ContaminantDB: Permethrin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (27)XML

Record Information

Version

1.0

Creation Date

2009-06-23 18:10:09 UTC

Update Date

2026-05-14 18:11:41 UTC

Accession Number

CHEM001599

Identification

Common Name

Permethrin

Class

Small Molecule

Description

Permethrin is only found in individuals that have used or taken this drug. It is a pyrethroid insecticide commonly used in the treatment of lice infestations and scabies. It is a yellow to light orange-brown, low melt-ing solid or viscous liquid.Permethrin acts on the nerve cell membrane to disrupt the sodium channel current by which the polarization of the membrane is regulated. Delayed repolarization and paralysis of the pests are the consequences of this disturbance.

Contaminant Sources

Clean Air Act Chemicals
EPA Endocrine Screening
HMDB Contaminants - Urine
HPV EPA Chemicals
IARC Carcinogens Group 3
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Drug
Ester
Ether
Household Toxin
Metabolite
Organic Compound
Organochloride
Pesticide
Pyrethroid
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3-Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate	ChEBI
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid, (3-phenoxyphenyl) methyl ester	ChEBI
Elimite	Kegg
(3-Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid	Generator
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylate, (3-phenoxyphenyl) methyl ester	Generator
(m-Phenoxybenzyl)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate	MeSH
3-Phenoxybenzyl-(+-)-cis,trans-2,2-dichlorovinyl-2,2-dimethyl-cyclopropylcarboxylic acid, ester	MeSH
3-Phenoxybenzyl-cis,trans-(1Rs)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate	MeSH
Ambush	MeSH
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester	MeSH
NRDC 143	MeSH
NRDC 147	MeSH
NRDC-143	MeSH
NRDC-147	MeSH
NRDC143	MeSH
NRDC147	MeSH
Nittifor	MeSH
Permethrin, (1R-cis)-isomer	MeSH
Permethrin, (1R-trans)-isomer	MeSH
Permethrin, (1S-cis)-isomer	MeSH
Permethrin, (1S-trans)-isomer	MeSH
Permethrin, (cis)-isomer	MeSH
Permethrin, (cis-(+-))-isomer	MeSH
Permethrin, (trans)-isomer	MeSH
Permethrin, (trans-(+-))-isomer	MeSH
Permethrin, trans-(1Rs)-isomer	MeSH
cis Permethrin	MeSH
cis-(1Rs)-Permethrin	MeSH
cis-Permethrin	MeSH
Permethrin, cis-(1Rs)-isomer	MeSH
trans Permethrin	MeSH
trans-(1Rs)-Permethrin	MeSH
trans-Permethrin	MeSH

Chemical Formula

C₂₁H₂₀Cl₂O₃

Average Molecular Mass

391.288 g/mol

Monoisotopic Mass

390.079 g/mol

CAS Registry Number

52645-53-1

IUPAC Name

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

Traditional Name

permethrin

SMILES

CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC(OC2=CC=CC=C2)=CC=C1

InChI Identifier

InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3

InChI Key

RLLPVAHGXHCWKJ-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
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
Chloroalkene
Haloalkene
Ether
Vinyl halide
Monocarboxylic acid or derivatives
Vinyl chloride
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organohalogen compound
Organochloride
Organooxygen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cyclopropanes (CHEBI:34911 )
cyclopropanecarboxylate ester (CHEBI:34911 )
a monoterpenoid (CPD-13115 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

pyrethroid ester insecticide

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Colourless crystals (11).

Experimental Properties

Property	Value
Melting Point	34°C
Boiling Point	220°C at 5.00E-02 mm Hg
Solubility	0.006 mg/L (at 20°C)

