Nonivamide

Base Information

• Chemical Name: Nonivamide
• CAS No.: 2444-46-4
• Deprecated CAS: 60806-29-3,618-92-8,497080-86-1,618-92-8
• Molecular Formula: C17H27NO3
• Molecular Weight: 293.406
• Hs Code.: 29242990
• European Community (EC) Number: 219-484-1
• NSC Number: 760391,172795
• UNII: S846B891OR
• DSSTox Substance ID: DTXSID1034769
• Nikkaji Number: J7.575B
• Wikipedia: Nonivamide
• Wikidata: Q420228
• NCI Thesaurus Code: C170227
• RXCUI: 31945
• Metabolomics Workbench ID: 44085
• ChEMBL ID: CHEMBL75124
• Mol file: 2444-46-4.mol

Synonyms:Nonanamide,N-vanillyl- (6CI,7CI,8CI);AH 23491X;N-Vanillylnonamide;NSC 172795;Nonanoylvanillyl amide;Vanillyl pelargonic amide;

Chemical Property of Nonivamide

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 2.48E-10mmHg at 25°C
• Melting Point: 54 °C
• Refractive Index: 1.513
• Boiling Point: 492.7 °C at 760 mmHg
• PKA: 9.76±0.20(Predicted)
• Flash Point: 251.8 °C
• PSA: 58.56000
• Density: 1.037 g/cm³
• LogP: 4.15850
• Storage Temp.: 2-8°C
• Solubility.: methanol: 100 mg/mL, clear to slightly hazy
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 293.19909372
• Heavy Atom Count: 21
• Complexity: 283

Purity/Quality:

99% ^*data from raw suppliers

Nonivamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 25-36/37/38-43
• Safety Statements: 26-45-37/39-36/37

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Food Additives
• Canonical SMILES: CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
• Recent ClinicalTrials: Efficacy and Safety of Finalgon? Cream Multiple Doses in Acute Low Back Pain
• Recent EU Clinical Trials: A multi-centre, double-blind, randomised, parallel group study to assess the efficacy and safety of multiple doses of topically applied hyperemisation-inducing ointment (2 cm ointment line per application; up to 3 times daily for up to 4 days) containing 2.5% Nicoboxil/0.4% Nonivamide versus 2.5% Nicoboxil, 0.4% Nonivamide and placebo in patients 18 to 65 years of age with acute low back pain
• Description: Nonivamide is also called pelargonic acid vanillylamide or PAVA. It is a capsaicinoid. Nonivamide, isolated from peppers, is a naturally occurring analog of capsaicin (sc-3577). Similar to capsaicin, nonivamide can activate the TRPV1 receptor, thus, stimulate the firing rate of dopaminergic neurons in the ventral tegmental area of the brain and to increase the expression of the serotonin receptor gene HTR2A. Nonivamide is with lower TRPV1 binding affinity, thus, a reduced pungency (9 200 000 scoville heat units) compared to capsaicin (16 000 000 scoville heat units). Nonivamide is used in the food production to add a hot sensation to flavoring agents and spice mixtures. It is also used in the sweets and confectionary industries to add hot sensation into products. In pharmaceutical industries, nonivamide is used as a cheaper alternative for capsaicin. Warming or heating ointment of nonivamide is used for temporary relief of pain from conditions such as rheumatism, arthritis, lumbao, muscular aches, sprains and strains, sporting injuries and other conditions where local warmth is beneficial. Finalgon is one of the common product utilizing nonivamide for this purpose. Nonivamide is also used as an incapacitant spray, affecting the assailed person’s eyes, causing intense pain and swelling. Nonanoyl-4-hydroxy-3-methoxybenzylamide is odorless with a pungent, burning taste. Synthesized from nonanyl chloride and vanillylamine.
• Uses: analgesic (topical), depletes Substance P N-Vanillylnonanamide is a synthetic analogue of Capsaicin (175680) with similar bioactivity.

Technology Process of Nonivamide

There total 23 articles about Nonivamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

Nonanoyl chloride (764-85-2) + Vanillylamin (1196-92-5) → Nonivamide (2444-46-4,618-92-8)

Guidance literature:

Vanillylamin; With sodium hydrogencarbonate; In chloroform; water; at 20 ℃; for 0.75h;

Nonanoyl chloride; In chloroform; water; at 20 - 40 ℃; for 1h;

DOI:10.1002/adsc.201301148

Reference yield: 91.5%

Nonanoyl chloride (764-85-2) + vanillylamine hydrochloride (7149-10-2) → Nonivamide (2444-46-4,618-92-8)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; water; at 20 - 42 ℃; for 2.5h; Temperature;

Reference yield: 84.0%

3-methoxy-4-(triisopropylsilyloxy)-N-(nonanoyl)benzylamine (871570-36-4) → Nonivamide (2444-46-4,618-92-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1039/b914981c

upstream raw materials:

Nonanoyl chloride

Vanillylamin

N-(4-benzyloxy-3-methoxy-benzyl)-nonanamide

2-methoxy-phenol

Downstream raw materials:

Glyceryl novinamide

N-(4-O-glycol-3-methoxybenzyl)-nonamide

Vanillylamin

nonanoic acid methyl ester

Refernces

• 1、 -. "Preparation method of capsaicin and capsaicin prepared by using method". Paragraph 0011; 0037; 0094-0126. . Retrieved 2021/06/26.
• 2、 -. "Vanilla amide synthesis method". Paragraph 0083-0086; 0099-0101. . Retrieved 2021/06/13.