Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H17NO |
Molecular Weight | 191.2695 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CC)C(=O)C1=CC(C)=CC=C1
InChI
InChIKey=MMOXZBCLCQITDF-UHFFFAOYSA-N
InChI=1S/C12H17NO/c1-4-13(5-2)12(14)11-8-6-7-10(3)9-11/h6-9H,4-5H2,1-3H3
DescriptionSources: https://www.drugs.com/mmx/diethyltoluamide.htmlCurator's Comment: description was created based on several sources, including:
https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/deet_508.pdf | https://www.epa.gov/insect-repellents/deet | http://www.swmosquito.org/pdf/PROT_DEET%20Toxicity.pdf
Sources: https://www.drugs.com/mmx/diethyltoluamide.html
Curator's Comment: description was created based on several sources, including:
https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/deet_508.pdf | https://www.epa.gov/insect-repellents/deet | http://www.swmosquito.org/pdf/PROT_DEET%20Toxicity.pdf
Diethyltoluamide (DEET) is an insect repellent used to keep insects away. This product is effective against mosquitoes, biting flies (gnats, sandflies, deer flies, stable flies, black flies), ticks, harvest mites, and fleas. DEET is absorbed through the skin. DEET has few adverse effects when applied as directed. The most common problem is local skin irritation, including erythema and pruritis, at the site of application.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: 1279770.0 Gene Symbol: OBP17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21671117 |
31.3 µM [Kd] | ||
Target ID: OR136 (Culex quinquefasciatus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25349401 |
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Target ID: Ionotropic receptor 40a (Fruit fly) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24089210 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | Unknown Approved UseDEET to protect humans from mosquito-borne illnesses like West Nile Virus, the Zika virus or malaria and tick-borne illnesses like Lyme disease and Rocky Mountain spotted fever. |
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Preventing | Unknown Approved UseDEET to protect humans from mosquito-borne illnesses like West Nile Virus, the Zika virus or malaria and tick-borne illnesses like Lyme disease and Rocky Mountain spotted fever. |
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Preventing | Unknown Approved UseDEET to protect humans from mosquito-borne illnesses like West Nile Virus, the Zika virus or malaria and tick-borne illnesses like Lyme disease and Rocky Mountain spotted fever. |
PubMed
Title | Date | PubMed |
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Chemical sensitivity in symptomatic Cambodia veterans. | 2003 Dec |
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Schistosomiasis prophylaxis in vivo using N,N-diethyl-m-toluamide (DEET). | 2003 Jul-Aug |
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Amphiphilic star-like macromolecules as novel carriers for topical delivery of nonsteroidal anti-inflammatory drugs. | 2003 Oct 16 |
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Inhibition of trans-permethrin hydrolysis in human liver fractions by chloropyrifos oxon and carbaryl. | 2004 |
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Analysis and fate of insect repellents. | 2004 |
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Protective behavior survey, West Nile virus, British Columbia. | 2004 Aug |
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A comparison of topical formulations for the prevention of human schistosomiasis. | 2004 Aug |
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Insect repellent [correction of repellant] interactions: sunscreens enhance DEET (N,N-diethyl-m-toluamide) absorption. | 2004 Aug |
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Determination of selected pharmaceuticals and caffeine in sewage and seawater from Tromsø/Norway with emphasis on ibuprofen and its metabolites. | 2004 Aug |
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Analysis and mass spectrometric characterization of the insect repellent Bayrepel and its main metabolite Bayrepel-acid. | 2004 Aug 13 |
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Effect of topical agents on cercariae of Schistosoma mansoni. | 2004 Dec |
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Acaricidal activity of Paeonia suffruticosa root bark-derived compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae). | 2004 Dec 29 |
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Repellency of aromatic medicinal plant extracts and a steam distillate to Aedes aegypti. | 2004 Jun |
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p-Anisaldehyde: acaricidal component of Pimpinella anisum seed oil against the house dust mites Dermatophagoides farinae and Dermatophagoides pteronyssinus. | 2004 Mar |
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Comparative activity of deet and AI3-37220 repellents against the ticks Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae) in laboratory bioassays. | 2004 Mar |
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DEET mosquito repellent sold through social marketing provides personal protection against malaria in an area of all-night mosquito biting and partial coverage of insecticide-treated nets: a case-control study of effectiveness. | 2004 Mar |
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DEET mosquito repellent provides personal protection against malaria: a household randomized trial in an Afghan refugee camp in Pakistan. | 2004 Mar |
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Evaluation of the sensitivity of Aedes aegypti and Anopheles gambiae complex mosquitoes to two insect repellents: DEET and KBR 3023. | 2004 Mar |
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Active ingredients in sunscreens act as topical penetration enhancers for the herbicide 2,4-dichlorophenoxyacetic acid. | 2004 Mar 15 |
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In vitro repellency of N,N-diethyl-3-methylbenzamide and N,N-diethylphenylacetamide analogs against Aedes aegypti and Anopheles stephensi (Diptera: Culicidae). | 2004 May |
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Comparative resistance of Anopheles albimanus and Aedes aegypti to N,N-diethyl-3-methylbenzamide (Deet) and 2-methylpiperidinyl-3-cyclohexen-1-carboxamide (AI3-37220) in laboratory human-volunteer repellent assays. | 2004 May |
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Field evaluation of repellent formulations containing deet and picaridin against mosquitoes in Northern Territory, Australia. | 2004 May |
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In-vitro permeation of the insect repellent N,N-diethyl-m-toluamide (DEET) and the sunscreen oxybenzone. | 2004 May |
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Repellency of aerosol and cream products containing fennel oil to mosquitoes under laboratory and field conditions. | 2004 Nov |
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Comparative efficacy of IR3535 and deet as repellents against adult Aedes aegypti and Culex quinquefasciatus. | 2004 Sep |
