Names | |
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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
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.017.713 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
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) |
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): | |
LD50 (median dose)
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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).
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Nonivamide | |
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Heat | Above 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.
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]