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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:44:47 UTC
Update Date2021-10-13 08:37:18 UTC
HMDB IDHMDB0041866
Secondary Accession Numbers
  • HMDB41866
Metabolite Identification
Common NameDeltamethrin
DescriptionDeltamethrin is a pyrethroid ester insecticide. Deltamethrin plays key role in controlling malaria vectors, and is used in the manufacture of long-lasting insecticidal mosquito nets. It is used as one of a battery of pyrethroid insecticides in control of malarial vectors, particularly Anopheles gambiae, and whilst being the most employed pyrethroid insecticide, can be used in conjunction with, or as an alternative to, permethrin, cypermethrin and other organophosphate-based insecticides, such as malathion and fenthion. Resistance to deltamethrin (and its counterparts) is now extremely widespread and threatens the success of worldwide vector control programmes. Deltamethrin products are among the most popular and widely used insecticides in the world[citation needed] and have become very popular with pest control operators and individuals in the United States. This material is a member of one of the safest classes of pesticides: synthetic pyrethroids. This pesticide is highly toxic to aquatic life, particularly fish, and therefore must be used with extreme caution around water. It is neurotoxic to humans and has been found in human breast milk. Since deltamethrin is a neurotoxin, it attacks the nervous system. Skin contact can lead to tingling or reddening of the skin local to the application. If taken in through the eyes or mouth, a common symptom is facial paraesthesia, which can feel like many different abnormal sensations, including burning, partial numbness, 'pins and needles', skin crawling, etc. There are no reports indicating that chronic intoxication from pyrethroid insecticides causes motor neuron damage or motor neuron disease. However, in 2011, a case report was published demonstrating pathologically proven motor neuron death in a Japanese woman after acute massive ingestion of pesticides containing pyrethroids and organochlorine. There are many uses for deltamethrin, ranging from agricultural uses to home pest control. Deltamethrin has been instrumental in preventing the spread of diseases carried by tick-infested prairie dogs, rodents and other burrowing animals[citation needed]. It is helpful in eliminating and preventing a wide variety of household pests, especially spiders, fleas, ticks, carpenter ants, carpenter bees, cockroaches and bedbugs. Deltamethrin is also one of the primary ingredients in ant chalk.
Structure
Data?1563863709
Synonyms
ValueSource
(S)-alpha-Cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylateChEBI
(S)-alpha-Cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylateChEBI
(S)-Cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylateChEBI
BallisticChEBI
Cropro D-sectChEBI
DecamethrinChEBI
DecamethrineChEBI
DecisChEBI
Decis optionsChEBI
DeltaGardChEBI
DeltashieldChEBI
ScaliborChEBI
(S)-a-Cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylateGenerator
(S)-a-Cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
(S)-alpha-Cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
(S)-Α-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylateGenerator
(S)-Α-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
(S)-a-Cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylateGenerator
(S)-a-Cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
(S)-alpha-Cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
(S)-Α-cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylateGenerator
(S)-Α-cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
(S)-Cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylic acidGenerator
(S)-Cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylateHMDB
ButoxHMDB
CislinHMDB
CrackdownHMDB
Decis 0.5ulvHMDB
Decis 1.5ulvHMDB
Decis 2.5ulvHMDB
DekametrinHMDB
DeltagranHMDB
DeltamethrineHMDB
EsbecythrinHMDB
Glossinex 200HMDB
K-ObiolHMDB
K-OthrinHMDB
K-OthrineHMDB
New musigieHMDB
Phagase 1HMDB
SuspendHMDB
ZorcisHMDB
Decamethrin, (1S-(1alpha(s*),3alpha))-isomerHMDB
alpha-Cyano-3-phenoxybenzyl (1R,3R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylateHMDB
Decamethrin, (1R-(1alpha(r*),3beta))-isomerHMDB
DifexonHMDB
Decamethrin, (1R-(1alpha(r*),3alpha))-isomerHMDB
