Nonivamide

Nonivamide
Nonivamide
Heat	Above Peak (SR: 9,200,000)

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
CAS Number	2444-46-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:46936 ;
ChemSpider	2891 ;
ECHA InfoCard	100.017.713
EC Number	219-46-4;
KEGG	D08282 ;
PubChem CID	2998;
UNII	S846B891OR ;
CompTox Dashboard (EPA)	DTXSID1034769 ;
	InChI 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) Key: RGOVYLWUIBMPGK-UHFFFAOYSA-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;
	SMILES CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC;
Properties
Chemical formula	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)
Solubility in water	Insoluble
Solubility	Soluble in methanol
Hazards
Flash point	190 °C (374 °F; 463 K) (closed cup)
Autoignition; temperature	330 °C (626 °F; 603 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	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). verify (what is ?) Infobox references

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.^{[weasel words]}

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).

References

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

[1] Howard L. Constant, Geoffrey A. Cordell and Dennis P. West (1996). J. Nat. Prod. 59 (4): 425–426. doi:10.1021/np9600816. {{cite journal}}: Missing or empty |title= (help)

[aversiontech-2] ttp://www.aversiontech.com/nonivamide.html Retrieved 16 July 2010

[fn303-3] ttp://www.fnhusa.com/r/training/training_faq_tabs/303-launcher Retrieved 13 April 2013

[1]

[2]

[3]

See also

References