Nonivamide

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.

Quick facts Names, Identifiers ...

Nonivamide

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
CAS Number	2444-46-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:46936 N
ChemSpider	2891 N
ECHA InfoCard	100.017.713
EC Number	219-46-4
KEGG	D08282 Y
PubChem CID	2998
UNII	S846B891OR Y
CompTox Dashboard (EPA)	DTXSID1034769
InChI 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) N Key: RGOVYLWUIBMPGK-UHFFFAOYSA-N N 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
SMILES CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
Properties
Chemical formula	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)
Solubility in water	Insoluble
Solubility	Soluble in methanol
Hazards
Flash point	190 °C (374 °F; 463 K) (closed cup)
Autoignition temperature	330 °C (626 °F; 603 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	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). N verify (what is YN ?) Infobox references

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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]