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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[Evaluation of the effect of Knox-Out microencapsulated V.O. 240 and K-othrine powder on rat lice in two villages in the Betafo region]. | 2001 |
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Gross fluxes and estuarine behaviour of pesticides in the Scheldt estuary (1995-1997). | 2001 |
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Optimization of headspace solid-phase microextraction conditions for the determination of organophosphorus insecticides in natural waters. | 2001 Jul 13 |
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Increasing uptake and bioactivation with development positively modulate diazinon toxicity in early life stage medaka (Oryzias latipes). | 2001 Jun |
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Topical application as a method for comparing the effectiveness of insecticides against cat flea (Siphonaptera: Pulicidae). | 2001 Mar |
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Fatty acid amide hydrolase inhibition by neurotoxic organophosphorus pesticides. | 2001 May 15 |
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Evaluating environmental hazards of land applying composted diazinon using earthworm bioassays. | 2001 Nov |
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A comparison of biomarker responses in the earthworm Aporrectodea caliginosa to the organophosphorus insecticides diazinon and chlorpyrifos. | 2001 Nov |
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Pollutants in house dust as indicators of indoor contamination. | 2002 |
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Kynurenine formamidase: determination of primary structure and modeling-based prediction of tertiary structure and catalytic triad. | 2002 Apr 29 |
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Vitamin C and E intake is associated with increased paraoxonase activity. | 2002 Aug 1 |
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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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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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Oxidation of diazinon by anodic Fenton treatment. | 2002 Jul |
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Increased toxicity to invertebrates associated with a mixture of atrazine and organophosphate insecticides. | 2002 Jul |
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Exposure apportionment: ranking food items by their contribution to dietary exposure. | 2002 Jul |
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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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Persistence of methamidophos, diazinon, and malathion in tomatoes. | 2002 Oct |
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Causes of ambient toxicity in the Calleguas Creek watershed of southern California. | 2002 Sep |
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Convenient and rapid detection of pesticides in extracts of sheep wool. | 2002 Sep |
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Determination of pesticide residues in nonfatty foods by supercritical fluid extraction and gas chromatography/mass spectrometry: collaborative study. | 2002 Sep-Oct |
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Histological examination of sublethal effects of diazinon on ovary of bluegill, Lepomis macrochirus. | 2003 |
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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
Wed Jul 05 22:42:23 UTC 2023
by
admin
on
Wed Jul 05 22:42:23 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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8938
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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 |