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    Chemistry

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    Also known as: 2444-46-4, N-vanillylnonanamide, Pseudocapsaicin, Pelargonic acid vanillylamide, N-vanillylnonamide, N-vanillylpelargonamide
    Molecular Formula
    C17H27NO3
    Molecular Weight
    293.4  g/mol
    InChI Key
    RGOVYLWUIBMPGK-UHFFFAOYSA-N
    FDA UNII
    S846B891OR
    Nonivamide
    nonivamide is a natural product found in Capsicum annuum with data available.
    1 2D Structure

    Nonivamide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
    2.1.2 InChI
    InChI=1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)
    2.1.3 InChI Key
    RGOVYLWUIBMPGK-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
    2.2 Other Identifiers
    2.2.1 UNII
    S846B891OR
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. N-vanillylnonanamide

    2. Vanillyl-n-nonylamide

    3. Vanillylnonanamide

    2.3.2 Depositor-Supplied Synonyms

    1. 2444-46-4

    2. N-vanillylnonanamide

    3. Pseudocapsaicin

    4. Pelargonic Acid Vanillylamide

    5. N-vanillylnonamide

    6. N-vanillylpelargonamide

    7. N-(4-hydroxy-3-methoxybenzyl)nonanamide

    8. Nonanoic Acid Vanillylamide

    9. N-nonanoyl Vanillylamide

    10. Vanillyl-n-nonylamide

    11. Vanillyl Pelargonic Amide

    12. Pelargonyl Vanillylamide

    13. Hydroxymethoxybenzyl Pelargonamide

    14. Nonylic Acid Vanillylamide

    15. Vanillyl N-nonoylamide

    16. Nonanamide, N-vanillyl-

    17. Nonivamide [inn]

    18. Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-

    19. Nonanoyl Vanillylamide

    20. Desmethyldihydrocapsaicin

    21. N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide

    22. Fema No. 2787

    23. N-vanillylnonanoamide

    24. Hansaplast

    25. Nsc 172795

    26. Nonanoyl 4-hydroxy-3-methoxybenzylamide

    27. N-vanillyl Nonanamide

    28. Nonylic Acid Vanillyamide

    29. N-((4-hydroxy-3-methoxyphenyl)methyl)nonanamide

    30. N-((hydroxy-3-methoxyphenyl)methyl)4-nonanamide

    31. Nsc-172795

    32. Chembl75124

    33. Chebi:46936

    34. S846b891or

    35. Nonivamide (inn)

    36. Ah-23491x

    37. Mfcd00017286

    38. Nonanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-

    39. Ncgc00016089-05

    40. Nonylvanylamide

    41. Dsstox_cid_14769

    42. Dsstox_rid_79200

    43. Dsstox_gsid_34769

    44. Nonivamida

    45. Nonivamidum

    46. Nonivamidum [inn-latin]

    47. Nonivamida [inn-spanish]

    48. Cas-2444-46-4

    49. Pava

    50. 8-nordihydrocapsaicin

    51. N-vanillyl-nonanamide

    52. Nonanoylvanillyl Amide

    53. Vanillyl N-nonylamide

    54. Capsaicin (synthetic)

    55. N-((4-hydroxy-3-methoxyphenyl)methyl)-nonanamide

    56. N-[(4-hydroxy-3-methoxyphenyl)methyl]-nonanamide

    57. Einecs 219-484-1

    58. Brn 2144300

    59. Capscaisin

    60. Unii-s846b891or

    61. N-nonylvanylamide

    62. Pava Spray

    63. Hansaplast (tn)

    64. Nonanoylvanilylamide

    65. Nonylic Vanillamide

    66. Synthetic Capsaicin

    67. Nonoyl Vanillylamide

    68. Psva

    69. Nonylicacidvanillylamide

    70. Spectrum_000311

    71. Pelargonoyl Vanillylamide

    72. Specplus_000799

    73. N-pelargonylvanillylamide

    74. Spectrum2_001091

    75. Spectrum4_000916

    76. Spectrum5_001853

    77. Lopac-v-9130

    78. N-vanillylnonanamide, 8ci

    79. Nonivamide [mart.]

    80. Nonivamide [who-dd]

    81. Lopac0_001218

    82. Schembl81939

    83. Kbiogr_001412

    84. Kbioss_000791

    85. Mls002153373

    86. Divk1c_006895

    87. Spectrum2300192

    88. Spbio_001162

    89. N-pelargonic Acid Vanillylamide

    90. Dtxsid1034769

    91. Fema 2787

    92. Kbio1_001839

    93. Kbio2_000791

    94. Kbio2_003359

    95. Kbio2_005927

    96. Hh 50

    97. Hms2234e23

    98. Hms3374k02

    99. Hms3885c14

    100. Pharmakon1600-01506172

    101. Albb-025790

    102. Zinc1697652

    103. Tox21_110302

    104. Tox21_301218

    105. Bdbm50044767

    106. Ccg-39764

    107. Nsc172795

    108. Nsc760391

    109. S3935

    110. Akos001719931

    111. N-vanillylnonanamide, >=97%, Powder

    112. Tox21_110302_1

    113. Ac-4807

    114. Db11324

    115. Nsc-760391

    116. 8-methyl-n-vanillyl-trans-b-nonenamide

    117. N-vanillylnonanamide, Analytical Standard

