Icaridin - Wikipedia

Icaridin, also known as picaridin, is an insect repellent which can be used directly on skin or clothing. ... It has broad efficacy against various insects such ... Icaridin FromWikipedia,thefreeencyclopedia Jumptonavigation Jumptosearch NottobeconfusedwithIcariin. Icaridin Names IUPACname 1-(1-Methylpropoxycarbonyl)-2-(2-hydroxyethyl)piperidine2-(2-Hydroxyethyl)-1-piperidinecarboxylicacid1-methylpropylester Othernames KBR3023Hydroxyethylisobutylpiperidinecarboxylatesec-Butyl2-(2-hydroxyethyl)piperidine-1-carboxylate Identifiers CASNumber 119515-38-7 Y 3Dmodel(JSmol) Interactiveimage ChEMBL ChEMBL2104314 N ChemSpider 111359 Y ECHAInfoCard 100.102.177 PubChemCID 125098 UNII N51GQX0837 Y CompToxDashboard(EPA) DTXSID0034227 InChI InChI=1S/C12H23NO3/c1-3-10(2)16-12(15)13-8-5-4-6-11(13)7-9-14/h10-11,14H,3-9H2,1-2H3 YKey: QLHULAHOXSSASE-UHFFFAOYSA-N YInChI=1/C12H23NO3/c1-3-10(2)16-12(15)13-8-5-4-6-11(13)7-9-14/h10-11,14H,3-9H2,1-2H3Key: QLHULAHOXSSASE-UHFFFAOYAQ SMILES O=C(OC(C)CC)N1C(CCO)CCCC1 Properties Chemicalformula C12H23NO3 Molarmass 229.320 g·mol−1 Appearance colorlessliquid Odor odorless Density 1.07g/cm3 Meltingpoint −170 °C(−274 °F;103 K) Boilingpoint 296 °C(565 °F;569 K) Solubilityinwater 0.82g/100mL Solubility 752g/100mL(acetone) Refractiveindex(nD) 1.4717 Exceptwhereotherwisenoted,dataaregivenformaterialsintheirstandardstate(at25 °C[77 °F],100 kPa). N verify (whatis YN ?) Infoboxreferences Chemicalcompound Icaridin,alsoknownaspicaridin,isaninsectrepellentwhichcanbeuseddirectlyonskinorclothing.[1]Ithasbroadefficacyagainstvariousinsectssuchasmosquitos,ticks,gnats,fliesandfleas,andisalmostcolorlessandodorless.Astudyperformedin2010showedthatpicaridinsprayandcreamatthe20%concentrationprovided12hoursofprotectionagainstticks.[2]Icaridindoesnotdissolveplastics,syntheticsorsealants.[3] ThenamepicaridinwasproposedasanInternationalNonproprietaryName(INN)totheWorldHealthOrganization(WHO),buttheofficialnamethathasbeenapprovedbytheWHOisicaridin.Thechemicalispartofthepiperidinefamily,[1]alongwithmanypharmaceuticalsandalkaloidssuchaspiperine,whichgivesblackpepperitsspicytaste. TradenamesincludeBayrepelandSaltidinamongothers.ThecompoundwasdevelopedbytheGermanchemicalcompanyBayerandwasgiventhenameBayrepel.In2005,LanxessAGanditssubsidiarySaltigoGmbHwerespunofffromBayer[4]andtheproductwasrenamedSaltidinin2008.[5] On23July2020,icaridinwasapprovedagainbytheEUCommissionforuseinrepellentproducts.Theapprovalenteredintoforceon1February2022andisvalidfortenyears.[6] Contents 1Effectiveness 2Larvalsalamandertoxicity 3Chemistry 4Commercialproducts 5Mechanism 6Seealso 7References 8Externallinks Effectiveness[edit] IcaridinhasbeenreportedtobeaseffectiveasDEETwithouttheirritationassociatedwithDEET.[7]AccordingtotheWHO,icaridin“demonstratesexcellentrepellentpropertiescomparableto,andoftensuperiorto,thoseofthestandardDEET.”IntheUnitedStates,theCentersforDiseaseControlandPreventionrecommendsusingrepellentsbasedonicaridin,DEET,ethylbutylacetylaminopropionate(IR3535),oroiloflemoneucalyptus(containingp-menthane-3,8-diol,PMD)foreffectiveprotectionagainstmosquitoesthatcarrytheWestNilevirus,easternequineencephalitisandotherillnesses.[8] Icaridin-basedproducts,firstusedinEuropein2001,havebeenevaluatedbyConsumerReportsin2016asamongthemosteffectiveinsectrepellentswhenusedata20%concentration.[9]IcaridinwasearlierreportedtobeeffectivebyConsumerReports(7%solution)[10]andtheAustralianArmy(20%solution).