DEET
N, N-diethyl-meta-toluamide (DEET) is used as an insect repellent. DEET was developed by the U.S. Army in 1946 and was registered for use by the general public in 1957. DEET is a poor acetylcholinesterase inhibitor (<10% inhibition), even at a concentration of 10 mM. IC50 values for DEET against Drosophila melanogaster, Musca domestica, and human acetylcholinesterases were 6-12 mM. DEET was shown to increase internal free calcium via the octopamine receptors of Sf21 cells, an effect blocked by phentolamine. DEET also blocked Na(+) and K(+) channels in patch clamped rat cortical neurons, with IC50 values in the micromolar range. Pyridostigmine bromide, N, N-diethyl-m-toluamide (DEET), and permethrin: a model of Gulf-War syndrome
General
Type : Not AlphaBeta Hydrolase target
Chemical_Nomenclature : N,N-diethyl-3-methylbenzamide
Canonical SMILES : CCN(CC)C(=O)C1=CC=CC(=C1)C
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
InChIKey : MMOXZBCLCQITDF-UHFFFAOYSA-N
Other name(s) : Diethyltoluamide || N,N-Diethyl-3-methylbenzamide || N,N-Diethyl-m-toluamide || Diethyl toluamide || Benzamide, N,N-diethyl-3-methyl- || Metadelphene || CHEBI:7071 || SCHEMBL29976 || DB11282 || SCHEMBL1531067 || SCHEMBL8541272 || CHEMBL1453317
MW : 191.27
Formula : C12H17NO
CAS_number : 134-62-3
PubChem : 4284
UniChem : MMOXZBCLCQITDF-UHFFFAOYSA-N
Target
References (17)
| Title : Toxicity assessment of N, N-Diethyl-meta-toluamide (DEET) in zebrafish embryos - Zhang_2025_Comp.Biochem.Physiol.C.Toxicol.Pharmacol__110293 |
| Author(s) : Zhang H , Liu C , Sun Y , Tang S , Lei Y , Zhang W , Cheng B , Zhao Y , Luo Q |
| Ref : Comparative Biochemistry & Physiology C Toxicol Pharmacol , :110293 , 2025 |
| Abstract : |
| PubMedSearch : Zhang_2025_Comp.Biochem.Physiol.C.Toxicol.Pharmacol__110293 |
| PubMedID: 40683430 |
| Title : Comparison of the cytotoxicity and zebrafish embryo toxicity of insect repellent ingredients: p-Menthane-3,8-diol synthesized by green chemistry from Eucalyptus citriodora and N,N-diethyl-meta-toluamide - Ozokan_2024_Drug.Chem.Toxicol__1 |
| Author(s) : Ozokan G , Bilginer A , Mizrak Z , Isikoglu S , Beler M , Unal I , Cansiz D , Alturfan AA , Emekli-Alturfan E |
| Ref : Drug & Chemical Toxicology , :1 , 2024 |
| Abstract : |
| PubMedSearch : Ozokan_2024_Drug.Chem.Toxicol__1 |
| PubMedID: 38738628 |
| Title : Is DEET a dangerous neurotoxicant? - Swale_2019_Pest.Manag.Sci_75_2068 |
| Author(s) : Swale DR , Bloomquist JR |
| Ref : Pest Manag Sci , 75 :2068 , 2019 |
| Abstract : |
| PubMedSearch : Swale_2019_Pest.Manag.Sci_75_2068 |
| PubMedID: 31069958 |
| Title : Neurotoxicity and Mode of Action of N, N-Diethyl-Meta-Toluamide (DEET) - Swale_2014_PLoS.One_9_e103713 |
| Author(s) : Swale DR , Sun B , Tong F , Bloomquist JR |
| Ref : PLoS ONE , 9 :e103713 , 2014 |
| Abstract : |
| PubMedSearch : Swale_2014_PLoS.One_9_e103713 |
| PubMedID: 25101788 |
| Title : Stress and combined exposure to low doses of pyridostigmine bromide, DEET, and permethrin produce neurochemical and neuropathological alterations in cerebral cortex, hippocampus, and cerebellum - Abdel-Rahman_2004_J.Toxicol.Environ.Health.A_67_163 |
| Author(s) : Abdel-Rahman A , Abou-Donia S , El-Masry E , Shetty A , Abou-Donia MB |
| Ref : J Toxicol Environ Health A , 67 :163 , 2004 |
| Abstract : |
| PubMedSearch : Abdel-Rahman_2004_J.Toxicol.Environ.Health.A_67_163 |
| PubMedID: 14675905 |
| Title : Neurological deficits induced by malathion, DEET, and permethrin, alone or in combination in adult rats - Abdel-Rahman_2004_J.Toxicol.Environ.Health.A_67_331 |
| Author(s) : Abdel-Rahman A , Dechkovskaia AM , Goldstein LB , Bullman SH , Khan W , El-Masry EM , Abou-Donia MB |
| Ref : J Toxicol Environ Health A , 67 :331 , 2004 |
| Abstract : |
| PubMedSearch : Abdel-Rahman_2004_J.Toxicol.Environ.Health.A_67_331 |
| PubMedID: 14713564 |
| Title : Co-exposure to pyridostigmine bromide, DEET, and\/or permethrin causes sensorimotor deficit and alterations in brain acetylcholinesterase activity - Abou-Donia_2004_Pharmacol.Biochem.Behav_77_253 |
| Author(s) : Abou-Donia MB , Dechkovskaia AM , Goldstein LB , Abdel-Rahman A , Bullman SL , Khan WA |
