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Chemistry

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Also known as: 2-picoline, 109-06-8, O-picoline, Alpha-picoline, Pyridine, 2-methyl-, Picoline
Molecular Formula
C6H7N
Molecular Weight
93.13  g/mol
InChI Key
BSKHPKMHTQYZBB-UHFFFAOYSA-N
FDA UNII
3716Q16Q6A

CAS 109-06-8
2-methylpyridine is a metabolite found in or produced by Saccharomyces cerevisiae.
1 2D Structure

CAS 109-06-8

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-methylpyridine
2.1.2 InChI
InChI=1S/C6H7N/c1-6-4-2-3-5-7-6/h2-5H,1H3
2.1.3 InChI Key
BSKHPKMHTQYZBB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC=CC=N1
2.2 Other Identifiers
2.2.1 UNII
3716Q16Q6A
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-picoline

2. 2-picolinium Bromide

2.3.2 Depositor-Supplied Synonyms

1. 2-picoline

2. 109-06-8

3. O-picoline

4. Alpha-picoline

5. Pyridine, 2-methyl-

6. Picoline

7. Methylpyridine

8. A-picoline

9. Pyridine, Methyl-

10. 2-methyl-pyridine

11. O-methylpyridine

12. Picoline, Alpha

13. .alpha.-picoline

14. Rcra Waste Number U191

15. 1333-41-1

16. Nsc 3409

17. 2-mepy

18. .alpha.-methylpyridine

19. Chebi:50415

20. Nsc-3409

21. 3716q16q6a

22. Ncgc00160644-01

23. Dsstox_cid_1899

24. Dsstox_rid_76392

25. Dsstox_gsid_21899

26. Alpha-methylpyridine

27. Cas-109-06-8

28. Ccris 1721

29. Hsdb 101

30. Einecs 203-643-7

31. Rcra Waste No. U191

32. Ai3-2409

33. Alpha Picoline

34. 2-methylpridine

35. Ai3-24109

36. Unii-3716q16q6a

37. 2--picoline

38. 2-methyl Pyridine

39. Picoline (related)

40. Picoline, .alpha.

41. Mfcd00006332

42. 2-picoline, 98%

43. 2-methylpyridine, 98%

44. Ec 203-643-7

45. Nciopen2_007826

46. Nciopen2_007919

47. Wln: T6nj B1

48. Bidd:er0295

49. Chembl15732

50. .alpha.-picoline [mi]

51. 2-picoline, Analytical Standard

52. 2-methylpyridine [hsdb]

53. Dtxsid9021899

54. Nsc3409

55. 2-picoline,(s);2-methylpyridine

56. Bcp26524

57. Tox21_111951

58. Tox21_201693

59. Stl268873

60. Zinc38192546

61. Akos000119190

62. Zinc328578702

63. Am81276

64. Ncgc00160644-02

65. Ncgc00259242-01

66. Db-023694

67. O-picoline [un2313] [flammable Liquid]

68. Ft-0613358

69. P0415

70. 2-methylpyridine, Lonza Quality, >=99.0% (gc)

71. J-510091

72. Q2216745

73. Amprolium Hydrochloride Impurity A [ep Impurity]

74. F0001-0192

75. 2-methylpyridine Pound>>o-picoline Pound>>pyridine, 2-methyl-

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 93.13 g/mol
Molecular Formula C6H7N
XLogP31.1
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass93.057849228 g/mol
Monoisotopic Mass93.057849228 g/mol
Topological Polar Surface Area12.9 Ų
Heavy Atom Count7
Formal Charge0
Complexity52.1
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

Alpha-picoline was rapidly absorbed by blood & penetrated into liver, heart, spleen, lungs, & muscles during 1St 10-20 min following oral admin of 0.5 g/kg to rats. It was excreted in urine during 1St 48 hr.

KUPOR VG; VOP PATOKHIMII BIOKHIM BELKOV DRUGIKH BIOL AKTIV SOEDIN: 51-2 (1972)


Addition of a methyl group onto the pyridine molecule increases the rate of absorption of the resultant picolines into the liver, kidney, & brain of rats. After ip injection of the picolines, pharmacokinetic parameters were greatly dependent upon the position of the methyl group. For example, the residence time for beta-picoline in liver, brain, & kidney was > that of alpha- or gamma-picoline. Elimination of all four pyridines was biphasic in nature, the first phase being more prolonged for pyridine & beta-picoline than for alpha- or gamma-picoline.

Zharikov GP et al; Deposited Doc (VINITI 1299-83): 11 pages (1983)


The substance is rapidly absorbed by the blood and penetrated into liver, heart, spleen, lungs, brain and muscles during the first 10 - 20 minutes after oral administration of 500 mg/kg to rats. It is excreted in urine mainly during the first 48 hrs after administration. Prevalent accumulation in the liver within 1 hr. Within 2 days however, the levels of the substance in the organs was decreased to traces.

European Commission/European Chemical Substances Information System (ESIS); IUCLID Dataset, 2-Methylpyridine (CAS 109-06-8) p. 36 (2000). Available from, as of October 20, 2014: https://esis.jrc.ec.europa.eu//


4.2 Metabolism/Metabolites

... In rabbits and dogs /2-methylpyridine/ is oxidized to alpha-picolinic acid which is excreted in the urine. alpha-Picolinuric acid is also excreted by frogs administered alpha-picoline, but only in amounts less than 1% of the dose. In hens it is excreted partly as alpha-pyridinornithuric acid.

ITC/USEPA; Information Review #425 (Draft) Methylpyridines p.34 (1984)


/It was observed that/ 96% of a 100 mg/kg oral dose of 2-methylpyridine administered to rats was excreted in the urine as picolinuric acid.

ITC/USEPA; Information Review #425 (Draft) Methylpyridines p.34 (1984)


There also is evidence that 2-methylpyridine forms an N-methylated derivative in dogs.

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. 220


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