[11]ConsumerReportsretestsin2006gaveasresultthata7%solutionoficaridinofferedlittleornoprotectionagainstAedesmosquitoes(vectorofdenguefever)andaprotectiontimeofabout2.5hoursagainstCulex(vectorofWestNilevirus),whilea15%solutionwasgoodforaboutonehouragainstAedesand4.8hoursagainstCulex.[12] Larvalsalamandertoxicity[edit] A2018studyfoundthatacommercialrepellentproductcontaining20%icaridin,inwhattheauthorsdescribedas"conservativeexposuredoses",ishighlytoxictosalamanderlarvae.[13] Sinceonlytheicaridincontentofthetestedrepellentproductisknown,theobservedeffectscannotbereadilyattributedtoicaridin.Furthermore,theeffectsoftherepellentproductshowednodose-responserelationship,i.e.,therewasneitheranincreaseofthemagnitudeorseverityoftheobservedeffects(mortality,taildeformation),nordidtheeffectsoccuratearliertimepoints.ThestudyhasbeenregardedasinvalidbytheDanishEnvironmentalProtectionAgency,[14][15]whichhasevaluatedicaridinpriortoitsapprovalundertheEUBiocidalProductRegulation.Thereasonsforrejectionwerethetestingofamixtureofundisclosedcomposition,theuseofanon-standardtestorganism,thelackofanalyticalverificationofactualtestconcentrations,andthefactthatthetestsolutionwasneverrenewedwiththe25daysofstudyduration. Thestudyobservedhighlarvalsalamandermortalityoccurringdelayedafterthefourdaysofexposure.BecausethewidelyusedLC50testforassessingachemical'senvironmentaltoxicityisbasedonmortalitywithinfourdays,theauthorssuggestedthaticaridinwouldbeincorrectlydeemedas"safe"underthetestprotocol.[16]However,icaridinwasalsonon-toxicina21-dayreproductiontestonthewaterfleaDaphniamagna[17]anda32-dayearlylife-stagetestinzebrafish.[18] Chemistry[edit] Stereoisomersoficaridin Icaridincontainstwostereocenters:onewherethehydroxyethylchainattachestothering,andonewherethesec-butylattachestotheoxygenofthecarbamate.Thecommercialmaterialcontainsamixtureofallfourstereoisomers. Commercialproducts[edit] CommercialproductscontainingicaridinincludeCutterAdvanced,SkinSoSoftBugGuardPlus,Off!FamilyCare,Autan,Smidge,PiActiveandMOK.O.[19] Mechanism[edit] Apotentialodorantreceptorforicaridin(andDEET),theCquiOR136•CquiOrco,hasbeensuggestedrecentlyforCulexquinquefasciatusmosquito.[20] RecentcrystalandsolutionstudiesshowedthaticaridinbindstoAnophelesgambiaeodorantbindingprotein1(AgamOBP1).ThecrystalstructureofAgamOBP1•icaridincomplex(PDB:5EL2)revealedthaticaridinbindstotheDEET-bindingsiteintwodistinctorientationsandalsotoasecondbindingsite(sIC-bindingsite)locatedattheC-terminalregionoftheAgamOBP1.[21] RecentevidencewithAnophelesgambiaemosquitoessuggestsicaridindoesnotstronglyactivateolfactoryreceptorsneurons,butinsteadfunctionstoreducethevolatilityoftheodorantstowhichitismixed.[22]Byreducingodorvolatility,icaridinfunctionsto"mask"theabilityofvolatileodorantsontheskintoactivateolfactoryneuronsandattractmosquitoes.[22] Seealso[edit] SS220,anothersubstituted-piperidineinsectrepellent References[edit] ^ab"Picaridin".npic.orst.edu.Retrieved2020-03-29. ^https://archive.epa.gov/hsrb/web/pdf/2a_lnx003_primary_report_mrid_480538011.pdf[bareURLPDF] ^Picaridin.ArchivedfromtheoriginalonAugust9,2011. ^"BayerCompletesSpinOffofLanxessAG".31January2005. ^Saltigorenamesinsectrepellant,Chemical&EngineeringNews ^"CommissionImplementingRegulation(EU)2020/1086of23July2020approvingicaridinasanexistingactivesubstanceforuseinbiocidalproductsofproduct-type19".Retrieved31August2020. ^JournalofDrugsinDermatology(Jan-Feb2004)http://jddonline.com/articles/dermatology/S1545961604P0059X/1 ^"Traveler'sHealth:Avoidbugbites".CentersforDiseaseControlandPrevention. ^"MosquitoRepellentsThatBestProtectAgainstZika".ConsumerReports,April,2016. ^-ConsumerReportsConfirmsEffectivenessOfNewAlternativeToDeet(linkrecreatedfromWaybackMachineInternetArchive-19May2019) ^Frances,S.P.;Waterson,D.G.E.;Beebe,N.W.;Cooper,R.D.