Spilanthol

Spilanthol
Names
	IUPAC name (2E,6Z,8E)-N-Isobutyl-2,6,8-decatrienamide
	Other names Affinin
Identifiers
CAS Number	25394-57-4;
3D model (JSmol)	Interactive image;
ChemSpider	4509783;
PubChem CID	5353001;
	InChI InChI=1S/C14H23NO/c1-4-5-6-7-8-9-10-11-14(16)15-12-13(2)3/h4-7,10-11,13H,8-9,12H2,1-3H3,(H,15,16)/b5-4+,7-6-,11-10+ Key: BXOCHUWSGYYSFW-HVWOQQCMSA-N; InChI=1/C14H23NO/c1-4-5-6-7-8-9-10-11-14(16)15-12-13(2)3/h4-7,10-11,13H,8-9,12H2,1-3H3,(H,15,16)/b5-4+,7-6-,11-10+ Key: BXOCHUWSGYYSFW-HVWOQQCMBC;
	SMILES O=C(/C=C/CC/C=C\C=C\C)NCC(C)C;
Properties
Chemical formula	C14H23NO
Molar mass	221.34 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.

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.

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[1] 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.

[2] 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.

[3] 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.

[4] 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.