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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
    Methyl Nicotinate
    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 Weight 137.14 g/mol
    Molecular Formula C7H7NO2
    XLogP30.8
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count2
    Exact Mass137.047678466 g/mol
    Monoisotopic Mass137.047678466 g/mol
    Topological Polar Surface Area39.2 Ų
    Heavy Atom Count10
    Formal Charge0
    Complexity125
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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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    09-Mar-2021
    20-Jun-2024
    KGS
    overview
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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