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Chemistry

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Also known as: 55-18-5, Diethylnitrosamine, Diethylnitrosoamine, Ndea, N-ethyl-n-nitrosoethanamine, N,n-diethylnitrous amide
Molecular Formula
C4H10N2O
Molecular Weight
102.14  g/mol
InChI Key
WBNQDOYYEUMPFS-UHFFFAOYSA-N
FDA UNII
3IQ78TTX1A

N-Nitrosodiethylamine
A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties.
1 2D Structure

N-Nitrosodiethylamine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N,N-diethylnitrous amide
2.1.2 InChI
InChI=1S/C4H10N2O/c1-3-6(4-2)5-7/h3-4H2,1-2H3
2.1.3 InChI Key
WBNQDOYYEUMPFS-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCN(CC)N=O
2.2 Other Identifiers
2.2.1 UNII
3IQ78TTX1A
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Diethylnitrosamine

2. N Nitrosodiethylamine

3. Nitrosodiethylamine

2.3.2 Depositor-Supplied Synonyms

1. 55-18-5

2. Diethylnitrosamine

3. Diethylnitrosoamine

4. Ndea

5. N-ethyl-n-nitrosoethanamine

6. N,n-diethylnitrous Amide

7. Nitrosodiethylamine

8. N,n-diethylnitrosamine

9. N,n-diethylnitrosoamine

10. Ethanamine, N-ethyl-n-nitroso-

11. Diethylamine, N-nitroso-

12. Diethylnitrosamide

13. Dena

14. Diaethylnitrosamin

15. N-nitroso-n,n-diethylamine

16. Den (mutagen)

17. Ethylamine, N-nitrosodi-

18. Den

19. Rcra Waste Number U174

20. Nsc 132

21. N-nitroso-diaethylamine

22. 3iq78ttx1a

23. 1,1-diethyl-2-oxohydrazine

24. Chebi:34873

25. Nsc-132

26. N-nitrosodiethlamine

27. Mfcd00013890

28. N-diethylnitrosamine

29. Dsstox_cid_1028

30. Dsstox_rid_75913

31. Dsstox_gsid_21028

32. N-nitrosodiethyl-d10-amine

33. Nitrosamine, Diethyl-

34. Diaethylnitrosamin [german]

35. Cas-55-18-5

36. N-ethyl-n-nitroso-ethanamine

37. Ccris 239

38. Hsdb 4001

39. N-nitroso-diaethylamine [german]

40. Einecs 200-226-1

41. Rcra Waste No. U174

42. Unii-3iq78ttx1a

43. Brn 1744991

44. N-nitrosodiethylamine (ndea)

45. Ai3-62031

46. Diethylnitrosamine

47. Diethyl-nitroso-amine

48. N-nitroso-diethylamine

49. Diaethylnitrosamin;ndma

50. N-ethyl-n-nitroso-ethylamine

51. N-nitrosodiethylamine, Liquid

52. Mls002415760

53. Bidd:er0527

54. Schembl106629

55. Wln: Onn2&2

56. Chembl164290

57. Nsc132

58. 1,1-diethyl-2-oxohydrazine #

59. Dtxsid2021028

60. Hms3039g08

61. N-nitrosodiethylamine [mi]

62. N-nitrosodiethylamine, Isopac(r)

63. Bcp19136

64. Hy-n7434

65. Zinc3875370

66. N-nitrosodiethylamine [hsdb]

67. N-nitrosodiethylamine [iarc]

68. Tox21_201255

69. Tox21_300533

70. Stl220642

71. Akos015903105

72. N-nitrosodiethylamine [usp-rs]

73. N-nitrosodiethylamine, >=99.0% (gc)

74. Ncgc00091350-01

75. Ncgc00091350-02

76. Ncgc00091350-03

77. Ncgc00091350-04

78. Ncgc00254309-01

79. Ncgc00258807-01

80. Bs-17234

81. N-nitrosodiethylamine, Analytical Standard

82. Smr001370919

83. Sy053647

84. Db-052695

85. Cs-0128799

86. D0516

87. Ft-0631240

88. N-nitrosodiethylamine 0.1 Mg/ml In Methanol

89. F14922

90. N-nitroso-diethylamine 100 Microg/ml In Methanol

91. N-nitroso-diethylamine 1000 Microg/ml In Methanol

92. Q22138388

93. N-nitroso-diethylamine 1000 Microg/ml In Dichloromethane

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 102.14 g/mol
Molecular Formula C4H10N2O
XLogP30.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Exact Mass102.079312947 g/mol
Monoisotopic Mass102.079312947 g/mol
Topological Polar Surface Area32.7 Ų
Heavy Atom Count7
Formal Charge0
Complexity51.7
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 MeSH Pharmacological Classification

Alkylating Agents

Highly reactive chemicals that introduce alkyl radicals into biologically active molecules and thereby prevent their proper functioning. Many are used as antineoplastic agents, but most are very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. They have also been used as components in poison gases. (See all compounds classified as Alkylating Agents.)


