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5 API Suppliers, 1 EU WC, 5 Listed Suppliers, $ API Reference Price

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RELATED EXCIPIENT COMPANIES

2 Nanjing Well Pharmaceutical, 2 Actylis, 1 BASF, 3 Gangwal Chemicals, 1 Nanjing Bold Chemical, 6 Seppic

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Chemistry

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Also known as: 93-60-7, Methyl pyridine-3-carboxylate, Nikomet, Methylnicotinate, Methyl-nicotinate, Nicometh

Molecular Formula

C₇H₇NO₂

Molecular Weight

137.14 g/mol

InChI Key

YNBADRVTZLEFNH-UHFFFAOYSA-N

FDA UNII

7B1AVU9DJN

heat spray is a natural product found in Chaenomeles speciosa, Coffea arabica, and other organisms with data available.

1 2D Structure

Methyl Nicotinate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl pyridine-3-carboxylate

2.1.2 InChI

InChI=1S/C7H7NO2/c1-10-7(9)6-3-2-4-8-5-6/h2-5H,1H3

2.1.3 InChI Key

YNBADRVTZLEFNH-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COC(=O)C1=CN=CC=C1

2.2 Other Identifiers

2.2.1 UNII

7B1AVU9DJN

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Methylnicotinate

2.3.2 Depositor-Supplied Synonyms

1. 93-60-7

2. Methyl Pyridine-3-carboxylate

3. Nikomet

4. Methylnicotinate

5. Methyl-nicotinate

6. Nicometh

7. Nicotinic Acid Methyl Ester

8. Methyl 3-pyridinecarboxylate

9. 3-(methoxycarbonyl)pyridine

10. 3-pyridinecarboxylic Acid, Methyl Ester

11. Heat Spray

12. Nicotinic Acid, Methyl Ester

13. 3-(carbomethoxy)pyridine

14. 3-picolinic Acid Methyl Ester

15. M-(methoxycarbonyl)pyridine

16. Fema No. 3709

17. Methyl Nicotinate [usan]

18. Nsc 13126

19. 3pyrcoome

20. 3-pyridinecarboxylic Acid Methyl Ester

21. Heat Spray (tn)

22. 3-carbomethoxypyridine

23. Nsc-13126

24. 7b1avu9djn

25. Methyl Nicotinate (usan)

26. Ncgc00159479-02

27. Methyl Ester Of Pyridine-3-carboxylic Acid

28. Wln: T6nj Cvo1

29. Dsstox_cid_24471

30. Dsstox_rid_80253

31. Dsstox_gsid_44471

32. Cas-93-60-7

33. Einecs 202-261-8

34. Unii-7b1avu9djn

35. Brn 0113951

36. Ai3-19241

37. Methyl Nicotinoate

38. Nicotinato De Metila

39. Nicotinato De Metilo

40. Nicotinato Di Metile

41. Mfcd00006388

42. Nicotinate De Methyle

43. Nicotinic Acid Methyl

44. Methyl Nicotinate, 99%

45. Methylpyridine-3-carboxylate

46. Schembl24566

47. 5-22-02-00059 (beilstein Handbook Reference)

48. Methyl Nicotinate [mi]

49. Chembl379845

50. Zinc1706

51. Dtxsid7044471

52. Methyl Nicotinate [fhfi]

53. Methyl Nicotinate [inci]

54. Fema 3709

55. Methyl Nicotinate [vandf]

56. Chebi:134761

57. Methyl Nicotinate [mart.]

58. Methyl Nicotinate, >=99%, Fg

59. Hms1775a18

60. Methyl Nicotinate [who-dd]

61. Cs-d1355

62. Hy-b1695

63. Nsc13126

64. Tox21_111702

65. Tox21_302038

66. Nsc403799

67. S6231

68. Stk803258

69. Methyl Nicotinate, Analytical Standard

70. Akos000119439

71. Tox21_111702_1

72. Db13882

73. Gs-3032

74. Nsc-403799

75. Methyl Nicotinate [ep Monograph]

76. Pyridine-3-carboxylic Acid Methyl Ester

77. Ncgc00159479-03

78. Ncgc00159479-05

79. Ncgc00255708-01

80. Ac-22482

81. Db-031973

82. Am20061626

83. Ft-0645164

84. N0086

85. Methyl Nicotinate Methyl 3-pyridinecarboxylate

86. Methyl Nicotinate, Puriss., >=99.0% (gc)

87. D04991

88. D87532

89. Ac-907/25014170

90. Sr-01000944497

91. Q-201381

92. Q3341206

93. Sr-01000944497-1

94. Methyl Nicotinate;methyl 3-pyridinecarboxylate

95. F0001-2240

96. Methyl Nicotinate, European Pharmacopoeia (ep) Reference Standard

97. Methyl Nicotinate, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₇H₇NO₂
Molecular Weight	137.14 g/mol
XLogP3	0.8
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Exact Mass	137.047678466 g/mol
Monoisotopic Mass	137.047678466 g/mol
Topological Polar Surface Area	39.2 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	125
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Indicated for the temporary relief of aches and pains in muscles, tendons, and joints.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Following topical administration, methyl nicotinate acts as a peripheral vasodilator to enhance local blood flow at the site of application. It induced vasodilation of the peripheral blood capillaries which are located in the dermal papillae of upper dermis layers adjacent to the epidermisdermis junction. During tissue penetration at the dermis, methyl nicotinate is hydrolyzed to nicotinic acid. In human volunteers, topical administration of methyl nicotinate caused vasodilation-induced generalized cutaneous erythema.

5.2 Absorption, Distribution and Excretion

Absorption

The presence of methyl group facilitates the penetration of methyl nicotinate through the skin with good lipophilicity, allowing rapid absorption following topical administration. _In vitro_, about 80-90% of the polar compounds methyl nicotinate rapidly penetrated the skin. It was demonstrated in excised skin of hairless mice that methyl nicotinate can effectively bypass the stratum corneum layer of the skin. In humans, nicotinic acid and nicotinamide were shown to be rapidly absorbed from the stomach and intestine via a sodium carrier-mediated mechanism at low concentrations.

Route of Elimination

Following epicutaneous administration of small radiolabelled dose of methyl nicotinate in human volunteers, approximately 15% of the dose was recovered in the urine within 108 hours after treatment. The excretion of nicotinic acid mainly takes place in the kidneys.

Volume of Distribution

According to the animal studies, nicotinic acid is mainly concentrated in the liver, kidneys, and adipose tissue.

Clearance

No pharmacokinetic data available.

5.3 Metabolism/Metabolites

Methyl nicotinate undergoes ester hydrolysis to form nicotinic acid and methanol. The hydrolysis is thought to be mediated by nonspecific -naphthylacetate-esterase at the dermis layer of the skin.

5.4 Biological Half-Life

_In vitro_, the half-life of methyl nicotinate in the dermis was 3 to 10 minutes.

5.5 Mechanism of Action

While the mechanism of action of methyl nicotinate and other topically-administered nicotinic acid esters is not clear, it is thought that methyl nicotinate promotes the release of prostaglandin D2 that is strictly locally-acting due to its short half-life. It was demonstrated in human subjects that the local cutaneous vascular response to methyl nicotinic was suppressed by inhibitors of prostaglandin biosynthesis, indicating that the effect of methyl nicotinate on vascular smooth muscles may be mediated by the release of local prostaglandins. Prostaglandins released from the skin and blood vessels induce cutaneous vasodilation.

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API Reference Price

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