27. Ccris 3564

28. Hsdb 127

29. Delta(sup 5,7,9)-naphthantriene

30. Einecs 204-340-2

31. Unii-ft6xmi58yq

32. 1,2,3,4-tetrahydronaphthalene, Reagent Grade, >=97%

33. Epa Pesticide Chemical Code 055901

34. Ai3-01257

35. Tetralin Solvent

36. Einecs 270-178-4

37. Mfcd00001733

38. Tetralin [hsdb]

39. Tetralin [mi]

40. Bmse000530

41. Tetralin [usp-rs]

42. Tetralin [who-dd]

43. Ec 204-340-2

44. Nciopen2_000650

45. 1,3,4-tetrahydronaphthalene

46. 1,2,3,4-tetrahydronapthalene

47. 5,6,7,8-tetrahydronaphthalene

48. Chembl1575635

49. Dtxsid1026118

50. Naphthalene 1,3,4-tetrahydride

51. Wln: L66 & Tj

52. 1,2,3,4 Tetrahyclronaphthalene

53. .delta.(5,7,9)-naphthantriene

54. .delta.(sup 5,9)-naphthantriene

55. Naphthalene-1,2,3,4-tetrahydride

56. Nsc77451

57. Zinc8437660

58. Tox21_201793

59. Tox21_303325

60. Stl264224

61. .delta.(sup 5,7,9)-naphthantriene

62. Akos000121383

63. Ncgc00091744-01

64. Ncgc00091744-02

65. Ncgc00256948-01

66. Ncgc00259342-01

67. Ft-0654145

68. T0107

69. T0713

70. 1,2,3,4-tetrahydronaphthalene, Tetralin, Thn

71. 1,2,3,4-tetrahydronaphthalene, Anhydrous, 99%

72. Q420416

73. 1,2,3,4-tetrahydronaphthalene, Analytical Standard

74. W-108503

75. 1,2,3,4-tetrahydronaphthalene, Reagentplus(r), 99%

76. F1908-0164

77. 1,2,3,4-tetrahydronaphthalene, Vetec(tm) Reagent Grade, 98%

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 132.20 g/mol
Molecular Formula C10H12
XLogP33.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count0
Exact Mass132.093900383 g/mol
Monoisotopic Mass132.093900383 g/mol
Topological Polar Surface Area0 Ų
Heavy Atom Count10
Formal Charge0
Complexity92.6
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

ABSORBED VAPOR IS EXCRETED BY KIDNEYS AS ALPHA- AND BETA-TETRAHYDRONAPHTHOLS ANDTHEIR GLUCURONIDES ... .

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-153


RADIOACTIVE TETRALIN, WHEN ADMIN TO RABBIT, WAS EXCRETED IN URINE AS GLUCURONIDEAT 87-99% AND IN FECES AT 0.6-1.8% OF ORIGINAL DOSE. ... WAS ABSORBED BY MUSSEL BUT NOT METABOLIZED; ... UP TO 80% WAS RELEASED IN UNCHANGED FORM WHEN THE ORGANISM WAS TRANSFERRED TO FRESH SEAWATER.

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. 3242


When radioactive tetralin was fed to rabbits, 87-90% of the activity was excreted in the urine in 2 days and 0.5-3.7% on the third day. The feces contained only 0.6-1.8%. No radioactivity was found in the breath, and negligible amounts were retained in the tissues. About 90-99% of the dose was accounted for.

Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 2. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991., p. 643


4.2 Metabolism/Metabolites

(1-(14)C)-TETRALIN IS METABOLIZED IN RABBITS BY HYDROXYLATION OF ALICYCLIC RING TO YIELD CONJUGATES OF AC-ALPHA-TETRALOL (60% OF DOSE), AC-BETA-TETRALOL (20%) & TETRALIN-1,2-DIOL (2.5%), & HYDROXYLATION OF AROMATIC RING ... YIELDING AR-BETA-TETRALOL (5,6,7,8-TETRAHYDRO-2-NAPHTHOL, 0.1%).

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 220


YIELDS 2-HYDROXYTETRALYLMERCAPTURIC ACID, 1,2,3,4-TETRAHYDRO-1-NAPHTHOL, 1,2,3,4-TETRAHYDRO-2-NAPHTHOL IN RABBIT. YIELDS 1,2,3,4-TETRAHYDRO-1,2-DIHYDROXYNAPHTHALENE, 5,6,7,8-TETRAHYDRO-2-NAPHTHOL IN RABBIT. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. T-10


In rabbits, the main urinary metabolite was the glucuronide of alpha-tetralol (52.4%). Other conjugated metabolites were beta-tetralol (25.3%), 4-hydroxy-alpha-tetralone (6.1%), and cis-tetralin-1,2-diol (0.4%). Using rat liver homogenates, it was shown that conversion of tetralin to tetralol requires reduced nicotinamide adenine dinucleotide phosphate and that tetralin hydroperoxide is a probable intermediate. Further study confirmed this possibility and indicated that tetralin hydroxylation proceeds via a radical mechanism similar to that of lipid peroxidation.

Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 2. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991., p. 643


Tetralin, a component of fuels, solvents, and varnishes, is metabolized in male Fischer 344 rats to 1-tetralol, 2-tetralol, 2-hydroxyl-1-tetralone, 4-hydroxyl-1-tetralone, 1,2-tetralindiol, and 1,4-tetralindiol.

PMID:2926829 Serve MP et al; J Toxicol Environ Health 26 (3): 267-75 (1989)


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