Open main menu

Wikipedia β

Icaridin, also known as picaridin, is an insect repellent. It has broad efficacy against various insects and is almost colorless and odorless.

Icaridin
IcaridinSVG.svg
Icaridin 3d structure.png
Names
IUPAC names
1-(1-methylpropoxycarbonyl)-2-(2-hydroxyethyl)piperidine

2-(2-hydroxyethyl)-1-piperidinecarboxylic acid 1-methylpropyl ester
Other names
KBR 3023

hydroxyethyl isobutyl piperidine carboxylate

sec-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.102.177
UNII
Properties
C12H23NO3
Molar mass 229.3 g/mol
Boiling point 296 °C (565 °F; 569 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

The name picaridin was proposed as an International Nonproprietary Name (INN) to the World Health Organization (WHO), but the official name that has been approved by the WHO is icaridin.

Trade names include Bayrepel and Saltidin among others. The compound was developed by the German chemical company Bayer and was given the name Bayrepel. In 2005, Lanxess AG and its subsidiary Saltigo GmbH were spun off from Bayer[1] and the product was renamed Saltidin in 2008.[2]

Contents

EffectivenessEdit

Icaridin has been reported to be as effective as DEET without the irritation associated with DEET.[3] According to the WHO, icaridin “demonstrates excellent repellent properties comparable to, and often superior to, those of the standard DEET.” In the United States, the Centers for Disease Control and Prevention recommends using repellents based on Icaridin, DEET, IR3535, or oil of lemon eucalyptus (containing p-menthane-3,8-diol, PMD) for effective protection against mosquitoes that carry the West Nile virus, Eastern Equine Encephalitis and other illnesses.[4]

Icaridin does not dissolve plastics.[5]

Icaridin-based products, first used in Europe in 1998, and the US in 2005 have been evaluated by Consumer Reports in 2016 as among the most effective insect repellents when used at a 20% concentration.[6] Icaridin was earlier reported to be effective by Consumer Reports (7% solution)[7] and the Australian Army (20% solution).[8] Consumer Reports retests in 2006 gave as result that a 7% solution of icaridin offered little or no protection against Aedes mosquitoes (vector of dengue fever) and a protection time of about 2.5 hours against Culex (vector of West Nile virus), while a 15% solution was good for about one hour against Aedes and 4.8 hours against Culex.[9]

ChemistryEdit

 
Stereoisomers of icaridin

Icaridin contains two stereocenters: one where the hydroxyethyl chain attaches to the ring, and one where the sec-butyl attaches to the oxygen of the carbamate. The commercial material contains a mixture of all four stereoisomers.

Commercial productsEdit

Commercial products containing icaridin include Cutter Advanced, Skin So Soft Bug Guard Plus, Autan, Smidge, PiActive and MOK.O.[10]

MechanismEdit

A potential odorant receptor•co-receptor of Ιcaridin (and DEET), the CquiOR136•CquiOrco, has been suggested recently for Culex quinquefasciatus mosquito. [11]

Recent crystal and solution studies showed that Icaridin binds to Anopheles gambiae odorant binding protein 1 (AgamOBP1). The crystal structure of AgamOBP1•Icaridin complex (PDB: 5EL2) revealed that Icaridin binds to the DEET-binding site in two distinct orientations and also to a second binding site (sIC-binding site) located at the C-terminal region of the AgamOBP1.[12]

See alsoEdit

  • SS220, another substituted-piperidine insect-repellant

ReferencesEdit

  1. ^ "Bayer Completes Spin Off of Lanxess AG". 31 January 2005. 
  2. ^ Saltigo renames insect repellant, Chemical & Engineering News
  3. ^ Journal of Drugs and Dermatology (Jan-Feb 2004) http://jddonline.com/articles/dermatology/S1545961604P0059X/1
  4. ^ "Traveler's Health: Avoid bug bites". Centers for Disease Control and Prevention. 
  5. ^ Picaridin. Archived from the original on August 9, 2011.
  6. ^ "Mosquito Repellents That Best Protect Against Zika". Consumer Reports, April, 2016. 
  7. ^ Consumerreports.Org - Consumer Reports Confirms Effectiveness Of New Alternative To Deet
  8. ^ Frances, S. P.; Waterson, D. G. E.; Beebe, N. W.; Cooper, R. D. (2004). "Field Evaluation of Repellent Formulations Containing Deet and Picaridin Against Mosquitoes in Northern Territory, Australia". Journal of Medical Entomology. 41 (3): 414. PMID 15185943. doi:10.1603/0022-2585-41.3.414. 
  9. ^ "Insect repellents: which keep bugs at bay?" Consumer Reports, June 2006, vol 71 (issue 6), p. 6.
  10. ^ Cha, Ariana Eunjung. "Zika virus FAQ: What is it, and what are the risks as it spreads? The Washington Post. January 21, 2016.
  11. ^ Xu, Pingxi; Choo, Young-Moo; de la Rosa, Alyssa; Leal, Walter S. (2014). "Mosquito odorant receptor for DEET and methyl jasmonate". Proceedings of the National Academy of Sciences. 111 (46): 16592–16597. doi:10.1073/pnas.1417244111. 
  12. ^ Drakou, CE; Tsitsanou, KE; Potamitis, C; Fessas, D; Zervou, M; Zographos, SE (2017). "The crystal structure of the AgamOBP1•Icaridin complex reveals alternative binding modes and stereo-selective repellent recognition". Cellular and Molecular Life Sciences. 74 (2): 319–338. PMID 27535661. doi:10.1007/s00018-016-2335-6. 

External linksEdit