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Preferred IUPAC name
Other names
Pseudocapsaicin; Vanillyl-N-nonylamide; Vanillylamide of n-nonanoic acid; VNA; Nonylic acid vanillyl amide; Pelargonic acid vanillylamide (PAVA); Pelargonyl vanillyl amide
3D model (JSmol)
ECHA InfoCard 100.017.713 Edit this at Wikidata
EC Number
  • 219-46-4
  • 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
  • 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)
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)
Solubility Soluble in methanol
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).
☒N verify (what is checkY☒N ?)
Infobox references
HeatAbove peak
Scoville scale9,200,000[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]


There are various treatments to combat the effects of nonivamide. One popular method includes administering a one-to-one solution of Milk of Magnesia and water to the eyes. Doctors also recommend not using oils or creams on the skin and to not wear contact lenses during nonivamide exposure. [7] However, One study found that Milk of Magnesia, baby shampoo, 2% lidocaine gel, or milk did not demonstrate significantly better performance than water.[8]

See also[edit]


  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. ^ a b 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. ^ 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: 831. doi:10.1186/s12889-017-4814-6. PMC 5649076. PMID 29052530.
  7. ^ Brown, Dr. Ernest (2020-05-31). "Bike-riding doctor helps protesters recover from pepper spray attacks". WUSA9. Retrieved 2020-06-01.
  8. ^ 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.