Icaridin
Encyclopedia
Icaridin, also known as picaridine, 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 and the product was renamed Saltidin in 2008.
without the irritation associated with DEET. 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 (which may require more applications), for effective protection against mosquito
es that carry the West Nile virus
, Eastern Equine Encephalitis and other illnesses.
Unlike DEET, icaridin does not dissolve plastics.
Picaridin, first used in Europe in 2001, has been reported to be effective by Consumer Reports
(7% solution) and the Australian Army (20% solution). Consumer Reports retests in 2006 gave as result that a 7% solution of picaridin 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. Natrapel 8 hour is a 20% based picaridin repellent that claims to be effective for 8 hours.
ester, not an isobutyl ester. Icaridin contains the substructure R2N-C(=O)-O-R, formally making it a substituted carbamate
. Icaridin is a 1:1-mixture of the two racemic diastereomer
s
Thus, icaridin is in fact a mixture of four isomeric compounds.
INCI
The International Nomenclature of Cosmetic Ingredients, abbreviated INCI, is a system of names for waxes, oils, pigments, chemicals, and other ingredients of soaps, cosmetics, and the like, based on scientific names and other Latin and English words...
name hydroxyethyl isobutyl piperidine carboxylate, and the trade names Bayrepel and Saltidin, is an insect repellent
Insect repellent
An insect repellent is a substance applied to skin, clothing, or other surfaces which discourages insects from landing or climbing on that surface. There are also insect repellent products available based on sound production, particularly ultrasound...
. It has broad efficacy against different insects and is almost colorless and odorless.
The name picaridin was proposed as an International Nonproprietary Name
International Nonproprietary Name
An International Nonproprietary Name is the official nonproprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization...
(INN) to the World Health Organization
World Health Organization
The World Health Organization is a specialized agency of the United Nations that acts as a coordinating authority on international public health. Established on 7 April 1948, with headquarters in Geneva, Switzerland, the agency inherited the mandate and resources of its predecessor, the Health...
(WHO), but the official name that has been approved by the WHO
Who
Who may refer to:* Who , an English-language pronoun* who , a Unix command* Who?, one of the Five Ws in journalism- Art and entertainment :* Who? , a 1958 novel by Algis Budrys...
is icaridin. The compound was developed by the German chemical company Bayer
Bayer
Bayer AG is a chemical and pharmaceutical company founded in Barmen , Germany in 1863. It is headquartered in Leverkusen, North Rhine-Westphalia, Germany and well known for its original brand of aspirin.-History:...
and was given the name Bayrepel. In 2005, Lanxess AG and its subsidiary Saltigo GmbH were spun off from Bayer and the product was renamed Saltidin in 2008.
Empirical findings
Icaridin has been reported to be as effective as DEETDEET
N,N-Diethyl-meta-toluamide, abbreviated DEET, is a slightly yellow oil. It is the most common active ingredient in insect repellents...
without the irritation associated with DEET. 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
Centers for Disease Control and Prevention
The Centers for Disease Control and Prevention are a United States federal agency under the Department of Health and Human Services headquartered in Druid Hills, unincorporated DeKalb County, Georgia, in Greater Atlanta...
recommends using repellents based on icaridin, DEET, or oil of lemon eucalyptus (which may require more applications), for effective protection against mosquito
Mosquito
Mosquitoes are members of a family of nematocerid flies: the Culicidae . The word Mosquito is from the Spanish and Portuguese for little fly...
es that carry the West Nile virus
West Nile virus
West Nile virus is a virus of the family Flaviviridae. Part of the Japanese encephalitis antigenic complex of viruses, it is found in both tropical and temperate regions. It mainly infects birds, but is known to infect humans, horses, dogs, cats, bats, chipmunks, skunks, squirrels, domestic...
, Eastern Equine Encephalitis and other illnesses.
Unlike DEET, icaridin does not dissolve plastics.
Picaridin, first used in Europe in 2001, has been reported to be effective by Consumer Reports
Consumer Reports
Consumer Reports is an American magazine published monthly by Consumers Union since 1936. It publishes reviews and comparisons of consumer products and services based on reporting and results from its in-house testing laboratory. It also publishes cleaning and general buying guides...
(7% solution) and the Australian Army (20% solution). Consumer Reports retests in 2006 gave as result that a 7% solution of picaridin offered little or no protection against Aedes
Aedes
Aedes is a genus of mosquito originally found in tropical and subtropical zones, but now found on all continents excluding Antarctica. Some species have been spread by human activity. Aedes albopictus, a most invasive species was recently spread to the New World, including the U.S., by the used...
mosquitoes (vector of dengue fever
Dengue fever
Dengue fever , also known as breakbone fever, is an infectious tropical disease caused by the dengue virus. Symptoms include fever, headache, muscle and joint pains, and a characteristic skin rash that is similar to measles...
) and a protection time of about 2.5 hours against Culex
Culex
Culex is a genus of mosquito, and is important in that several species serve as vectors of important diseases, such as West Nile virus, filariasis, Japanese encephalitis, St. Louis encephalitis and avian malaria....
(vector of West Nile virus), while a 15% solution was good for about one hour against Aedes and 4.8 hours against Culex. Natrapel 8 hour is a 20% based picaridin repellent that claims to be effective for 8 hours.
Chemistry
The INCI name for icaridin is hydroxyethyl isobutyl piperidine carboxylate. This chemical name is wrong as icaridin is an sec-butylButyl
In organic chemistry, butyl is a four-carbon alkyl radical or substituent group with general chemical formula -C4H9, derived from either of the two isomers of butane....
ester, not an isobutyl ester. Icaridin contains the substructure R2N-C(=O)-O-R, formally making it a substituted carbamate
Carbamate
Carbamates are organic compounds derived from carbamic acid . A carbamate group, carbamate ester, and carbamic acids are functional groups that are inter-related structurally and often are interconverted chemically. Carbamate esters are also called urethanes.-Synthesis:Carbamic acids are derived...
. Icaridin is a 1:1-mixture of the two racemic diastereomer
Diastereomer
Diastereomers are stereoisomers that are not enantiomers.Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more of the equivalent stereocenters and are not mirror images of each other.When two diastereoisomers differ from each other at...
s
- (R,R)-isomer and its enantiomerEnantiomerIn chemistry, an enantiomer is one of two stereoisomers that are mirror images of each other that are non-superposable , much as one's left and right hands are the same except for opposite orientation. It can be clearly understood if you try to place your hands one over the other without...
(S,S)-isomer - (R,S)-isomer and its enantiomer (S,R)-isomer
Thus, icaridin is in fact a mixture of four isomeric compounds.