{{Chembox | ImageFile = Spilanthol skeletal.svg | ImageClass = skin-invert-image | ImageSize = 200px | PIN = (2''E'',6''Z'',8''E'')-''N''-(2-Methylpropyl)deca-2,6,8-trienamide | OtherNames = Affinin |Section1={{Chembox Identifiers | CASNo = 25394-57-4 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 4W9L3S4856 | PubChem = 5353001 | ChemSpiderID = 4509783 | SMILES = O=C(/C=C/CC/C=C\C=C\C)NCC(C)C | 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+ | InChIKey = BXOCHUWSGYYSFW-HVWOQQCMBC | StdInChI = 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+ | StdInChIKey = BXOCHUWSGYYSFW-HVWOQQCMSA-N }} |Section2={{Chembox Properties | C=14 | H=23 | N=1 | O=1 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Spilanthol''' (affinin) is a fatty acid amide isolated from ''Acmella oleracea''.<ref>{{Cite journal |pmid=10389272 |year=1999 |last1=Ramsewak |first1=RS |last2=Erickson |first2=AJ |last3=Nair |first3=MG |title=Bioactive N-isobutylamides from the flower buds of Spilanthes acmella |volume=51 |issue=6 |pages=729–32 |journal=Phytochemistry |doi=10.1016/S0031-9422(99)00101-6 |bibcode=1999PChem..51..729R}}</ref> It is believed to be responsible for the local anesthetic properties of the plant.<ref>{{Cite journal |doi=10.1002/ptr.3395 |title=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 |year=2011 |last1=Spelman |first1=Kevin |last2=Depoix |first2=Delphine |last3=McCray |first3=Megan |last4=Mouray |first4=Elisabeth |last5=Grellier |first5=Philippe |journal=Phytotherapy Research |volume=25 |issue=7 |pages=1098–101 |pmid=22692989 |pmc=3374932}}</ref>
Spilanthol permeates the human skin<ref>{{Cite journal |doi=10.1016/j.jep.2009.09.046 |title=Transdermal behaviour of the N-alkylamide spilanthol (affinin) from Spilanthes acmella (Compositae) extracts |year=2010 |last1=Boonen |first1=Jente |last2=Baert |first2=Bram |last3=Roche |first3=Nathalie |last4=Burvenich |first4=Christian |last5=De Spiegeleer |first5=Bart |journal=Journal of Ethnopharmacology |volume=127 |issue=1 |pages=77–84 |pmid=19808085}}</ref> and the inside lining of the cheeks in the mouth (buccal mucosa),<ref>{{Cite journal |doi=10.1016/j.jpba.2010.02.010 |title=LC-MS profiling of N-alkylamides in Spilanthes acmella extract and the transmucosal behaviour of its main bio-active spilanthol |year=2010 |last1=Boonen |first1=Jente |last2=Baert |first2=Bram |last3=Burvenich |first3=Christian |last4=Bondeel |first4=Phillip |last5=De Saeger |first5=Sarah |last6=De Spiegeleer |first6=Bart |journal=Journal of Pharmaceutical and Biomedical Analysis |volume=53 |issue=3 |pages=243–249 |pmid=20227845}}</ref> 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.<ref name=":0">{{Cite journal |last1=Bakondi |first1=Edina |last2=Singh |first2=Salam Bhopen |last3=Hajnády |first3=Zoltán |last4=Nagy-Pénzes |first4=Máté |last5=Regdon |first5=Zsolt |last6=Kovács |first6=Katalin |last7=Hegedűs |first7=Csaba |last8=Madácsy |first8=Tamara |last9=Maléth |first9=József |last10=Hegyi |first10=Péter |last11=Demény |first11=Máté Á |date=2019-09-03 |title=Spilanthol Inhibits Inflammatory Transcription Factors and iNOS Expression in Macrophages and Exerts Anti-inflammatory Effects in Dermatitis and Pancreatitis |journal=International Journal of Molecular Sciences |volume=20 |issue=17 |article-number=E4308 |doi=10.3390/ijms20174308 |issn=1422-0067 |pmc=6747447 |pmid=31484391 |doi-access=free}}</ref> 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.<ref name=":0" />
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.<ref>{{cite journal |url=https://www.thieme-connect.de/products/ejournals/abstract/10.1055/a-2244-8855 |doi=10.1055/a-2244-8855 |title=Affinin, isolated from Heliopsis longipes, induces an antihypertensive effect that involves CB1 cannabinoid receptors and TRPA1 and TRPV1 channels activation |date=2024 |last1=Luz-Martínez |first1=Beatriz A. |last2=Marrero-Morfa |first2=Dailenys |last3=Luna-Vázquez |first3=Francisco J. |last4=Rojas-Molina |first4=Alejandra |last5=Ibarra-Alvarado |first5=Cesar |journal=Planta Medica |pmid=38219731 |s2cid=266983561|url-access=subscription }}</ref>
==See also== * Hydroxy alpha sanshool
==References== {{reflist}}
Category:Fatty acid amides Category:Local anesthetics