DIETHYLTOLUAMIDE

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 Search

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
AGAP003309-PA 1 Target ID: 1279770 Gene Symbol: OBP17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21671117	Binding Agent 994	Malaria West Nile virus infectious disease	31.3000000000000007 µM [Kd]
Target ID: OR136 (Culex quinquefasciatus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25349401	Activator 1335
Target ID: Ionotropic receptor 40a (Fruit fly) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24089210	Activator 1335

Conditions

Condition	Modality	Targets	Highest Phase	Product
Malaria 89 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9180612 https://www.ncbi.nlm.nih.gov/pubmed/21418669	Preventing	AGAP003309-PA	Approved 7997	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 7997	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	AGAP003309-PA	Approved 7997	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
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	12539864
High performance liquid chromatographic determination of diazinon, permethrin, DEET (N, N-diethyl-m-toluamide), and their metabolites in rat plasma and urine.	2001 Jun	11495064
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
Acaricidal activity of butylidenephthalide identified in Cnidium officinale rhizome against dermatophagoides farinae and dermatophagoides pteronyssinus (Acari: Pyroglyphidae).	2002 Jul 31	12137464
Comparative efficacy of insect repellents against mosquito bites.	2002 Jul 4	12097535
Cardiorespiratory effects following acute exposure to pyridostigmine bromide and/or N,N-diethyl-m-toluamide (DEET) in rats.	2002 Jul-Aug	12171630
Pyridostigmine bromide modulates the dermal disposition of [14C]permethrin.	2002 Jun 15	12079425
Genotoxicity studies on permethrin, DEET and diazinon in primary human nasal mucosal cells.	2002 Mar	12003267
Malaria outbreak control in an African village by community application of 'deet' mosquito repellent to ankles and feet.	2002 Mar	11963976
In vitro human metabolism and interactions of repellent N,N-diethyl-m-toluamide.	2002 Mar	11854147
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
Repellent activity of constituents identified in Foeniculum vulgare fruit against Aedes aegypti (Diptera: Culicidae).	2002 Nov 20	12428949
Gulf War related exposure factors influencing topical absorption of 14C-permethrin.	2002 Sep 5	12243864
Human Exposures to N,N-diethyl-m-toluamide insect repellents reported to the American Association of Poison Control Centers 1993-1997.	2002 Sep-Oct	12396679
Effectiveness of a repellent containing DEET and EBAAP for preventing tick bites.	2002 Spring	11929056
Pyridostigmine bromide modulates topical irritant-induced cytokine release from human epidermal keratinocytes and isolated perfused porcine skin.	2003 Feb 1	12504339
Acaricidal activity of clove bud oil compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).	2003 Feb 12	12568544
Acaricidal activity of Cnidium officinale rhizome-derived butylidenephthalide against Tyrophagus putrescentiae (Acari: Acaridae).	2003 Jan	12558107
Testicular germ-cell apoptosis in stressed rats following combined exposure to pyridostigmine bromide, N,N-diethyl m-toluamide (DEET), and permethrin.	2003 Jan 10	12587291
Schistosomiasis prophylaxis in vivo using N,N-diethyl-m-toluamide (DEET).	2003 Jul-Aug	15259480
Comparison of the mosquito-repelling efficacy of methyl neodecanamide (MNDA) to that of Deet.	2003 May-Jun	12858227
Amphiphilic star-like macromolecules as novel carriers for topical delivery of nonsteroidal anti-inflammatory drugs.	2003 Oct 16	15198514
Analysis and fate of insect repellents.	2004	15497861
Protective behavior survey, West Nile virus, British Columbia.	2004 Aug	15496260
A comparison of topical formulations for the prevention of human schistosomiasis.	2004 Aug	15285838
Insect repellent [correction of repellant] interactions: sunscreens enhance DEET (N,N-diethyl-m-toluamide) absorption.	2004 Aug	15258101
Determination of selected pharmaceuticals and caffeine in sewage and seawater from Tromsø/Norway with emphasis on ibuprofen and its metabolites.	2004 Aug	15212901
Analysis and mass spectrometric characterization of the insect repellent Bayrepel and its main metabolite Bayrepel-acid.	2004 Aug 13	15387185
Neurological deficits induced by malathion, DEET, and permethrin, alone or in combination in adult rats.	2004 Feb 27	14713564
Repellency of aromatic medicinal plant extracts and a steam distillate to Aedes aegypti.	2004 Jun	15264623
Comparative study of the topical effectiveness of the Andiroba oil (Carapa guianensis) and DEET 50% as repellent for Aedes sp.	2004 Sep-Oct	15517027
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
Survey of repellent use by service members arriving in Kuwait for Operation Iraqi Freedom 2.	2005 Jun	16001599
Repellency of deet and SS220 applied to skin involves olfactory sensing by two species of ticks.	2005 Mar	15752184
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
Mosquito repellents and superwarfarin rodenticides--are they really toxic in children?	2006 Apr	16601500
Repelling properties of some plant materials on the tick Ixodes ricinus L.	2006 Jan	16360943

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 `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

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

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