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2D Structure
Also known as: 504-29-0, Pyridin-2-amine, 2-pyridinamine, 2-pyridylamine, Aminopyridine, Pyridinamine
Molecular Formula
C5H6N2
Molecular Weight
94.11  g/mol
InChI Key
ICSNLGPSRYBMBD-UHFFFAOYSA-N
FDA UNII
WSX981HEWU

1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
pyridin-2-amine
2.1.2 InChI
InChI=1S/C5H6N2/c6-5-3-1-2-4-7-5/h1-4H,(H2,6,7)
2.1.3 InChI Key
ICSNLGPSRYBMBD-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=NC(=C1)N
2.2 Other Identifiers
2.2.1 UNII
WSX981HEWU
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Alpha-aminopyridine

2. Alpha-aminopyridine, Hydrochloride

3. Alpha-aminopyridine, Mononitrate

4. Alpha-aminopyridine, Sulfate

5. Ortho-aminopyridine

2.3.2 Depositor-Supplied Synonyms

1. 504-29-0

2. Pyridin-2-amine

3. 2-pyridinamine

4. 2-pyridylamine

5. Aminopyridine

6. Pyridinamine

7. O-aminopyridine

8. 2-aminopyridin

9. 2-aminopryidine

10. Amino-2 Pyridine

11. Pyridine, 2-amino-

12. 1,2-dihydro-2-iminopyridine

13. 2-pyridinylnitrene

14. Pyridin-2-ylamine

15. .alpha.-aminopyridine

16. 26445-05-6

17. Nsc 431

18. 2-pyridinylamine

19. .beta.-pyridylamine

20. Pyridin-2-yl-amine

21. .alpha.-pyridinamine

22. .alpha.-pyridylamine

23. Wsx981hewu

24. Chembl21619

25. Nsc-431

26. 2-amino Pyridine

27. Alpha-pyridinamine

28. Alpha-pyridylamine

29. Alpha-aminopyridine

30. Pyridin-2-amine (2-pyridylamine)

31. Pyridine, Amino-

32. Ccris 4747

33. Hsdb 2068

34. Einecs 207-988-4

35. Unii-wsx981hewu

36. Aminopyridin

37. Iminopyridine

38. Pyridineamine

39. Pyridinylamine

40. Aminopyridines

41. Amino Pyridine

42. Amino-pyridine

43. Pyridyl Amine

44. Pyridyl Nitrogen

45. Ai3-15287

46. 2-pyridyl Amine

47. 2-amino-pyridine

48. 2-aminopyr-idine

49. Pyridine-2-amine

50. 2- Aminopyridine

51. Pyridine-2-ylamine

52. Aminopyridine, 2-

53. Mfcd00006312

54. 2-aminopyridine, 99%

55. Dsstox_cid_4505

56. Un 2671 (related)

57. Ec 207-988-4

58. 2-aminopyridine, >=99%

59. Dsstox_rid_77434

60. Dsstox_gsid_24505

61. Bidd:gt0578

62. Nsc431

63. 2-aminopyridine [hsdb]

64. Dtxsid0024505

65. .alpha.-aminopyridine [mi]

66. Act09785

67. Bcp22964

68. Str00201

69. Tox21_200880

70. Bbl011573

71. Bdbm50013712

72. Stk286012

73. Zinc13952160

74. Akos000119615

75. Am81273

76. Cs-w020569

77. Pb47078

78. 2-ap, 2-pyridinamine, 2-pyridylamine

79. O-aminopyridine [un2671] [poison]

80. Ncgc00248863-01

81. Ncgc00258434-01

82. 24843-39-8

83. Bp-13063

84. Cas-504-29-0

85. Piroxicam Impurity A [ep Impurity]

86. Tenoxicam Impurity A [ep Impurity]

87. 2-aminopyridine, Purum, >=98.0% (nt)

88. Db-020545

89. A0411

90. Ft-0611271

91. Ft-0662050

92. Piroxicam Related Compound A [usp-rs]

93. P17100

94. Ac-907/25014346

95. 2-aminopyridine, Pestanal(r), Analytical Standard

96. Mepyramine Maleate Impurity C [ep Impurity]

97. Q2393470

98. W-105962

99. W-106097

100. F1995-0206

101. Mepyramine Impurity C, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 94.11 g/mol
Molecular Formula C5H6N2
XLogP30.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass94.053098200 g/mol
Monoisotopic Mass94.053098200 g/mol
Topological Polar Surface Area38.9 Ų
Heavy Atom Count7
Formal Charge0
Complexity54
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

Fluorescent Dyes

Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags. (See all compounds classified as Fluorescent Dyes.)


