(+/-)-cis-Permethrin (CED0002972)

Record Information

Version

1.0

Creation Date

2016-05-22 07:30:13 UTC

Update Date

2026-04-05 14:18:22 UTC

Accession Number

CHEM020855

Identification

Common Name

(+/-)-cis-Permethrin

Class

Small Molecule

Description

(+/-)-cis-Permethrin is an organic compound with the formula C21H20Cl2O3 and an average molecular weight of 391.29 g/mol. (+/-)-cis-Permethrin belongs to the fatty acid esters, a subclass of fatty acyls within the organic compounds. Industrially, the compound is utilized as a biocide and a pyrethroid insecticide (PMC9487696). Regarding environmental presence and human exposure, (+/-)-cis-Permethrin is recorded in indoor air, dust, and atmospheric transport. Inhalation is a recorded exposure route, a finding supported by literature (PMC3447599).

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

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

Chemical Formula

C₂₁H₂₀Cl₂O₃

Average Molecular Mass

391.290 g/mol

Monoisotopic Mass

390.079 g/mol

CAS Registry Number

61949-76-6

IUPAC Name

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

Traditional Name

acticin

SMILES

[H][C@]1(C=C(Cl)Cl)[C@@]([H])(C(=O)OCC2=CC(OC3=CC=CC=C3)=CC=C2)C1(C)C

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/t17-,19-/m0/s1

InChI Key

RLLPVAHGXHCWKJ-HKUYNNGSSA-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

Pyrethroid insecticides (C14388 )
Pyrethroid pesticides (C14388 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	39.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0519000000-0f6eb9a687fe3c0d66c4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-1923000000-a400c6833ac566d7a622	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052e-2900000000-7758be41aece58f5d5d1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0109000000-fdac422c546f05b83ceb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-1709000000-f755eb7d0bee859d0bb8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9500000000-97e9860533a91746241d	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
241.0	Log mg/kg	[140:430]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
19	Indoor air	Air, dust & atmospheric transport	Not Available
602	Molluscicides	Agriculture & land management	Not Available
607	Rodenticides(1)	Agriculture & land management	Not Available
608	Rodenticides	Agriculture & land management	Not Available
609	Aftershave	Personal care & cosmetics	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	499.481
Click to view 3D structure	Prolyl endopeptidase	P27028	Elizabethkingia meningoseptica	Predicted (SEA)	15.5698
Click to view 3D structure	E3 ubiquitin-protein ligase RNF4	P78317	Humans	Predicted (SEA)	15.3363
Click to view 3D structure	Fatty-acid amide hydrolase 1	O00519	Humans	Predicted (SEA)	144.021
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	389.635
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	646.149
Click to view 3D structure	Monoglyceride lipase	Q99685	Humans	Predicted (SEA)	55.1172
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	777.947
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	334.596
Click to view 3D structure	Free fatty acid receptor 1	O14842	Humans	Predicted (SEA)	98.3236
Click to view 3D structure	Mas-related G-protein coupled receptor member X4	Q96LA9	Humans	Predicted (SEA)	41.805
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	688.421
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	1071.44
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	908.968
Click to view 3D structure	Aldo-keto reductase family 1 member B1	P15121	Humans	Predicted (SEA)	103.695
Click to view 3D structure	Fatty-acid amide hydrolase 1	O08914	Mus musculus	Predicted (SEA)	87.0354
Click to view 3D structure	15-cis-phytoene desaturase	P26294	Synechococcus elongatus (strain PCC 7942) (Anacystis nidulans R2)	Predicted (SEA)	45.4639
Click to view 3D structure	Solute carrier family 12 member 5	Q63633	Rattus norvegicus	Predicted (SEA)	16.4262
Click to view 3D structure	Peroxisome proliferator-activated receptor gamma	P37231	Humans	Predicted (SEA)	393.839
Click to view 3D structure	Sodium/iodide cotransporter	Q63008	Rattus norvegicus	Predicted (SEA)	32.0739
Click to view 3D structure	Free fatty acid receptor 4	Q5NUL3	Humans	Predicted (SEA)	120.121
Click to view 3D structure	Fatty-acid amide hydrolase 1	P97612	Rattus norvegicus	Predicted (SEA)	211.283
Click to view 3D structure	Heat shock factor protein 1	P38532	Mus musculus	Predicted (SEA)	281.347
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	2753.29
Click to view 3D structure	Sigma intracellular receptor 2	Q5BJF2	Humans	Predicted (SEA)	684.217