Pirimiphos-methyl (CHEM003485)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (18)XML
Record Information
Version1.0
Creation Date2014-08-29 06:51:44 UTC
Update Date2016-11-09 01:09:09 UTC
Accession NumberCHEM003485
Identification
Common NamePirimiphos-methyl
ClassSmall Molecule
DescriptionPirimiphos-methyl is an organophosphate and fumigant insecticide with pirimiphos-methyl and no longer in production. It is used to control a wide range of insects and mites in stores, animal houses, domestic and industrial premisies. It is considered to be an acetylcholinesterase (AChE) inhibitor with contact and respiratory action. This is one of several compounds used for vector control of Triatoma.
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Industrial/Workplace Toxin
  • Insecticide
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
O-[2-(Diethylamino)-6-methylpyrimidin-4-yl] O,O-dimethyl thiophosphateChEBI
PirimifosmethylChEBI
Pirimiphos methylChEBI
PirimiphosmethylChEBI
Pyrimiphos methylChEBI
O-[2-(Diethylamino)-6-methylpyrimidin-4-yl] O,O-dimethyl thiophosphoric acidGenerator
PiritioneMeSH
O-(2-(diethylamino)-6-Methyl-4-pyrimidinyl) O,O- dimethylphosphorothioate licMeSH
ActellicMeSH
AktelMeSH
Chemical FormulaC11H20N3O3PS
Average Molecular Mass305.334 g/mol
Monoisotopic Mass305.096 g/mol
CAS Registry Number29232-93-7
IUPAC NameO-2-(diethylamino)-6-methylpyrimidin-4-yl O,O-dimethyl phosphorothioate
Traditional NameO-2-(diethylamino)-6-methylpyrimidin-4-yl O,O-dimethyl phosphorothioate
SMILESCCN(CC)C1=NC(OP(=S)(OC)OC)=CC(C)=N1
InChI IdentifierInChI=1S/C11H20N3O3PS/c1-6-14(7-2)11-12-9(3)8-10(13-11)17-18(19,15-4)16-5/h8H,6-7H2,1-5H3
InChI KeyQHOQHJPRIBSPCY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidinyl phosphorothioates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where R= pyrimidine, R' = organyl group , and R\" = any atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
Sub ClassThiophosphoric acid esters
Direct ParentPyrimidinyl phosphorothioates
Alternative Parents
Substituents
  • Pyrimidinyl phosphorothioate
  • Dialkylarylamine
  • Thiophosphate triester
  • Aminopyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Actin Filament
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Aflatoxin BiosynthesisNot AvailableNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point15-18°C
Boiling Pointdecomposes before boiling
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP3.91ALOGPS
logP2.96ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)5.09ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area56.71 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity81.31 m³·mol⁻¹ChemAxon
Polarizability30.71 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-1490000000-30fac2b7c9208b9d4e6eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0200-0790000000-784b40098216be79a581Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03ki-0900000000-895cdb27adc01302a330Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-0911000000-ba5b0672e4bab27ca388Spectrum
LC-MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-0200-0790000000-952c08c209a5666e2f14Spectrum
LC-MS/MSLC-MS/MS Spectrum - 80V, Positivesplash10-0a4i-1900000000-4e8a11388a8353420139Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-3966cebde88daac933fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0209000000-6dbf3dcfe0e322198dabSpectrum
LC-MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-0bt9-1900000000-51e7080196d96c82db04Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0gb9-0900000000-7101d86decc6c087bc16Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0fkc-0900000000-396ee6ab0c0839693cffSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a4i-1719000000-3aed70af03fb848971a8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0fkc-0900000000-ffa782226105d26603d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0359000000-416ae91c212df63bf10bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0692000000-54185c472d72dd012c95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-7940000000-945d6b4e6fff3fd05f1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0569000000-3f964fdb65d2baa50628Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btc-0691000000-b6717f4381802607d73cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-1920000000-9714a9ea8031c043cca8Spectrum
MSMass Spectrum (Electron Ionization)splash10-004l-9671000000-db466e16c69b326f2d7bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityPirimiphos-methyl is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.
MetabolismMetabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Spraying and application of nonarsenical insecticides entail exposures that are probably carcinogenic to humans (Group 2A). (1)
Uses/SourcesThis is a man-made compound that is used as a pesticide.
Minimum Risk LevelNot Available
Health EffectsAcute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.
SymptomsSymptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.
TreatmentIf the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0256600
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPirimiphos-methyl
Chemspider ID31773
ChEBI ID38843
PubChem Compound IDNot Available
Kegg Compound IDC18403
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23343221
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24476070
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24685163
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24711991