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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

Description

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

CNS Penetrant
2523
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.

Originator

Approval Year

Unknown
134361
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8228
 1900.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Predicting insecticide resistance: mutagenesis, selection and response.
1998 Oct 29
[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
Gross fluxes and estuarine behaviour of pesticides in the Scheldt estuary (1995-1997).
2001
Optimization of headspace solid-phase microextraction conditions for the determination of organophosphorus insecticides in natural waters.
2001 Jul 13
Increasing uptake and bioactivation with development positively modulate diazinon toxicity in early life stage medaka (Oryzias latipes).
2001 Jun
Topical application as a method for comparing the effectiveness of insecticides against cat flea (Siphonaptera: Pulicidae).
2001 Mar
Fatty acid amide hydrolase inhibition by neurotoxic organophosphorus pesticides.
2001 May 15
Evaluating environmental hazards of land applying composted diazinon using earthworm bioassays.
2001 Nov
A comparison of biomarker responses in the earthworm Aporrectodea caliginosa to the organophosphorus insecticides diazinon and chlorpyrifos.
2001 Nov
Pollutants in house dust as indicators of indoor contamination.
2002
Kynurenine formamidase: determination of primary structure and modeling-based prediction of tertiary structure and catalytic triad.
2002 Apr 29
Vitamin C and E intake is associated with increased paraoxonase activity.
2002 Aug 1
Simple method for the determination of trace levels of pesticides in honeybees using matrix solid-phase dispersion and gas chromatography.
2002 Dec 27
Simple determination of 22 organophosphorous pesticides in human blood using headspace solid-phase microextraction and gas chromatography with mass spectrometric detection.
2002 Jan
Oxidation of diazinon by anodic Fenton treatment.
2002 Jul
Increased toxicity to invertebrates associated with a mixture of atrazine and organophosphate insecticides.
2002 Jul
Exposure apportionment: ranking food items by their contribution to dietary exposure.
2002 Jul
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
Persistence of methamidophos, diazinon, and malathion in tomatoes.
2002 Oct
Causes of ambient toxicity in the Calleguas Creek watershed of southern California.
2002 Sep
Convenient and rapid detection of pesticides in extracts of sheep wool.
2002 Sep
Determination of pesticide residues in nonfatty foods by supercritical fluid extraction and gas chromatography/mass spectrometry: collaborative study.
2002 Sep-Oct
Histological examination of sublethal effects of diazinon on ovary of bluegill, Lepomis macrochirus.
2003
Predicting children's short-term exposure to pesticides: results of a questionnaire screening approach.
2003 Jan
The effects of acute pesticide exposure on neuroblastoma cells chronically exposed to diazinon.
2003 Mar 14
Patents

Patents

JP1015654A
1
JP2000026722A
1
JP2011509971A
151
JP2011527307A
41
JPH02138391A
1
JPH02247102A
2
JPH0240353A
1
JPH06263606A
1
JPH06263609A
1
JPH08231303A
1
JPH08299304A
1
JPH10182677A
1
JPS56113703A
1
JPS56166102A
1
JPS5745102A
2
JPS6013701A
1
JPS6122003A
1
JPS6235346A
1

Sample Use Guides

In Vivo Use Guide
Dimpylate (diazinon) is a contact insecticide. It is administered by spraying the crops.
Route of Administration: Topical
In Vitro Use Guide
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 Wed Jul 05 22:42:23 UTC 2023
Edited
by admin
on Wed Jul 05 22:42:23 UTC 2023
Record UNII
YUS1M1Q929
Record Status Validated (UNII)
Record Version
  • Download
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 Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
EPA PESTICIDE CODE 57801
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
Code System Code Type Description
INN
2045
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
MESH
D003976
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
EPA CompTox
DTXSID9020407
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
CHEBI
34682
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
ALANWOOD
diazinon
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
WIKIPEDIA
DIAZINON
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
PUBCHEM
3017
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
HSDB
303
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
NSC
8938
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
CAS
333-41-5
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
EVMPD
SUB07189MIG
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-373-8
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
SMS_ID
100000082650
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
NCI_THESAURUS
C169912
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
FDA UNII
YUS1M1Q929
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
DAILYMED
YUS1M1Q929
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
ChEMBL
CHEMBL388560
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY
MERCK INDEX
M4268
Created by admin on Wed Jul 05 22:42:23 UTC 2023 , Edited by admin on Wed Jul 05 22:42:23 UTC 2023
PRIMARY Merck Index
Related Record Type Details
CYTOCHROME P450 2B6
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 1A1
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of 2-ISOPROPYL-6-METHYL-4-PYRIMIDONE
METABOLITE -> PARENT
Related Record Type Details
Structure of DIMPYLATE
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