Nonivamide, also called pelargonic acid vanillylamide or PAVA, is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
and a
capsaicinoid
Capsaicin (8-methyl-''N''-vanillyl-6-nonenamide) ( or ) is an active component of chili peppers, which are plants belonging to the genus ''Capsicum''. It is a chemical irritant for mammals, including humans, and produces a sensation of burning ...
. It is an
amide
In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is ...
of
pelargonic acid
Pelargonic acid, also called nonanoic acid, is an organic compound with structural formula CH3(CH2)7CO2H. It is a nine-carbon fatty acid. Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, ...
(n-nonanoic acid) and
vanillyl amine
Vanillylamine is a chemical compound that is an intermediate in the biosynthesis of capsaicin. Vanillylamine is produced from vanillin by the enzyme vanillin aminotransferase. It is then converted with 8-methyl-6-nonenoic acid into capsaicin b ...
. It is present in
chili pepper
Chili peppers (also chile, chile pepper, chilli pepper, or chilli), from Nahuatl '' chīlli'' (), are varieties of the berry-fruit of plants from the genus ''Capsicum'', which are members of the nightshade family Solanaceae, cultivated for ...
s, but is commonly manufactured synthetically. It is more heat-stable than
capsaicin
Capsaicin (8-methyl-''N''-vanillyl-6-nonenamide) ( or ) is an active component of chili peppers, which are plants belonging to the genus ''Capsicum''. It is a chemical irritant for mammals, including humans, and produces a sensation of burning ...
.
Nonivamide is used as a
food additive
Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt (salt ...
to add
pungency
Pungency () refers to the taste of food commonly referred to as spiciness, hotness or heat, found in foods such as chili peppers. Highly pungent tastes may be experienced as unpleasant. The term piquancy () is sometimes applied to foods with a l ...
to
seasoning
Seasoning is the process of supplementing food via herbs, spices, salts, and/or sugar, intended to enhance a particular flavour.
General meaning
Seasonings include herbs and spices, which are themselves frequently referred to as "seasonings". Ho ...
s,
flavoring
A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of the gusta ...
s, and
spice
A spice is a seed, fruit, root, bark, or other plant substance primarily used for flavoring or coloring food. Spices are distinguished from herbs, which are the leaves, flowers, or stems of plants used for flavoring or as a garnish. Spices a ...
blends. It is also used in the
confectionery
Confectionery is the art of making confections, which are food items that are rich in sugar and carbohydrates. Exact definitions are difficult. In general, however, confectionery is divided into two broad and somewhat overlapping categories ...
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).
[http://www.aversiontech.com/hot-and-spicy/nonivamide-pava/Retrieved 16 July 2010 ] This is consistent with nonivamide's role as a
TRPV1
The transient receptor potential cation channel subfamily V member 1 (TrpV1), also known as the capsaicin receptor and the vanilloid receptor 1, is a protein that, in humans, is encoded by the ''TRPV1'' gene. It was the first isolated member of th ...
ion channel agonist. Mammalian TRPV1 is activated by heat and capsaicin, but the avian form is insensitive to capsaicin.
Nonivamide is used (under the name PAVA) as the payload in "less-lethal munitions" such as the
FN Herstal
Fabrique Nationale Herstal (), trading as FN Herstal and often referred to as Fabrique Nationale or simply FN, is a leading firearms manufacturer based in Herstal, Belgium. It is currently the largest exporter of military small arms in Europe.
F ...
's
FN 303
The FN 303 is a semi-automatic less-lethal riot gun designed and manufactured by Fabrique Nationale de Herstal.
The FN 303 uses compressed air to fire projectiles from a 15-round drum magazine. It is designed to incapacitate the target through b ...
projectiles
or as the active ingredient in most
pepper spray
Pepper spray, oleoresin capsicum spray, OC spray, capsaicin spray, or capsicum spray is a lachrymatory agent (a compound that irritates the eyes to cause a burning sensation, pain, and temporary blindness) used in policing, riot control, cr ...
s,
[ which may be used as a ]chemical weapon
A chemical weapon (CW) is a specialized munition that uses chemicals formulated to inflict death or harm on humans. According to the Organisation for the Prohibition of Chemical Weapons (OPCW), this can be any chemical compound intended as a ...
.riot control
Riot control measures are used by law enforcement, military, paramilitary or security forces to control, disperse, and arrest people who are involved in a riot, unlawful demonstration or unlawful protest.
If a riot is spontaneous and irration ...
munition and also a weapon to disperse peaceful demonstrators; they have also been used in other contexts, such as military or police training exercises.[ While irritants commonly cause only "transient ]lacrimation
Tears are a clear liquid secreted by the lacrimal glands (tear gland) found in the eyes of all land mammals. Tears are made up of water, electrolytes, proteins, lipids, and mucins that form layers on the surface of eyes. The different types of ...
, blepharospasm
Blepharospasm is any abnormal contraction of the orbicularis oculi muscle. The condition should be distinguished from the more common, and milder, involuntary quivering of an eyelid, known as myokymia, or fasciculation. In most cases, blepharosp ...
, superficial pain, and disorientation," their use and misuse also presents serious risks of more severe injury and disability.[
]
Treatment
Nonivamide is not soluble in water, however water will dilute it and wash it away. One study found that milk of magnesia, baby shampoo, 2% lidocaine gel, or milk, did not demonstrate significantly better performance than water, when used on pepper spray.
See also
*PAVA spray
PAVA spray is an incapacitant spray similar to pepper spray. It is dispensed from a handheld canister, in a liquid stream. It contains a 0.3% solution of pelargonic acid vanillylamide (PAVA), also called nonivamide, a synthetic capsaicinoid (analo ...
*Phenylacetylrinvanil
Phenylacetylrinvanil (IDN-5890) is a synthetic analogue of capsaicin which acts as a potent and selective agonist for the TRPV1 receptor, with slightly lower potency than resiniferatoxin, though still around 300 times the potency of capsaicin. It ...
References
{{Transient receptor potential channel modulators
Riot control agents
Lachrymatory agents
Capsaicinoids
Phenol ethers