Icaridin

From Wikipedia, the free encyclopedia
Not to be confused with Icariin.
Icaridin
IUPAC name

1-piperidinecarboxylic acid 2-(2-hydroxyethyl)-1-­methylpropylester

Identifiers
CAS number 119515-38-7 YesY
PubChem 125098
ChemSpider 111359 YesY
Jmol-3D images Image 1
Properties
Molecular formula C12H23NO3
Molar mass 229.3 g/mol
Boiling point 296 °C; 565 °F; 569 K
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Icaridin, also known as picaridin, KBR 3023, under the INCI name hydroxyethyl isobutyl piperidine carboxylate, and the trade names Bayrepel and Saltidin, is an insect repellent. It has broad efficacy against different insects and is almost colorless and odorless.

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. 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]

Empirical findings

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, or oil of lemon eucalyptus for effective protection against mosquitoes that carry the West Nile virus, Eastern Equine Encephalitis and other illnesses.

Unlike DEET, icaridin does not dissolve plastics.[4]

Icaridin, first used in Europe in 2001, has been reported to be effective by Consumer Reports (7% solution)[5] and the Australian Army (20% solution).[6] 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.[7]

Chemistry

Stereoisomers of icaridin

The INCI name for icaridin is hydroxyethyl isobutyl piperidine carboxylate.[8] This chemical name is wrong as icaridin is an sec-butyl ester, not an isobutyl ester.[citation needed] Icaridin contains the substructure R2N-C(=O)-O-R, formally making it a substituted carbamate. Icaridin is a 1:1-mixture[8] of the two racemic diastereomers

  • (R,R)-isomer and its enantiomer (S,S)-isomer
  • (R,S)-isomer and its enantiomer (S,R)-isomer

Thus, icaridin is in fact a mixture of four isomeric compounds, each with its own unique pharmacological properties.

See also

References

  1. ↑ Bayer completes spin off of Lanxess AG
  2. ↑ C&EN News: Saltigo renames insect repellant
  3. ↑ Journal of Drugs and Dermatology (Jan-Feb 2004)
  4. ↑ Picaridin.
  5. ↑ Consumerreports.Org - Consumer Reports Confirms Effectiveness Of New Alternative To Deet
  6. ↑ http://www.bioone.org/perlserv/?request=get-document&issn=0022-2585&volume=041&issue=03&page=0414
  7. ↑ "Insect repellents: which keep bugs at bay?" Consumer Reports, June 2006, vol 71 (issue 6), p. 6.
  8. ↑ 8.0 8.1 WHO. "WHO SPECIFICATIONS AND EVALUATIONS FOR PUBLIC HEALTH PESTICIDES: ICARIDIN" (PDF) (in English). p. 18. Retrieved 2009-08-09. 

External links

This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.