Guthion (CHEM000125)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (14)XML
Record Information
Version1.0
Creation Date2009-03-06 18:58:08 UTC
Update Date2026-03-31 19:49:30 UTC
Accession NumberCHEM000125
Identification
Common NameGuthion
ClassSmall Molecule
DescriptionGuthion, also called azinphos-methyl, is a synthetic organophosphorous pesticide. It has been used on many different crops, especially apples, pears, cherries, peaches, almonds, and cotton. Due to its toxicity, its use has been banned or tightly regulated in most areas today. (3)
Contaminant Sources
  • Clean Air Act Chemicals
  • EAFUS Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Food Toxin
  • Organic Compound
  • Organophosphate
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-(Mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one, O,O-dimethyl phosphorodithioateChEBI
Azinphos methylChEBI
AzinphosmethylChEBI
GuthionChEBI
O,O-Dimethyl S-(3,4-dihydro-4-keto-1,2,3-benzotriazinyl-3-methyl) dithiophosphateChEBI
O,O-Dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] dithiophosphateChEBI
Phosphorodithioic acid, O,O-dimethyl S-((4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl) esterChEBI
3-(Mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one, O,O-dimethyl phosphorodithioic acidGenerator
O,O-Dimethyl S-(3,4-dihydro-4-keto-1,2,3-benzotriazinyl-3-methyl) dithiophosphoric acidGenerator
O,O-Dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] dithiophosphoric acidGenerator
Phosphorodithioate, O,O-dimethyl S-((4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl) esterGenerator
Chemical FormulaC10H12N3O3PS2
Average Molecular Mass317.324 g/mol
Monoisotopic Mass317.006 g/mol
CAS Registry Number86-50-0
IUPAC NameO,O-dimethyl {[(4-oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)methyl]sulfanyl}phosphonothioate
Traditional NameO,O-dimethyl [(4-oxo-1,2,3-benzotriazin-3-yl)methyl]sulfanylphosphonothioate
SMILESCOP(=S)(OC)SCN1N=NC2=CC=CC=C2C1=O
InChI IdentifierInChI=1S/C10H12N3O3PS2/c1-15-17(18,16-2)19-7-13-10(14)8-5-3-4-6-9(8)11-12-13/h3-6H,7H2,1-2H3
InChI KeyCJJOSEISRRTUQB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzotriazine organothiophosphates. These are aromatic compounds containing a benzo-1,2,3-triazine, which is substituted by an organothiophosphate group at the 3-position. Their general structure is R-CSP(=S)(OR')OR'', where R=benzo-1,2,3-triazine, R',R\" = any atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzo-1,2,3-triazines
Sub ClassBenzotriazine organothiophosphates
Direct ParentBenzotriazine organothiophosphates
Alternative Parents
Substituents
  • Benzotriazine organothiophosphate
  • Triazinone
  • Triazine
  • Dithiophosphate s-ester
  • Benzenoid
  • 1,2,3-triazine
  • Dithiophosphate o-ester
  • Heteroaromatic compound
  • Organic dithiophosphate
  • Lactam
  • Azacycle
  • Sulfenyl compound
  • Organothiophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceColorless to white crystals.
Experimental Properties
PropertyValue
Melting Point73°C
Boiling PointNot Available
Solubility0.0209 mg/mL at 20 °C [BOWMAN,BT & SANS,WW (1983)]
Predicted Properties
PropertyValueSource
Water Solubility0.035 g/LALOGPS
logP2.75ALOGPS
logP3.24ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area63.49 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.64 m³·mol⁻¹ChemAxon
Polarizability29.62 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-08fr-0910000000-8a90862fb34d7f1de4d6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-008c-0900000000-c3d2041851aea43793d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-0900000000-d45bfd942d49cb4291aeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0kdj-9300000000-8aab23fdf42981012983Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-008c-0900000000-1af926d96f15ea4fe029Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0kdm-9600000000-87f03e4a5118de93472bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-65ca1a571d6e6181a088Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0900000000-c34b6732021b15900ca6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-0900000000-7cfe94f327d288d4482cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-56fb2b538788f6a5dd63Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000x-0900000000-02de58086414fbca0a4bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000x-1900000000-eacce6bcbada6302fcfbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-03ec-0910000000-4f5411792d4477abc588Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0006-1900000000-0d479bb903e25e1f854eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0kbg-5900000000-3e0b563fe56090b9433aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-0639000000-d7afc7588998311cc61fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-6908000000-2adf23de316e0ef841d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-6900000000-ab0ac3300b9628fd5fa4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0119000000-6b01cea6b4efafb87ffcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0390000000-2c07ac5163df5ab1dc15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1900000000-4a556662783ce60fac92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0900000000-c86324755309401cbaeaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0900000000-558e5a824d096c620192Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-5900000000-6248de11ddfc5a8e385eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0902000000-8064bfc10805102a22bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2900000000-e2f755731cfbdd47a562Spectrum
MSMass Spectrum (Electron Ionization)splash10-0in9-8900000000-dcab6b11e3ab3e51c6c8Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (3) ; dermal (3) ; inhalation (3)
Mechanism of ToxicityGuthion 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 ValuesLD50: 11 mg/kg (Oral, Rat) (6) LD50: 4900 ug/kg (Intraperitoneal, Rat) (5) LD50: 7500 ug/kg (Intravenous, Rat) (5) LD50: 65 mg/kg (Dermal, Mouse) (5) LC50: 0.15 mg/L over 4 hours (Inhalation, Rat) (6)
Lethal Dose5 to 50 mg/kg for an adult human. (4)
Carcinogenicity (IARC Classification)Spraying and application of nonarsenical insecticides entail exposures that are probably carcinogenic to humans (Group 2A). (2)
Uses/SourcesGuthion is used as a pesticide, thus exposure usually occurs from eating contaminated food. (3)
Minimum Risk LevelAcute Inhalation: 0.02 mg/m3 (1) Intermediate Inhalation: 0.01 mg/m3 (1) Chronic Inhalation: 0.01 mg/m3 (1) Acute Oral: 0.01 mg/kg/day (1) Intermediate Oral: 0.003 mg/kg/day (1) Chronic Oral: mg/kg/day (1)
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.
SymptomsGuthion interferes with the nerves and brain normal way. Exposure to very high levels of guthion for a short period in air, water, or food may cause difficulty breathing, chest tightness, vomiting, cramps, diarrhea, blurred vision, sweating, headaches, dizziness, loss of consciousness, and death. (3)
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 IDHMDB0248807
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAzinphos-methyl
Chemspider ID2181
ChEBI ID2953
PubChem Compound ID2268
Kegg Compound IDC11018
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17097717
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24177216
3. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.