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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=CC(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 191.2695
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.

Originator

Approval Year

2015
472
Targets

Targets

Primary TargetPharmacologyConditionPotency
AGAP003309-PA
1
Target ID: 1279770.0
Gene Symbol: OBP17
Binding Agent
1076
 31.3 µM [Kd]
OR136 (Culex quinquefasciatus)
1
Target ID: OR136 (Culex quinquefasciatus)
Activator
1447
Ionotropic receptor 40a (Fruit fly)
1
Target ID: Ionotropic receptor 40a (Fruit fly)
Activator
1447
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8583
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
Approved
8583
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
Approved
8583
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.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
196.5 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9109058/
15 mg/kg single, topical
dose: 15 mg/kg
route of administration: Topical
experiment type: SINGLE
co-administered:
DIETHYLTOLUAMIDE plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2.26 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9109058/
6 mg/kg single, intravenous
dose: 6 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
DIETHYLTOLUAMIDE plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.03 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9109058/
15 mg/kg single, topical
dose: 15 mg/kg
route of administration: Topical
experiment type: SINGLE
co-administered:
DIETHYLTOLUAMIDE plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.56 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9109058/
6 mg/kg single, intravenous
dose: 6 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
DIETHYLTOLUAMIDE plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.73 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9109058/
15 mg/kg single, topical
dose: 15 mg/kg
route of administration: Topical
experiment type: SINGLE
co-administered:
DIETHYLTOLUAMIDE plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
50 % single, topical
Studied dose
Dose: 50 %
Route: topical
Route: single
Dose: 50 %
Sources:
https://pubmed.ncbi.nlm.nih.gov/19744033/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/19744033/
Sources:
https://pubmed.ncbi.nlm.nih.gov/19744033/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252

