Nonivamide , also called pelargonic acid vanillamide or VAPK, is an organic compound and capsaicinoid (an analog of capsaicin ). An amide of pelargonic acid ( n- nonanoic acid) and vanilla amine. Present in chili peppers [1] , but is usually produced synthetically. Nonivamide is more thermostable than capsaicin.
| Nonivamide | |
|---|---|
 | |
| General | |
| Systematic name | N - [(4-hydroxy-3-methoxyphenyl) methyl] nonanamide |
| Chem. formula | C 17 H 27 N O 3 |
| Physical properties | |
| condition | white or off-white powder |
| Molar mass | 293.41 g / mol |
| Density | 1.10 g / cm³ |
| Thermal properties | |
| T. melt. | 57–61 ° C |
| T. Kip. ' | 492.7 ° C at 760 mm Hg. Art. |
| T. aux. | 251.8 ° C |
| T. svpl. | 330 ° C |
| Steam pressure | 10 mmHg Art. at 25 ° C |
| Chemical properties | |
| Solubility in water | insoluble |
| Solubility in methanol | Yes |
| Optical properties | |
| Refractive index | 1,513 |
| Classification | |
| Reg. CAS number | |
| PubChem | |
| Reg. EINECS number | |
| Smiles | |
| Inchi | |
| Reg. EC number | 219-46-4 |
| RTECS | RA5955000 |
| Chebi | CHEBI: 46936 |
| UN number | 2811 |
| ChemSpider | |
| Security | |
| LD 50 | 511 mg / kg ( rat , oral ) 1000 mg / kg ( rabbit , dermal ) |
| Toxicity | irritant |
| R phrases | R25 , R36 / 37/38 , R41 |
| S-phrases | S26 , S45 |
| H phrases | H315 , H317 , H319 , H335 |
| P-phrases | P261 , P280 , P305 + P351 + P338 |
| NFPA 704 |  one 3 0 |
Other names:
- pseudocapsaicin
- vanilla N- nonylamide
- Nonyl Acid Vanilla
- pelargonic acid vanillamide (VAPK)
- pelargonyl vanillamide
Application
Nonivamide is used together with nicoboxyl as active substances in ointments under the brand name Finalgon, which is used to relieve arthritis and muscle pain. A small drop of ointment is applied to the skin, quickly absorbed, causing heat, and relieves pain for several hours.
Nonivamide is used as a food supplement to add pungency to seasonings , flavors, and spice mixtures. It is also used in the confectionery industry to create a sensation of pungency, and in the pharmaceutical industry as a cheap alternative to capsaicin.
Like capsaicin, it can deter mammals (but not birds or insects that seem to be immune to it) from plant pests or seeds. This is consistent with the role of nonivamide as an ion channel agonist of . Mammalian TRPV1 is activated by heat and capsaicin, but birds are insensitive to capsaicin [2] .
Nonivamide is used (called VAPK) as a payload in “non-lethal equipment” , such as FN 303 from FN Herstal [3] , or as an active ingredient in most pepper cans [2] - both uses are temporary incapacitate people who can either be detained or refrain from acts of violence against law enforcement agencies or third parties (for example, riots or other situations / groups of violence).
Takes fifth place on the Scovilla burning scale from 9.200.000ECU .
Notes
- ↑ Howard L. Constant, Geoffrey A. Cordell, and Dennis P. West. Nonivamide, a Constituent of Capsicum oleoresin (English) // J. Nat. Prod .. - 1996. - T. 59 , No. 4 . - S. 425-426 . - DOI : 10.1021 / np9600816 .
- ↑ 1 2 nonivamide (synthetic capsaicin) Archived December 31, 2015. - aversiontech.com
- ↑ FN 303® System on fnamerica.com