U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of DIETHYLTOLUAMIDE

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

HIDE SMILES / InChI

Molecular Formula C12H17NO
Molecular Weight 191.2695
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: 1279770.0
Gene Symbol: OBP17
31.3 µM [Kd]
Target ID: OR136 (Culex quinquefasciatus)
Target ID: Ionotropic receptor 40a (Fruit fly)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

DEET 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.
Preventing
Unknown

Approved Use

DEET 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.
Preventing
Unknown

Approved Use

DEET 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

PubMed

TitleDatePubMed
Development of a high-performance liquid chromatographic method for the quantification of chlorpyrifos, pyridostigmine bromide, N,N-diethyl-m-toluamide and their metabolites in rat plasma and urine.
2001 Apr 25
Induction of urinary excretion of 3-nitrotyrosine, a marker of oxidative stress, following administration of pyridostigmine bromide, DEET (N,N-diethyl-m-toluamide) and permethrin, alone and in combination in rats.
2001 Apr 30
Toxic encephalopathy associated with use of DEET insect repellents: a case analysis of its toxicity in children.
2001 Jan
Repellency of volatile oils from plants against three mosquito vectors.
2001 Jun
Combined exposure to DEET (N,N-diethyl-m-toluamide) and permethrin-induced release of rat brain mitochondrial cytochrome c.
2001 Jun 22
Subchronic dermal application of N,N-diethyl m-toluamide (DEET) and permethrin to adult rats, alone or in combination, causes diffuse neuronal cell death and cytoskeletal abnormalities in the cerebral cortex and the hippocampus, and Purkinje neuron loss in the cerebellum.
2001 Nov
DEET (N,N-diethyl-m-toluamide) alone and in combination with permethrin increased urinary excretion of 6beta-hydroxycortisol in rats, a marker of hepatic CYP3A induction.
2001 Nov 9
Safety of the insect repellent N,N-diethyl-M-toluamide (DEET) in pregnancy.
2001 Oct
Laboratory and field evaluations of the insect repellent 3535 (ethyl butylacetylaminopropionate) and deet against mosquito vectors in Thailand.
2001 Sep
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.
2002 Aug
Repellent activities of essential oils and monoterpenes against Culex pipiens pallens.
2002 Dec
Comparative efficacy of insect repellents against mosquito bites.
2002 Jul 4
Pyridostigmine bromide modulates the dermal disposition of [14C]permethrin.
2002 Jun 15
Binding of pyridostigmine bromide, N,N-diethyl-m-toluamide and permethrin, alone and in combinations, to human serum albumin.
2002 May
Analysis of N,N-diethyl-m-toluamide in porcine skin perfusates using solid-phase extraction disks and reversed-phase high-performance liquid chromatography.
2002 Nov 15
Repellent activity of constituents identified in Foeniculum vulgare fruit against Aedes aegypti (Diptera: Culicidae).
2002 Nov 20
Pyridostigmine bromide modulates topical irritant-induced cytokine release from human epidermal keratinocytes and isolated perfused porcine skin.
2003 Feb 1
Acaricidal activity of Cnidium officinale rhizome-derived butylidenephthalide against Tyrophagus putrescentiae (Acari: Acaridae).
2003 Jan
Testicular germ-cell apoptosis in stressed rats following combined exposure to pyridostigmine bromide, N,N-diethyl m-toluamide (DEET), and permethrin.
2003 Jan 10
Schistosomiasis prophylaxis in vivo using N,N-diethyl-m-toluamide (DEET).
2003 Jul-Aug
Olfactory stimulation of Africanized honey bee (Hymenoptera: Apidae) attacks by insect repellents.
2003 May
Amphiphilic star-like macromolecules as novel carriers for topical delivery of nonsteroidal anti-inflammatory drugs.
2003 Oct 16
Inhibition of trans-permethrin hydrolysis in human liver fractions by chloropyrifos oxon and carbaryl.
2004
Analysis and fate of insect repellents.
2004
Protective behavior survey, West Nile virus, British Columbia.
2004 Aug
Insect repellent [correction of repellant] interactions: sunscreens enhance DEET (N,N-diethyl-m-toluamide) absorption.
2004 Aug
Effect of topical agents on cercariae of Schistosoma mansoni.
2004 Dec
Co-exposure to pyridostigmine bromide, DEET, and/or permethrin causes sensorimotor deficit and alterations in brain acetylcholinesterase activity.
2004 Feb
Repellency of aromatic medicinal plant extracts and a steam distillate to Aedes aegypti.
2004 Jun
Comparative activity of deet and AI3-37220 repellents against the ticks Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae) in laboratory bioassays.
2004 Mar
Evaluation of the sensitivity of Aedes aegypti and Anopheles gambiae complex mosquitoes to two insect repellents: DEET and KBR 3023.
2004 Mar
Field evaluation of repellent formulations containing deet and picaridin against mosquitoes in Northern Territory, Australia.
2004 May
Repellency of aerosol and cream products containing fennel oil to mosquitoes under laboratory and field conditions.
2004 Nov
Biodegradation of the insecticide N,N-diethyl-m-toluamide by fungi: identification and toxicity of metabolites.
