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 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
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
Repellency of volatile oils from plants against three mosquito vectors.	2001 Jun	11469188
Laboratory and field evaluation of insect repellents as oviposition deterrents against the mosquito Aedes albopictus.	2001 Jun	11434545
Combined exposure to DEET (N,N-diethyl-m-toluamide) and permethrin-induced release of rat brain mitochondrial cytochrome c.	2001 Jun 22	11437058
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
Simultaneous determination of malathion, permethrin, DEET (N,N-diethyl-m-toluamide), and their metabolites in rat plasma and urine using high performance liquid chromatography.	2001 Sep	11470206
Repellent activities of essential oils and monoterpenes against Culex pipiens pallens.	2002 Dec	12542193
Pyridostigmine bromide modulates the dermal disposition of [14C]permethrin.	2002 Jun 15	12079425
In vitro human metabolism and interactions of repellent N,N-diethyl-m-toluamide.	2002 Mar	11854147
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
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
DEET: a review and update of safety and risk in the general population.	2003	14677793
DEET-based insect repellents: safety implications for children and pregnant and lactating women.	2003 Aug 5	12900480
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
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
Percutaneous absorption of topical N,N-diethyl-m-toluamide (DEET): effects of exposure variables and coadministered toxicants.	2003 Jan 24	12653019
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
Repellent efficacy of DEET and KBR 3023 against Amblyomma hebraeum (Acari: Ixodidae).	2003 Mar	12693855
Olfactory stimulation of Africanized honey bee (Hymenoptera: Apidae) attacks by insect repellents.	2003 May	12943104
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
Semen quality in relation to biomarkers of pesticide exposure.	2003 Sep	12948887
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
Neurological deficits induced by malathion, DEET, and permethrin, alone or in combination in adult rats.	2004 Feb 27	14713564
p-Anisaldehyde: acaricidal component of Pimpinella anisum seed oil against the house dust mites Dermatophagoides farinae and Dermatophagoides pteronyssinus.	2004 Mar	15114512
Active ingredients in sunscreens act as topical penetration enhancers for the herbicide 2,4-dichlorophenoxyacetic acid.	2004 Mar 15	15020197
In vitro repellency of N,N-diethyl-3-methylbenzamide and N,N-diethylphenylacetamide analogs against Aedes aegypti and Anopheles stephensi (Diptera: Culicidae).	2004 May	15185946
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
Absorption and evaporation of N,N-diethyl-m-toluamide from human skin in vitro.	2005 Apr 1	15781296
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
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
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
Acaricidal activity of active constituent isolated in Chamaecyparis obtusa leaves against Dermatophagoides spp.	2005 Mar 23	15769116
Comparison of contact and spatial repellency of catnip oil and N,N-diethyl-3-methylbenzamide (deet) against mosquitoes.	2005 May	15962779
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

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 15 15:17:19 GMT 2023` Edited by `admin` on `Fri Dec 15 15:17:19 GMT 2023`
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