Predicted Properties

Property	Value	Source
Water Solubility	6.9e-05 g/L	ALOGPS
logP	6.24	ALOGPS
logP	5.7	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	114.28 m³·mol⁻¹	ChemAxon
Polarizability	39.43 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-3900000000-469dc103f8f391a6bb7f	Spectrum
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
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-QFT , positive	splash10-0002-1900000000-956860faa94e3dea2ee2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-1900000000-ce2901f0a3049806d95f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-1900000000-b5846ca870454df7f44f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0900000000-474995c2ccb155f0975c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-1900000000-261c3708f1e50c4a8418	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-006t-2900000000-4915b2e2cee108c117a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0002-0900000000-a73154cdccdc124955c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0002-1900000000-2f9800db80661116530a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0002-1900000000-bf65bfc29edf7e8f72d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-1900000000-91cb4c87ae286d88f203	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0002-1900000000-2546d86434c241ad989e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0519000000-0f6eb9a687fe3c0d66c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-1923000000-a400c6833ac566d7a622	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052e-2900000000-7758be41aece58f5d5d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0109000000-fdac422c546f05b83ceb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1709000000-f755eb7d0bee859d0bb8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9500000000-97e9860533a91746241d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0536-0429000000-98939aa3532b9312d6ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-2923000000-0cd57653df5af5d7ac42	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001l-8911000000-9f85adb3775c89af21a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0119000000-eda907ff628cd2b35844	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03ki-1902000000-84bc834f9310543ce7d7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9211000000-bcaffb823cfb3efededa	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (10) ; oral (10) ; dermal (10) ; eye contact (10). Poorly absorbed through the skin.

Mechanism of Toxicity

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. (12, 10)

Metabolism

The proposed metabolic pathway for cis- and trans-permethrin are as follows. The five principle sites of metabolic attack in both permethrin isomers is ester cleavage, oxidation at the trans- and cis-methyl of the geminal dimethyl group of the acid moiety, and oxidation at 2'- and 4'- position of the phenoxy group. Conjugation of the resultant carboxylic acids, alcohols, and phenols with glucuronic acid, glycine, and sulfuric acid occurs to varying extent. cis-Permethrin is more stable then trans-permethrin, and the cis isomer yields four faecally excreted ester metabolites that results from hydroxylation at the 2'- or 4'-position of the phenoxy group or at the trans- or cis methyl group on the cyclopropane ring. The estercleaved metabolites are extensively excreted into the urine whereas the metabolites retaining an ester bond are found only in the feces. The major metabolite from the acid moiety of both isomers was Cl2CA in free (1-8%) and glucuronide (14-42%) forms. Other significant metabolites are trans-OH-Cl2CA (1-5%) and cis-OH-Cl2CA in the free (3-5%), lactone (0-4%) and glucuronide (1-2%) forms. On the other hand, the alcohol moiety released after cleavage of the ester bond of both isomers is converted mainly to the sulfate of 3-(4'-hydroxyphenoxy)benzoic acid (4'-OH-PBacid) (29-43% of the dose) and PBacid in the free (1-10%) and glucuronide (7-15%) forms. Other significant metabolites of the alcohol moiety are PBalc, PBacid-glycine and the sulfate of 3-(2'-hydroxyphenoxy) benzoic acid (2'-OH-PBacid). A study by Nakamura et al. proposed that permethrin was hydrolyzed by CES (carboxylesterase), then PBAlc formed was oxidized to PBAld, and further, PBAld was oxidized to PBAcid by the P450 system in rat liver microsomes. (5, 2) Route of Elimination: Permethrin is rapidly metabolized by ester hydrolysis to inactive metabolites which are excreted primarily in the urine.

Toxicity Values

Oral, rat LD₅₀: 430 - 4000 mg/kg Skin, rabbit LD₅₀: 2000 mg/kg LD50: 3 801 mg/kg (Oral, Rat) (10)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (7)

Uses/Sources

For the treatment of infestation with Sarcoptes scabiei (scabies). Pyrethroids are used as insecticides. (10)

Minimum Risk Level

Intermediate Oral: 0.2 mg/kg/day (Rat) (10)

Health Effects

As for every type I pyrethroids , permethrin 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, severe corneal damage, hypotension and tachycardia, associated with anaphylaxis can also occur following permethrin poisoning. (10)

Symptoms

Following oral exposure, severe fine tremor, marked reflex hyperexcitability, sympathetic activation can occur. Nausea, vomiting and abdominal pain commonly occur and develop following ingestion. Sudden bronchospasm, swelling of oral and laryngeal mucous membranes, and anaphylactoid reactions have been reported after inhalation. Hypersensitivity reactions characterized by pneumonitis, cough, dyspnea, wheezing, chest pain, and bronchospasm may occur too . Dermatitis is the main effect of a dermal exposure to permethrin. (13)

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. (13)

Concentrations

Not Available

External Links

DrugBank ID

DB04930

HMDB ID

HMDB0250296

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID