Diethyltoluamide (CHEM002788)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:51 UTC
Update Date2016-10-28 10:04:30 UTC
Accession NumberCHEM002788
Identification
Common NameDiethyltoluamide
ClassSmall Molecule
DescriptionDiethyltoluamide, abbreviated DEET, is a slightly yellow oil. It is the most common active ingredient in insect repellents. It is intended to be applied to the skin or to clothing, and provides protection against mosquitos, ticks, fleas, chiggers, and many other biting insects.
Contaminant Sources
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • Suspected Compounds - Waste Water
  • Suspected Compounds – Schymanski Project
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Ester
  • Household Toxin
  • Insect Repellent
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Methyl-N,N-diethylbenzamideChEBI
AutanChEBI
DeetChEBI
DetamideChEBI
Diethyl toluamideChEBI
DiethyltoluamidumChEBI
DietiltoluamidaChEBI
FlypelChEBI
m-DelpheneChEBI
MetadelpheneChEBI
MuscolChEBI
OffChEBI
OFF!ChEBI
RepelChEBI
DEET, 2,5-di-me-analogMeSH
DETMeSH
DETAMeSH
N,N Diethyl 3 methylbenzamideMeSH
N,N Diethyl m toluamideMeSH
N,N DiethyltoluamideMeSH
N,N-Diethyl-2,5-dimethylbenzamideMeSH
N,N-Diethyl-3-methylbenzamideMeSH
N,N-Diethyl-m-toluamideMeSH
N,N-DiethyltoluamideMeSH
Chemical FormulaC12H17NO
Average Molecular Mass191.270 g/mol
Monoisotopic Mass191.131 g/mol
CAS Registry Number134-62-3
IUPAC NameN,N-diethyl-3-methylbenzamide
Traditional NameDETA
SMILESCCN(CC)C(=O)C1=CC=CC(C)=C1
InChI IdentifierInChI=1S/C12H17NO/c1-4-13(5-2)12(14)11-8-6-7-10(3)9-11/h6-9H,4-5H2,1-3H3
InChI KeyMMOXZBCLCQITDF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n,n-dialkyl-m-toluamides. These are aromatic that contain a m-toluamide, where the carboxamide group is N- substituted with two alkyl chains.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassToluenes
Direct ParentN,N-dialkyl-m-toluamides
Alternative Parents
Substituents
  • N,n-dialkyl-m-toluamide
  • Benzoic acid or derivatives
  • Benzamide
  • Benzoyl
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-33°C
Boiling Point288-292°C
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.68 g/LALOGPS
logP2.1ALOGPS
logP2.5ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)-0.082ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.47 m³·mol⁻¹ChemAxon
Polarizability22.16 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-016r-4900000000-1934ae23aef1d6d58a78Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014l-9711100000-6efb069e880ace92d4cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-995982de47cfbcedff66Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014l-0900000000-49b97cb5b12bcd0757bbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-5c845107ddf24f631344Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-4e7d4be8f6085796f370Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-281ad1f50c96e62d93dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0900000000-6f014def377ae48a45e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0900000000-3ec7134a184c674a70e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014l-0900000000-be3e4ba15c24f2ff7ae3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-1900000000-c118ef147fc9025ced44Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-3900000000-53c7c6316dce45b27287Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00kf-9800000000-2b501045198b5f22a55eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0900000000-3c12af86f43b00cea820Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0900000000-84ab99b187682ae43e94Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014l-0900000000-604acf0d90339752c932Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-1900000000-31f8aee182e7dcf3c1f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-3900000000-6482109d03926fb851eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00kf-9800000000-03e78de19a2c02564209Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-c8cb356261079f7901ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-5fac2adeeb5001907efbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-2900000000-2bea2538593d9d0ab98eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-073f8dc5b247cf0353e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-3d63f65bd039fddb1ac7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-26e810492d4e8f73c0f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9500000000-b6215ccf9c1980e72db5Spectrum
MSMass Spectrum (Electron Ionization)splash10-014l-4900000000-c13868bc7a5900810817Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
StatusValueUnitSample LocationReference
DrugBank IDDB11282
HMDB IDHMDB0250930
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDEET
Chemspider ID4133
ChEBI ID7071
PubChem Compound ID4284
Kegg Compound IDC10935
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20797533
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20963476
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21937991
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22289669
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23167529
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23261834
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23407786
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23437043
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=2499696
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=25748344
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=26467804
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=27138630
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=27345502
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=27510858
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=27639850
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=27657095
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=28676765
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=29077936
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=30395919
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=3352115
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=7564300
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=8187533
23.