ChemIDplus A TOXNET DATABASE

Substance Name: Permethrin [USAN:INN:BAN]
RN: 52645-53-1
InChIKey: RLLPVAHGXHCWKJ-HKUYNNGSSA-N

Note

  • A pyrethroid insecticide commonly used in the treatment of LICE INFESTATIONS and SCABIES.

Molecular Formula

  • C21-H20-Cl2-O3

Molecular Weight

  • 391.292
 

Classification Codes

Classification Codes

  • Agricultural Chemical
  • Ectoparasiticide
  • Enzyme Inhibitors
  • Human Data
  • Insecticide
  • Insecticides
  • Mutation data
  • Pesticides
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • Permethrin
  • Permethrin [ANSI:BSI:ISO]
  • Permethrin [USAN:INN:BAN]

MeSH Heading

  • Permethrin

Synonyms

  • (+-)-3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
  • (3-Phenoxyphenyl)methyl 3-(2,2-dichlorethenyl)-2,2-dimethylcyclopropanecarboxylate
  • 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid (3-phenoxyphenyl)methyl ester
  • 3-(Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
  • 3-Phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
  • 3-Phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
  • 3-Phenoxybenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate
  • 3-Phenoxybenzyl(+-)-cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate
  • Acticin
  • AI3-29158
  • Ambush
  • Ambushfog
  • Anomethrin N
  • Antiborer 3768
  • Bematin 987
  • BRN 2063148
  • BW-21-Z
  • Caswell No. 652BB
  • CCRIS 2001
  • Chinetrin
  • Coopex
  • Corsair
  • Cosair
  • Diffusil H
  • Dragnet
  • Dragnet FT
  • Dragon
  • Ecsumin
  • Ectiban
  • Efmethrin
  • EINECS 258-067-9
  • Eksmin
  • Elimite
  • EPA Pesticide Chemical Code 109701
  • Exmin
  • Expar
  • Exsmin
  • FMC 33297
  • FMC 41655
  • HSDB 6790
  • ICI-PP 557
  • Imperator
  • Indothrin
  • Insorbcid MP
  • Ipitox
  • JF 7065
  • Kafil
  • Kaleait
  • Kavil
  • Kestrel
  • Kestrel (pesticide)
  • Kudos
  • LE 79-519
  • Lyclear
  • m-Phenoxybenzyl (+-)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
  • m-Phenoxybenzyl (+1)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
  • Mitin BC
  • MP79
  • NIA 33297
  • Nix
  • NRDC 143
  • OMS 1821
  • Outflank
  • Outflank-stockade
  • Perigen
  • Perigen W
  • Permanone 80
  • Permasect
  • Permasect-25EC
  • Permethrin
  • Permethrin,racemic
  • Permethrine
  • Permethrine [ISO-French]
  • Permethrinum
  • Permethrinum [Latin]
  • Permetrin (Hungarian)
  • Permetrina
  • Permetrina [Portuguese]
  • Permit
  • Permitrene (Hungarian)
  • Perthrine
  • Picket
  • Picket G
  • Pounce
  • PP 557
  • Pramex
  • Pynosect
  • Quamlin
  • Ridect Pour-On
  • S 3151
  • S-3151
  • SBP 15131TEC
  • SBP-1513
  • SBP-1513TEC
  • Stomoxi
  • Stomoxin
  • Stomoxin P
  • Stomozan
  • Talcord
  • UNII-509F88P9SZ
  • WL 43479

Systematic Names

  • Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester
  • Cyclopropanecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, 3-phenoxybenzyl ester, (+-)-, (cis,trans)-
  • m-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
  • Permethrin

Superlist Names

  • (3-Phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
  • 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid, (3-phenoxyphenyl) methyl ester
  • Permethrin

