Nonivamide
Nonivamide, also called pelargonic acid vanillylamide or PAVA, is an organic compound and a capsaicinoid. It is an amide of pelargonic acid (n-nonanoic acid) and vanillyl amine. It is present in chili peppers, but is commonly manufactured synthetically. It is more heat-stable than capsaicin. Nonivamide is used as a food additive to add pungency to seasonings, flavorings, and spice blends. It is also used in the confectionery industry to create a hot sensation, and in the pharmaceutical industry in some formulations as a cheaper alternative to capsaicin. Like capsaicin, it can deter mammals (but not birds or insects) from consuming plants or seeds (e.g. squirrels and bird feeder seeds). This is consistent with nonivamide's role as a TRPV1 ion channel agonist. Mammalian TRPV1 is activated by heat and capsaicin, but the avian form is insensitive to capsaicin. Nonivamide is used (under the name PAVA) as the payload in "less-lethal munitions" such as the FN Herstal's FN 303 projectiles or as the active ingredient in most pepper sprays, which may be used as a chemical weapon. As a chemical irritant, pepper sprays have been used both as a riot control munition and also a weapon to disperse peaceful demonstrators; they have also been used in other contexts, such as military or police training exercises. While irritants commonly cause only "transient lacrimation, blepharospasm, superficial pain, and disorientation," their use and misuse also presents serious risks of more severe injury and disability.
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| Names | |
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| Preferred IUPAC name
N-[(4-Hydroxy-3-methoxyphenyl)methyl]nonanamide | |
| Other names
Pseudocapsaicin; Vanillyl-N-nonylamide; Vanillylamide of n-nonanoic acid; VNA; Nonylic acid vanillyl amide; Pelargonic acid vanillylamide (PAVA); Pelargonyl vanillyl amide
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.017.713 |
| EC Number |
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| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C17H27NO3 | |
| Molar mass | 293.407 g·mol−1 |
| Appearance | White to off-white powder |
| Odor | Pungent |
| Density | 1.10 g/cm3 |
| Melting point | 54 °C (129 °F; 327 K) |
| Insoluble | |
| Solubility | Soluble in methanol |
| Hazards | |
| Flash point | 190 °C (374 °F; 463 K) (closed cup) |
| 330 °C (626 °F; 603 K) | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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511 mg/kg (rat, oral) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Nonivamide | |
|---|---|
| Heat | Above peak |
| Scoville scale | 9,200,000[1] SHU |
Nonivamide, also called pelargonic acid vanillylamide or PAVA, is an organic compound and a capsaicinoid. It is an amide of pelargonic acid (n-nonanoic acid) and vanillyl amine. It is present in chili peppers,[2] but is commonly manufactured synthetically. It is more heat-stable than capsaicin.
Nonivamide is used as a food additive to add pungency to seasonings, flavorings, and spice blends. It is also used in the confectionery industry to create a hot sensation, and in the pharmaceutical industry in some formulations as a cheaper alternative to capsaicin.
Like capsaicin, it can deter mammals (but not birds or insects) from consuming plants or seeds (e.g. squirrels and bird feeder seeds).[3] This is consistent with nonivamide's role as a TRPV1 ion channel agonist. Mammalian TRPV1 is activated by heat and capsaicin, but the avian form is insensitive to capsaicin.[4]
Nonivamide is used (under the name PAVA) as the payload in "less-lethal munitions" such as the FN Herstal's FN 303 projectiles[5] or as the active ingredient in most pepper sprays,[3] which may be used as a chemical weapon.[6] As a chemical irritant, pepper sprays have been used both as a riot control munition and also a weapon to disperse peaceful demonstrators; they have also been used in other contexts, such as military or police training exercises.[6] While irritants commonly cause only "transient lacrimation, blepharospasm, superficial pain, and disorientation," their use and misuse also presents serious risks of more severe injury and disability.[6]
Treatment
[edit]Nonivamide is not soluble in water, however water will dilute it and wash it away. One study found that milk of magnesia, baby shampoo, 2% lidocaine gel, or milk, did not demonstrate significantly better performance than water, when used on pepper spray.[7]
See also
[edit]- PAVA spray, a type of pepper spray
- Phenylacetylrinvanil, a synthetic analogue of capsaicin
References
[edit]- ^ Govindarajan, Sathyanarayana (1991). "Capsicum — Production, Technology, Chemistry, and Quality. Part V. Impact on Physiology, Pharmacology, Nutrition, and Metabolism; Structure, Pungency, Pain, and Desensitization Sequences". Critical Reviews in Food Science and Nutrition. 29 (6): 435–474. doi:10.1080/10408399109527536. PMID 2039598.
- ^ Howard L. Constant, Geoffrey A. Cordell and Dennis P. West (1996). "Nonivamide, a Constituent of Capsicum oleoresin". J. Nat. Prod. 59 (4): 425–426. doi:10.1021/np9600816.
- ^ a b "nonivamide (synthetic capsaicin)". www.aversiontech.com. Archived from the original on 2015-12-31. Retrieved 16 July 2010.
- ^ Rohm, Barbara; Riedel, Annett; Ley, Jakob P; Widder, Sabine; Krammer, Gerhard E; Somoza, Veronika (2015). "Capsaicin, nonivamide and trans-pellitorine decrease free fatty acid uptake without TRPV1 activation and increase acetyl-coenzyme a synthetase activity in Caco-2 cells". Food & Function. 6 (1): 172–184. doi:10.1039/C4FO00435C. PMID 25422952.
- ^ "The FN 303 Less Lethal Launcher". Archived from the original on 2013-05-04. Retrieved 2013-04-14.
- ^ a b c Haar, Rohini J.; Iacopino, Vincent; Ranadive, Nikhil; Weiser, Sheri D.; Dandu, Madhavi (19 October 2017). "Health impacts of chemical irritants used for crowd control: a systematic review of the injuries and deaths caused by tear gas and pepper spray". BMC Public Health. 17 (1): 831. doi:10.1186/s12889-017-4814-6. PMC 5649076. PMID 29052530.
- ^ Barry, James D.; Hennessy, Robert; McManus, John G. (January 2008). "A Randomized Controlled Trial Comparing Treatment Regimens for Acute Pain for Topical Oleoresin Capsaicin (Pepper Spray) Exposure in Adult Volunteers". Prehospital Emergency Care. 12 (4): 432–437. doi:10.1080/10903120802290786. PMID 18924005. S2CID 12262260.