Nonivamide

Nonivamide
Names
IUPAC name
N-[(4-Hydroxy-3-methoxyphenyl)methyl]nonanamide
Other names
Pseudocapsaicin; Vanillyl-N-nonylamide; Nonylic acid vanillyl amide; Pelargonic acid vanillylamide (PAVA); Pelargonyl vanillyl amide
Identifiers
2444-46-4 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:46936 N
ChemSpider 2891 N
ECHA InfoCard 100.017.713
EC Number 219-46-4
KEGG D08282 YesY
PubChem 2998
UNII S846B891OR YesY
Properties
C17H27NO3
Molar mass 293.41 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).
N verify (what is YesYN ?)
Infobox references
Nonivamide
Heat Above Peak (SR: 9,200,000)

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

Ointment sold under trade name Finalgon is used to relieve arthritis and muscle pain. A small drop of the ointment applied on the skin is absorbed quickly causing warm to burning sensation and pain relief for several hours.

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.[2]

Nonivamide is used (under the name PAVA) as the payload in "less-lethal munitions" such as the Fabrique Nationale Herstal FN 303 [3] or as the active ingredient in most pepper sprays [2] - in both applications, the idea is to temporarily incapacitate people so that they can either be detained prior to arrest or deterred from acts of violence toward law-enforcement personnel or third parties (such as rioting or other group violence).

See also

References

  1. ↑ Howard L. Constant, Geoffrey A. Cordell and Dennis P. West (1996). J. Nat. Prod. 59 (4): 425–426. doi:10.1021/np9600816. Missing or empty |title= (help)
  2. 1 2 http://www.aversiontech.com/nonivamide.html Retrieved 16 July 2010
  3. ↑ http://www.fnhusa.com/r/training/training_faq_tabs/303-launcher Retrieved 13 April 2013
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