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2D Structure
Also known as: 693-98-1, 2-methyl-1h-imidazole, 1h-imidazole, 2-methyl-, Imidazole, 2-methyl-, 2-methyl imidazole, 2-methylglyoxaline
Molecular Formula
C4H6N2
Molecular Weight
82.10  g/mol
InChI Key
LXBGSDVWAMZHDD-UHFFFAOYSA-N
FDA UNII
T0049Z45LZ

1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-methyl-1H-imidazole
2.1.2 InChI
InChI=1S/C4H6N2/c1-4-5-2-3-6-4/h2-3H,1H3,(H,5,6)
2.1.3 InChI Key
LXBGSDVWAMZHDD-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=NC=CN1
2.2 Other Identifiers
2.2.1 UNII
T0049Z45LZ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-methylimidazole Hydrochloride

2. 2-methylimidazole, Silver (1+) Salt

3. Zn(2-methylimidazole)2

2.3.2 Depositor-Supplied Synonyms

1. 693-98-1

2. 2-methyl-1h-imidazole

3. 1h-imidazole, 2-methyl-

4. Imidazole, 2-methyl-

5. 2-methyl Imidazole

6. 2-methylglyoxaline

7. Mfcd00005190

8. Chembl293391

9. Dtxsid4022107

10. T0049z45lz

11. Nsc 21394-d5

12. Nsc-21394

13. 2mz

14. Ncgc00091456-01

15. Dtxcid202107

16. Methylimidazole

17. 2-methyl-1h-imidazole; 1h-2-methylimidazole; 2-methylimidazole; 2mi; 2mz; 2mz-h

18. Cas-693-98-1

19. Ccris 2459

20. Einecs 211-765-7

21. Nsc 21394

22. Methylimidazol

23. Methyl Imidazol

24. Unii-t0049z45lz

25. 2methylimidazole

26. Methyl-imidazole

27. Ai3-50033

28. 2-methylimidazol

29. 2-metylimidazole

30. 2-methylimdazole

31. Hsdb 7756

32. 2-methyl-imidazol

33. 2-methyl-imidazole

34. 2-methyl Glyoxaline

35. 2-methyl-1h-imidazol

36. Curezol-2mz-p

37. Imicure-ami 2

38. Epicure-mi 2

39. Epikure-mi 2

40. 2-methylimidazole, 99%

41. Ec 211-765-7

42. Methylimidazole, 2-

43. Wln: T5m Cnj B1

44. Mls001065618

45. 2-methylimidazole [hsdb]

46. 2-methylimidazole [iarc]

47. Hms3039f06

48. Nsc21394

49. Str02220

50. Tox21_111136

51. Tox21_201316

52. Tox21_302808

53. Bbl013047

54. Bdbm50295560

55. Stk301707

56. Akos000118836

57. Cs-w019983

58. Pb43299

59. Ncgc00091456-02

60. Ncgc00256531-01

61. Ncgc00258868-01

62. Pd063450

63. Smr000568464

64. 2-methylimidazole (ondansetron Impurity F)

65. Am20100647

66. Ft-0613056

67. Ft-0671849

68. M0345

69. Ns00010845

70. En300-21278

71. C19261

72. D77862

73. A833348

74. A836474

75. W-104630

76. Q21099566

77. F2190-0640

78. Z104494990

79. Inchi=1/c4h6n2/c1-4-5-2-3-6-4/h2-3h,1h3,(h,5,6

80. Ondansetron Hydrochloride Dihydrate Impurity F [ep Impurity]

81. 2-methylimidazole, >=95.0% (hplc), Pharmaceutical Impurity Standard

82. Ondansetron Impurity F, European Pharmacopoeia (ep) Reference Standard

83. Ondansetron Hydrochloride Impurity, 2-methylimidazole- [usp Impurity]

84. 2-methylimidazole (ondansetron Impurity F), Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 82.10 g/mol
Molecular Formula C4H6N2
XLogP30.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area28.7
Heavy Atom Count6
Formal Charge0
Complexity44.8
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

... The disposition of [2-(14)C]-2-methylimidazole (2-MI) has been investigated following po administration of either 5, 50, or 150 mg/kg to male F344 rats. Excretion data indicated that absorption of 2-MI was both rapid and proportional to dose in the range studied. Approximately 90% of the total dose was eliminated in urine within 24 hr. Most of the remaining 14C was excreted in feces and as expired 14CO2. Excretion data were similar following iv administration of 5 mg/kg. Little or no enterohepatic circulation of compound occurred, since biliary excretion of 2-MI-derived 14C was negligible. Approximately 70% of the 14C excreted in urine, following all dosing, consisted of parent compound. High-performance liquid chromatography (HPLC) chromatograms for all treatment groups were similar, indicating that metabolism of 2-MI in rats was not affected by dose or route of administration.

PMID:9652548 Sanders JM et al; J Toxicol Environ Health A 54 (2): 121-32 (1998).


The toxicokinetics of 2-methylimidazole (2-MI) were studied in male and female Fischer 344 rats after a single iv dose of 10 mg/kg or gavage dose of 25, 50, or 100 mg/kg. The 2-MI was formulated in 0.05 M phosphate-buffered saline (pH 7.4). The iv profiles could be best described by a two-compartment model with first-order elimination. The terminal elimination half-life, volume of distribution at steady state, and clearance values were 0.78 and 0.85/hr, 1.5 and 1.9 L, and 4.97 and 12.0 L/hr/kg for males and females, respectively. After a gavage dose, the plasma concentration time profiles could be best described by a one-compartment model, no lag phase, and first-order absorption and elimination. The peak 2-MI plasma concentrations increased proportionately with dose and were reached within 35 to 50 min (T(max)) for all groups. The estimated half-life value for 2-MI was about 1 hr for the iv group and the male 25-, 50-, or 100-mg/kg groups and female 25-mg/kg groups. Clearance increased for the male 100- and female 50- and 100- mg/kg groups. For a given dose group, clearance was also two to three times greater for female rats when compared to male rats. Absolute bioavailability for 2-MI was estimated to approach 97%. The results of this study indicated that 2-MI was (1) rapidly and completely absorbed, (2) quickly eliminated, (3) cleared differently for females than for males, (4) affected somewhat by dose for females, and (5) unlikely to undergo tissue accumulation following repeated exposure.

PMID:12079612 Johnson JD et al; J Toxicol Environ Health A 65 (12): 869-79 (2002).


4.2 Biological Half-Life

The toxicokinetics of 2-methylimidazole (2-MI) were studied in male and female Fischer 344 rats after a single iv dose of 10 mg/kg or gavage dose of 25, 50, or 100 mg/kg. The 2-MI was formulated in 0.05 M phosphate-buffered saline (pH 7.4) ... The estimated half-life value for 2-MI was about 1 hr for the iv group and the male 25-, 50-, or 100-mg/kg groups and female 25-mg/kg groups ...

PMID:12079612 Johnson JD et al; J Toxicol Environ Health A 65 (12): 869-79 (2002).