Nonivamide

Last updated
Nonivamide
Nonivamide.svg
Names
Preferred IUPAC name
N-[(4-Hydroxy-3-methoxyphenyl)methyl]nonanamide
Other names
Pseudocapsaicin; Vanillyl-N-nonylamide; Vanillylamide of n-nonanoic acid; VNA; Nonylic acid vanillyl amide; Pelargonic acid vanillylamide (PAVA); Pelargonyl vanillyl amide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.017.713 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 219-46-4
KEGG
PubChem CID
UNII
  • 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) X mark.svgN
    Key: RGOVYLWUIBMPGK-UHFFFAOYSA-N X mark.svgN
  • 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
  • CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
Properties
C17H27NO3
Molar mass 293.407 g·mol−1
AppearanceWhite 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Nonivamide
HeatAbove peak
Scoville scale 9,200,000 [1] SHU

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

Contents

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). [3] 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. [4]

Nonivamide is used (under the name PAVA) as the payload in "less-lethal munitions" such as the FN Herstal's FN 303 projectiles [5] or as the active ingredient in most pepper sprays, [3] which may be used as a chemical weapon. [6] As a chemical irritant, pepper sprays have been used both as a riot control munition and also a weapon to disperse peaceful demonstrators; they have also been used in other contexts, such as military or police training exercises. [6] While irritants commonly cause only "transient lacrimation, blepharospasm, superficial pain, and disorientation," their use and misuse also presents serious risks of more severe injury and disability. [6]

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. [7]

See also

Related Research Articles

<span class="mw-page-title-main">Scoville scale</span> Scale for measuring spiciness of peppers

The Scoville scale is a measurement of pungency of chili peppers and other substances, recorded in Scoville heat units (SHU). It is based on the concentration of capsaicinoids, among which capsaicin is the predominant component.

<span class="mw-page-title-main">Capsaicin</span> Pungent chemical compound in chili peppers

Capsaicin (8-methyl-N-vanillyl-6-nonenamide) is an active component of chili peppers, which are plants belonging to the genus Capsicum. It is a chemical irritant and neurotoxin for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related amides (capsaicinoids) are produced as secondary metabolites by chili peppers, probably as deterrents against certain mammals and fungi. Pure capsaicin is a hydrophobic, colorless, highly pungent, crystalline to waxy solid compound.

<span class="mw-page-title-main">Chili pepper</span> Varieties of peppers belonging to several species of Capsicum genus

Chili peppers, 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 their pungency. Chili peppers are widely used in many cuisines as a spice to add "heat" to dishes. Capsaicin and related compounds known as capsaicinoids are the substances giving chili peppers their intensity when ingested or applied topically. Chili peppers exhibit a wide range of heat and flavor profiles. This diversity is the reason behind the availability of different types of paprika and chili powder, each offering its distinctive taste and heat level.

Pepper spray, oleoresin capsicum spray, OC spray, capsaicin spray, or capsicum spray is a lacrimator product containing the compound capsaicin as the active ingredient that irritates the eyes to cause burning and pain sensations, and temporary blindness. Pepper spray is used as a less lethal weapon in policing, riot control, crowd control, and self-defense, including defense against dogs and bears. Its inflammatory effects cause the eyes to close, temporarily taking away vision. This temporary blindness allows officers to more easily restrain subjects and permits people in danger to use pepper spray in self-defense for an opportunity to escape. It also causes temporary discomfort and burning of the lungs which causes shortness of breath.

<span class="mw-page-title-main">Riot control</span> Measures taken against unlawful or violent crowds of people

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.

<span class="mw-page-title-main">Piperine</span> Alkaloid responsible for the pungency of black pepper

Piperine, possibly along with its isomer chavicine, is the compound responsible for the pungency of black pepper and long pepper. It has been used in some forms of traditional medicine.

<span class="mw-page-title-main">Tear gas</span> Non-lethal chemical weapon

Tear gas, also known as a lachrymator agent or lachrymator, sometimes colloquially known as "mace" after the early commercial self-defense spray, is a chemical weapon that stimulates the nerves of the lacrimal gland in the eye to produce tears. In addition, it can cause severe eye and respiratory pain, skin irritation, bleeding, and blindness. Common lachrymators both currently and formerly used as tear gas include pepper spray, PAVA spray (nonivamide), CS gas, CR gas, CN gas, bromoacetone, xylyl bromide and Mace.

<span class="mw-page-title-main">Pepper-spray projectile</span> Law enforcement weapon

A pepper-spray projectile, also called a pepper-spray ball, pepper-ball, pepper bomb, or pepper-spray pellet, is a frangible projectile containing a powdered chemical that irritates the eyes and nose in a manner similar to pepper spray. These projectiles are fired from specially designed forced compliance weapons or modified paintball guns.

<span class="mw-page-title-main">Dihydrocapsaicin</span> Chemical compound

Dihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin, it is an irritant. It accounts for about 22% of the total capsaicinoid mixture and has the same pungency as capsaicin. Pure dihydrocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. It is soluble in dimethyl sulfoxide and 100% ethanol.

Nordihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum).

Homodihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin it is an irritant. Homodihydrocapsaicin accounts for about 1% of the total capsaicinoids mixture and has about half the pungency of capsaicin. Pure homodihydrocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. It produces "numbing burn" in the throat and is one of the most prolonged and difficult to rinse out. On the Scoville scale it has 8,600,000 SHU.