Decamethrin, (1R-(1alpha(s*),3beta))-isomerHMDB
Decamethrin, (1S-(1alpha(r*),3alpha))-isomerHMDB
NRDC 161HMDB
Chemical FormulaC22H19Br2NO3
Average Molecular Weight505.199
Monoisotopic Molecular Weight502.973168773
IUPAC Name(S)-cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Traditional Namestricker
CAS Registry Number52918-63-5
SMILES
[H][C@@](OC(=O)[C@]1([H])[C@]([H])(C=C(Br)Br)C1(C)C)(C#N)C1=CC(OC2=CC=CC=C2)=CC=C1
InChI Identifier
InChI=1S/C22H19Br2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/t17-,18+,20-/m0/s1
InChI KeyOWZREIFADZCYQD-NSHGMRRFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentPyrethroids
Alternative Parents
Substituents
  • Pyrethroid skeleton
  • Diphenylether
  • Diaryl ether
  • Benzyloxycarbonyl
  • Phenoxy compound
  • Phenol ether
  • Monocyclic benzene moiety
  • Cyclopropanecarboxylic acid or derivatives
  • Benzenoid
  • Carboxylic acid ester
  • Ketene acetal or derivatives
  • Carboxylic acid derivative
  • Ether
  • Bromoalkene
  • Monocarboxylic acid or derivatives
  • Carbonitrile
  • Nitrile
  • Haloalkene
  • Vinyl halide
  • Vinyl bromide
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organohalogen compound
  • Organobromide
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point100 °CNot Available
Boiling Point535.80 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility2.0e-06 mg/mL at 25 °CNot Available
LogP6.20Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP10(6.13) g/LALOGPS
logP10(5.74) g/LChemAxon
logS10(-5.6) g/LALOGPS
pKa (Strongest Acidic)10.62ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.32 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity124.29 m³·mol⁻¹ChemAxon
Polarizability42.76 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Deltamethrin[H][C@@](OC(=O)[C@]1([H])[C@]([H])(C=C(Br)Br)C1(C)C)(C#N)C1=CC(OC2=CC=CC=C2)=CC=C13519.6Standard polar33892256
Deltamethrin[H][C@@](OC(=O)[C@]1([H])[C@]([H])(C=C(Br)Br)C1(C)C)(C#N)C1=CC(OC2=CC=CC=C2)=CC=C12898.1Standard non polar33892256
Deltamethrin[H][C@@](OC(=O)[C@]1([H])[C@]([H])(C=C(Br)Br)C1(C)C)(C#N)C1=CC(OC2=CC=CC=C2)=CC=C13105.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Deltamethrin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfr-3290000000-fc2670ebdafd72059d492017-09-01Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0ff3-7940000000-0aa3b4a622f8410e5b432014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deltamethrin 10V, Positive-QTOFsplash10-0udi-0060190000-d06e22076d1773eb0a442016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deltamethrin 20V, Positive-QTOFsplash10-0fb9-0190220000-42d1b03d814ec594ac382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deltamethrin 40V, Positive-QTOFsplash10-004s-2390000000-81cbf54d9ff1579aaee82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deltamethrin 10V, Negative-QTOFsplash10-0udi-0010190000-74170f71f0cac166e6c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deltamethrin 20V, Negative-QTOFsplash10-0uk9-3151590000-565197ea502710a2b39e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deltamethrin 40V, Negative-QTOFsplash10-0006-9430000000-f63f1a3abdb315fa7b1a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deltamethrin 10V, Positive-QTOFsplash10-0zfr-0050290000-ae219751f7022f5de5c32021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deltamethrin 20V, Positive-QTOFsplash10-0zi1-3291140000-49559be6170bc80632d42021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deltamethrin 40V, Positive-QTOFsplash10-0a59-2980000000-38996b5e6c79b7a6a39a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deltamethrin 10V, Negative-QTOFsplash10-0udi-0050290000-dabcbd6a2915829d16b42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deltamethrin 20V, Negative-QTOFsplash10-0udj-3290150000-1ee946d210b195df7f8c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deltamethrin 40V, Negative-QTOFsplash10-0006-9010100000-1b3ae98f2c93d34b79a92021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13600
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID37079
KEGG Compound IDC10985
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDeltamethrin
METLIN IDNot Available
PubChem Compound40585
PDB IDNot Available
ChEBI ID4388
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1349811
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.