Identification
- Summary
Diethyltoluamide is an insect repellant, also known as DEET.
- Generic Name
- Diethyltoluamide
- DrugBank Accession Number
- DB11282
- Background
Diethyltoluamide (DEET) is the common active ingredient in many insect repellent products. It is widely used to repel biting pests such as mosquitoes and ticks. Every year, DEET formulations are used to protect populations from mosquito-borne illnesses like West Nile Virus, the Zika virus, malaria, and/or tick-borne illnesses like Lyme disease and Rocky Mountain spotted fever. And, despite concerns over excessive exposure to the chemical, appropriate usage of the chemical at the recommended dosages and routes of administration have generally proven to be safe - even when most DEET products are largely designed to be applied directly to human skin, where the exact mechanisms of actions in which DEET is capable of repelling insects and causing toxicity to humans is still not fully elucidated.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Diethyltoluamide (DB11282)
- Weight
- Average: 191.2695
Monoisotopic: 191.131014171 - Chemical Formula
- C12H17NO
- Synonyms
- 3-methyl-N,N-diethylbenzamide
- DEET
- diethyl toluamide
- diéthyltoluamide
- Diethyltoluamide
- diethyltoluamidum
- dietiltoluamida
- N,N-diethyl-m-toluamide
- External IDs
- ENT-20218
- ENT-22542
- NSC-33840
Pharmacology
- Indication
Diethyltoluamide, or DEET, is an active ingredient that is predominantly indicated for as an insect repellant used to repel biting pests like mosquitoes and ticks 5. Products containing DEET currently are available to the public in a variety of liquids, lotions, sprays, and impregnated materials like towelettes or roll-ons 5.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prevention of Insect bites ••• ••• •••••••• ••••• Used in combination to prevent Sunburn ••• ••• - Contraindications & Blackbox Warnings
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When used appropriately, diethyltoluamide (DEET) containing products are designed to be applied directly to people's skin as a means to elicit a repelling action to keep insects from targeting human skin 5. At the amounts and doses recommended for use on human children and adults, noticeable absorption or systemic exposure is not expected 5,6. Owing to the proportional difference in size between humans and insects, however, the exposure of insects to the applied DEET (whether topically or via inhalation of DEET) is expected to be enough to interfere with the insects' sensory attraction to human skin 5,6.
- Mechanism of action
The exact mechanism(s) of action by which both (a) insects are repelled by diethyltoluamide (DEET), and (b) humans can be affected deleteriously by exposure to toxic amounts of DEET have not yet been formally elucidated 5,6,8.
Research is ongoing regarding the exact mechanism of action by which DEET is capable of repelling insects. However, the most longstanding mechanism proposes that the DEET chemical blocks the olfactory receptors of insects for the volatile 1-octen-3-ol compound that is an element in human sweat and breath 1. As a consequence, this proposed mechanism suggests that the blockade of insects' senses for this 1-octen-3-ol blinds and prevents the triggering of their biting and/or feeding instinct on humans and other animals that produce that compound 1. Nevertheless, this theory has not yet been fully elucidated.
Furthermore, recent studies have demonstrated that DEET binds to certain molecular targets like the Anopheles gambiae odorant binding protein 1 (AgamOBP1) with high shape complementarity 2 and the antennae-specific odorant receptor CquiOR136 of the southern house mosquito, Culex quinquefasciatus 9. In southern house mosquitos with reduced CquiOR136 transcript levels, behavioral tests demonstrated that this phenotype showed demonstrably lower responses/repulsion to DEET 9. Again, however, such findings require continued research and do not formally elucidate the mechanism of action by which DEET can repel insects.
And finally, the mechanism of toxicity in which DEET is capable of eliciting effects of neurotoxicity in humans who have been exposed to toxic levels of the agent is also poorly understood 6,3. A recent study proposes that DEET is capable of blocking Na+ and K+ channels in the rat animal model 3. This ion channel blocking activity of DEET in neurons may subsequently contribute to the kind of neuro-sensory adverse effects like numbness experienced after inadvertent application to the lips or mouth of humans 3.
- Absorption
Most diethyltoluamide (DEET) formulations employ the agent as a liquid to be applied onto human skin in an effort to repel mosquitoes from feeding on the skin. Topical application and absorption is consequently the most common route of absorption. When used appropriately, DEET formulations are generally not indicated for too many other routes of absorption or administration, like parenterally or orally.
DEET is absorbed quickly through intact skin; 48% of the applied dose is totally absorbed within 6 hours 6. Topical absorption is the usual route of entry as DEET is normally applied to the skin as a mosquito repellent 6. DEET applied to the skin has also been shown to accumulate in the dermis 6. DEET is rapidly absorbed after oral ingestion 6. Additionally, animal experiments demonstrate that DEET can cross the placenta 6.
