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Chemistry

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Also known as: 57-14-7, N,n-dimethylhydrazine, Dimazine, Gem-dimethylhydrazine, Unsymmetrical dimethylhydrazine, 1,1-dimethylhydrazin
Molecular Formula
C2H8N2
Molecular Weight
60.10  g/mol
InChI Key
RHUYHJGZWVXEHW-UHFFFAOYSA-N
FDA UNII
4WPQ90N53J

1,1-Dimethylhydrazine
1,1-Dimethylhydrazine is a clear, colorless, flammable, hygroscopic liquid with a fishy smell that emits toxic fumes of nitrogen oxides when heated to decomposition, and turns yellow upon contact with air. 1,1-Dimethylhydrazine is mainly used as a high-energy fuel in jets and rockets, but is also used in chemical synthesis, in photography and to control the growth of vegetation. This substance is also found in tobacco products. Exposure to 1,1-dimethylhydrazine results in irritation of skin, eyes and mucous membranes, and can affect liver and central nervous system. 1,1-Dimethylhydrazine is reasonably anticipated to be a human carcinogen. (NCI05)
1 2D Structure

1,1-Dimethylhydrazine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1,1-dimethylhydrazine
2.1.2 InChI
InChI=1S/C2H8N2/c1-4(2)3/h3H2,1-2H3
2.1.3 InChI Key
RHUYHJGZWVXEHW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(C)N
2.2 Other Identifiers
2.2.1 UNII
4WPQ90N53J
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,1-dimethyhydrazine

2. Dimazine

3. Dimazine Dihydrochloride

4. Dimazine Hydrochloride

5. Unsymmetrical Dimethylhydrazine

2.3.2 Depositor-Supplied Synonyms

1. 57-14-7

2. N,n-dimethylhydrazine

3. Dimazine

4. Gem-dimethylhydrazine

5. Unsymmetrical Dimethylhydrazine

6. 1,1-dimethylhydrazin

7. Udmh

8. Unsym-dimethylhydrazine

9. Hydrazine, 1,1-dimethyl-

10. U-dimethylhydrazine

11. 1,1-dimethyl Hydrazine

12. Uns-dimethylhydrazine

13. Dimazin

14. As-dimethylhydrazine

15. Hydrazine, N,n-dimethyl-

16. Asymmetric Dimethylhydrazine

17. Rcra Waste Number U098

18. Unsymmetrical-dimethylhydrazine

19. Dimethylhydrazine, Unsym.

20. Nsc 60517

21. 1.1-dimethylhydrazine

22. Niesymetryczna Dwu Metylohydrazyna

23. (ch3)2nnh2

24. 4wpq90n53j

25. Dimethylhydrazine, Unsymmetrical

26. Dtxsid1020516

27. Nsc-60517

28. As-dimethyl Hydrazine

29. Asymmetric-dimethylhydrazine

30. Ccris 258

31. Dimethylhydrazine Unsymmetrical

32. N,n-dimetilidrazina

33. N,n-dimetilidrazina [italian]

34. Hsdb 528

35. 1,1-dimethylhydrazin [german]

36. Einecs 200-316-0

37. Un1163

38. Dimethyl Hydrazine (dmh)

39. Rcra Waste No. U098

40. Brn 0605261

41. Unii-4wpq90n53j

42. Niesymetryczna Dwu Metylohydrazyna [polish]

43. 1,1-dimethyldiazane

44. Dimethylhydrazine, As

45. Asym-dimethylhydrazine

46. Hydrazine,n-dimethyl-

47. Hydrazine,1-dimethyl-

48. N,n-dimethyl Hydrazine

49. N,n-dimethyl-hydrazine

50. 1,1-dimethyl-hydrazine

51. Me2nnh2

52. N',n'-dimethylhydrazine

53. Dsstox_cid_516

54. Ec 200-316-0

55. Dsstox_rid_75637

56. Dsstox_gsid_20516

57. Unsymmetrical-dimethylhyrazine

58. N,n-dimethylhydrazine, 98%

59. Wln: Zn1&1

60. Chebi:18853

61. Nsc60517

62. 1,1-dimethylhydrazine [mi]

63. Tox21_302358

64. Mfcd00007628

65. Zinc59447665

66. 1,1-dimethylhydrazine [hsdb]

67. 1,1-dimethylhydrazine [iarc]

68. Akos000119664

69. Un 1163

70. Cas-57-14-7

71. Ncgc00255194-01

72. D0740

73. C19233

74. A831327

75. Q161296

76. Q-200052

77. Dimethylhydrazine, Unsymmetrical [un1163] [poison]

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 60.10 g/mol
Molecular Formula C2H8N2
XLogP3-0.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass60.068748264 g/mol
Monoisotopic Mass60.068748264 g/mol
Topological Polar Surface Area29.3 Ų
Heavy Atom Count4
Formal Charge0
Complexity11.5
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

