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

Details

Stereochemistry ACHIRAL
Molecular Formula C12H17NO
Molecular Weight 191.2699
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIETHYLTOLUAMIDE

SMILES

CCN(CC)C(=O)c1cccc(C)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 191.2699
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: 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
Gene Symbol: OBP17
31.3000000000000007 µM [Kd]
Target ID: OR136 (Culex quinquefasciatus)
Target ID: Ionotropic receptor 40a (Fruit fly)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing

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

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

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
Locomotor and sensorimotor performance deficit in rats following exposure to pyridostigmine bromide, DEET, and permethrin, alone and in combination.
2001 Apr
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
Evaluation of immunotoxicity induced by single or concurrent exposure to N,N-diethyl-m-toluamide (DEET), pyridostigmine bromide (PYR), and JP-8 jet fuel.
2001 Jun
High performance liquid chromatographic determination of diazinon, permethrin, DEET (N, N-diethyl-m-toluamide), and their metabolites in rat plasma and urine.
2001 Jun
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
Drugs and personal care products as ubiquitous pollutants: occurrence and distribution of clofibric acid, caffeine and DEET in the North Sea.
2002 Aug 5
Repellent activities of essential oils and monoterpenes against Culex pipiens pallens.
2002 Dec
Acaricidal activity of butylidenephthalide identified in Cnidium officinale rhizome against dermatophagoides farinae and dermatophagoides pteronyssinus (Acari: Pyroglyphidae).
2002 Jul 31
Comparative efficacy of insect repellents against mosquito bites.
2002 Jul 4
Cardiorespiratory effects following acute exposure to pyridostigmine bromide and/or N,N-diethyl-m-toluamide (DEET) in rats.
2002 Jul-Aug
Pyridostigmine bromide modulates the dermal disposition of [14C]permethrin.
2002 Jun 15
Genotoxicity studies on permethrin, DEET and diazinon in primary human nasal mucosal cells.
2002 Mar
Malaria outbreak control in an African village by community application of 'deet' mosquito repellent to ankles and feet.
2002 Mar
In vitro human metabolism and interactions of repellent N,N-diethyl-m-toluamide.
2002 Mar
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
Gulf War related exposure factors influencing topical absorption of 14C-permethrin.
2002 Sep 5
Human Exposures to N,N-diethyl-m-toluamide insect repellents reported to the American Association of Poison Control Centers 1993-1997.
2002 Sep-Oct
Effectiveness of a repellent containing DEET and EBAAP for preventing tick bites.
2002 Spring
Pyridostigmine bromide modulates topical irritant-induced cytokine release from human epidermal keratinocytes and isolated perfused porcine skin.
2003 Feb 1
Acaricidal activity of clove bud oil compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).
2003 Feb 12
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
Comparison of the mosquito-repelling efficacy of methyl neodecanamide (MNDA) to that of Deet.
2003 May-Jun
Amphiphilic star-like macromolecules as novel carriers for topical delivery of nonsteroidal anti-inflammatory drugs.
2003 Oct 16
Analysis and fate of insect repellents.
2004
Protective behavior survey, West Nile virus, British Columbia.
2004 Aug
A comparison of topical formulations for the prevention of human schistosomiasis.
2004 Aug
Insect repellent [correction of repellant] interactions: sunscreens enhance DEET (N,N-diethyl-m-toluamide) absorption.
2004 Aug
Determination of selected pharmaceuticals and caffeine in sewage and seawater from Tromsø/Norway with emphasis on ibuprofen and its metabolites.
2004 Aug
Analysis and mass spectrometric characterization of the insect repellent Bayrepel and its main metabolite Bayrepel-acid.
2004 Aug 13
Neurological deficits induced by malathion, DEET, and permethrin, alone or in combination in adult rats.
2004 Feb 27
Repellency of aromatic medicinal plant extracts and a steam distillate to Aedes aegypti.
2004 Jun
Comparative study of the topical effectiveness of the Andiroba oil (Carapa guianensis) and DEET 50% as repellent for Aedes sp.
2004 Sep-Oct
Solid lipid nanoparticles (SLN) for topical drug delivery: incorporation of the lipophilic drugs N,N-diethyl-m-toluamide and vitamin K.
2005 Dec
Nitric oxide regulates prolidase activity by serine/threonine phosphorylation.
2005 Dec 1
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
Evaluation of West Nile virus education campaign.
2005 Nov
Bioengineering of a cellulosic fabric for insecticide delivery via grafted cyclodextrin.
2005 Nov-Dec
Field-user acceptability of new camouflage face paint formulations in the Republic of Korea.
2005 Oct
Mosquito repellents and superwarfarin rodenticides--are they really toxic in children?
2006 Apr
Repelling properties of some plant materials on the tick Ixodes ricinus L.
2006 Jan
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 Sat Jun 26 08:03:51 UTC 2021
Edited
by admin
on Sat Jun 26 08:03:51 UTC 2021
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
DIETHYLTOLUAMIDE [WHO-DD]
Common Name English
BENZAMIDE, N,N-DIETHYL-3-METHYL-
Systematic Name English
DIETHYLTOLUAMIDUM [WHO-IP LATIN]
Common Name English
DIETHYLTOLUAMIDE [USP]
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
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 Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
EPA PESTICIDE CODE 80301
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
NCI_THESAURUS C737
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
WHO-VATC QP53GX01
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
Code System Code Type Description
CAS
134-62-3
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY
LACTMED
Diethyltoluamide
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY
RXCUI
3129
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY RxNorm
WHO INTERNATIONAL PHARMACOPEIA
DIETHYLTOLUAMIDE
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
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.
USP_CATALOG
1197007
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY USP-RS
INN
6685
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY
FDA UNII
FB0C1XZV4Y
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY
DRUG CENTRAL
4418
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY
DRUG BANK
DB11282
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY
PUBCHEM
4284
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY
EVMPD
SUB07114MIG
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY
EPA CompTox
134-62-3
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-149-7
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY
MESH
D003671
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY
MERCK INDEX
M4129
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C80601
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY
WIKIPEDIA
DEET
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY
ChEMBL
CHEMBL1453317
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY
HSDB
1582
Created by admin on Sat Jun 26 08:03:51 UTC 2021 , Edited by admin on Sat Jun 26 08:03:51 UTC 2021
PRIMARY
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