A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (-)-cis-Permethrin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the (-)-cis-Permethrin?

The molecule (-)-cis-Permethrin presents a molecular formula of C21H20Cl2O3 and its IUPAC name is (3-phenoxyphenyl)methyl (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate.

-)-cis-Permethrin molecule is an insecticide that is used to kill a variety of insects. It works by causing nerve damage in insects, which results in death. Permethrin is considered to be relatively safe for humans and animals, but can be harmful to fish and other aquatic organisms..

3D structure

Cartesian coordinates

Geometry of (-)-cis-Permethrin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing


(-)-cis-Permethrin RLLPVAHGXHCWKJ-HKUYNNGSSA-N chemical compound 2D structure molecule svg


Molecule descriptors

IUPAC name(3-phenoxyphenyl)methyl (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
InChI codeInChI=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

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (-)-cis-Permethrin
  • (.+/-.)-3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
  • (.+/-.)-m-Phenoxybenzyl-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxylate
  • (3-phenoxyphenyl)methyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate
  • (?)-cis-Permethrin
  • (SS)-trans-Permethrin
  • 1S-cis-Permethrin
  • 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid (3-phenoxy-phenyl)methyl ester
  • 3-Phenoxybenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate
  • 3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate #
  • 54774-46-8
  • Acticin
  • Adion
  • Ambushfog
  • Anomethrin N
  • Coopex
  • Corsair
  • Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester
  • Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester, (1S-cis)-
  • Dragnet
  • Ectiban
  • Eksmin
  • Elimite
  • Expar
  • FMC-33297
  • Jureong
  • Kafil
  • Kaleait
  • Kavil
  • Kestrel
  • LE 79-519
  • NIA-33297
  • Outflank
  • PP-557
  • Perigen
  • Permanone
  • Permasect
  • Permethrin, (-)-cis-
  • Permethrine
  • Permetrina
  • Permitrine
  • Perthrine
  • Picket
  • Pulvex
  • Pynosect
  • Q27290439
  • Qamlin
  • Quamilin
  • Repel Permanone
  • Ridect pour-on
  • S-3151
  • SBP-1513
  • Sharkesuper
  • Stomoxin
  • Stomozan
  • Tornade
  • cis-(-)-permethrin
  • m-Phenoxybenzyl (.+/-.)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
  • m-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1850377
  • DTXSID2058253
  • CHEMBL601463
  • SCHEMBL9669087

Physico-Chemical properties

IUPAC name(3-phenoxyphenyl)methyl (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Molecular formulaC21H20Cl2O3
Molecular weight391.288
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity104.41
Topological polar surface area35.5

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.