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:: 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
Isolation of a deet-insensitive mutant of Drosophila melanogaster (Diptera: Drosophilidae).
2001 Dec
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
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
The effects of pyridostigmine bromide, permethrin, and DEET alone, or in combination, on fixed-ratio and fixed-interval behavior in male and female rats.
2001 May-Jun
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
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
Genotoxicity studies on permethrin, DEET and diazinon in primary human nasal mucosal cells.
2002 Mar
Chemical sensitivity in symptomatic Cambodia veterans.
2003 Dec
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
Repellent efficacy of DEET and KBR 3023 against Amblyomma hebraeum (Acari: Ixodidae).
2003 Mar
Comparison of the mosquito-repelling efficacy of methyl neodecanamide (MNDA) to that of Deet.
2003 May-Jun
A comparison of topical formulations for the prevention of human schistosomiasis.
2004 Aug
Effect of topical agents on cercariae of Schistosoma mansoni.
2004 Dec
Acaricidal activity of Paeonia suffruticosa root bark-derived compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).
2004 Dec 29
Comparative activity of deet and AI3-37220 repellents against the ticks Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae) in laboratory bioassays.
2004 Mar
DEET mosquito repellent provides personal protection against malaria: a household randomized trial in an Afghan refugee camp in Pakistan.
2004 Mar
Evaluation of the sensitivity of Aedes aegypti and Anopheles gambiae complex mosquitoes to two insect repellents: DEET and KBR 3023.
2004 Mar
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 May
Repellency of aerosol and cream products containing fennel oil to mosquitoes under laboratory and field conditions.
2004 Nov
Comparative study of the topical effectiveness of the Andiroba oil (Carapa guianensis) and DEET 50% as repellent for Aedes sp.
2004 Sep-Oct
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
Field evaluation of commercial repellent formulations against mosquitoes (Diptera: Culicidae) in Northern Territory, Australia.
2005 Dec
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
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
Food protective effect of acaricidal components isolated from anise seeds against the stored food mite, Tyrophagus putrescentiae (Schrank).
2005 Jun
In vitro evaluation of concurrent use of commercially available insect repellent and sunscreen preparations.
2005 Jun
Monoterpenes from thyme (Thymus vulgaris) as potential mosquito repellents.
2005 Mar
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
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
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
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 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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