4.2 Absorption, Distribution and Excretion

/MILK/ In goats, 1 hr after oral administration of 30 mg/kg bw nitrosodiethylamine, there were 11.4 mg/kg nitrosodiethylamine in milk and 11.9 mg/kg in blood. Only traces were found in milk and none in blood after 24 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. V17 104 (1978)


Autoradiographic studies indicated that non-metabolized N-nitrosodiethylamine passed to fetuses with even distribution in most fetal tissues on all studied days of gestation (day 12, 14, 16, 16 and 18) in mice. Results also indicated metabolism of the substance in mucosa of fetal bronchial tree and liver on day 18 of gestation.

Brittebo EB et al; Acta Pharmacacol Toxicol 48 (4): 355-63 (1981)


4.3 Metabolism/Metabolites

Inhibition of sulfotransferase by 2,6-dichloro-4-nitrophenol completely abolished the genotoxic potential of N-nitrosodiethanolamine in rat liver as indicated by the induction of DNA single-strand breaks. The DNA strand-breaking potential of N-nitroso-2-hydroxymorpholine, a metabolite of N-nitrosodiethanolamine formed by alcohol dehydrogenase -mediated oxidation, was also almost quantitatively abolished. In contrast to these beta-hydroxylated nitrosamines, the effectiveness of N-nitrosodiethylamine remained unaffected by 2,6-dichloro-4-nitrophenol with respect to its DNA damaging potential. ... A new activation mechanism for N-nitrosodiethanolamine is proposed: N-nitrosodiethanolamine is transformed at first by alcohol dehydrogenase into the cyclic hemiacetal N-nitroso-2-hydroxymorpholine. This cyclic beta-hydroxynitrosamine appears to be a substrate for sulfotransferase. The resulting sulfate conjugate is suggested to be ultimate genotoxic electrophile. However, the results do not exclude the possibility that N-nitrosodiethanolamine itself undergoes sulfate conjugation.

PMID:3456349 Sterzel W, Eisenbrand G; J Cancer Res Clin Oncol 111 (1): 20-4 (1986)


Oxidative N-deethylation of NDEA accounts for the production of CO2 and alkylating species in vivo. The rate of metabolism of NDEA by slices of organs from rats and hamsters in vitro has been measured, and a correlation made between the degree of metabolism and the distribution of induced tumors. After administration of NDEA to rats or hamsters, several ethylated derivatives were produced in liver and kidney nucleic acids. These included 7-ethylguanine, O6-ethylguanine and 3-ethyladenine.

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. V17 105 (1978)


... Evidence suggests that nitrosodiethylamine requires metabolic activation in order to exert its carcinogenic and toxic effects. ... N-nitrosoethyl-N-(2-hydroxyethyl)amine and N-nitrosoethyl-N-(carboxymethyl)amine have been detected in urine of rats. ...

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. V17 105 (1978)


Possible relationships between structure and metabolism of nitrosamines have been investigated in the rat small intestine. Isolated segments of jejunum and ileum were perfused from the luminal side for 2 hr with a Tyrode solution containing one of four symmetrical dialkylnitrosamines with 2-5 carbon atoms per side chain, all (14)C-labeled at the alpha position, or one of two unsymmetrical nitrosamines, N-nitroso-tert-butylmethylamine and N-nitrosomethylbenzylamine, (14)C-labeled in the methyl group. Besides measurement of (14)C to intestinal tissue, the absorbed fluid (absorbate) as well as the perfusion medium and tissue homogenates were analyzed by for the presence of polar metabolites to assess the intestinal metabolism of nitrosamines. Neither N-nitrosodiethylamine nor the two unsymmetrical nitrosamines were metabolized to any significant extent.

PMID:3087650 Richter E et al; Carcinogenesis 7 (7): 1207-14 (1986)


Nitrosodiethylamine has known human metabolites that include N-Nitrosoethanamine.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


4.4 Mechanism of Action

... It is shown that the two nitrosamines N-nitrosodiethylamine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone bind to nicotinic cholinergic receptors in hamster lung. Binding of the nitrosamines as well as nicotine to this receptor stimulates proliferation of human lung carcinoid cells in vitro. These data suggest chronic stimulation of nicotinic receptors by nicotine and nitrosamines in smokers as one of the molecular events responsible for stimulation of neuroendocrine cell proliferation and ultimately the development of lung tumors with neuroendocrine differentiation. ...

Schuller HM; Cancer Res 52 (9 Suppl): 2723s-6s (1992)


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