ContaminantDB: Allethrin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (57)XML

Record Information

Version

1.0

Creation Date

2009-06-18 17:03:34 UTC

Update Date

2026-05-14 19:36:42 UTC

Accession Number

CHEM000882

Identification

Common Name

Allethrin

Class

Small 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester	ChEBI
3-Allyl-2-methyl-4-oxo-2-cyclopenten-1-yl chrysanthemate	ChEBI
3-Allyl-2-methyl-4-oxocyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate	ChEBI
3-Allyl-4-keto-2-methylcyclopentenyl chrysanthemum monocarboxylate	ChEBI
Bioallethrin	ChEBI
Pynamin	ChEBI
Duocide	Kegg
2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester	Generator
3-Allyl-2-methyl-4-oxo-2-cyclopenten-1-yl chrysanthemic acid	Generator
3-Allyl-2-methyl-4-oxocyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylic acid	Generator
3-Allyl-4-keto-2-methylcyclopentenyl chrysanthemum monocarboxylic acid	Generator
Allethrins	MeSH
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester	MeSH

Chemical Formula

C₁₉H₂₆O₃

Average Molecular Mass

302.408 g/mol

Monoisotopic Mass

302.188 g/mol

CAS Registry Number

584-79-2

IUPAC Name

2-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 Name

pyrethrin

SMILES

CC(C)=CC1C(C(=O)OC2CC(=O)C(CC=C)=C2C)C1(C)C

InChI Identifier

InChI=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 Key

ZCVAOQKBXKSDMS-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Pyrethroids

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 Framework

Aliphatic homomonocyclic compounds

External Descriptors

cyclopropanes (CHEBI:34572 )
Cyclopropane and cyclobutane monoterpenoids (C14337 )
Pyrethroid insecticides (C14337 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

pyrethroid ester insecticide

Biological Roles

pyrethroid ester insecticide

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Pale yellow viscous liquid.

Experimental Properties

Property	Value
Melting Point	-40°C
Boiling Point	Not Available
Solubility	0.0046 mg/mL at 25°C [TOMLIN,C (1997)]

Predicted Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	3.58	ALOGPS
logP	4.06	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	18.09	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	88.71 m³·mol⁻¹	ChemAxon
Polarizability	34.56 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-0f79-0901000000-317e8414ec3cd132d7d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-000i-0900000000-f5727e43a4d8157c607c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive	splash10-000i-0900000000-ccfeff4119a4c59853d8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive	splash10-000i-0900000000-d64f9f20926490a9787d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 50V, positive	splash10-014r-0900000000-6acd9ccaecebc333612b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 27V, positive	splash10-000i-0900000000-bc7a51d3398423a54c1e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-014r-0900000000-6acd9ccaecebc333612b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900000000-2c710a00995495b7f28d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-0900000000-aeb33847108dca4a3e1f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-0901000000-317e8414ec3cd132d7d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-f5727e43a4d8157c607c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-0900000000-f92fa7a2cc19a82f4e76	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-2956000000-ea6ab3754b3d6b73987b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-9410000000-f84a167828224c1c4c4d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zi0-9300000000-7aaddaff4b5285bab8da	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0419000000-e90978f635724728e791	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-5923000000-02cc94654ba7f61c64f0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00r2-3900000000-4ea3fa3c947c8af18c6c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-3891000000-eb1696e2adee8d74c943	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0cei-8911000000-52077304a781c1864357	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ap3-9500000000-ecaa094f13d20305c522	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0901000000-09a7aa08a386d1ad542c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-a13a3b88213fa1a0638c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-1930000000-adcb10f3f736d0680083	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0096-9500000000-70a98d42082c3f4b3c4e	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (9) ; oral (9) ; dermal (9) ; eye contact (9).

Mechanism of Toxicity

Both 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)

Metabolism

Upon 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 Values

LD50: 1100 mg/kg (Oral, Rat) (10) LD50: 480 mg/kg (Oral, Mouse) (10) LD50: >2500 mg/kg (Dermal, Rat) (10)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC.

Uses/Sources

Pyrethroids are used as insecticides. (8)

Minimum Risk Level

Not Available

Health Effects

As 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)

Symptoms

Following 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)

Treatment

Following 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 ID

Not Available

HMDB ID

HMDB0243551

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Allethrin (CHEM000882)

Structure for CHEM000882: Allethrin