Record Information
Version1.0
Creation Date2009-06-18 17:03:34 UTC
Update Date2026-05-14 19:36:42 UTC
Accession NumberCHEM000882
Identification
Common NameAllethrin
ClassSmall Molecule
Description
Allethrin is a pyrethroid (type I) insecticide. 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. (7)
Contaminant Sources
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Household Toxin
  • Organic Compound
  • Pesticide
  • Pyrethroid
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl esterChEBI
3-Allyl-2-methyl-4-oxo-2-cyclopenten-1-yl chrysanthemateChEBI
3-Allyl-2-methyl-4-oxocyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylateChEBI
3-Allyl-4-keto-2-methylcyclopentenyl chrysanthemum monocarboxylateChEBI
BioallethrinChEBI
PynaminChEBI
DuocideKegg
2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl esterGenerator
3-Allyl-2-methyl-4-oxo-2-cyclopenten-1-yl chrysanthemic acidGenerator
3-Allyl-2-methyl-4-oxocyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylic acidGenerator
3-Allyl-4-keto-2-methylcyclopentenyl chrysanthemum monocarboxylic acidGenerator
AllethrinsMeSH
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl esterMeSH
Chemical FormulaC19H26O3
Average Molecular Mass302.408 g/mol
Monoisotopic Mass302.188 g/mol
CAS Registry Number584-79-2
IUPAC Name2-methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
Traditional Namepyrethrin
SMILESCC(C)=CC1C(C(=O)OC2CC(=O)C(CC=C)=C2C)C1(C)C
InChI IdentifierInChI=1S/C19H26O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h7,9,14,16-17H,1,8,10H2,2-6H3
InChI KeyZCVAOQKBXKSDMS-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
  • Monoterpenoid
  • Monocyclic monoterpenoid
  • Cyclopropanecarboxylic acid or derivatives
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic 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
StateLiquid
AppearancePale yellow viscous liquid.
Experimental Properties
PropertyValue
Melting Point-40°C
Boiling PointNot Available
Solubility0.0046 mg/mL at 25°C [TOMLIN,C (1997)]
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP3.58ALOGPS
logP4.06ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.09ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity88.71 m³·mol⁻¹ChemAxon
Polarizability34.56 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureInhalation (9) ; oral (9) ; dermal (9) ; eye contact (9).
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. (11, 12, 8)
MetabolismUpon absorption of allethrine , biotransformation takes place through hydrolysis of the central ester bond, oxidative attacks at several sites, and conjugation reactions to produce a complex array of primary and secondary water-soluble metabolites that undergo urinary and biliary excretion. Allethrin is oxidized not only at the chrysanthemate isobutenyl moiety to the corresponding primary alcohol but also at the allyl group to 1'-hydroxyprop-2'-enyl and 2',3'-dihydroxy-propyl derivatives, or at a methyl group on the cyclopropyl moiety to a hydroxy derivative. It is widely accepted that metabolism results in the formation of compounds that have little or no demonstrable toxicity, although the formation of reactive or toxic intermediates cannot be ruled out, and it appears that cleavage of the ester bond results in substantial detoxification. Allethrin is also converted to chrysanthemum dicarboxylic acid and allethrolone. Allethrin leaves the body quickly, mainly in the urine, but also in feces and breath. (8, 5)
Toxicity ValuesLD50: 1100 mg/kg (Oral, Rat) (10) LD50: 480 mg/kg (Oral, Mouse) (10) LD50: >2500 mg/kg (Dermal, Rat) (10)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC.
Uses/SourcesPyrethroids are used as insecticides. (8)
Minimum Risk LevelNot Available
Health EffectsAs for every type I pyrethroid, allethrin effects typically include rapid onset of aggressive behavior and increased sensitivity to external stimuli, followed by fine tremor, prostration with coarse whole body tremor, elevated body temperature, coma, and death. Paresthesia can also occur after dermal exposure to allethrin. It is likely to be a human carcinogen by the oral route. (8)
SymptomsFollowing dermal exposure to allethrin, feelings of numbness, itching, burning, stinging, tingling, or warmth may occur, that could last for a few hours. Dizziness, headache, nausea, muscle twitching, reduced energy, and changes in awareness can result from inhalation or ingestion of large amounts of allethrin. (8)
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. (6)
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0243551
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAllethrins
Chemspider ID10958
ChEBI ID34572
PubChem Compound ID11442
Kegg Compound IDC14337
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References