substrate
1946

inducer
1087
inhibitor
2438
inhibitor
2507

substrate
1388
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP19A1
429

OATP1B1
1079

OATP1B3
961

CYP2C19
2057

CYP1A2
2153
P-gp
2052

CYP2A6
626

CYP2E1
729

CYP1A2
1197

CYP2B6
776

CYP2C19
1119

CYP3A5
446
CYP1A2
832

CYP2A6
86

CYP2B6
669

CYP1A1
151
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 inconclusive [IC50 27.5404 uM]
CYP2C19
2141
 inconclusive [IC50 70.9799 uM]
CYP3A4
2633
 no [IC50 15.8904 uM]
CYP19A1
430
 no
CYP2C9
2497
 no
CYP2D6
2546
 no
OATP1B1
1095
 yes [Inhibition 10 uM]
OATP1B3
970
 yes [Inhibition 10 uM]
CYP1A1
272
 yes
CYP1A2
2333
 yes
CYP2A6
911
 yes
CYP2B6
1160
 yes
CYP3A4
2633
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 no
CYP2B6
776
 yes [Km 40.2 uM]
CYP1A2
1197
 yes [Km 41 uM]
CYP2D6
1388
 yes [Km >1000 uM]
CYP2A6
626
 yes
CYP2C19
1119
 yes
CYP2E1
729
 yes
CYP3A4
1946
 yes
CYP3A5
446
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
Mosquito repellents and superwarfarin rodenticides--are they really toxic in children?
2006-04
Hodgkin lymphoma, multiple myeloma, soft tissue sarcomas, insect repellents, and phenoxyherbicides.
2006-03
Initial evaluation of N,N-diethyl-m-toluamide and permethrin absorption in human volunteers under stress conditions.
2006-02
Repelling properties of some plant materials on the tick Ixodes ricinus L.
2006-01
Bioengineering of a cellulosic fabric for insecticide delivery via grafted cyclodextrin.
2005-12-03
Nitric oxide regulates prolidase activity by serine/threonine phosphorylation.
2005-12-01
Field evaluation of commercial repellent formulations against mosquitoes (Diptera: Culicidae) in Northern Territory, Australia.
2005-12
Solid lipid nanoparticles (SLN) for topical drug delivery: incorporation of the lipophilic drugs N,N-diethyl-m-toluamide and vitamin K.
2005-12
Evaluation of West Nile virus education campaign.
2005-11
Field-user acceptability of new camouflage face paint formulations in the Republic of Korea.
2005-10
Repellent efficacy of four commercial DEET lotions against Amblyomma hebraeum (Acari: Ixodidae), the principal vector of Rickettsia africae in southern Africa.
2005-09
Insect repellents, phenoxyherbicide exposure, and non-Hodgkin's lymphoma.
2005-08
Feeding deterrent effects of catnip oil components compared with two synthetic amides against Aedes aegypti.
2005-07
Survey of repellent use by service members arriving in Kuwait for Operation Iraqi Freedom 2.
2005-06
Food protective effect of acaricidal components isolated from anise seeds against the stored food mite, Tyrophagus putrescentiae (Schrank).
2005-06
In vitro evaluation of concurrent use of commercially available insect repellent and sunscreen preparations.
2005-06
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.
2005-05
Comparison of contact and spatial repellency of catnip oil and N,N-diethyl-3-methylbenzamide (deet) against mosquitoes.
2005-05
Absorption and evaporation of N,N-diethyl-m-toluamide from human skin in vitro.
2005-04-01
Biodegradation of the insecticide N,N-diethyl-m-toluamide by fungi: identification and toxicity of metabolites.
2005-04
Acaricidal activity of active constituent isolated in Chamaecyparis obtusa leaves against Dermatophagoides spp.
2005-03-23
Monoterpenes from thyme (Thymus vulgaris) as potential mosquito repellents.
2005-03
Repellency of deet and SS220 applied to skin involves olfactory sensing by two species of ticks.
2005-03
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.
2005-02-10
Acaricidal activity of Paeonia suffruticosa root bark-derived compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).
2004-12-29
Effect of topical agents on cercariae of Schistosoma mansoni.
2004-12
Comparative study of the topical effectiveness of the Andiroba oil (Carapa guianensis) and DEET 50% as repellent for Aedes sp.
2004-11-02
Repellency of aerosol and cream products containing fennel oil to mosquitoes under laboratory and field conditions.
2004-11
Comparative efficacy of IR3535 and deet as repellents against adult Aedes aegypti and Culex quinquefasciatus.
2004-09
Analysis and mass spectrometric characterization of the insect repellent Bayrepel and its main metabolite Bayrepel-acid.
2004-08-13
Protective behavior survey, West Nile virus, British Columbia.
2004-08
A comparison of topical formulations for the prevention of human schistosomiasis.
2004-08
Insect repellent [correction of repellant] interactions: sunscreens enhance DEET (N,N-diethyl-m-toluamide) absorption.
2004-08
Determination of selected pharmaceuticals and caffeine in sewage and seawater from Tromsø/Norway with emphasis on ibuprofen and its metabolites.
2004-08
Schistosomiasis prophylaxis in vivo using N,N-diethyl-m-toluamide (DEET).
2004-07-21
Repellency of aromatic medicinal plant extracts and a steam distillate to Aedes aegypti.
2004-06
In vitro repellency of N,N-diethyl-3-methylbenzamide and N,N-diethylphenylacetamide analogs against Aedes aegypti and Anopheles stephensi (Diptera: Culicidae).
2004-05
Comparative resistance of Anopheles albimanus and Aedes aegypti to N,N-diethyl-3-methylbenzamide (Deet) and 2-methylpiperidinyl-3-cyclohexen-1-carboxamide (AI3-37220) in laboratory human-volunteer repellent assays.
2004-05
Field evaluation of repellent formulations containing deet and picaridin against mosquitoes in Northern Territory, Australia.
2004-05
In-vitro permeation of the insect repellent N,N-diethyl-m-toluamide (DEET) and the sunscreen oxybenzone.
2004-05
Active ingredients in sunscreens act as topical penetration enhancers for the herbicide 2,4-dichlorophenoxyacetic acid.
2004-03-15
p-Anisaldehyde: acaricidal component of Pimpinella anisum seed oil against the house dust mites Dermatophagoides farinae and Dermatophagoides pteronyssinus.
2004-03
Comparative activity of deet and AI3-37220 repellents against the ticks Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae) in laboratory bioassays.
2004-03
DEET mosquito repellent sold through social marketing provides personal protection against malaria in an area of all-night mosquito biting and partial coverage of insecticide-treated nets: a case-control study of effectiveness.
2004-03
DEET mosquito repellent provides personal protection against malaria: a household randomized trial in an Afghan refugee camp in Pakistan.
2004-03
Evaluation of the sensitivity of Aedes aegypti and Anopheles gambiae complex mosquitoes to two insect repellents: DEET and KBR 3023.
2004-03
Inhibition of trans-permethrin hydrolysis in human liver fractions by chloropyrifos oxon and carbaryl.
2004
Analysis and fate of insect repellents.
2004
Chemical sensitivity in symptomatic Cambodia veterans.
2003-12
Amphiphilic star-like macromolecules as novel carriers for topical delivery of nonsteroidal anti-inflammatory drugs.
2003-10-16
Patents

Patents

JP2001302409A
1
JP2002535268A
3
JP2004107267A
1
JP2004352351A
1
JP2008195707A
3
JP2010195766A
1
JP2685353B2
1
JP4271869B2
10
JPH00193505A
1
JPH02283229A
1
JPH04224712A
1
JPH0489429A
1
JPH05132402A
3
JPH05255026A
2
JPH09165301A
1
JPH09227305A
1
JPH099853A
1
JPH11269007A
1
JPS0661509A
1
JPS5615203A
1
JPS5629501A
1
JPS63316706A
1

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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 Mon Mar 31 17:52:55 GMT 2025
Edited
by admin
on Mon Mar 31 17:52:55 GMT 2025
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
DIETHYL TOLUAMIDE
INCI  
INCI  
Preferred 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
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
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 Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
EPA PESTICIDE CODE 80301
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
NCI_THESAURUS C737
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
WHO-VATC QP53GX01
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
Code System Code Type Description
CAS
134-62-3
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
LACTMED
Diethyltoluamide
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
ALANWOOD
diethyltoluamide
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
RXCUI
3129
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY RxNorm
DAILYMED
FB0C1XZV4Y
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DIETHYLTOLUAMIDE
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
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 Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
CHEBI
7071
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
INN
6685
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
FDA UNII
FB0C1XZV4Y
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
DRUG CENTRAL
4418
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
DRUG BANK
DB11282
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
PUBCHEM
4284
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
EVMPD
SUB07114MIG
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
EPA CompTox
DTXSID2021995
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
SMS_ID
100000083130
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
ECHA (EC/EINECS)
205-149-7
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
MESH
D003671
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
MERCK INDEX
m4129
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C80601
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
WIKIPEDIA
DEET
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
RS_ITEM_NUM
1197007
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
ChEMBL
CHEMBL1453317
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
HSDB
1582
Created by admin on Mon Mar 31 17:52:55 GMT 2025 , Edited by admin on Mon Mar 31 17:52:55 GMT 2025
PRIMARY
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ACTIVE MOIETY
NIH
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