Human Metabolome Database Version 3.5

Showing metabocard for Deltamethrin (HMDB41866)

Record Information
Version 3.5
Creation Date 2012-09-13 05:44:47 -0600
Update Date 2013-05-29 22:29:39 -0600
Secondary Accession Numbers None
Metabolite Identification
Common Name Deltamethrin
Description Deltamethrin 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
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Display: 2D Structure | 3D Structure
  1. (S)-cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate
  2. Butox
  3. Cislin
  4. Crackdown
  5. Decamethrin
  6. Decamethrine
  7. Decis
  8. Decis 0.5ULV
  9. Decis 1.5ULV
  10. Decis 2.5ULV
  11. Dekametrin
  12. DeltaGard
  13. Deltagran
  14. Deltamethrin
  15. Deltamethrine
  16. Esbecythrin
  17. Glossinex 200
  18. K-Obiol
  19. K-Othrin
  20. K-Othrine
  21. New Musigie
  22. Phagase 1
  23. Suspend
  24. Zorcis
Chemical Formula C22H19Br2NO3
Average Molecular Weight 505.199
Monoisotopic Molecular Weight 502.973168773
IUPAC Name (S)-cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Traditional IUPAC Name deltamethrin
CAS Registry Number 52918-63-5
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
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Pyrethroids
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • Pyrethroid insecticides(KEGG)
  • aromatic ether(ChEBI)
  • carboxylic ester(ChEBI)
  • nitrile(ChEBI)
  • organobromine compound(ChEBI)
  • Benzyl Alcohol Derivative
  • Benzyl Cyanide
  • Benzyloxycarbonyl
  • Carboxylic Acid Ester
  • Cyclopropane
  • Halogen Derivative
  • Ketene Acetal Or Derivative
  • Nitrile
  • Organic Halide
  • Organobromide
Direct Parent Pyrethroids
Status Expected and Not Quantified
  • Toxin/Pollutant
  • Nutrient
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 100 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 2e-06 mg/mL at 25 °C Not Available
LogP 6.20 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0013 g/L ALOGPS
LogP 6.13 ALOGPS
LogP 5.74 ChemAxon
LogS -5.61 ALOGPS
pKa (strongest acidic) 10.62 ChemAxon
pKa (strongest basic) -7.1 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 59.32 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 124.29 ChemAxon
Polarizability 42.76 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Not Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 37079 Link_out
KEGG Compound ID C10985 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link deltamethrin Link_out
NuGOwiki Link HMDB41866 Link_out
Metagene Link HMDB41866 Link_out
METLIN ID Not Available
PubChem Compound 40585 Link_out
PDB ID Not Available
ChEBI ID 4388 Link_out
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available