Nonivamide

Source: Wikipedia, the free encyclopedia.
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
3D model (
JSmol
)
ChEBI
ChemSpider
ECHA InfoCard
 100.017.713 Edit this at Wikidata
EC Number
  • 219-46-4
KEGG
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) ☒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
  • CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
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):
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
HeatAbove peak
Scoville scale9,200,000[1] SHU

Nonivamide, also called pelargonic acid vanillylamide or PAVA, is an

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

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

References

  1. PMID 2039598
    .
  2. doi:10.1021/np9600816
    .
  3. ^ a b http://www.aversiontech.com/hot-and-spicy/nonivamide-pava/Retrieved 16 July 2010 Archived 31 December 2015 at the Wayback Machine
  4. PMID 25422952
    .
  5. ^ "The FN 303 Less Lethal Launcher". Archived from the original on 2013-05-04. Retrieved 2013-04-14.
  6. ^
    PMID 29052530
    .
  7. S2CID 12262260
    .
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