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Details

Stereochemistry RACEMIC
Molecular Formula C22H26O3
Molecular Weight 338.44
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RESMETHRIN, TRANS-(±)-

SMILES

CC(C)=C[C@@H]1[C@@H](C(=O)OCC2=COC(CC3=CC=CC=C3)=C2)C1(C)C

InChI

InChIKey=VEMKTZHHVJILDY-UXHICEINSA-N
InChI=1S/C22H26O3/c1-15(2)10-19-20(22(19,3)4)21(23)25-14-17-12-18(24-13-17)11-16-8-6-5-7-9-16/h5-10,12-13,19-20H,11,14H2,1-4H3/t19-,20+/m1/s1

HIDE SMILES / InChI
Bioresmethrin is a synthetic pyrethroid insecticide. It is the (+)-trans isomer of resmethrin which itself contains a minimum of 30% bioresmethrin. Bioresmethrin is the [1R, trans] isomer of resmethrin and has greater insecticidal activity than the racemic mixture. Bioresmethrin is a potent contact insecticide effective against a wide range of household insects, plant pests, grain pests and insects found in animal housing. It exhibits a high order of insecticidal activity, which when coupled with its excellent toxicological properties, makes it potentially one of the safest and most useful insecticides now being produced.

CNS Activity

Curator's Comment: As for every type I pyrethroid, bioresmethrin effects typically include rapid onset of aggressive behavior and increased sensitivity to external stimuli.

Originator

Curator's Comment: Bioresmethrin was discovered in England by M. Elliott and co-workers at the Rothamsted Experimental Station in collaboration with the National Research and Development Corporation (NRDC).

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Enhanced efficiency of electrostatically charged insecticide aerosols.
2001 May
Long-term effectiveness of grain protectants and structural treatments against Liposcelis decolor (Pearman) (Psocoptera: Liposcelididae), a pest of stored products.
2002 Dec
Synergized bifenthrin plus chlorpyrifos-methyl for control of beetles and psocids in sorghum in Australia.
2003 Apr
Pyrethroid stimulation of ion transport across frog skin.
2003 Jun
Glutathione S-transferase and insecticide resistance in laboratory strains and field populations of Musca domestica.
2005 Aug
Hydrolytic metabolism of pyrethroids by human and other mammalian carboxylesterases.
2006 Feb 28
Hydrolysis of pyrethroids by human and rat tissues: examination of intestinal, liver and serum carboxylesterases.
2007 May 15
Impact of urban agriculture on malaria vectors in Accra, Ghana.
2008 Aug 4
Susceptibility to thiamethoxam of Musca domestica from Danish livestock farms.
2008 Feb
In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms.
2009 Jan
Pyrethroid insecticides: isoform-dependent hydrolysis, induction of cytochrome P450 3A4 and evidence on the involvement of the pregnane X receptor.
2009 May 15
Inhibition of carboxylesterase activity of THP1 monocytes/macrophages and recombinant human carboxylesterase 1 by oxysterols and fatty acids.
2010 Jan
Patents

Patents

Sample Use Guides

2 groups each of 3 rats received i.v. injections into the lateral tail vein of 2.5 mg/kg ([U-14C]phenyl, 2uCi/rat) cismethrin or bioresmethrin as a solution in glycerin formal (3.75 mg/ml).
Route of Administration: Intravenous
In Vitro Use Guide
Glial cells in the ganglia and ventral connectives of Periplaneta americana treated with 5 uM bioresmethrin were found to be swollen and even more electron lucent than the control cells.
Name Type Language
RESMETHRIN, TRANS-(±)-
Common Name English
CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)-, (5-(PHENYLMETHYL)-3-FURANYL)METHYL ESTER, (1R,3R)-REL-
Common Name English
TRANS-(5-BENZYL-3-FURYL)METHYL 2,2-DIMETHYL-3-(2-METHYLPROPENYL)CYCLOPROPANECARBOXYLATE
Common Name English
CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYLPROPENYL)-, (5-BENZYL-3-FURYL)METHYL ESTER, TRANS-(±)-
Common Name English
3-FURANMETHANOL, 5-BENZYL-, 2,2-DIMETHYL-3-(2-METHYLPROPENYL)CYCLOPROPANECARBOXYLATE, TRANS-(±)-
Common Name English
DL-TRANS-RESMETHRIN
Common Name English
TRANS-RESMETHRIN
Common Name English
CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYL-1-PROPEN-1-YL)-, (5-(PHENYLMETHYL)-3-FURANYL)METHYL ESTER, (1R,3R)-REL-
Common Name English
CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)-, (5-(PHENYLMETHYL)-3-FURANYL)METHYL ESTER, TRANS-(±)-
Common Name English
5-BENZYL-3-FURYLMETHYL (±)-TRANS-CHRYSANTHEMATE
Common Name English
Code System Code Type Description
PUBCHEM
162381
Created by admin on Sat Dec 16 01:47:14 GMT 2023 , Edited by admin on Sat Dec 16 01:47:14 GMT 2023
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EPA CompTox
DTXSID4091524
Created by admin on Sat Dec 16 01:47:14 GMT 2023 , Edited by admin on Sat Dec 16 01:47:14 GMT 2023
PRIMARY
FDA UNII
8535H601Y7
Created by admin on Sat Dec 16 01:47:14 GMT 2023 , Edited by admin on Sat Dec 16 01:47:14 GMT 2023
PRIMARY
CAS
10453-55-1
Created by admin on Sat Dec 16 01:47:14 GMT 2023 , Edited by admin on Sat Dec 16 01:47:14 GMT 2023
PRIMARY