    118. Ncgc00016089-01

    119. Ncgc00016089-02

    120. Ncgc00016089-03

    121. Ncgc00016089-04

    122. Ncgc00016089-06

    123. Ncgc00094463-01

    124. Ncgc00094463-02

    125. Ncgc00094463-03

    126. Ncgc00094463-04

    127. Ncgc00255553-01

    128. As-13519

    129. Hy-17568

    130. Smr001230764

    131. N-(4-hydroxy-3-methoxybenzyl)nonanamide #

    132. Eu-0101218

    133. Ft-0603609

    134. Ft-0623446

    135. M0900

    136. Nonanamide, N-(4-hydroxy-3-methoxybenzyl)-

    137. 4-hydroxy-3-methoxy-n-(1-oxononyl)-benzamide

    138. D08282

    139. V 9130

    140. V-3000

    141. Ab00053157_06

    142. Hydroxymethoxybenzyl Pelargonamide [inci]

    143. N-((4-hydroxy-3-methoxyphenyl)methyl)-nonanamid

    144. Nonanamide, N-((4-hydroxy-3-methoxyphenyl)meth

    145. 444n464

    146. A817309

    147. Nonivamide (constituent Of Capsicum) [dsc]

    148. Q420228

    149. Sr-01000076196

    150. Sr-01000076196-1

    151. N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide, 9ci

    152. Z373586944

    153. N-nonanoyl-4-hydroxy-3-methoxybenzyl-amide [fhfi]

    154. Nonivamide, European Pharmacopoeia (ep) Reference Standard

    155. N-(4-hydroxy-3-methoxybenzyl)nonanamide, N-vanillylpelargonamide, Nonanoic Acid Vanillylamide, Nonylvanylamide, Pelargonic Acid Vanillylamide

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 293.4 g/mol
    Molecular Formula C17H27NO3
    XLogP34.2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count10
    Exact Mass293.19909372 g/mol
    Monoisotopic Mass293.19909372 g/mol
    Topological Polar Surface Area58.6 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity283
    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

    Nonivamide is used as a topical analgesic and is also used as a flavoring ingredient,,.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Relieves minor aches and pains of muscles and joints,.

    5.2 Metabolism/Metabolites

    Limited information is available on pharmacokinetics and metabolism of nonivamide. For the closely related [DB06774] and other capsaicinoids, gastrointestinal absorption is rapid and almost entirely complete in studies of rats (oral dose of about 10 to 15 mg/kg of combined capsaicin and dihydrocapsaicin) with about 85% of the dose being absorbed within 3 hours. Both substances undergo first-pass metabolism in the liver and partly metabolized at the site of absorption.

    5.3 Biological Half-Life

    About 7 minutes.

    5.4 Mechanism of Action

    Nonivamide is a naturally occurring analog of [DB06774], isolated from peppers, described to produce effects similar to [DB06774]. It is an agonist of the VR1 (vanilloid/TRPV1 receptor). It serves as a transient agonist of these receptors, which are potentiated by pro-inflammatory drugs, a phenomenon that leads to thermal hyperalgesia, or increased heat sensation. Nonivamide has been shown to stimulate afferent neurons with about half the potency of [DB06774]. Agonism of the VR1 (TRPV1) (vanilloid) receptor by Nonivamide was demonstrated to induce the release of Ca2+ from the endoplasmic reticulum (ER) of human lung cells, producing ER stress and cell death [MSDS]. Nonivamide, like other capsaicinoids, acts on the vanilloid receptors located in the peripheral afferent nerve fibers, providing short-acting irritant and algesic properties. Applied dermally, these substances act by stimulating sensitive chemoreceptors of the skin and by reflex, hyperemia and a local elevation in temperature. After repetitive administration, capsaicinoids have been reported to lead to desensitization to nociceptive stimuli possibly by long-acting depletion of peptide neurotransmitters (substance P) from peripheral sensory neurons. Capsaicinoids can modulate muscle tone (in bladder, bronchus etc.). Intravenous injection of nonivamide to rats (10 g/kg) has been found to lead to bradycardia. The cardiovascular effects are partly explained by substance P release. Nonivamide given to rats subcutaneously (1 mg/kg) was found to cause body temperature decrease, vasodilatation, and increased salivation. Capsaicinoids have shown to illicit bronchospastic effects in guinea pigs. Capsaicin and its analogs were reported to increase barbiturate sleeping time in rats by interacting with hepatic metabolizing enzymes.

