Spilanthol
Chemical compound From Wikipedia, the free encyclopedia
Chemical compound From Wikipedia, the free encyclopedia
Spilanthol (affinin) is a fatty acid amide isolated from Acmella oleracea.[1] It is believed to be responsible for the local anesthetic properties of the plant.[2]
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Names | |
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Preferred IUPAC name
(2E,6Z,8E)-N-(2-Methylpropyl)deca-2,6,8-trienamide | |
Other names
Affinin | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C14H23NO | |
Molar mass | 221.344 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Spilanthol permeates the human skin[3] and the inside lining of the cheeks in the mouth (buccal mucosa),[4] resulting in local as well as systemic pharmacological concentrations. In the skin and in the pancreas, spilanthol has also been shown to exert anti-inflammatory effects.[5] The underlying mechanism involves inhibition of nitric oxide production due to reduced expression of inducible nitric oxide synthase enzyme (iNOS) in macrophages. Transcription factor array experiments revealed that spilanthol inhibits the activation of several transcription factors (NFκB, ATF4, FOXO1, IRF1, ETS1, and AP-1) which may explain the effect of spilanthol on gene expression.[5]
The antihypertensive effect of spilanthol was blocked by CB1 antagonist rimonabant and TRPV1 antagonist capsazepine, suggesting spilanthol mediates some activity by interaction with the cannabinoid receptors and TRPV1 channels.[6]
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