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:: 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 Target ID: 1279770.0 Gene Symbol: OBP17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21671117	Binding Agent 413	31.3 µM [Kd]
Target ID: OR136 (Culex quinquefasciatus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25349401	Activator 560
Target ID: Ionotropic receptor 40a (Fruit fly) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24089210	Activator 560

Conditions

Condition	Modality	Highest Phase	Product
Malaria 39 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9180612 https://www.ncbi.nlm.nih.gov/pubmed/21418669	Preventing	Approved 4033	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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22962880 https://www.epa.gov/insect-repellents/deet	Preventing	Approved 4033	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 Sources: https://www.epa.gov/insect-repellents/deet http://www.swmosquito.org/pdf/PROT_DEET%20Toxicity.pdf	Preventing	Approved 4033	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
Isolation of a deet-insensitive mutant of Drosophila melanogaster (Diptera: Drosophilidae).	2001 Dec	11777068
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
Repellency of volatile oils from plants against three mosquito vectors.	2001 Jun	11469188
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
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	11420065
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	11700004
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
Genotoxicity studies on permethrin, DEET and diazinon in primary human nasal mucosal cells.	2002 Mar	12003267
Chemical sensitivity in symptomatic Cambodia veterans.	2003 Dec	15859508
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
Repellent efficacy of DEET and KBR 3023 against Amblyomma hebraeum (Acari: Ixodidae).	2003 Mar	12693855
Comparison of the mosquito-repelling efficacy of methyl neodecanamide (MNDA) to that of Deet.	2003 May-Jun	12858227
A comparison of topical formulations for the prevention of human schistosomiasis.	2004 Aug	15285838
Effect of topical agents on cercariae of Schistosoma mansoni.	2004 Dec	15587316
Acaricidal activity of Paeonia suffruticosa root bark-derived compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).	2004 Dec 29	15612767
Comparative activity of deet and AI3-37220 repellents against the ticks Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae) in laboratory bioassays.	2004 Mar	15061285
DEET mosquito repellent provides personal protection against malaria: a household randomized trial in an Afghan refugee camp in Pakistan.	2004 Mar	14996362
Evaluation of the sensitivity of Aedes aegypti and Anopheles gambiae complex mosquitoes to two insect repellents: DEET and KBR 3023.	2004 Mar	14996361
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
Repellency of aerosol and cream products containing fennel oil to mosquitoes under laboratory and field conditions.	2004 Nov	15532688
Comparative study of the topical effectiveness of the Andiroba oil (Carapa guianensis) and DEET 50% as repellent for Aedes sp.	2004 Sep-Oct	15517027
Biodegradation of the insecticide N,N-diethyl-m-toluamide by fungi: identification and toxicity of metabolites.	2005 Apr	15750774
Absorption and evaporation of N,N-diethyl-m-toluamide from human skin in vitro.	2005 Apr 1	15781296
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
Food protective effect of acaricidal components isolated from anise seeds against the stored food mite, Tyrophagus putrescentiae (Schrank).	2005 Jun	15954709
In vitro evaluation of concurrent use of commercially available insect repellent and sunscreen preparations.	2005 Jun	15948991
Monoterpenes from thyme (Thymus vulgaris) as potential mosquito repellents.	2005 Mar	15825766
Repellency of deet and SS220 applied to skin involves olfactory sensing by two species of ticks.	2005 Mar	15752184
Acaricidal activity of active constituent isolated in Chamaecyparis obtusa leaves against Dermatophagoides spp.	2005 Mar 23	15769116
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 `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

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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