    API SUPPLIERS

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    Transo-Pharm Handels GmbH

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    Formosa Laboratories

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    Registration Number : 222MF10228

    Registrant's Address : 36 Hoping Street, Louchu, Taoyuan 33842, Taiwan

    Initial Date of Registration : 2010-09-10

    Latest Date of Registration : --

     EU-WC NDC KDMF VMF Others AUDIT
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    FORMOSA LABORATORIES, INC.

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    Nonyl Vanillylamide

    Registration Number : 222MF10228

    Registrant's Address : 36 Hoping Street, Louchu, Taoyuan 33842, Taiwan

    Initial Date of Registration : 2010-09-10

    Latest Date of Registration : 2010-09-10

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    Nonivamide

    About the Company : Founded in 1987, Transo-Pharm is a fully licensed and certified global distributor of pharmaceutical components for the health and veterinary industries. The company supports its c...

    Founded in 1987, Transo-Pharm is a fully licensed and certified global distributor of pharmaceutical components for the health and veterinary industries. The company supports its customers throughout the complete lifecycle of APIs, from product development to market research, sourcing, import-export and sales. Transo-Pharm offers a diverse range of products. It qualifies manufacturers for full compliance and serves both as a valuable sourcing agent for its clients and a regulatory marketing agent for API manufacturers. It has offices in Shanghai, Hong Kong, Singapore, the United States, and an affiliated office in Mumbai.
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    Formosa Laboratories

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    Nonivamide

    About the Company : Formosa Laboratories Inc. founded in Taiwan since 1995 started with API business and has been serving customers worldwide. As an established API manufacturer receiving GMP inspecti...

    Formosa Laboratories Inc. founded in Taiwan since 1995 started with API business and has been serving customers worldwide. As an established API manufacturer receiving GMP inspections from regulatory authorities around the world, Formosa now provides CDMO service extending from APIs and ADCs (Antibody Drug Conjugates) to cytotoxic and non-cytotoxic injectables of aseptic liquid filling and lyophilization. Formosa Laboratories is able to offer full-service GMP manufacturing for drug substance, ADCs and drug product with its API and injectable facilities that accommodates small molecules, biologics and ADCs etc.
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    API Reference Price

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    [{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1711909800,"product":"NONIVAMIDE(SYNTHETIC CAPSAICIN) GRANULAR 98%HPLC (FOR INDUSTRIAL USE & NOT FOR MEDICAL AND PHARMA USE)","address":"7, DEVKARAN MANSION, 24, VITHALDAS","city":"MUMBAI. MAHARASHTRA","supplier":"SANMIK GROUP LIMITED","supplierCountry":"CHINA","foreign_port":"QINGDAO","customer":"IMPEX CHEMICAL CORPORATION","customerCountry":"INDIA","quantity":"500.00","actualQuantity":"500","unit":"KGS","unitRateFc":"63.5","totalValueFC":"31947.1","currency":"USD","unitRateINR":"5335.6","date":"01-Apr-2024","totalValueINR":"2667814.8","totalValueInUsd":"31947.1","indian_port":"JNPT","hs_no":"29241900","bill_no":"2827488","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"QINGDAO","supplierAddress":"ROOM 3112, HUAGANG INTERNATIONALN ROAD,JIANGYIN CITY , JIANGSU PRO CHINA","customerAddress":"7, DEVKARAN MANSION, 24, VITHALDAS"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1715538600,"product":"NONIVAMIDE 1% (99% MALTODEXTRIN)","address":"1\/17, KAMANA COOP. HSG. SCTY.,","city":"MUMBAI, MAHARASHTRA","supplier":"SHAANXI UNDERSUN BIOMEDTECH CO.,LTD","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"NIKITA TRANSPHASE ADDUCTS PVT LTD","customerCountry":"INDIA","quantity":"25.00","actualQuantity":"25","unit":"KGS","unitRateFc":"190","totalValueFC":"4806.7","currency":"USD","unitRateINR":"16026.5","date":"13-May-2024","totalValueINR":"400662.5","totalValueInUsd":"4806.7","indian_port":"Bombay Air","hs_no":"29242990","bill_no":"3460285","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"Building#3, Wanke Cloud Valley, No.1 Deng Ling Road, Xian, Shaanxi, 710075, China. China, Peoples Republic","customerAddress":"1\/17, KAMANA COOP. HSG. SCTY.,"}]
    01-Apr-2024
    13-May-2024
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