Spilanthol
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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
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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). | |
Infobox references | |
Spilanthol 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]
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.
See also[]
References[]
- ^ Ramsewak, RS; Erickson, AJ; Nair, MG (1999). "Bioactive N-isobutylamides from the flower buds of Spilanthes acmella". Phytochemistry. 51 (6): 729–32. doi:10.1016/S0031-9422(99)00101-6. PMID 10389272.
- ^ Spelman, Kevin; Depoix, Delphine; McCray, Megan; Mouray, Elisabeth; Grellier, Philippe (2011). "The Traditional Medicine Spilanthes acmella, and the Alkylamides Spilanthol and Undeca-2E-ene-8,10-diynoic Acid Isobutylamide, Demonstrate in Vitro and in Vivo Antimalarial Activity". Phytotherapy Research. 25 (7): 1098–101. doi:10.1002/ptr.3395. PMC 3374932. PMID 22692989.
- ^ Boonen, Jente; Baert, Bram; Roche, Nathalie; Burvenich, Christian; De Spiegeleer, Bart (2010). "Transdermal behaviour of the N-alkylamide spilanthol (affinin) from Spilanthes acmella (Compositae) extracts". Journal of Ethnopharmacology. 127 (1): 77–84. doi:10.1016/j.jep.2009.09.046. PMID 19808085.
- ^ Boonen, Jente; Baert, Bram; Burvenich, Christian; Bondeel, Phillip; De Saeger, Sarah; De Spiegeleer, Bart (2010). "LC-MS profiling of N-alkylamides in Spilanthes acmella extract and the transmucosal behaviour of its main bio-active spilanthol". Journal of Pharmaceutical and Biomedical Analysis. 53 (3): 243–249. doi:10.1016/j.jpba.2010.02.010. PMID 20227845.
Categories:
- Fatty acid amides
- Local anesthetics
- Organic compound stubs