# Vanilloid

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The **vanilloids** are compounds which possess a [vanillyl group](/source/Vanillyl_group). They include [vanillyl alcohol](/source/Vanillyl_alcohol), [vanillin](/source/Vanillin), [vanillic acid](/source/Vanillic_acid), [acetovanillon](/source/Acetovanillon), [vanillylmandelic acid](/source/Vanillylmandelic_acid), [homovanillic acid](/source/Homovanillic_acid), [capsaicin](/source/Capsaicin), etc. Isomers are the [isovanilloids](/source/Isovanilloids).

- {| class="wikitable" style="text-align:center; font-size:90%"

|- | || || || || || |- | vanillyl alcohol || vanillin || vanillic acid || acetovanillon || [Vanillylamine](/source/Vanillylamine) || [Capsaicin](/source/Capsaicin) |}

A number of vanilloids, most notably capsaicin, bind to the [transient receptor potential vanilloid type 1](/source/TRPV1) (TRPV1) receptor, an [ion channel](/source/Ion_channel) which naturally responds to noxious stimuli such as high temperatures and acidic [pH](/source/PH).[1] This action is responsible for the burning sensation experienced after eating [spicy peppers](/source/Capsicum). Endogenously generated chemicals that trigger the TRPV1 channel of the vanilloids class are referred to as **endovanilloids**[2] including [anandamide](/source/Anandamide), [20-hydroxyeicosatetraenoic acid](/source/20-hydroxyeicosatetraenoic_acid) (20-HETE),[3] [N-arachidonoyl dopamine](/source/N-arachidonoyl_dopamine) (NADA) and N-oleoyl-dopamine ().[4]

[Fatty acid amide hydrolase](/source/Fatty-acid_amide_hydrolase_1) (FAAH), is a crucial [enzyme](/source/Enzyme) for endovanilloid, and the [*N*-acylethanolamines](/source/N-Acylethanolamine) (NAEs), [catabolism](/source/Catabolism) at TRPV1, and other [cannabinoid receptors](/source/Cannabinoid_receptor).[5]

- {| class="wikitable" style="text-align:center; font-size:90%"

|- | |- | [Anandamide](/source/Anandamide) |} Outside the food industry vanilloids such as [nonivamide](/source/Nonivamide) are used commercially in [pepper spray](/source/Pepper_spray) formulations.

Other vanilloids which act at TRPV1 include [resiniferatoxin](/source/Resiniferatoxin) and [olvanil](/source/Olvanil).[6]

## References

1. Pingle, SC; Matta, JA; Ahern, GP (2007). *Capsaicin receptor: TRPV1 a promiscuous TRP channel*. Vol. 179, no. 179. Handbook of Experimental Pharmacology. pp. 155–171. [doi:10.1007/978-3-540-34891-7_9](https://doi.org/10.1007/978-3-540-34891-7_9). ISBN 978-3-540-34889-4. [PMID 17217056](https://pubmed.ncbi.nlm.nih.gov/17217056)

1. Van Der Stelt M, Di Marzo V (2004). "Endovanilloids. Putative endogenous ligands of transient receptor potential vanilloid 1 channels.". *Eur J Biochem*. **271** (10): 1827–34. [doi:10.1111/j.1432-1033.2004.04081.x](https://doi.org/10.1111/j.1432-1033.2004.04081.x). [PMID 15128293](https://pubmed.ncbi.nlm.nih.gov/15128293)

1. Hamers A, Primus CP, Whitear C, Kumar NA, Masucci M, Montalvo Moreira SA et al. (2022). "20-hydroxyeicosatetraenoic acid (20-HETE) is a pivotal endogenous ligand for TRPV1-mediated neurogenic inflammation in the skin.". *Br J Pharmacol*. **179** (7): 1450–1469. [doi:10.1111/bph.15726](https://doi.org/10.1111/bph.15726). [PMID 34755897](https://pubmed.ncbi.nlm.nih.gov/34755897). [S2CID 243939400](https://api.semanticscholar.org/CorpusID:243939400)

1. De Petrocellis L, Chu CJ, Moriello AS, Kellner JC, Walker JM, Di Marzo V (2004). "Actions of two naturally occurring saturated N-acyldopamines on transient receptor potential vanilloid 1 (TRPV1) channels.". *Br J Pharmacol*. **143** (2): 251–6. [doi:10.1038/sj.bjp.0705924](https://doi.org/10.1038/sj.bjp.0705924). [PMC 1575334](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1575334). [PMID 15289293](https://pubmed.ncbi.nlm.nih.gov/15289293)

1. Silva, M.; Martins, D.; Charrua, A.; Piscitelli, F.; Tavares, I.; Morgado, C.; Di Marzo, V. (2016-08-01). ["Endovanilloid control of pain modulation by the rostroventromedial medulla in an animal model of diabetic neuropathy"](https://www.sciencedirect.com/science/article/pii/S002839081630079X). *Neuropharmacology*. **107**: 49–57. [doi:10.1016/j.neuropharm.2016.03.007](https://doi.org/10.1016/j.neuropharm.2016.03.007). [ISSN 0028-3908](https://www.worldcat.org/issn/0028-3908). [PMID 26965218](https://pubmed.ncbi.nlm.nih.gov/26965218)

1. Carlson, Neil R. & Birkett, Melissa A. (2017). *Physiology of Behavior*. 12 ed. Pearson. p. 212. ISBN 9780134320823.

## Literature

- Lee, Jeewoo; Uk Kang, Sang; Yeon Kim, Su; Eun Kim, Sung; Joon Jo, Yeong; Kim, Sunghoon (2001). ["Vanilloid and Isovanilloid Analogues as Inhibitors of Methionyl-tRNA and Isoleucyl-tRNA Synthetases"](http://144.206.159.178/ft/116/34385/588514.pdf). *[Bioorganic & Medicinal Chemistry Letters](/source/Bioorganic_%26_Medicinal_Chemistry_Letters)*. **11** (8): 965–968. [doi:10.1016/S0960-894X(01)00096-8](https://doi.org/10.1016/S0960-894X(01)00096-8). [PMID 11327601](https://pubmed.ncbi.nlm.nih.gov/11327601)[dead link]

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Adapted from the Wikipedia article [Vanilloid](https://en.wikipedia.org/wiki/Vanilloid) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Vanilloid?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.