| Ref : Pharmacol Biochem Behav , 77 :253 , 2004 |
| Abstract : |
| PubMedSearch : Abou-Donia_2004_Pharmacol.Biochem.Behav_77_253 |
| PubMedID: 14751452 |
| Title : Pyridostigmine bromide modulates the dermal disposition of [14C]permethrin - Baynes_2002_Toxicol.Appl.Pharmacol_181_164 |
| Author(s) : Baynes RE , Monteiro-Riviere NA , Riviere JE |
| Ref : Toxicol Appl Pharmacol , 181 :164 , 2002 |
| Abstract : |
| PubMedSearch : Baynes_2002_Toxicol.Appl.Pharmacol_181_164 |
| PubMedID: 12079425 |
| Title : Cardiorespiratory Effects Following Acute Exposure to Pyridostigmine Bromide and\/or N,N-Diethyl-m-toluamide (DEET) in Rats - Chaney_2002_Int.J.Toxicol_21_287 |
| Author(s) : Chaney LA , Rockhold RW , Hume AS |
| Ref : Int J Toxicol , 21 :287 , 2002 |
| Abstract : |
| PubMedSearch : Chaney_2002_Int.J.Toxicol_21_287 |
| PubMedID: 12171630 |
| Title : Disruption of the blood-brain barrier and neuronal cell death in cingulate cortex, dentate gyrus, thalamus, and hypothalamus in a rat model of gulf-war syndrome - Abdel-Rahman_2002_Neurobiol.Dis_10_306 |
| Author(s) : Abdel-Rahman A , Shetty A , Abou-Donia MB |
| Ref : Neurobiol Dis , 10 :306 , 2002 |
| Abstract : |
| PubMedSearch : Abdel-Rahman_2002_Neurobiol.Dis_10_306 |
| PubMedID: 12270692 |
| Title : Locomotor and sensorimotor performance deficit in rats following exposure to pyridostigmine bromide, DEET, and permethrin, alone and in combination - Abou-Donia_2001_Toxicol.Sci_60_305 |
| Author(s) : Abou-Donia MB , Goldstein LB , Jones KH , Abdel-Rahman AA , Damodaran TV , Dechkovskaia AM , Bullman SL , Amir BE , Khan WA |
| Ref : Toxicol Sci , 60 :305 , 2001 |
| Abstract : |
| PubMedSearch : Abou-Donia_2001_Toxicol.Sci_60_305 |
| PubMedID: 11248143 |
| Title : Evaluation of immunotoxicity induced by single or concurrent exposure to N,N-diethyl-m-toluamide (DEET), pyridostigmine bromide (PYR), and JP-8 jet fuel - Peden-Adam_2001_Toxicol.Ind.Health_17_192 |
| Author(s) : Peden-Adam MM , Eudaly J , Eudaly E , Dudley A , Zeigler J , Lee A , Robbs J , Gilkeson G , Keil DE |
| Ref : Toxicol Ind Health , 17 :192 , 2001 |
| Abstract : |
| PubMedSearch : Peden-Adam_2001_Toxicol.Ind.Health_17_192 |
| PubMedID: 12539864 |
| Title : Interactions of bovine brain tubulin with pyridostigmine bromide and N,N'-diethyl-m-toluamide - Prasad_2000_Neurochem.Res_25_19 |
| Author(s) : Prasad V , Scotch R , Chaudhuri AR , Walss C , Fathy DB , Miller C , Luduena RF |
| Ref : Neurochem Res , 25 :19 , 2000 |
| Abstract : |
| PubMedSearch : Prasad_2000_Neurochem.Res_25_19 |
| PubMedID: 10685600 |
| Title : Acute effects of an insect repellent, N,N-diethyl-m-toluamide, on cholinesterase inhibition induced by pyridostigmine bromide in rats - Chaney_2000_Toxicol.Appl.Pharmacol_165_107 |
| Author(s) : Chaney LA , Wineman RW , Rockhold RW , Hume AS |
| Ref : Toxicol Appl Pharmacol , 165 :107 , 2000 |
| Abstract : |
| PubMedSearch : Chaney_2000_Toxicol.Appl.Pharmacol_165_107 |
| PubMedID: 10828206 |
| Title : Molecular similarity analysis between insect juvenile hormone and N, N-diethyl-m-toluamide (DEET) analogs may aid design of novel insect repellents - Bhattacharjee_2000_J.Mol.Recognit_13_213 |
| Author(s) : Bhattacharjee AK , Gupta RK , Ma D , Karle JM |
| Ref : J Mol Recognit , 13 :213 , 2000 |
| Abstract : |
| PubMedSearch : Bhattacharjee_2000_J.Mol.Recognit_13_213 |
| PubMedID: 10931558 |
| Title : Influence of inert ingredients in pesticide formulations on dermal absorption of carbaryl - Baynes_1998_Am.J.Vet.Res_59_168 |
| Author(s) : Baynes RE , Riviere JE |
| Ref : American Journal of Veterinary Research , 59 :168 , 1998 |
| Abstract : |
| PubMedSearch : Baynes_1998_Am.J.Vet.Res_59_168 |
| PubMedID: 9492931 |
| Title : The influence of diethyl-m-toluamide (DEET) on the percutaneous absorption of permethrin and carbaryl - Baynes_1997_Toxicol.Appl.Pharmacol_144_332 |
| Author(s) : Baynes RE , Halling KB , Riviere JE |
| Ref : Toxicol Appl Pharmacol , 144 :332 , 1997 |
| Abstract : |
| PubMedSearch : Baynes_1997_Toxicol.Appl.Pharmacol_144_332 |
| PubMedID: 9194417 |