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
Isolation of a deet-insensitive mutant of Drosophila melanogaster (Diptera: Drosophilidae).
2001 Dec
Toxic encephalopathy associated with use of DEET insect repellents: a case analysis of its toxicity in children.
2001 Jan
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
Repellency of volatile oils from plants against three mosquito vectors.
2001 Jun
Laboratory & field evaluation of controlled release formulation of the insect repellents N,N-diethyl-m-toluamide (DEET) & N,N-diethyl phenylacetamide (DEPA) against mosquito vectors.
2001 Mar
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
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
Topical formulation studies with DEET (N,N-diethyl-3-methylbenzamide) and cyclodextrins.
2002 Jan
Acaricidal activity of butylidenephthalide identified in Cnidium officinale rhizome against dermatophagoides farinae and dermatophagoides pteronyssinus (Acari: Pyroglyphidae).
2002 Jul 31
In vitro human metabolism and interactions of repellent N,N-diethyl-m-toluamide.
2002 Mar
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
DEET: a review and update of safety and risk in the general population.
2003
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
Repellent efficacy of DEET and KBR 3023 against Amblyomma hebraeum (Acari: Ixodidae).
2003 Mar
Olfactory stimulation of Africanized honey bee (Hymenoptera: Apidae) attacks by insect repellents.
2003 May
Biological activity of tropolone.
2003 Oct
Semen quality in relation to biomarkers of pesticide exposure.
2003 Sep
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
Acaricidal activity of Paeonia suffruticosa root bark-derived compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).
2004 Dec 29
Co-exposure to pyridostigmine bromide, DEET, and/or permethrin causes sensorimotor deficit and alterations in brain acetylcholinesterase activity.
2004 Feb
Neurological deficits induced by malathion, DEET, and permethrin, alone or in combination in adult rats.
2004 Feb 27
p-Anisaldehyde: acaricidal component of Pimpinella anisum seed oil against the house dust mites Dermatophagoides farinae and Dermatophagoides pteronyssinus.
2004 Mar
Comparative activity of deet and AI3-37220 repellents against the ticks Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae) in laboratory bioassays.
2004 Mar
In vitro repellency of N,N-diethyl-3-methylbenzamide and N,N-diethylphenylacetamide analogs against Aedes aegypti and Anopheles stephensi (Diptera: Culicidae).
2004 May
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
Solid lipid nanoparticles (SLN) for topical drug delivery: incorporation of the lipophilic drugs N,N-diethyl-m-toluamide and vitamin K.
2005 Dec
In vitro evaluation of concurrent use of commercially available insect repellent and sunscreen preparations.
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
Repellent efficacy of four commercial DEET lotions against Amblyomma hebraeum (Acari: Ixodidae), the principal vector of Rickettsia africae in southern Africa.
2005 Sep
Repelling properties of some plant materials on the tick Ixodes ricinus L.
2006 Jan
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 Wed Jul 05 22:48:30 UTC 2023
Edited
by admin
on Wed Jul 05 22:48:30 UTC 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 Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
EPA PESTICIDE CODE 80301
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
NCI_THESAURUS C737
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
WHO-VATC QP53GX01
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
Code System Code Type Description
CAS
134-62-3
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
LACTMED
Diethyltoluamide
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
ALANWOOD
diethyltoluamide
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
RXCUI
3129
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY RxNorm
DAILYMED
FB0C1XZV4Y
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DIETHYLTOLUAMIDE
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 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 Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
CHEBI
7071
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
INN
6685
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
FDA UNII
FB0C1XZV4Y
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
DRUG CENTRAL
4418
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
DRUG BANK
DB11282
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
PUBCHEM
4284
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
EVMPD
SUB07114MIG
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
EPA CompTox
DTXSID2021995
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
SMS_ID
100000083130
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-149-7
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
MESH
D003671
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
MERCK INDEX
M4129
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C80601
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
WIKIPEDIA
DEET
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
RS_ITEM_NUM
1197007
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
ChEMBL
CHEMBL1453317
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
HSDB
1582
Created by admin on Wed Jul 05 22:48:30 UTC 2023 , Edited by admin on Wed Jul 05 22:48:30 UTC 2023
PRIMARY
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