4.2 Absorption, Distribution and Excretion

It may enter the body through the skin.

Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981., p. 1


PYRIDINE & ITS ALKYL DERIVATIVES ARE ABSORBED FROM GI TRACT, INTRAPERITONEAL CAVITY & LUNGS. PERITONEAL ABSORPTION IS APPARENTLY ONLY SLIGHTLY MORE RAPID & COMPLETE THAN GI ABSORPTION... IN GENERAL THE BASES ARE RAPIDLY ABSORBED THROUGH INTACT SKIN. /ALKYL DERIVATIVES OF PYRIDINE/

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2719


MAJORITY OF /PYRIDINE/ DERIVATIVES TESTED ... PENETRATE INTACT GUINEA PIG SKIN READILY. AMINOPYRIDINES, VINYLPYRIDINES & 4-PICOLINE PENETRATE SKIN MOST RAPIDLY & AMYL DERIV & 5-ETHYL-2-METHYLPYRIDINE ARE LEAST READILY ABSORBED. /AMINOPYRIDINES/

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2724


4.3 Metabolism/Metabolites

Rats were fed 100 or 1000 ppm methapyrilene in their diet for 1, 2, 4, 8 or 16 weeks. Liver microsomes were prepared from both control and treated rats. After incubation with 1 mM methapyrilene, eight metabolites were detected and six were quantitated. /One/ ... metabolites /was/ identified as ... 2-aminopyridine. ...

PMID:3802404 Lampe MA, Kammerer RC; Carcinogenesis 8 (2): 221-6 (1987)


4.4 Mechanism of Action

AMINOPYRIDINES @ CONCN ABOVE 1X10-5 MOLAR CAUSED CONTRACTIONS OF GUINEA PIG ILEUM. AMINOPYRIDINES MAY ACT ON CHOLINERGIC NERVES IN ILEUM, CAUSING INCR RELEASE OF ACETYLCHOLINE BY FACILITATING CALCIUM MOVEMENT, NOT BLOCKING POTASSIUM CONDUCTANCE.

MORITOKI ET AL; ARCH INT PHARM THER 232 (1): 28-41 (1978)


THE EFFECTS OF 2-, 3-, AND 4-AMINOPYRIDINES WERE INVESTIGATED ON THE ISOLATED CHICK NERVE-MUSCLE PREPARATION AND ON NERVE-FREE CELL CULTURES OF EMBRYONIC CHICK SKELETAL MUSCLE. ALL 3 COMPOUNDS REVERSED TUBOCURARINE BLOCKADE & AUGMENTED TWITCH HEIGHT IN INDIRECTLY STIMULATED ISOLATED NERVE-MUSCLE PREPN. THE AMINOPYRIDINES MAY FACILITATE NEUROMUSCULAR TRANSMISSION BY INCR ACETYLCHOLINE RELEASE IN RESPONSE TO NERVE STIMULATION.

BOWMAN ET AL; NAUNYN-SCHMIEDEBERG'S ARCH PHARMACOL 297 (1): 99-103 (1977)


2-AMINOPYRIDINE BLOCKED POTASSIUM CHANNELS OF SQUID AXON MEMBRANES IN MANNER DEPENDENT ON MEMBRANE POTENTIAL & DURATION & FREQUENCY OF VOLTAGE CLAMP PULSES. BINDING IS TO CLOSED K CHANNELS, RELEASED FROM OPEN CHANNELS IN VOLTAGE-DEPENDENT MANNER.

PMID:993770 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2228444 YEH ET AL; J GEN PHYSIOL 68(5): 519-35 (1976)