Showing Compound Card for Thiamethoxam (CDB006231)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-07-28 20:21:38 UTC
Updated at2020-11-18 16:40:15 UTC
CannabisDB IDCDB006231
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameThiamethoxam
DescriptionThiamethoxam belongs to the class of organic compounds known as 2,5-disubstituted thiazoles. 2,5-disubstituted thiazoles are compounds containing a thiazole ring substituted at positions 2 and 5 only. The use of neonicotinoids has been linked in a range of studies to adverse ecological effects, including honey-bee colony collapse disorder (CCD) and loss of birds due to a reduction in insect populations. Thiamethoxam is a neonicotinoid insecticide, which is a class of neuro-active insecticides modeled after nicotine. Thiamethoxam is an extremely weak basic (essentially neutral) compound (based on its pKa). Neonicotinoids are currently used on corn, canola, cotton, sorghum, sugar beets and soybeans. Thiamethoxam is a potentially toxic compound. Acetylcholine is broken down by acetylcholinesterase to terminate signals from these receptors. In mammals, nicotinic acetylcholine receptors are located in cells of both the central and peripheral nervous systems. Nicotinic acetylcholine receptors are activated by the neurotransmitter acetylcholine.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ACTARA 25 WGMeSH
3-(2-chloro-Thiazol-5-ylmethyl)-5-methyl-(1,3,5)oxadiazinan-4-yldene-N-nitroamineMeSH
ActaraMeSH
Chemical FormulaC8H10ClN5O3S
Average Molecular Weight291.715
Monoisotopic Molecular Weight291.019287608
IUPAC Name(4Z)-3-[(2-chloro-1,3-thiazol-5-yl)methyl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine
Traditional Namethiamethoxam
CAS Registry Number153719-23-4
SMILES
CN1COCN(CC2=CN=C(Cl)S2)\C1=N/[N+]([O-])=O
InChI Identifier
InChI=1S/C8H10ClN5O3S/c1-12-4-17-5-13(8(12)11-14(15)16)3-6-2-10-7(9)18-6/h2H,3-5H2,1H3/b11-8-
InChI KeyNWWZPOKUUAIXIW-FLIBITNWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2,5-disubstituted thiazoles. 2,5-Disubstituted thiazoles are compounds containing a thiazole ring substituted at positions 2 and 5 only.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassThiazoles
Direct Parent2,5-disubstituted thiazoles
Alternative Parents
Substituents
  • 2,5-disubstituted 1,3-thiazole
  • Aryl chloride
  • Aryl halide
  • Heteroaromatic compound
  • Guanidine
  • Organic nitro compound
  • Allyl-type 1,3-dipolar organic compound
  • Oxacycle
  • Azacycle
  • Organic 1,3-dipolar compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point139.1°CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.54ALOGPS
logP1.07ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)0.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area84.1 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.81 m³·mol⁻¹ChemAxon
Polarizability25.74 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSThiamethoxam, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 10V, positivesplash10-01ox-0090000000-b96956c5f01f7b4d87b82020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 20V, positivesplash10-001i-0930000000-c2368eb9e2ec01afe97d2020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 30V, positivesplash10-001i-0900000000-d8c26cd5c80e6ba674552020-08-04View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 40V, positivesplash10-053r-0900000000-29bc8a1fa27dbbd0e44b2020-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-9352dc604b386f6ac9a12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-1090000000-3bb13ae0dfd8f9be65ec2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-6900000000-1b53cccfd2735db5c0df2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-3090000000-958ae188a575a58163bc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9100000000-5621eb62e7c5584c2a8a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-6c00dbb61be83b615c662016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThiamethoxam
METLIN IDNot Available
PubChem Compound5485188
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Moulins JR, Blais M, Montsion K, Tully J, Mohan W, Gagnon M, McRitchie T, Kwong K, Snider N, Blais DR: Multiresidue Method of Analysis of Pesticides in Medical Cannabis. J AOAC Int. 2018 Nov 1;101(6):1948-1960. doi: 10.5740/jaoacint.17-0495. Epub 2018 May 29. [PubMed:29843862 ]