DEET is efficiently absorbed across the skin and by the gut 10. Blood concentrations of about 3 mg/L have been reported several hours after dermal application in the prescribed fashion 10.
Between 9% and 56% of dermally applied DEET is absorbed through the skin with peak blood levels being attained within 1 hour 6. Absorption through the skin varies according to the site exposed to the DEET 6. In animal model surfaces corresponding to the human palmar surface (an area that is typically heavily exposed during the application of liquid DEET), 68% of administered topical DEET was absorbed 6. As a consequence, small children are at increased risk of excessive absorption of DEET applied to the skin because of their relatively higher surface to volume ratio compared to adults 6.
- Volume of distribution
After dermal application, about 17% of the absorbed diethyltoluamide (DEET) dose enters the bloodstream 6. DEET accumulates in the skin, contributing to local irritation and possibly even bullous dermatitis 6. Accumulation within the body, however, has not been reported and experimentally there have been no cumulative effects of subtoxic doses of DEET; but various case reports of toxicity in man suggests that accumulation of the repellent could occur, and with deleterious effects 6.
- Protein binding
Readily accessible data regarding the protein binding of diethyltoluamide (DEET) is not available.
- Metabolism
Diethyltoluamide (DEET) is metabolized in humans by cytochrome P450 enzymes into the primary metabolites N,N-diethyl-m-hydroxymethylbenzamide (BALC) and Nethyl-m-toluamide (ET) 7. Although several P450 isoenzymes have elicited activity in DEET metabolism, it appears that the CYP2B6 and CYP2C19 enzymes are the principal P450s responsible for the transformation of DEET to BALC and ET, respectively 7. Most of the body load is metabolized by such hepatic P450 enzymes, with only 10%–14% recovered unchanged in the urine 4.
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- Route of elimination
Diethyltoluamide (DEET) is principally excreted via the kidneys, where the initial phase is initially rapid but not more than 50% of the absorbed dose is excreted during the first 5 days 6. In a study with a human volunteer weighing 65.8 kg and having been treated with 15 g of 95% DEET, urinary levels of DEET and a metabolite were measurable 4 hours after the initial exposure and persisted 48 hours later 6. Maximum urinary levels of DEET observed were 207 mg/L at 8 hours 6.
- Half-life
The elimination half-life of diethyltoluamide (DEET) is observed to be about 2.5 hours 4.
- Clearance
Readily accessible data regarding the clearance of diethyltoluamide (DEET) is not available.
- Adverse Effects
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Ingestion of diethyltoluamide (DEET) in adults may lead to hypotension, seizures, and/or coma within as little as an hour 4. Deaths have been associated with serum concentrations of 1 mmol/L 4. Psychosis was described in an adult who had applied a product containing 70% DEET to the skin 4.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareOxybenzone Oxybenzone can cause an increase in the absorption of Diethyltoluamide resulting in an increased serum concentration and potentially a worsening of adverse effects. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Autan / Detamide / Flypel / m-Delphene / Metadelphene / Muscol / Off! / Repel
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Insect Repellent Insect Block Aerosol 9 g/100mL Topical MOD DESIGN BUILD 2021-03-23 Not applicable US 
Mosquite Bug Off Liquid 10 g/100mL Topical Lydia Co., Ltd. 2019-03-23 2019-03-28 US Mosquito Bug Off Liquid 10 g/100mL Topical Lydia Co., Ltd. 2019-03-23 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Croc Bloc Combinator SPF 15 Diethyltoluamide (10 %) + Octinoxate (6.5 %) + Oxybenzone (2 %) Lotion Topical Croc Bloc Products Inc. 1999-05-21 2002-07-11 Canada 
Sunsect Insect Repellent Sunscreen Diethyltoluamide (20 g/100g) + Octinoxate (7.5 g/100g) + Octisalate (5 g/100g) + Oxybenzone (6 g/100g) Lotion Topical Iguana Llc 2015-06-01 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Insect Repellent Insect Block Diethyltoluamide (9 g/100mL) Aerosol Topical MOD DESIGN BUILD 2021-03-23 Not applicable US Mosquite Bug Off Diethyltoluamide (10 g/100mL) Liquid Topical Lydia Co., Ltd. 2019-03-23 2019-03-28 US Mosquito Bug Off Diethyltoluamide (10 g/100mL) Liquid Topical Lydia Co., Ltd. 2019-03-23 Not applicable US
