Cypermethrin (CHEM000892)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (40)XML
Record Information
Version1.0
Creation Date2009-06-18 17:03:35 UTC
Update Date2026-04-14 19:30:57 UTC
Accession NumberCHEM000892
Identification
Common NameCypermethrin
ClassSmall Molecule
DescriptionCypermethrin is a synthetic pyrethroid primarily used as an insecticide. It acts as a fast-acting neurotoxin in insects. It is easily degraded on soil and plants but can be effective for weeks when applied to indoor inert surfaces. Exposure to sunlight, water and oxygen will accelerate its decomposition. It is a synthetic pyrethroid. Cypermethrin is highly toxic to fish, bees and aquatic insects, according to the National Pesticides Telecommunications Network (NPTN). Cypermethrin is found in many household ant and cockroach killers, including Raid and ant chalk. Some subsets of isomers of this substance are alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin and zeta-cypermethrin. A pyrethroid is a synthetic chemical compound similar to the natural chemical pyrethrins produced by the flowers of pyrethrums (Chrysanthemum cinerariaefolium and C. coccineum). Pyrethroids are common in commercial products such as household insecticides and insect repellents. In the concentrations used in such products, they are generally harmless to human beings but can harm sensitive individuals. They are usually broken apart by sunlight and the atmosphere in one or two days, and do not significantly affect groundwater quality except for being toxic to fish. (5, 8, 9)
Contaminant Sources
  • EPA Endocrine Screening
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Household Toxin
  • Insecticide
  • Nitrile
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pyrethroid
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
alpha-Cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateChEBI
ZetagardKegg
a-Cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateGenerator
a-Cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
alpha-Cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
Α-cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateGenerator
Α-cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
(1S,3S)-(R)-Cyano(3-phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
CymbushHMDB
alpha-CypermethrinHMDB
AlphacypermethrinHMDB
beta-CipermetrinaHMDB
SupercypermethrinHMDB
FastacHMDB
NRDC 149HMDB
Cypermethrin, (1R-(1alpha(r*),3beta))-isomerHMDB
Cypermethrin, (1R-(1alpha(s*),3beta))-isomerHMDB
FendonaHMDB
RipcordHMDB
SherpaHMDB
SupermethrinHMDB
Fastac 50EcHMDB
AlphamethrinHMDB
Cypermethrin, (1alpha(s*),3alpha)-(+-)-isomerHMDB
Chemical FormulaC22H19Cl2NO3
Average Molecular Mass416.297 g/mol
Monoisotopic Mass415.074 g/mol
CAS Registry Number52315-07-8
IUPAC Namecyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Traditional Nameustaad
SMILESCC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC2=CC=CC=C2)=C1
InChI IdentifierInChI=1S/C22H19Cl2NO3/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
InChI KeyKAATUXNTWXVJKI-UHFFFAOYSA-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
  • Chloroalkene
  • Monocarboxylic acid or derivatives
  • Carbonitrile
  • Nitrile
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen 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 Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceLight, amber coloured viscous liquid (11).
Experimental Properties
PropertyValue
Melting Point80.5°C
Boiling PointNot Available
Solubility4e-06 mg/mL at 20°C [WAUCHOPE,RD et al. (1991A)]
Predicted Properties
PropertyValueSource
Water Solubility0.00086 g/LALOGPS
logP5.81ALOGPS
logP5.44ChemAxon
logS-5.7ALOGPS
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
Refractivity119.09 m³·mol⁻¹ChemAxon
Polarizability40.57 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0512900000-3c26550cde83f141de05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-1912200000-b3b26bde64fbc63423e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052e-1900000000-a8aceee4a43e1d313973Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0011900000-32f3cf0f9235364f299fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3346900000-98416964f4d22c0b7018Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9520000000-1bb5c04c6247a934fc53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0038900000-53fc8b1c4fc4bcdfd216Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0691-3391400000-39611d4b3cb6d43d0b1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-3890100000-3e4509fe741515b0ca5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0211900000-db6771eccb17edab98b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2860900000-dfb133d3ec704df3980fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9110000000-3657fc947a30f3439e8eSpectrum
MSMass Spectrum (Electron Ionization)splash10-02cr-4910000000-8849f1db9e07694cee2fSpectrum
Toxicity Profile
Route of ExposureInhalation (6) ; oral (6) ; dermal (6) ; eye contact (6).
Mechanism of ToxicityBoth type I and type II pyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. They also inhibit calium channels and Ca2+, Mg2+-ATPase. (12, 13, 6)
MetabolismCypermethrin has been shown to be well absorbed after oral administration, extensively metabolized, and eliminated as polar conjugates in urine. The main route of metabolism was, as anticipated, via hydrolysis of the ester linkage. The cyclopropane-carboxylic acid moiety is subsequently excreted via the urine as the glucuronide conjugate (6).
Toxicity ValuesLD50: 250-300 mg/kg (Oral, Mouse) (10)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Spraying and application of nonarsenical insecticides entail exposures that are probably carcinogenic to humans (Group 2A). (3)
Uses/SourcesPyrethroids are used as insecticides. (6)
Minimum Risk LevelAcute Oral: 0.02 mg/kg/day (Rat) (6)
Health EffectsAt high doses, signs of poisoning attributable to cypermethrin include profuse salivation and pulmonary edema, clonic seizures, opisthotonos (i.e., the spine is bent forward such that a supine body rests on its head and heels), coma, and death. At lower doses, commonly observed effects include paresthesia and erythema (7).
SymptomsFollowing dermal exposure to cypermethrin, feelings of numbness, itching, burning, stinging, tingling, or warmth may occur, that could last for a few hours. Ddizziness, headache, nausea, muscle twitching, reduced energy, and changes in awareness can reult from inhalation or ingestion of large amounts of cypermethrin. Paralysis can occur after exposure (6).
TreatmentFollowing oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis. (4)
Concentrations
Not Available
DrugBank IDDB13721
HMDB IDHMDB0243566
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCypermethrin
Chemspider ID2809
ChEBI ID4042
PubChem Compound ID2912
Kegg Compound IDC10984
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17420035
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18922205
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20508922
4. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.