nonivamide

{{chembox

|Verifiedfields = changed

|Watchedfields = changed

|verifiedrevid = 444309931

|ImageFile = nonivamide.svg

|ImageSize = 250px

|PIN = N-[(4-Hydroxy-3-methoxyphenyl)methyl]nonanamide

|OtherNames = Pseudocapsaicin; Vanillyl-N-nonylamide; Vanillylamide of n-nonanoic acid; VNA; Nonylic acid vanillyl amide; Pelargonic acid vanillylamide (PAVA); Pelargonyl vanillyl amide

|Section1={{Chembox Identifiers

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = S846B891OR

|CASNo_Ref = {{cascite|correct|??}}

|CASNo = 2444-46-4

|PubChem = 2998

|EINECS = 219-46-4

|KEGG_Ref = {{keggcite|correct|kegg}}

|KEGG = D08282

|ChEBI_Ref = {{ebicite|changed|EBI}}

|ChEBI = 46936

|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

|ChemSpiderID = 2891

|SMILES = CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC

|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)

|InChIKey = RGOVYLWUIBMPGK-UHFFFAOYAC

|StdInChI_Ref = {{stdinchicite|changed|chemspider}}

|StdInChI = 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)

|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

|StdInChIKey = RGOVYLWUIBMPGK-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

|C=17 | H=27 | N=1 | O=3

|Appearance = White to off-white powder

|Odor = Pungent

|Density = 1.10 g/cm³

|MeltingPtC = 54

|Solubility = Insoluble

|SolubleOther = Soluble in methanol

}}

|Section3={{Chembox Hazards

|FlashPtC = 190

|FlashPt_notes = (closed cup)

|AutoignitionPtC = 330

|AutoignitionPt_notes =

|LD50 = 511 mg/kg (rat, oral)

}}

}}

{{Infobox pepper

|heat = Above peak

|scoville = 9,200,000{{cite journal | vauthors = Govindarajan, Sathyanarayana | date = 1991 | title = Capsicum — Production, Technology, Chemistry, and Quality. Part V. Impact on Physiology, Pharmacology, Nutrition, and Metabolism; Structure, Pungency, Pain, and Desensitization Sequences | journal = Critical Reviews in Food Science and Nutrition | volume = 29 | issue = 6 | pages = 435–474 | doi=10.1080/10408399109527536 | pmid = 2039598}}

}}

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,{{cite journal | author = Howard L. Constant, Geoffrey A. Cordell and Dennis P. West |title = Nonivamide, a Constituent of Capsicum oleoresin |journal = J. Nat. Prod. | date = 1996 | volume = 59 | issue = 4 | pages = 425–426 | doi = 10.1021/np9600816}} 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).http://www.aversiontech.com/hot-and-spicy/nonivamide-pava/Retrieved 16 July 2010 {{Webarchive|url=https://web.archive.org/web/20151231223740/http://www.aversiontech.com/hot-and-spicy/nonivamide-pava/ |date=31 December 2015 }} 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.{{cite journal | doi = 10.1039/C4FO00435C | title = Capsaicin, nonivamide and trans-pellitorine decrease free fatty acid uptake without TRPV1 activation and increase acetyl-coenzyme a synthetase activity in Caco-2 cells | journal = Food & Function | volume = 6 | pages = 172–184 | year = 2015 | last1 = Rohm | first1 = Barbara | last2 = Riedel | first2 = Annett | last3 = Ley | first3 = Jakob P | last4 = Widder | first4 = Sabine | last5 = Krammer | first5 = Gerhard E | last6 = Somoza | first6 = Veronika | issue = 1 | pmid = 25422952 | url = http://phaidra.univie.ac.at/o:475368 | doi-access = free}}

Nonivamide is used (under the name PAVA) as the payload in "less-lethal munitions" such as the FN Herstal's FN 303 projectiles{{cite web|title=The FN 303 Less Lethal Launcher|url=http://www.fnhusa.com/r/training/training_faq_tabs/303-launcher|url-status=dead|archive-url=https://web.archive.org/web/20130504083508/http://www.fnhusa.com/r/training/training_faq_tabs/303-launcher/|archive-date=2013-05-04|access-date=2013-04-14}} or as the active ingredient in most pepper sprays, which may be used as a chemical weapon.{{cite journal |last1=Haar |first1=Rohini J. |last2=Iacopino |first2=Vincent |last3=Ranadive |first3=Nikhil |last4=Weiser |first4=Sheri D. |last5=Dandu |first5=Madhavi |title=Health impacts of chemical irritants used for crowd control: a systematic review of the injuries and deaths caused by tear gas and pepper spray |journal=BMC Public Health |date=19 October 2017 |volume=17 |issue=1 |page=831 |doi=10.1186/s12889-017-4814-6 |pmid=29052530 |pmc=5649076 |doi-access=free }} 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. 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.