Nonivamide

Nonivamide
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
PubChem	2998
KEGG	D08282 Y
Jmol-3D images	Image 1
SMILES CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
Properties
Molecular formula	C17H27NO3
Molar mass	293.4 g mol−1
Melting point	54°C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

Nonivamide is used as a food additive to add pungency to seasonings, flavorings, and spice blends. It is also used in the confectionary industry to create a hot sensation, and in the pharmaceutical industry in some formulations as a cheaper alternative to capsaicin.

As a potent lachrymatory agent, nonivamide finds use as the active ingredient of some oleoresin capsicum-based riot control agents (pepper spray). Within the UK, nonivamide is used as the PAVA spray by the British Transport Police and some other territorial forces, such as Suffolk Police, Wiltshire Police and Northamptonshire Police, although many still use CS Incapacitant Spray.

Like capsaicin, it can deter mammals (but not birds or insects, which seem immune) from consuming plants or seeds (e.g. squirrels and bird feeder seeds^[2]).

References

1. ^ Howard L. Constant, Geoffrey A. Cordell and Dennis P. West. J. Nat. Prod., 1996, 59 (4), pp 425–426 DOI: 10.1021/np9600816 Publication Date (Web): April 22, 1996 Retrieved 16 July 2010
2. ^ http://www.aversiontech.com/nonivamide.html Retrieved 16 July 2010