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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
Structure of DIMPYLATE

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

HIDE SMILES / InChI

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

Curator's Comment: Animal tissue studies and autopsy reports of human deaths from diazinon have shown that it is widely and rapidly distributed throughout the body. Rats exposed orally to 23 mg/kg diazinon had detectable levels of diazinon in the blood, adipose tissue, muscle, liver and brain.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1900.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Agricultural use of organophosphate pesticides and the risk of non-Hodgkin's lymphoma among male farmers (United States).
2001 Aug
Influence of sebum and stratum corneum hydration on pesticide/herbicide collection efficiencies of the human hand.
2001 Aug
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
High performance liquid chromatographic determination of diazinon, permethrin, DEET (N, N-diethyl-m-toluamide), and their metabolites in rat plasma and urine.
2001 Jun
Diazinon is activated by CYP2C19 in human liver.
2001 Nov 15
Acute toxicity and bioaccumulation of pesticide Diazinon in red tilapia (Oreochromis niloticus x Mossambicus albina).
2002
Exposure to the organophosphate diazinon: data from a human volunteer study with oral and dermal doses.
2002 Aug 5
Community exposures to airborne agricultural pesticides in California: ranking of inhalation risks.
2002 Dec
Modeling of single-step and multistep adsorption isotherms of organic pesticides on soil.
2002 Dec 4
Removal of organophosphate pesticides from wastewater by supercritical carbon dioxide extraction.
2002 Feb
Simple determination of 22 organophosphorous pesticides in human blood using headspace solid-phase microextraction and gas chromatography with mass spectrometric detection.
2002 Jan
Size exclusion chromatographic cleanup for GC/MS determination of organophosphorus pesticide residues in household and vehicle dust.
2002 Jan-Feb
Determination of insecticides in honey by matrix solid-phase dispersion and gas chromatography with nitrogen-phosphorus detection and mass spectrometric confirmation.
2002 Jan-Feb
Exposure apportionment: ranking food items by their contribution to dietary exposure.
2002 Jul
Diazinon and its degradation products in agricultural water courses in British Columbia, Canada.
2002 Jul
Application of solid-phase microextraction in the monitoring of priority pesticides in the Kalamas River (N.W. Greece).
2002 Jul 19
Effect of some organophosphorus pesticides on oxygen consumption of shrimp, Litopenaeus vannamei.
2002 Jun
Genotoxicity studies on permethrin, DEET and diazinon in primary human nasal mucosal cells.
2002 Mar
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
Interactions between pesticides and components of pesticide formulations in an in vitro neurotoxicity test.
2002 May 1
Pesticide residues in agricultural products monitored in Hyogo Prefecture, Japan, FYs 1995-1999.
2002 May-Jun
Sublethal responses of wolf spiders (Lycosidae) to organophosphorous insecticides.
2002 Oct
Persistence of methamidophos, diazinon, and malathion in tomatoes.
2002 Oct
Prevalence of fetal exposure to environmental toxins as determined by meconium analysis.
2002 Sep
Histological examination of sublethal effects of diazinon on ovary of bluegill, Lepomis macrochirus.
2003
Patents

Sample Use Guides

Dimpylate (diazinon) is a contact insecticide. It is administered by spraying the crops.
Route of Administration: Topical
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 Fri Dec 15 15:10:44 GMT 2023
Edited
by admin
on Fri Dec 15 15:10:44 GMT 2023
Record UNII
YUS1M1Q929
Record Status Validated (UNII)
Record Version
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Name Type Language
DIMPYLATE
INN   MART.   WHO-DD  
INN  
Official Name English
DIETHYL 2-ISOPROPYL-4-METHYL-6-PYRIMIDYL THIONOPHOSPHATE
Common Name English
DIAZINON [ISO]
Common Name English
O,O-DIETHYL 2-ISOPROPYL-6-METHYL-4-PYRIMIDINYLPHOSPHOROTHIOATE
Systematic Name English
OPTIMIZER INSECTICIDE
Brand Name English
Dimpylate [WHO-DD]
Common Name English
dimpylate [INN]
Common Name English
DIAZINON [HSDB]
Common Name English
O,O-DIETHYL O-(6-METHYL-2-(1-METHYLETHYL)-4-PYRIMIDINYL) PHOSPHOROTHIOATE
Systematic Name English
DIAZINON [MI]
Common Name English
DIMPYLATE [MART.]
Common Name English
DIAZINON
HSDB   ISO   MI  
Systematic Name English
PHOSPHOROTHIOIC ACID O,O-DIETHYL O-(6-METHYL-2-(1-METHYLETHYL)-4-PYRIMIDINYL) ESTER
Systematic Name English
NSC-8938
Code English
NEW Z DIAZINON
Brand Name English
DIAZINON [IARC]
Common Name English
G-24480
Code English
Classification Tree Code System Code
WHO-VATC QP53AF03
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
EPA PESTICIDE CODE 57801
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
Code System Code Type Description
INN
2045
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
MESH
D003976
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PRIMARY
EPA CompTox
DTXSID9020407
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PRIMARY
CHEBI
34682
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
ALANWOOD
diazinon
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
WIKIPEDIA
DIAZINON
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
PUBCHEM
3017
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PRIMARY
HSDB
303
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
NSC
8938
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PRIMARY
CAS
333-41-5
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
EVMPD
SUB07189MIG
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-373-8
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
SMS_ID
100000082650
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
NCI_THESAURUS
C169912
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
FDA UNII
YUS1M1Q929
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
DAILYMED
YUS1M1Q929
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
ChEMBL
CHEMBL388560
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
MERCK INDEX
m4268
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY Merck Index
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