Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H25NO3 |
Molecular Weight | 375.4602 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)=C[C@@H]1[C@@H](C(=O)O[C@H](C#N)C2=CC(OC3=CC=CC=C3)=CC=C2)C1(C)C
InChI
InChIKey=FJDPATXIBIBRIM-VSKRKVRLSA-N
InChI=1S/C24H25NO3/c1-16(2)13-20-22(24(20,3)4)23(26)28-21(15-25)17-9-8-12-19(14-17)27-18-10-6-5-7-11-18/h5-14,20-22H,1-4H3/t20-,21-,22+/m1/s1
Molecular Formula | C24H25NO3 |
Molecular Weight | 375.4602 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
http://onlinelibrary.wiley.com/doi/10.1002/ps.2780110214/full | https://www.ncbi.nlm.nih.gov/pubmed/2449265
Curator's Comment: description was created based on several sources, including
http://onlinelibrary.wiley.com/doi/10.1002/ps.2780110214/full | https://www.ncbi.nlm.nih.gov/pubmed/2449265
Cyphenothrin, (+)-trans- (d,d,trans-cyphenothrin) is the type II pyrethroid insecticide, acting by contact poisoning Cyphenothrin, (+)-trans- is used in public health against flies, mosquitoes, cockroaches, etc. Cyphenothrin is the ISO common name for a racemic mixture of 4 pairs of diastereoisomers, designated as (±)-α-cyano-3- phenoxybenzyl (±)-cis-trans- chrysanthemate. The name Cyphenothrin, (+)-trans- refers to an enantio-enriched mixture, comprised mainly of the single stereoisomer (S)-α-cyano-3- phenoxybenzyl (1R, 3R)-2,2-dimethyl-3-(2-methylprop-1-enyl) cyclopropanecarboxylate, with only small proportions of the other stereoisomers, as defined by the WHO specification.
Cyphenothrin, (+)-trans- is almost insoluble in water but highly soluble in organic solvents, such as hexane, ethanol, acetone, toluene etc.
Cyphenothrin, (+)-trans- stable under normal storage conditions but is readily hydrolyzed in water at higher pH and is sensitive to light.
Cyphenothrin, (+)-trans- has a low potential for bioaccumulation due to hydrolysis, photolysis and metabolism in water, soil and in biota.
The data for toxicology of Cyphenothrin, (+)-trans- partly rely on studies conducted with cyphenothrin. Cyphenothrin, (+)-trans- generally shows low mammalian toxicity and is not a sensitizer in the Buehler and is not irritating to the rabbit eye and skin. There was no evidence of carcinogenicity in the rat or mouse. There was no evidence of mutagenic responses in bacterial, micronucleus or sister chromatid exchange tests. In a 2-generation reproduction study in the rat, no reproductive effects were observed at any dose level. There was no evidence of teratogenicity or developmental effects in rats or rabbits, although there was a decrease in maternal weight gain and a consequential decrease in rat offspring viability at the high dose tested. Cyphenothrin, (+)-trans- is very toxic to Daphnia magna and fish but it has a low toxicity to bobwhite quails. On the basis of the one-year dog study, a NOEL of 16.8 to 19.6 mg/kg bw/d is established by the Swiss Office of Public Health. The Cyphenothrin, (+)-trans- TC was classified as moderately toxic (Class 3) in Switzerland and, although it has not been classified by the International Programme on Chemical Safety (IPCS), this organization has classified the closely related cyphenothrin (1R-isomers) as Class II, moderately hazardous.
CNS Activity
Approval Year
Sample Use Guides
Rat NOAEL = 300 ppm 16.8 mg/kg bw/day (male); 19.6 mg/kg bw/day (female)
Mouse NOAEL = 500 mg/m³ (male, female).
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2449265
Experiments were performed using the mouse neuroblastoma cell line NIE-115. Three main effects of the cyphenothrin (25 uM) was found: (1) the peak amplitude of the sodium current increased; (2) the declining phase of the sodium current during depolarization was greatly slowed down resuilting in a marked residual current towards the end of tlhe 15 ms pulse; and (3) after repolarization of the membrane to the holding potential a large, slowly decaying sodium tail current remained.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 05:03:42 GMT 2023
by
admin
on
Sat Dec 16 05:03:42 GMT 2023
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Record UNII |
K18840IATQ
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Record Status |
Validated (UNII)
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Record Version |
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