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Record Information
Version4.0
Creation Date2012-09-13 11:44:47 UTC
Update Date2017-09-27 08:33:40 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
Thumb
Synonyms
ValueSource
DecamethrinChEBI
(S)-cyano(3-Phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylateHMDB
ButoxHMDB
CislinHMDB
CrackdownHMDB
DecamethrineHMDB
DecisHMDB
Decis 0.5ulvHMDB
Decis 1.5ulvHMDB
Decis 2.5ulvHMDB
DekametrinHMDB
DeltaGardHMDB
DeltagranHMDB
DeltamethrineHMDB
EsbecythrinHMDB
Glossinex 200HMDB
K-ObiolHMDB
K-OthrinHMDB
K-OthrineHMDB
New musigieHMDB
Phagase 1HMDB
SuspendHMDB
ZorcisHMDB
Decamethrin, (1S-(1alpha(s*),3alpha))-isomerMeSH
alpha-cyano-3-Phenoxybenzyl (1R,3R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylateMeSH
Decamethrin, (1R-(1alpha(r*),3beta))-isomerMeSH
DifexonMeSH
Decamethrin, (1R-(1alpha(r*),3alpha))-isomerMeSH
Decamethrin, (1R-(1alpha(s*),3beta))-isomerMeSH
Decamethrin, (1S-(1alpha(r*),3alpha))-isomerMeSH
NRDC 161MeSH
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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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

Biological Location:

  Subcellular:

Route of exposure:

  Parenteral:

  Enteral:

Source:

Role

Biological role:

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Environmental role:

Physiological effect

Health effect:

  Observation:

  Health condition:

    Gastrointestinal disorders:

    Nervous system disorders:

    Skin and subcutaneous tissue disorders:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point100 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.0e-06 mg/mL at 25 °CNot Available
LogP6.20Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0013 g/LALOGPS
logP6.13ALOGPS
logP5.74ChemAxon
logS-5.6ALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0060190000-d06e22076d1773eb0a44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0190220000-42d1b03d814ec594ac38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004s-2390000000-81cbf54d9ff1579aaee8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0010190000-74170f71f0cac166e6c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-3151590000-565197ea502710a2b39eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9430000000-f63f1a3abdb315fa7b1aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0ff3-7940000000-0aa3b4a622f8410e5b43View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
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 ]