Registry Numbers

CAS Registry Number

  • 52645-53-1

Other Registry Numbers

  • 57608-04-5
  • 60018-94-2
  • 63364-00-1
  • 75497-64-2
  • 93388-66-0

System Generated Number

  • 0052645531

Structure Descriptors

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

InChIKey

RLLPVAHGXHCWKJ-HKUYNNGSSA-N

Smiles

CC1([C@H]([C@H]1C(=O)OCc2cccc(c2)Oc3ccccc3)C=C(Cl)Cl)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - domestic LD50 oral 32gm/kg (32000mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 168, 1978.
chicken LD50 oral 7gm/kg (7000mg/kg) BEHAVIORAL: IRRITABILITY

BEHAVIORAL: TREMOR

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
JAT, Journal of Applied Toxicology. Vol. 7, Pg. 367, 1987.
Link to PubMed
duck LD50 oral 11300mg/kg (11300mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 168, 1978.
guinea pig LD50 oral 4gm/kg (4000mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A316, Pg. 1984,
man LD50 unreported > 4gm/kg (4000mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 168, 1978.
man TDLo oral 2270mg/kg (2270mg/kg)   Journal of Toxicology, Clinical Toxicology. Vol. 36, Pg. 57, 1998.
Link to PubMed
man TDLo oral 2270mg/kg (2270mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: COMA
Journal of Toxicology, Clinical Toxicology. Vol. 36, Pg. 57, 1998.
Link to PubMed
mouse LC50 inhalation 685mg/m3 (685mg/m3)   Yakkyoku. Pharmacy. Vol. 30, Pg. 1635, 1979.
mouse LD50 intraperitoneal 429mg/kg (429mg/kg)   Ecotoxicology and Environmental Safety. Vol. 18, Pg. 27, 1989.
Link to PubMed
mouse LD50 intravenous 31mg/kg (31mg/kg)   Toxicology and Applied Pharmacology. Vol. 66, Pg. 153, 1982.
Link to PubMed
mouse LD50 oral 424mg/kg (424mg/kg)   Ecotoxicology and Environmental Safety. Vol. 18, Pg. 27, 1989.
Link to PubMed
mouse LD50 skin > 10gm/kg (10000mg/kg)   Yakkyoku. Pharmacy. Vol. 30, Pg. 1635, 1979.
mouse LD50 subcutaneous 10gm/kg (10000mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: TREMOR
Bochu Kagaku. Scientific Pest Control. Vol. 41, Pg. 143, 1976.
mouse LD50 unreported 680mg/kg (680mg/kg) BEHAVIORAL: COMA

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(9), Pg. 69, 1988.
mouse LDLo intracrebral 600ug/kg (.6mg/kg)   Toxicology and Applied Pharmacology. Vol. 66, Pg. 290, 1982.
Link to PubMed
quail LD50 oral 13500mg/kg (13500mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 168, 1978.
rabbit LD50 oral 4gm/kg (4000mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A316, Pg. 1984,
rabbit LD50 skin > 2gm/kg (2000mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C233, 1991.
rat LC50 inhalation 485mg/m3 (485mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(12), Pg. 21, 1990.
rat LD intravenous > 270mg/kg (270mg/kg)   Nature. Vol. 246, Pg. 169, 1973.
Link to PubMed
rat LD50 oral 383mg/kg (383mg/kg)   National Technical Information Service. Vol. AD-A047-284,
rat LD50 skin 1750mg/kg (1750mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(9), Pg. 69, 1988.
rat LD50 subcutaneous 6600mg/kg (6600mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: TREMOR
Bochu Kagaku. Scientific Pest Control. Vol. 41, Pg. 143, 1976.
rat LD50 unreported 537mg/kg (537mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(9), Pg. 69, 1988.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 34 deg C   EXP
log P (octanol-water) 6.5 (none)   EXP
Water Solubility 0.006 mg/L 20 EXP
Vapor Pressure 2.18E-08 mm Hg 25 EXP
Henry's Law Constant 1.87E-06 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.90E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by Syracuse Research Corporation.
See all available property data for this compound, including references.