(2004)."FieldEvaluationofRepellentFormulationsContainingDeetandPicaridinAgainstMosquitoesinNorthernTerritory,Australia".JournalofMedicalEntomology.41(3):414–7.doi:10.1603/0022-2585-41.3.414.PMID 15185943. ^"Insectrepellents:whichkeepbugsatbay?"ConsumerReports,June2006,vol71(issue6),p. 6. ^Almeida,Rafael;Han,Barbara;Reisinger,Alexander;Kagemann,Catherine;Rosi,Emma(1October2018)."Highmortalityinaquaticpredatorsofmosquitolarvaecausedbyexposuretoinsectrepellent".BiologyLetters.14(10):20180526.doi:10.1098/rsbl.2018.0526.PMC 6227861.PMID 30381452. ^"ECHA-Informationonbiocides".echa.europa.eu.p. 3.Retrieved2020-08-31. ^"OpinionontheapplicationforapprovaloftheactivesubstanceIcaridin,Producttype:19".10December2019.Retrieved31August2020. ^"Widelyusedmosquitorepellentproveslethaltolarvalsalamanders".ScienceNews.ScienceDaily.CaryInstituteofEcosystemStudies.31October2018.Retrieved12December2018. ^"ECHA-Informationonbiocides".pp. 231–245.Retrieved31August2020. ^"ECHA-Informationonbiocides".pp. 220–229.Retrieved31August2020. ^Cha,ArianaEunjung."ZikavirusFAQ:Whatisit,andwhataretherisksasitspreads?TheWashingtonPost.January21,2016. ^Xu,Pingxi;Choo,Young-Moo;delaRosa,Alyssa;Leal,WalterS.(2014)."MosquitoodorantreceptorforDEETandmethyljasmonate".ProceedingsoftheNationalAcademyofSciences.111(46):16592–16597.Bibcode:2014PNAS..11116592X.doi:10.1073/pnas.1417244111.PMC 4246313.PMID 25349401. ^Drakou,CE;Tsitsanou,KE;Potamitis,C;Fessas,D;Zervou,M;Zographos,SE(2017)."ThecrystalstructureoftheAgamOBP1•Icaridincomplexrevealsalternativebindingmodesandstereo-selectiverepellentrecognition".CellularandMolecularLifeSciences.74(2):319–338.doi:10.1007/s00018-016-2335-6.PMID 27535661.S2CID 12211128. ^abAfify,Ali;Betz,JoshuaF.;Riabinina,Olena;Lahondère,Chloé;Potter,ChristopherJ.(2019)."CommonlyUsedInsectRepellentsHideHumanOdorsfromAnophelesMosquitoes".CurrentBiology.29(21):3669–3680.e5.doi:10.1016/j.cub.2019.09.007.PMC 6832857.PMID 31630950. Externallinks[edit] PicaridinGeneralFactSheet-NationalPesticideInformationCenter ChoosingandUsingInsectRepellents-NationalPesticideInformationCenter EPAfactsheet Retrievedfrom"https://en.wikipedia.org/w/index.php?title=Icaridin&oldid=1096142164" Categories:HouseholdchemicalsInsectrepellentsCarbamatesPiperidinesPrimaryalcoholsHiddencategories:AllarticleswithbareURLsforcitationsArticleswithbareURLsforcitationsfromMarch2022ArticleswithPDFformatbareURLsforcitationsArticleswithoutKEGGsourceArticleswithchangedEBIidentifierECHAInfoCardIDfromWikidataPagesusingcollapsiblelistwithbothbackgroundandtext-alignintitlestyleArticlescontainingunverifiedchemicalinfoboxesArticleswithshortdescriptionShortdescriptionisdifferentfromWikidata Navigationmenu Personaltools NotloggedinTalkContributionsCreateaccountLogin Namespaces ArticleTalk English Views ReadEditViewhistory More Search Navigation MainpageContentsCurrenteventsRandomarticleAboutWikipediaContactusDonate Contribute HelpLearntoeditCommunityportalRecentchangesUploadfile Tools WhatlinkshereRelatedchangesUploadfileSpecialpagesPermanentlinkPageinformationCitethispageWikidataitem Print/export DownloadasPDFPrintableversion Inotherprojects WikimediaCommons Languages العربيةتۆرکجهDeutschEspañolفارسیFrançaisItaliano日本語PortuguêsСрпски/srpskiSrpskohrvatski/српскохрватскиSuomi中文 Editlinks