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,[2] but is commonly manufactured synthetically. It is more heat-stable than capsaicin.

Nonivamide
Names
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
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.017.713
EC Number
  • 219-46-4
KEGG
UNII
  • 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) ☒N
    Key: RGOVYLWUIBMPGK-UHFFFAOYSA-N ☒N
  • InChI=1/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)
    Key: RGOVYLWUIBMPGK-UHFFFAOYAC
  • CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
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):
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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Infobox references
Nonivamide
HeatAbove peak
Scoville scale9,200,000[1] SHU

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

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

References
  1. 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.
  2. 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.
  3. http://www.aversiontech.com/hot-and-spicy/nonivamide-pava/Retrieved 16 July 2010 Archived 31 December 2015 at the Wayback Machine
  4. 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.
  5. "The FN 303 Less Lethal Launcher". Archived from the original on 2013-05-04. Retrieved 2013-04-14.
  6. 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: 831. doi:10.1186/s12889-017-4814-6. PMC 5649076. PMID 29052530.
  7. 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.
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