DIETHYLTOLUAMIDE

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 Search

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
Sources: https://www.drugs.com/mmx/diethyltoluamide.html
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

Targets

Primary Target	Pharmacology	Potency
AGAP003309-PA 1 Target ID: 1279770.0 Gene Symbol: OBP17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21671117	Binding Agent 1037	31.3 µM [Kd]
Target ID: OR136 (Culex quinquefasciatus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25349401	Activator 1404
Target ID: Ionotropic receptor 40a (Fruit fly) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24089210	Activator 1404

Conditions

Condition	Modality	Highest Phase	Product
Malaria 92 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9180612 https://www.ncbi.nlm.nih.gov/pubmed/21418669	Preventing	Approved 8307	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.
Lyme disease 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22962880 https://www.epa.gov/insect-repellents/deet	Preventing	Approved 8307	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.
West Nile virus infectious disease 1 Sources: https://www.epa.gov/insect-repellents/deet http://www.swmosquito.org/pdf/PROT_DEET%20Toxicity.pdf	Preventing	Approved 8307	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

Title	Date	PubMed
Locomotor and sensorimotor performance deficit in rats following exposure to pyridostigmine bromide, DEET, and permethrin, alone and in combination.	2001 Apr	11248143
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	11325563
Isolation of a deet-insensitive mutant of Drosophila melanogaster (Diptera: Drosophilidae).	2001 Dec	11777068
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	11525153
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	12270692
Drugs and personal care products as ubiquitous pollutants: occurrence and distribution of clofibric acid, caffeine and DEET in the North Sea.	2002 Aug 5	12186282
Repellent activities of essential oils and monoterpenes against Culex pipiens pallens.	2002 Dec	12542193
Topical formulation studies with DEET (N,N-diethyl-3-methylbenzamide) and cyclodextrins.	2002 Jan	11782901
Binding of pyridostigmine bromide, N,N-diethyl-m-toluamide and permethrin, alone and in combinations, to human serum albumin.	2002 May	12029383
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	12383479
Gulf War related exposure factors influencing topical absorption of 14C-permethrin.	2002 Sep 5	12243864
Combined exposure to DEET (N,N-diethyl-m-toluamide) and permethrin: pharmacokinetics and toxicological effects.	2003 Jan-Feb	12587253
Analysis and mass spectrometric characterization of the insect repellent Bayrepel and its main metabolite Bayrepel-acid.	2004 Aug 13	15387185
Evaluation of the sensitivity of Aedes aegypti and Anopheles gambiae complex mosquitoes to two insect repellents: DEET and KBR 3023.	2004 Mar	14996361
Active ingredients in sunscreens act as topical penetration enhancers for the herbicide 2,4-dichlorophenoxyacetic acid.	2004 Mar 15	15020197
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	15185944
In-vitro permeation of the insect repellent N,N-diethyl-m-toluamide (DEET) and the sunscreen oxybenzone.	2004 May	15142339
Biodegradation of the insecticide N,N-diethyl-m-toluamide by fungi: identification and toxicity of metabolites.	2005 Apr	15750774
Insect repellents, phenoxyherbicide exposure, and non-Hodgkin's lymphoma.	2005 Aug	16093930
Field evaluation of commercial repellent formulations against mosquitoes (Diptera: Culicidae) in Northern Territory, Australia.	2005 Dec	16506580
Solid lipid nanoparticles (SLN) for topical drug delivery: incorporation of the lipophilic drugs N,N-diethyl-m-toluamide and vitamin K.	2005 Dec	16398266
Nitric oxide regulates prolidase activity by serine/threonine phosphorylation.	2005 Dec 1	16167338
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	15733541
Feeding deterrent effects of catnip oil components compared with two synthetic amides against Aedes aegypti.	2005 Jul	16119554
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	16110978
Comparison of contact and spatial repellency of catnip oil and N,N-diethyl-3-methylbenzamide (deet) against mosquitoes.	2005 May	15962779
Evaluation of West Nile virus education campaign.	2005 Nov	16318730
Bioengineering of a cellulosic fabric for insecticide delivery via grafted cyclodextrin.	2005 Nov-Dec	16321057
Field-user acceptability of new camouflage face paint formulations in the Republic of Korea.	2005 Oct	16435753
Repellent efficacy of four commercial DEET lotions against Amblyomma hebraeum (Acari: Ixodidae), the principal vector of Rickettsia africae in southern Africa.	2005 Sep	15993907
Mosquito repellents and superwarfarin rodenticides--are they really toxic in children?	2006 Apr	16601500
Initial evaluation of N,N-diethyl-m-toluamide and permethrin absorption in human volunteers under stress conditions.	2006 Feb	16578980
Repelling properties of some plant materials on the tick Ixodes ricinus L.	2006 Jan	16360943
Hodgkin lymphoma, multiple myeloma, soft tissue sarcomas, insect repellents, and phenoxyherbicides.	2006 Mar	16531830

Patents

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 `Fri Dec 16 16:42:32 UTC 2022` Edited by `admin` on `Fri Dec 16 16:42:32 UTC 2022`
Record UNII	FB0C1XZV4Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIETHYLTOLUAMIDE

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

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

Common Name

English

DIETHYLTOLUAMIDE [HSDB]

Common Name

English

diethyltoluamide [INN]

Common Name

English

DEET	Locators: MI Sources:

Common Name

English

N,N-DIETHYL-M-TOLUAMIDE

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

P03BX01