N-Vanillylnonamide

N-Vanillylnonamide Uses, Dosage, Side Effects, Food Interaction and all others data.

N-Vanillylnonamide is found in herbs and spices. It is an alkaloid from the Capsicum species. The structures of Capsaicin and nonivamide differ only slightly with respect to the fatty acid moiety of the side chain (8-methyl nonenoic acid versus nonanoic acid) .

N-Vanillylnonamide is a flavoring ingredient. N-Vanillylnonamide is an organic compound and a capsaicinoid. It is an amide of pelargonic acid and vanillylamine. It is naturally found in chili peppers but manufactured to produce a synthetic form for various pharmacologic preparations .

This drug has been studied in combination with Nicarboxil in the treatment of lower back pain .

N-Vanillylnonamide
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Uses during Pregnancy
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Trade Name	N-Vanillylnonamide
Generic	Nonivamide
Nonivamide Other Names	Hydroxymethoxybenzyl pelargonamide, N-Nonanoyl vanillylamide, N-Vanillylnonamide, N-Vanillylpelargonamide, Nonivamide, Pelargonyl vanillylamide, Pseudocapsaicin, Vanillyl-N-nonylamide
Type
Formula	C₁₇H₂₇NO₃
Weight	Average: 293.4012 Monoisotopic: 293.199093735
Groups	Investigational
Therapeutic Class
Manufacturer
Available Country
Last Updated:	September 19, 2023 at 7:00 am

Uses

N-Vanillylnonamide is used as a topical analgesic and is also used as a flavoring ingredient , , .

N-Vanillylnonamide is also used to associated treatment for these conditions: Back Pain Lower Back, Back Pain, Acute, Contusions, Joint Pain, Rheumatism, Soreness, Muscle, Sprains, Stiff Shoulder, Poor blood circulation, Topical Analgesia

How N-Vanillylnonamide works

N-Vanillylnonamide is a naturally occurring analog of Capsaicin, isolated from peppers, described to produce effects similar to Capsaicin. 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 .

N-Vanillylnonamide has been shown to stimulate afferent neurons with about half the potency of Capsaicin. Agonism of the VR1 (TRPV1) (vanilloid) receptor by N-Vanillylnonamide was demonstrated to induce the release of Ca2+ from the endoplasmic reticulum (ER) of human lung cells, producing ER stress and cell death .

N-Vanillylnonamide, 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 μg/kg) has been found to lead to bradycardia. The cardiovascular effects are partly explained by substance P release. N-Vanillylnonamide 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 .

Toxicity

N-Vanillylnonamide appears to be of low acute toxicity, according to the EMA summary report . The oral LD50 in rats is reported with 5110 mg/kg and the dermal LD50 in rabbits is greater than 10 000 mg/kg. Administered intraperitoneally, the LD50 in rats was measured to be about 90 mg/kg. In combination with nicoboxil, the acute dermal toxicity of nonivamide was increased. Signs of toxicity (depression, labored respiration, diarrhea) were observed at doses as low as 32 mg/kg body weight of nonivamide combined 200 mg nicoboxil/kg body weight .

Allergic reactions in humans following administration of capsaicin or capsicum extracts are reported to be rare .

No information on carcinogenic properties of nonivamide was available. Tumorigenic properties have been reported in literature for Capsaicin or chili .