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 Y
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, but is commonly manufactured synthetically. It is more heat-stable than capsaicin.

Ointment sold under trade name Finalgon is used to relieve arthritis and muscule 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 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 the active ingredient in PAVA spray, used by British Transport Police, Ministry of Defence Police and some territorial forces; such as, Suffolk Police, Wiltshire Police and Northamptonshire Police—although many forces 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). It has been shown to be effective against some kinds of tumors.