Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H21N2O3PS |
Molecular Weight | 304.346 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOP(=S)(OCC)OC1=CC(C)=NC(=N1)C(C)C
InChI
InChIKey=FHIVAFMUCKRCQO-UHFFFAOYSA-N
InChI=1S/C12H21N2O3PS/c1-6-15-18(19,16-7-2)17-11-8-10(5)13-12(14-11)9(3)4/h8-9H,6-7H2,1-5H3
Molecular Formula | C12H21N2O3PS |
Molecular Weight | 304.346 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Dimpylate (diazinon) is a nonsystemic organophosphate insecticide, an inhibitor of the enzyme acetylcholinesterase (AChE), which hydrolyzes the neurotransmitter acetylcholine (ACh) in cholinergic synapses and neuromuscular junctions. This results in abnormal accumulation of ACh in the nervous system. Dimpylate was first registered for use in the USA in 1956. It was developed as an insecticide, acaricide, and nematicide for use on a variety of pests for control of soil insects and pests of fruit, vegetables, and forage and field crops. It had been used extensively in home and garden applications, in formulations designed to prevent such pests as crickets or cockroaches from infesting homes or offices, and in pet collars. Due to the emerging health and ecological risks posed by diazinon, manufacturers agreed to phase out and cancel all residential products. Manufacturing of indoor use products containing dimpylatewas discontinued in 2001; manufacture of non-agricultural outdoor use products containing dimpylate was discontinued in 2003.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24704612 |
1900.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Agricultural use of organophosphate pesticides and the risk of non-Hodgkin's lymphoma among male farmers (United States). | 2001 Aug |
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Influence of sebum and stratum corneum hydration on pesticide/herbicide collection efficiencies of the human hand. | 2001 Aug |
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Overproduction of a P450 that metabolizes diazinon is linked to a loss-of-function in the chromosome 2 ali-esterase (MdalphaE7) gene in resistant house flies. | 2001 Dec |
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High performance liquid chromatographic determination of diazinon, permethrin, DEET (N, N-diethyl-m-toluamide), and their metabolites in rat plasma and urine. | 2001 Jun |
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Diazinon is activated by CYP2C19 in human liver. | 2001 Nov 15 |
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Acute toxicity and bioaccumulation of pesticide Diazinon in red tilapia (Oreochromis niloticus x Mossambicus albina). | 2002 |
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Exposure to the organophosphate diazinon: data from a human volunteer study with oral and dermal doses. | 2002 Aug 5 |
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Community exposures to airborne agricultural pesticides in California: ranking of inhalation risks. | 2002 Dec |
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Modeling of single-step and multistep adsorption isotherms of organic pesticides on soil. | 2002 Dec 4 |
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Removal of organophosphate pesticides from wastewater by supercritical carbon dioxide extraction. | 2002 Feb |
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Simple determination of 22 organophosphorous pesticides in human blood using headspace solid-phase microextraction and gas chromatography with mass spectrometric detection. | 2002 Jan |
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Size exclusion chromatographic cleanup for GC/MS determination of organophosphorus pesticide residues in household and vehicle dust. | 2002 Jan-Feb |
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Determination of insecticides in honey by matrix solid-phase dispersion and gas chromatography with nitrogen-phosphorus detection and mass spectrometric confirmation. | 2002 Jan-Feb |
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Exposure apportionment: ranking food items by their contribution to dietary exposure. | 2002 Jul |
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Diazinon and its degradation products in agricultural water courses in British Columbia, Canada. | 2002 Jul |
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Application of solid-phase microextraction in the monitoring of priority pesticides in the Kalamas River (N.W. Greece). | 2002 Jul 19 |
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Effect of some organophosphorus pesticides on oxygen consumption of shrimp, Litopenaeus vannamei. | 2002 Jun |
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Genotoxicity studies on permethrin, DEET and diazinon in primary human nasal mucosal cells. | 2002 Mar |
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Human blood and environmental media screening method for pesticides and polychlorinated biphenyl compounds using liquid extraction and gas chromatography-mass spectrometry analysis. | 2002 Mar 25 |
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Interactions between pesticides and components of pesticide formulations in an in vitro neurotoxicity test. | 2002 May 1 |
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Pesticide residues in agricultural products monitored in Hyogo Prefecture, Japan, FYs 1995-1999. | 2002 May-Jun |
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Sublethal responses of wolf spiders (Lycosidae) to organophosphorous insecticides. | 2002 Oct |
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Persistence of methamidophos, diazinon, and malathion in tomatoes. | 2002 Oct |
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Prevalence of fetal exposure to environmental toxins as determined by meconium analysis. | 2002 Sep |
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Histological examination of sublethal effects of diazinon on ovary of bluegill, Lepomis macrochirus. | 2003 |
Sample Use Guides
Dimpylate (diazinon) is a contact insecticide. It is administered by spraying the crops.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24704612
The Ellman assay was used to test AchE inhibition activity. The assay is based on chromophores generated in situ after enzymatic cleavage of acetylthiocholine and the resulting thiocholine with Ellman’s reagent, DTNB (5,50-dithio-bis-2-nitrobenzoic acid). The plates were incubated at room temperature and the enzymatic activity was determined by spectrophotometric reading at 412 nm.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:10:44 GMT 2023
by
admin
on
Fri Dec 15 15:10:44 GMT 2023
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Record UNII |
YUS1M1Q929
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QP53AF03
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EPA PESTICIDE CODE |
57801
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2045
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D003976
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DTXSID9020407
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34682
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diazinon
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DIAZINON
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3017
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8938
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333-41-5
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SUB07189MIG
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206-373-8
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100000082650
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C169912
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YUS1M1Q929
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YUS1M1Q929
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CHEMBL388560
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m4268
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |