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

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 1064	31.3 µM [Kd]
OR136 (Culex quinquefasciatus) 1 Target ID: OR136 (Culex quinquefasciatus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25349401	Activator 1430
Ionotropic receptor 40a (Fruit fly) 1 Target ID: Ionotropic receptor 40a (Fruit fly) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24089210	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Malaria 95 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9180612 https://www.ncbi.nlm.nih.gov/pubmed/21418669	Preventing	Approved 8429	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 8429	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 8429	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
Development of a high-performance liquid chromatographic method for the quantification of chlorpyrifos, pyridostigmine bromide, N,N-diethyl-m-toluamide and their metabolites in rat plasma and urine.	2001 Apr 25	11339298
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
Safety of the insect repellent N,N-diethyl-M-toluamide (DEET) in pregnancy.	2001 Oct	11693870
Laboratory and field evaluations of the insect repellent 3535 (ethyl butylacetylaminopropionate) and deet against mosquito vectors in Thailand.	2001 Sep	14529087
Soldier acceptability of a camouflage face paint combined with DEET insect repellent.	2001 Sep	11569440
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
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
Cardiorespiratory effects following acute exposure to pyridostigmine bromide and/or N,N-diethyl-m-toluamide (DEET) in rats.	2002 Jul-Aug	12171630
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
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
Combined exposure to DEET (N,N-diethyl-m-toluamide) and permethrin: pharmacokinetics and toxicological effects.	2003 Jan-Feb	12587253
Schistosomiasis prophylaxis in vivo using N,N-diethyl-m-toluamide (DEET).	2003 Jul-Aug	15259480
Biological activity of tropolone.	2003 Oct	14519960
Inhibition of trans-permethrin hydrolysis in human liver fractions by chloropyrifos oxon and carbaryl.	2004	15663293
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
Analysis and mass spectrometric characterization of the insect repellent Bayrepel and its main metabolite Bayrepel-acid.	2004 Aug 13	15387185
Acaricidal activity of Paeonia suffruticosa root bark-derived compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).	2004 Dec 29	15612767
Co-exposure to pyridostigmine bromide, DEET, and/or permethrin causes sensorimotor deficit and alterations in brain acetylcholinesterase activity.	2004 Feb	14751452
Repellency of aromatic medicinal plant extracts and a steam distillate to Aedes aegypti.	2004 Jun	15264623
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
Field evaluation of repellent formulations containing deet and picaridin against mosquitoes in Northern Territory, Australia.	2004 May	15185943
Survey of repellent use by service members arriving in Kuwait for Operation Iraqi Freedom 2.	2005 Jun	16001599
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
Repellent efficacy of four commercial DEET lotions against Amblyomma hebraeum (Acari: Ixodidae), the principal vector of Rickettsia africae in southern Africa.	2005 Sep	15993907
Initial evaluation of N,N-diethyl-m-toluamide and permethrin absorption in human volunteers under stress conditions.	2006 Feb	16578980

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).

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