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.
[1] https://www.scbt.com/scbt/product/nonivamide-2444-46-4
[2] https://pubchem.ncbi.nlm.nih.gov/compound/N-Vanillylnonanamide#section=Clinical-Trials
[3] https://cot.food.gov.uk/sites/default/files/cot/cotsection.pdf
Nonanoyl-4-hydroxy-3-methoxybenzylamide is odorless with a pungent, burning taste. Synthesized from nonanyl chloride and vanillylamine.
n-Nonanyl-4-hydroxy-3-methoxybenzyl-amide is an odorless compound, but has a pungent, burning taste
N-Vanillylnonanamide is a synthetic analogue of Capsaicin (175680) with similar bioactivity.
analgesic (topical), depletes Substance P
From nonanyl chloride and vanillylamine.
ChEBI: A capsaicinoid that is the carboxamide resulting from the formal condensation of the amino group of 4-hydroxy-3-methoxybenzylamine with the carboxy group of nonanoic acid. It is the active ingredient in many pepper sprays.
The general procedure for the synthesis of N-(4-hydroxy-3-methoxybenzyl)nonanamide from nonanoyl chloride and 4-(aminomethyl)-2-methoxyphenol was as follows: first, the hydrochloride or hydrobromide of 4-(aminomethyl)-2-methoxyphenol (1 mmol) was dissolved in anhydrous N,N-dimethylformamide (DMF) (2 mL). Subsequently, N,N-diisopropylethylamine (DIPEA) (2 mmol) was added to neutralize the salt and release the free amine. After stirring the reaction mixture for 10 minutes at room temperature, nonanoyl chloride (1 mmol) was slowly added. The reaction continued to be stirred at room temperature for 6 to 24 hours. Upon completion of the reaction, water (40 mL) was added to the reaction mixture to quench the reaction. The mixture was transferred to a partition funnel and extracted with dichloromethane (CH2Cl2) (3 x 6 mL). The organic phases were combined and concentrated under reduced pressure to obtain the crude product. Finally, the crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate, 2:1 v/v) or preparative high-performance liquid chromatography (HPLC) (according to the analytical scheme described above) to afford the target compound N-(4-hydroxy-3-methoxybenzyl)nonanamide.
1. m. j. caterina, m. a. schumacher, m. tominaga, t. a. rosen, j. d. levine and d. julius, nature 1997, 389, 816-824. 2. y. g. gil and m. k. kang, life sci 2008, 82, 997-1003. 3. y. s. lee, d. h. nam and j. a. kim, cancer lett 2000, 161, 121-130. 4. h. c. chang, s. t. chen, s. y. chien, s. j. kuo, h. t. tsai and d. r. chen, hum exp toxicol 2011, 30, 1657-1665. 5. k. c. brown, t. r. witte, w. e. hardman, h. luo, y. c. chen, a. b. carpenter, j. k. lau and p. dasgupta, plos one 2010, 5, e10243.>