Categories
- ATC Codes
- P03BX01 — Diethyltoluamide
- Drug Categories
- Acids, Carbocyclic
- Agrochemicals
- Amides
- Antiparasitic Products, Insecticides and Repellents
- Benzamides and benzamide derivatives
- Benzene Derivatives
- Benzoates
- Compounds used in a research, industrial, or household setting
- Ectoparasiticides, Incl. Scabicides, Insecticides and Repellents
- Insect Repellents
- Insecticides and Repellents
- Pesticides
- Protective Agents
- Toxic Actions
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n,n-dialkyl-m-toluamides. These are aromatic that contain a m-toluamide, where the carboxamide group is N- substituted with two alkyl chains.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Toluenes
- Direct Parent
- N,N-dialkyl-m-toluamides
- Alternative Parents
- Benzamides / Benzoyl derivatives / Tertiary carboxylic acid amides / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aromatic homomonocyclic compound / Benzamide / Benzoic acid or derivatives / Benzoyl / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative / N,n-dialkyl-m-toluamide / Organic nitrogen compound / Organic oxide
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- monocarboxylic acid amide, benzamides (CHEBI:7071) / Insect repellents (C10935)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- FB0C1XZV4Y
- CAS number
- 134-62-3
- InChI Key
- MMOXZBCLCQITDF-UHFFFAOYSA-N
- InChI
- InChI=1S/C12H17NO/c1-4-13(5-2)12(14)11-8-6-7-10(3)9-11/h6-9H,4-5H2,1-3H3
- IUPAC Name
- N,N-diethyl-3-methylbenzamide
- SMILES
- CCN(CC)C(=O)C1=CC(C)=CC=C1
References
- General References
- Ditzen M, Pellegrino M, Vosshall LB: Insect odorant receptors are molecular targets of the insect repellent DEET. Science. 2008 Mar 28;319(5871):1838-42. doi: 10.1126/science.1153121. Epub 2008 Mar 13. [Article]
- Tsitsanou KE, Thireou T, Drakou CE, Koussis K, Keramioti MV, Leonidas DD, Eliopoulos E, Iatrou K, Zographos SE: Anopheles gambiae odorant binding protein crystal complex with the synthetic repellent DEET: implications for structure-based design of novel mosquito repellents. Cell Mol Life Sci. 2012 Jan;69(2):283-97. doi: 10.1007/s00018-011-0745-z. Epub 2011 Jun 14. [Article]
- Swale DR, Sun B, Tong F, Bloomquist JR: Neurotoxicity and mode of action of N, N-diethyl-meta-toluamide (DEET). PLoS One. 2014 Aug 7;9(8):e103713. doi: 10.1371/journal.pone.0103713. eCollection 2014. [Article]
- Koren G, Matsui D, Bailey B: DEET-based insect repellents: safety implications for children and pregnant and lactating women. CMAJ. 2003 Aug 5;169(3):209-12. [Article]
- United States Environmental Protection Agency: DEET Profile [Link]
- IPCS INCHEM: DEET Profile [Link]
- In Vitro Human Metabolism and Interactions of Repellent N,N-Diethyl-m-Toluamide [Link]
- National Pesticide Information Centre: DEET Technical Fact Sheet [Link]
- "Mosquito odorant receptor for DEET and methyl jasmonate." Proceedings of the National Academy of Sciences. [Link]
- NIH Toxnet: Diethyltoluamide Profile [Link]
- External Links
- KEGG Drug
- D02379
- KEGG Compound
- C10935
- ChemSpider
- 4133
- 3129
- ChEBI
- 7071
- ChEMBL
- CHEMBL1453317
- ZINC
- ZINC000000001291
- PDBe Ligand
- DE3
- Wikipedia
- DEET
- PDB Entries
- 3n7h / 7lig
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Unknown Status Prevention Dengue Fever / Japanese Encephalitis / Malaria 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Aerosol Topical 9 g/100mL Liquid Topical 10 g/100mL Lotion Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.68 mg/mL ALOGPS logP 2.1 ALOGPS logP 2.5 Chemaxon logS -2.1 ALOGPS pKa (Strongest Basic) -0.95 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 20.31 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 59.47 m3·mol-1 Chemaxon Polarizability 22.16 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 153.3050573 predictedDarkChem Lite v0.1.0 [M-H]- 154.5132573 predictedDarkChem Lite v0.1.0 [M-H]- 154.1527573 predictedDarkChem Lite v0.1.0 [M-H]- 141.89958 predictedDeepCCS 1.0 (2019) [M+H]+ 153.7110573 predictedDarkChem Lite v0.1.0 [M+H]+ 154.2979573 predictedDarkChem Lite v0.1.0 [M+H]+ 154.4408573 predictedDarkChem Lite v0.1.0 [M+H]+ 144.46217 predictedDeepCCS 1.0 (2019) [M+Na]+ 153.5367573 predictedDarkChem Lite v0.1.0 [M+Na]+ 154.2720573 predictedDarkChem Lite v0.1.0 [M+Na]+ 154.3355573 predictedDarkChem Lite v0.1.0 [M+Na]+ 152.65456 predictedDeepCCS 1.0 (2019)
Drug created at December 03, 2015 16:52 / Updated at February 21, 2021 18:53