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Tox21_300026
Also known as: Hexanedinitrile, 1,4-dicyanobutane, 111-69-3, Adipyldinitrile, Adipodinitrile, Adipic acid dinitrile
Molecular Formula
C6H8N2
Molecular Weight
108.14  g/mol
InChI Key
BTGRAWJCKBQKAO-UHFFFAOYSA-N
FDA UNII
SYT33B891I

1 2D Structure

Tox21_300026

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
hexanedinitrile
2.1.2 InChI
InChI=1S/C6H8N2/c7-5-3-1-2-4-6-8/h1-4H2
2.1.3 InChI Key
BTGRAWJCKBQKAO-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(CCC#N)CC#N
2.2 Other Identifiers
2.2.1 UNII
SYT33B891I
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Hexanedinitrile

2.3.2 Depositor-Supplied Synonyms

1. Hexanedinitrile

2. 1,4-dicyanobutane

3. 111-69-3

4. Adipyldinitrile

5. Adipodinitrile

6. Adipic Acid Dinitrile

7. Tetramethylene Dicyanide

8. Nitrile Adipico

9. Tetramethylene Cyanide

10. Adipic Acid Nitrile

11. Hexanedioic Acid, Dinitrile

12. Nsc 7617

13. Syt33b891i

14. Nsc-7617

15. Hexanedinitrile, Hydrogenated, High-boiling Fraction

16. Mfcd00001975

17. Dsstox_cid_1936

18. Dsstox_rid_76412

19. Adipinsaeuredinitril

20. Dsstox_gsid_21936

21. 68411-90-5

22. Nitrile Adipico [italian]

23. Adipinsaeuredinitril [german]

24. Cas-111-69-3

25. Ccris 4570

26. Hsdb 627

27. Einecs 203-896-3

28. Hexanedioic Acid Dinitrile

29. Un2205

30. Brn 1740005

31. Unii-syt33b891i

32. Adipic Dinitrile

33. Ai3-11080

34. Einecs 270-153-8

35. 4-cyanobutyl Cyanide

36. Adiponitrile, 99%

37. Hexane-1,6-dinitrile

38. Reaction Product (adiponitrile-hydrogen)

39. Adiponitrile [mi]

40. Butanedicarbonitrile

41. Wln: Nc4cn

42. Adiponitrile [hsdb]

43. Ec 203-896-3

44. Schembl59340

45. 4-02-00-01975 (beilstein Handbook Reference)

46. Mls002415709

47. 1,4-butanedicarbonitrile

48. Chembl2132938

49. Dtxsid3021936

50. Nsc7617

51. Hms2268i10

52. Zinc1683668

53. Tox21_202183

54. Tox21_300026

55. Adiponitrile [un2205] [poison]

56. Adiponitrile, Reaction Product With Hydrogen, High-boiling Fraction

57. Akos009031175

58. Un 2205

59. Ncgc00090882-01

60. Ncgc00090882-02

61. Ncgc00090882-03

62. Ncgc00254080-01

63. Ncgc00259732-01

64. Ms-20979

65. Smr001252282

66. A0168

67. Ft-0606865

68. Q84062

69. J-503989

70. Adiponitrile, >99%, Acid <200 Ppm, H2o <100 Ppm

71. F1908-0128

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 108.14 g/mol
Molecular Formula C6H8N2
XLogP3-0.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Exact Mass108.068748264 g/mol
Monoisotopic Mass108.068748264 g/mol
Topological Polar Surface Area47.6 Ų
Heavy Atom Count8
Formal Charge0
Complexity113
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

Seventy nine percent of dose /about 50 mg/kg sc admin to guinea pigs/ was eliminated as thiocyanate in urine. ... Skin penetration was suggested by incr in thiocyanate in urine ... after application to depilated skin. Greater quantities were absorbed when skin was abraded.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3152


The concentrations of thiocyanate in the blood and urine of guinea pigs injected with adiponitrile were proportional to the doses administered. Following administration of adiponitrile, 79% was eliminated as thiocyanate in the urine of guinea pigs. Of the cyanide antidotes, thiosulfate was most effective. However, on the basis of the ratio between administered adiponitrile dose and quantity of cyanide detected, /it was/ concluded that a greater part of the dose was metabolized to cyanide.

Snyder, R. (ed.). Ethel Browning's Toxicity and Metabolism of Industrial Solvents. 2nd ed. Volume II: Nitrogen and Phosphorus Solvents. Amsterdam-New York-Oxford: Elsevier, 1990., p. 325


4.2 Metabolism/Metabolites

... In guinea pigs ... it is hydrolyzed to hydrogen cyanide in the body giving rise to thiocyanate in urine.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3152


Male ddY mice were pretreated with carbon tetrachloride or olive oil and administered adiponitrile orally in concentrations sufficient to determine its median lethal dose (LD50). Brain cyanide concentrations were determined. The distribution coefficient (P) for partitioning adiponitrile between water and n-octanol was measured. Mice were pretreated as before and dosed with adiponitrile at 3 to 5 times its LD50. Mean survival times were determined. Hepatic microsomes were obtained from mice pretreated with carbon tetrachloride or olive oil and incubated with adiponitrile. The rate of release of free cyanide was investigated. The oral LD50 for animals pretreated with olive oil was 1.592 mmol/kg. The LD50 for the carbon tetrachloride treated mice was 2.652 mmol/kg. Brain cyanide concentrations in olive oil pretreated mice ranged from 0.35 to 0.74 ug/g. Carbon tetrachloride pretreatment lengthened survival and reduced brain cyanide concentrations. Dinitriles are metabolized to cyanides in vivo and in vitro.

Tanii H, Hashimoto K; Archives of Toxicol 57 (2): 88-93 (1985)


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