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Comparative study of the topical effectiveness of the Andiroba oil (Carapa guianensis) and DEET 50% as repellent for Aedes sp. | 2004 Sep-Oct |
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Biodegradation of the insecticide N,N-diethyl-m-toluamide by fungi: identification and toxicity of metabolites. | 2005 Apr |
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Absorption and evaporation of N,N-diethyl-m-toluamide from human skin in vitro. | 2005 Apr 1 |
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Insect repellents, phenoxyherbicide exposure, and non-Hodgkin's lymphoma. | 2005 Aug |
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Field evaluation of commercial repellent formulations against mosquitoes (Diptera: Culicidae) in Northern Territory, Australia. | 2005 Dec |
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Solid lipid nanoparticles (SLN) for topical drug delivery: incorporation of the lipophilic drugs N,N-diethyl-m-toluamide and vitamin K. | 2005 Dec |
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Nitric oxide regulates prolidase activity by serine/threonine phosphorylation. | 2005 Dec 1 |
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The metabolism of nonane, a JP-8 jet fuel component, by human liver microsomes, P450 isoforms and alcohol dehydrogenase and inhibition of human P450 isoforms by JP-8. | 2005 Feb 10 |
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Feeding deterrent effects of catnip oil components compared with two synthetic amides against Aedes aegypti. | 2005 Jul |
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Survey of repellent use by service members arriving in Kuwait for Operation Iraqi Freedom 2. | 2005 Jun |
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Food protective effect of acaricidal components isolated from anise seeds against the stored food mite, Tyrophagus putrescentiae (Schrank). | 2005 Jun |
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In vitro evaluation of concurrent use of commercially available insect repellent and sunscreen preparations. | 2005 Jun |
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Monoterpenes from thyme (Thymus vulgaris) as potential mosquito repellents. | 2005 Mar |
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Repellency of deet and SS220 applied to skin involves olfactory sensing by two species of ticks. | 2005 Mar |
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Acaricidal activity of active constituent isolated in Chamaecyparis obtusa leaves against Dermatophagoides spp. | 2005 Mar 23 |
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Widespread detection of N,N-diethyl-m-toluamide in U.S. streams: comparison with concentrations of pesticides, personal care products, and other organic wastewater compounds. | 2005 May |
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Comparison of contact and spatial repellency of catnip oil and N,N-diethyl-3-methylbenzamide (deet) against mosquitoes. | 2005 May |
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Evaluation of West Nile virus education campaign. | 2005 Nov |
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Bioengineering of a cellulosic fabric for insecticide delivery via grafted cyclodextrin. | 2005 Nov-Dec |
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Field-user acceptability of new camouflage face paint formulations in the Republic of Korea. | 2005 Oct |
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Repellent efficacy of four commercial DEET lotions against Amblyomma hebraeum (Acari: Ixodidae), the principal vector of Rickettsia africae in southern Africa. | 2005 Sep |
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Mosquito repellents and superwarfarin rodenticides--are they really toxic in children? | 2006 Apr |
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Initial evaluation of N,N-diethyl-m-toluamide and permethrin absorption in human volunteers under stress conditions. | 2006 Feb |
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Repelling properties of some plant materials on the tick Ixodes ricinus L. | 2006 Jan |
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Hodgkin lymphoma, multiple myeloma, soft tissue sarcomas, insect repellents, and phenoxyherbicides. | 2006 Mar |
Patents
Sample Use Guides
Sparingly to exposed area(s) of skin. Reapply when necessary. Use a product that contains low amounts (less than 30%) of diethyltoluamide. One application using a product that contains low amounts of diethyltoluamide will last about 4 to 8 hours.
Route of Administration:
Topical
DEET-containing formulations applied at a concentration of 320-360 ug/cm^2 1.6 (7-1.88 uM/cm^2) using human and pig skin. A minimum evaporation rate of 5 ug/cm^2/h (0.03 uM/cm^2/h) for DEET over 5-15 minutes was determined for human and pig skin. In vitro, penetration of DEET in the mouse (33.3 ug/cm^2; 0.174 uM/cm^2), rat (38.7 ug/cm^2; 0.202 uM/cm^2), hairless guinea pig (12.5 ug/cm^2; 0.0653 uM/cm^2), pig (19.4 ug/cm^2; 0.101 uM/cm^2), human (44.7 ug/cm^2; 0.234 uM/cm^2), as well as cultured human skin (27.9 ug/cm^2; 0.146 uM/cm^2) was assessed using an automated, flow-through skin penetration apparatus (AIDA).
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Classification Tree | Code System | Code | ||
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WHO-ATC |
P03BX01
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EPA PESTICIDE CODE |
80301
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NCI_THESAURUS |
C737
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WHO-VATC |
QP53GX01
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134-62-3
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Diethyltoluamide
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diethyltoluamide
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3129
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FB0C1XZV4Y
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DIETHYLTOLUAMIDE
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PRIMARY | Description: Colourless or faintly yellow liquid.Solubility: Practically immiscible in water and glycerol R; miscible with ethanol (~750 g/l) TS and ether R.Category: Insect repellent.Storage: Diethyltoluamide should be kept in a tightly closed container.Additional information: CAUTION: Diethyltoluamide is an irritant to eyes and mucous membranes.Requirements: Diethyltoluamide contains not less than 97.0% and not more than 103.0% of C12H17NO, calculated with reference to the anhydrous substance. | ||
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DB11282
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D003671
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m4129
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C80601
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DEET
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1197007
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1582
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)