Dimethylhydrazine administered by injection to a variety of species, including rat, rabbit, cat, dog, and monkey was rapidly absorbed into the blood and quite rapidly excreted via the kidneys. No preferential organ of storage was seen, and the urinary concentration was considered a more sensitive indication of exposure than blood levels. In rats given low doses (0.78 mg/kg), 30% of the injected radioactivity appeared as respiratory CO2 in 10 hr. Again, urine was the major excretory route. The urinary product was unchanged dimethylhydrazine. Other compounds identified in the urine of both rats and dogs following injections of dimethylhydrazine include a glucose hydrazine of dimethylhydrazine (3-10%) and an undetermined hydrazine (20-25%), and dimethylhydrazine accounted for 50-60%. Dogs and rats showed the same absorption and excretion patterns.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V4 1298


Dimethylhydrazine showed first order absorption processes when applied /dermally/. Subcutaneous administration resulted in much higher blood levels and almost complete absorption. In vitro application to rabbit skin showed evaporation of 85% of the dose, thus accounting for the low observed absorption. Elimination of dimethylhydrazine was rapid, and the terminal elimination half-life was 0.3-1.5 hours. From 3-19% of the dose was eliminated in urine.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V4 1299


Approximately 50% of the absorbed dose is excreted in 24 hr.

International Labour Office. Encyclopedia of Occupational Health and Safety. Vols. I&II. Geneva, Switzerland: International Labour Office, 1983., p. 1070


Unsymmetrical dimethylhydrazine is /biotransformed/ ...to carbon dioxide and unknown metabolites which are excreted with free... /1,1-dimethylhydrazine/ into the urine.

Thienes, C., and T.J. Haley. Clinical Toxicology. 5th ed. Philadelphia: Lea and Febiger, 1972., p. 140


For more Absorption, Distribution and Excretion (Complete) data for 1,1-DIMETHYLHYDRAZINE (8 total), please visit the HSDB record page.


4.2 Metabolism/Metabolites

Formaldehyde was formed by oxidative demethylation of 1,1-dimethylhydrazine by rat liver microsomes. Phenobarbital or 3-methylcholanthrene pretreatment enhanced demethylase activity.

PMID:4391185 Wittkop JA et al; Arch Biochem Biophys 134 (2): 308-15 (1969)


Rats admin low dose of (14)C 1,1-dimethylhydrazine metabolized approx 30% to (14)C labeled carbon dioxide in 10 hr. Conversion of convulsive dose to carbon dioxide amounted to slightly more than 13% at end of 20 hr. At least 50% of administered radioactivity appeared in urine in 2-day period.

Dost FN et al; Biochem Pharmacol 15 (9): 1325 (1966)


N-oxidation of alkylhydrazines was catalyzed by mouse liver microsomal mixed function oxidase. At pH 7.7 and 25 C, methylhydrazine and 1,1-dimethylhydrazine have nearly the same maximal n-oxidation rate as dimethylaniline.

PMID:4729304 Prough RA; Arch Biochem Biophys 158 (1): 442-4 (1973)


1,1-Dimethylhydrazine when added to suspension of rat liver microsomes exhibited binding spectra like those seen for nitrogenous ligands to cytochrome P450.

PMID:7391974 Hines RN, Prough RA; J Pharmacol Exp Ther 214 (1): 80-86 (1980)


For more Metabolism/Metabolites (Complete) data for 1,1-DIMETHYLHYDRAZINE (6 total), please visit the HSDB record page.


4.3 Biological Half-Life

Elimination of dimethylhydrazine was rapid, and the terminal elimination half-life was 0.3-1.5 hours.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V4 1299


4.4 Mechanism of Action

The precise mechanism of dimethylhydrazine toxicity is uncertain. In addition to the contact irritant effects, the acute effects of dimethylhydrazine exposure may involve the central nervous system as exemplified by tremors and convulsions and behavioral changes at sublethal doses. /It was/... noted that the deaths probably involve respiratory arrest and cardiovascular collapse. The central nervous system as a target is consistent with the delayed latency in response reported for dimethylhydrazine. There is some evidence that 1,1-dimethylhydrazine may act as an inhibitor of glutamic acid decarboxylase, thereby adversely affecting the aminobutyric acid shunt, and could explain the latency of CNS effects. Furthermore, vitamin B6 analogues that act as coenzymes in the aminobutyric acid shunt have been shown to be effective antagonists to 1,1-dimethylhydrazine toxicity.

CLS/NAS; Acute Exposure Guideline Levels for Selected Airborne Chemicals: Volume 1; Dimethylhydrazine p.173 (2000)


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