vanilloid

{{Short description|Chemical compounds containing a vanillyl group}}

The vanilloids are compounds which possess a vanillyl group. They include vanillyl alcohol, vanillin, vanillic acid, acetovanillon, vanillylmandelic acid, homovanillic acid, capsaicin, etc. Isomers are the isovanilloids.

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File:Vanillylalkohol.svg	File:Vanillin2.svg	File:Vanillinsäure.svg	File:Acetovanillone.svg	File:Vanillylamine.svg	File:kapsaicyna.svg
vanillyl alcohol	vanillin	vanillic acid	acetovanillon	Vanillylamine	Capsaicin

A number of vanilloids, most notably capsaicin, bind to the transient receptor potential vanilloid type 1 (TRPV1) receptor, an ion channel which naturally responds to noxious stimuli such as high temperatures and acidic pH.{{cite book | last1 = Pingle | first1 = SC | last2 = Matta | first2 = JA | last3 = Ahern | first3 = GP | title = Capsaicin receptor: TRPV1 a promiscuous TRP channel | volume = 179 | issue = 179 | pages = 155–171 | year = 2007 | pmid = 17217056 | doi = 10.1007/978-3-540-34891-7_9 | series = Handbook of Experimental Pharmacology | isbn = 978-3-540-34889-4 }} This action is responsible for the burning sensation experienced after eating spicy peppers. Endogenously generated chemicals that trigger the TRPV1 channel of the vanilloids class are referred to as endovanilloids{{cite journal| author=Van Der Stelt M, Di Marzo V| title=Endovanilloids. Putative endogenous ligands of transient receptor potential vanilloid 1 channels. | journal=Eur J Biochem | year= 2004 | volume= 271 | issue= 10 | pages= 1827–34 | pmid=15128293 | doi=10.1111/j.1432-1033.2004.04081.x | pmc= | doi-access=free }} including anandamide, 20-hydroxyeicosatetraenoic acid (20-HETE),{{cite journal| author=Hamers A, Primus CP, Whitear C, Kumar NA, Masucci M, Montalvo Moreira SA | display-authors=etal| title=20-hydroxyeicosatetraenoic acid (20-HETE) is a pivotal endogenous ligand for TRPV1-mediated neurogenic inflammation in the skin. | journal=Br J Pharmacol | year= 2022 | volume= 179 | issue= 7 | pages= 1450–1469 | pmid=34755897 | doi=10.1111/bph.15726 | pmc= | s2cid=243939400| doi-access=free }} N-arachidonoyl dopamine (NADA) and N-oleoyl-dopamine ({{PubChem|5282106}}).{{cite journal| author=De Petrocellis L, Chu CJ, Moriello AS, Kellner JC, Walker JM, Di Marzo V| title=Actions of two naturally occurring saturated N-acyldopamines on transient receptor potential vanilloid 1 (TRPV1) channels. | journal=Br J Pharmacol | year= 2004 | volume= 143 | issue= 2 | pages= 251–6 | pmid=15289293 | doi=10.1038/sj.bjp.0705924 | pmc=1575334 }}

Fatty acid amide hydrolase (FAAH), is a crucial enzyme for endovanilloid, and the N-acylethanolamines (NAEs), catabolism at TRPV1, and other cannabinoid receptors.{{Cite journal |last1=Silva |first1=M. |last2=Martins |first2=D. |last3=Charrua |first3=A. |last4=Piscitelli |first4=F. |last5=Tavares |first5=I. |last6=Morgado |first6=C. |last7=Di Marzo |first7=V. |date=2016-08-01 |title=Endovanilloid control of pain modulation by the rostroventromedial medulla in an animal model of diabetic neuropathy |url=https://www.sciencedirect.com/science/article/pii/S002839081630079X |journal=Neuropharmacology |language=en |volume=107 |pages=49–57 |doi=10.1016/j.neuropharm.2016.03.007 |pmid=26965218 |issn=0028-3908|url-access=subscription }}

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File:Anandamide_skeletal.svg

Anandamide

Outside the food industry vanilloids such as nonivamide are used commercially in pepper spray formulations.

Other vanilloids which act at TRPV1 include resiniferatoxin and olvanil.{{cite book|last1=Carlson|first1=Neil R.|last2=Birkett|first2=Melissa A.|title=Physiology of Behavior|date=2017|publisher=Pearson|isbn=9780134320823|page=212|edition=12}}