2005 Apr
Absorption and evaporation of N,N-diethyl-m-toluamide from human skin in vitro.
2005 Apr 1
Insect repellents, phenoxyherbicide exposure, and non-Hodgkin's lymphoma.
2005 Aug
Field evaluation of commercial repellent formulations against mosquitoes (Diptera: Culicidae) in Northern Territory, Australia.
2005 Dec
Nitric oxide regulates prolidase activity by serine/threonine phosphorylation.
2005 Dec 1
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
Feeding deterrent effects of catnip oil components compared with two synthetic amides against Aedes aegypti.
2005 Jul
Survey of repellent use by service members arriving in Kuwait for Operation Iraqi Freedom 2.
2005 Jun
Repellency of deet and SS220 applied to skin involves olfactory sensing by two species of ticks.
2005 Mar
Acaricidal activity of active constituent isolated in Chamaecyparis obtusa leaves against Dermatophagoides spp.
2005 Mar 23
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
Comparison of contact and spatial repellency of catnip oil and N,N-diethyl-3-methylbenzamide (deet) against mosquitoes.
2005 May
Bioengineering of a cellulosic fabric for insecticide delivery via grafted cyclodextrin.
2005 Nov-Dec
Repellent efficacy of four commercial DEET lotions against Amblyomma hebraeum (Acari: Ixodidae), the principal vector of Rickettsia africae in southern Africa.
2005 Sep
Mosquito repellents and superwarfarin rodenticides--are they really toxic in children?
2006 Apr
Initial evaluation of N,N-diethyl-m-toluamide and permethrin absorption in human volunteers under stress conditions.
2006 Feb
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:17:19 GMT 2023
Edited
by admin
on Fri Dec 15 15:17:19 GMT 2023
Record UNII
FB0C1XZV4Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIETHYLTOLUAMIDE
HSDB   INN   MART.   USP   USP-RS   WHO-DD   WHO-IP  
INN  
Official Name English
N,N-DIETHYL-3-METHYLBENZAMIDE
Systematic Name English
NSC-33840
Code English
BENZAMIDE, N,N-DIETHYL-3-METHYL-
Systematic Name English
DIETHYLTOLUAMIDUM [WHO-IP LATIN]
Common Name English
DIETHYLTOLUAMIDE [USP MONOGRAPH]
Common Name English
DIETHYL TOLUAMIDE [INCI]
Common Name English
DEET N,N-DIETHYL-META-TOLUAMIDE [VANDF]
Common Name English
ENT-20218
Code English
N,N-DIETHYL 3-METHYL BENZAMIDE
Common Name English
DIETHYLTOLUAMIDE [USP-RS]
Common Name English
DIETHYLTOLUAMIDE [MART.]
Common Name English
DIETHYLTOLUAMIDE [WHO-IP]
Common Name English
DEET [MI]
Common Name English
Diethyltoluamide [WHO-DD]
Common Name English
DIETHYL TOLUAMIDE
INCI  
INCI  
Official Name English
N,N-DIETHYL-META-TOLUAMIDE
Systematic Name English
ORISTAR DEET
Brand Name English
ENT-22542
Code English
DEET N,N-DIETHYL-META-TOLUAMIDE
VANDF  
Common Name English
DIETHYLTOLUAMIDE [HSDB]
Common Name English
diethyltoluamide [INN]
Common Name English
DEET
MI  
Common Name English
N,N-DIETHYL-M-TOLUAMIDE
Systematic Name English
Classification Tree Code System Code
WHO-ATC P03BX01
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
EPA PESTICIDE CODE 80301
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
NCI_THESAURUS C737
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
WHO-VATC QP53GX01
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
Code System Code Type Description
CAS
134-62-3
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
LACTMED
Diethyltoluamide
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
ALANWOOD
diethyltoluamide
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
RXCUI
3129
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY RxNorm
DAILYMED
FB0C1XZV4Y
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DIETHYLTOLUAMIDE
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
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.
NSC
33840
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
CHEBI
7071
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
INN
6685
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
FDA UNII
FB0C1XZV4Y
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
DRUG CENTRAL
4418
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
DRUG BANK
DB11282
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
PUBCHEM
4284
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
EVMPD
SUB07114MIG
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID2021995
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
SMS_ID
100000083130
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-149-7
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
MESH
D003671
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
MERCK INDEX
m4129
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C80601
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
WIKIPEDIA
DEET
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
RS_ITEM_NUM
1197007
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
ChEMBL
CHEMBL1453317
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
HSDB
1582
Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023
PRIMARY
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