<span class="mw-page-title-main">Homocapsaicin</span> Chemical compound

Homocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin it is an irritant. Homocapsaicin accounts for about 1% of the total capsaicinoids mixture and has about half the pungency of capsaicin. Pure homocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. On the Scoville scale it has 8,600,000 SHU. Homocapsaicin isolated from chili pepper has been found in two isomeric forms, both with a carbon-carbon double bond at the 6 position on the 10-carbon acyl chain. One isomer has an additional carbon, a methyl group, at the 8 position and the other has a methyl group at the 9 position. Homocapsaicin (6-ene-8-methyl) is the more abundant isomer. Homocapsaicin with the double bond at the 7 position has never been found in nature, though its structure is widely reported on the Internet and in the scientific literature. Details of this misidentification have been published.

<span class="mw-page-title-main">Resiniferatoxin</span> Chemical compound

Resiniferatoxin (RTX) is a naturally occurring chemical found in resin spurge, a cactus-like plant commonly found in Morocco, and in Euphorbia poissonii found in northern Nigeria. It is a potent functional analog of capsaicin, the active ingredient in chili peppers.

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, in a solvent of aqueous ethanol. The propellant is nitrogen. This solution has been selected because this is the minimum concentration which will fulfill the purpose of the equipment; namely to minimise a person's capacity for resistance, without unnecessarily prolonging their discomfort.

<span class="mw-page-title-main">Shogaol</span> Chemical compound

Shogaols are pungent constituents of ginger similar in chemical structure to gingerol. The most common of the group is [6]-shogaol. Like zingerone, it is produced when ginger is dried or cooked. Moreover, shogaol are converted to other constituents when heat is applied over time, which is why ginger loses its spiciness as it is cooked.

Capsinoids are alkaloid substances naturally present in chili peppers. Although they are structurally similar to capsaicin, the substance that causes pungency in hot peppers, they largely lack that characteristic. Capsinoids have an estimated "hot taste threshold" which is about 1/1000 that of capsaicin. Capsinoids were not reported in the scientific literature until 1989, when biologists first isolated them in a unique variety of chili peppers, CH-19 Sweet, which does not contain capsaicin. Capsinoids include capsiate, dihydrocapsiate, and nordihydrocapsiate.

<span class="mw-page-title-main">Pungency</span> Sharp smell or flavor

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 lower degree of pungency that are "agreeably stimulating to the palate". Examples of piquant food include mustard and curry.

<span class="mw-page-title-main">Vanilloids</span> Chemical compounds containing a vanillyl group

The vanilloids are compounds which possess a vanillyl group. They include vanillyl alcohol, vanillin, vanillic acid, acetovanillon, vanillylmandelic acid, homovanillic acid, capsaicin, etc. Isomers are the isovanilloids.

<span class="mw-page-title-main">Vanillylamine</span> Chemical compound

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 by the enzyme capsaicin synthase.

<span class="mw-page-title-main">Hot pepper challenge</span>

The hot pepper challenge is an Internet viral video fad, consisting of a food challenge that involves filming oneself while eating and swallowing a chili pepper that is high on the Scoville scale and known for its piquant (spicy-hot) qualities, in particular the cayenne pepper, Thai pepper, habanero, ghost pepper, and the Trinidad moruga scorpion pepper; the video is then uploaded to the Internet. Hot pepper challenges have been featured on television series, including Man v. Food.

References

  1. ↑ Govindarajan, Sathyanarayana (1991). "Capsicum — Production, Technology, Chemistry, and Quality. Part V. Impact on Physiology, Pharmacology, Nutrition, and Metabolism; Structure, Pungency, Pain, and Desensitization Sequences". Critical Reviews in Food Science and Nutrition. 29 (6): 435–474. doi:10.1080/10408399109527536. PMID   2039598.
  2. ↑ Howard L. Constant, Geoffrey A. Cordell and Dennis P. West (1996). "Nonivamide, a Constituent of Capsicum oleoresin". J. Nat. Prod. 59 (4): 425–426. doi:10.1021/np9600816.
  3. 1 2 http://www.aversiontech.com/hot-and-spicy/nonivamide-pava/Retrieved 16 July 2010 Archived 31 December 2015 at the Wayback Machine
  4. ↑ Rohm, Barbara; Riedel, Annett; Ley, Jakob P; Widder, Sabine; Krammer, Gerhard E; Somoza, Veronika (2015). "Capsaicin, nonivamide and trans-pellitorine decrease free fatty acid uptake without TRPV1 activation and increase acetyl-coenzyme a synthetase activity in Caco-2 cells". Food & Function. 6 (1): 172–184. doi: 10.1039/C4FO00435C . PMID   25422952.
  5. ↑ "The FN 303 Less Lethal Launcher". Archived from the original on 2013-05-04. Retrieved 2013-04-14.
  6. 1 2 3 Haar, Rohini J.; Iacopino, Vincent; Ranadive, Nikhil; Weiser, Sheri D.; Dandu, Madhavi (19 October 2017). "Health impacts of chemical irritants used for crowd control: a systematic review of the injuries and deaths caused by tear gas and pepper spray". BMC Public Health. 17: 831. doi:10.1186/s12889-017-4814-6. PMC   5649076 . PMID   29052530.
  7. ↑ Barry, James D.; Hennessy, Robert; McManus, John G. (January 2008). "A Randomized Controlled Trial Comparing Treatment Regimens for Acute Pain for Topical Oleoresin Capsaicin (Pepper Spray) Exposure in Adult Volunteers". Prehospital Emergency Care. 12 (4): 432–437. doi:10.1080/10903120802290786. PMID   18924005. S2CID   12262260.
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