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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Predicting insecticide resistance: mutagenesis, selection and response. | 1998 Oct 29 |
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Gross fluxes and estuarine behaviour of pesticides in the Scheldt estuary (1995-1997). | 2001 |
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Response of bobwhite quail and gray-tailed voles to granular and flowable diazinon applications. | 2001 Feb |
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Effects of field exposure to diazinon on small mammals inhabiting a semienclosed prairie grassland ecosystem. I. Ecological and reproductive effects. | 2001 Feb |
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Effect of insulin resistance on serum paraoxonase activity in a nondiabetic population. | 2001 Jul |
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Fatty acid amide hydrolase inhibition by neurotoxic organophosphorus pesticides. | 2001 May 15 |
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Diazinon is activated by CYP2C19 in human liver. | 2001 Nov 15 |
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Levels of persistent organic pollutants in several child day care centers. | 2001 Nov-Dec |
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Topical insecticide treatments to protect dogs from sand fly vectors of leishmaniasis. | 2001 Sep-Oct |
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Pattern recognition of the movement tracks of medaka (Oryzias latipes) in response to sub-lethal treatments of an insecticide by using artificial neural networks. | 2002 |
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Sorption behaviour of acetochlor, atrazine, carbendazim, diazinon, imidacloprid and isoproturon on Hungarian agricultural soil. | 2002 Aug |
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Vitamin C and E intake is associated with increased paraoxonase activity. | 2002 Aug 1 |
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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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Biological monitoring of exposure to organophosphate pesticides. | 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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Simple method for the determination of trace levels of pesticides in honeybees using matrix solid-phase dispersion and gas chromatography. | 2002 Dec 27 |
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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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Oxidation of diazinon by anodic Fenton treatment. | 2002 Jul |
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Herbicide and insecticide loadings from the Susquehanna River to the northern Chesapeake Bay. | 2002 Jul 17 |
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Paraoxonase (PON1) polymorphisms in farmers attributing ill health to sheep dip. | 2002 Mar 2 |
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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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Chronic diazinon exposure: pathologies of spleen, thymus, blood cells, and lymph nodes are modulated by dietary protein or lipid in the mouse. | 2002 Mar 5 |
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Identification of alternatives for the management of foliar nematodes in floriculture. | 2002 May |
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Predicting children's short-term exposure to pesticides: results of a questionnaire screening approach. | 2003 Jan |
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The effects of acute pesticide exposure on neuroblastoma cells chronically exposed to diazinon. | 2003 Mar 14 |
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 UTC 2023
by
admin
on
Fri Dec 15 15:10:44 UTC 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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303
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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 |