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Record Information
Version2.0
Creation Date2009-06-17 23:53:04 UTC
Update Date2014-12-24 20:23:00 UTC
Accession NumberT3D0981
Identification
Common NameMethiocarb
ClassSmall Molecule
DescriptionMethiocarb is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. (4)
Compound Type
  • Amine
  • Carbamate
  • Ester
  • Ether
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
3,5-Dimethyl-4-(methylsulfanyl)phenyl methylcarbamate
3,5-Dimethyl-4-(methylthio)phenol methylcarbamate
3,5-Dimethyl-4-(Methylthio)phenyl methylcarbamate
3,5-Dimethyl-4-methyl-thiophenyl-N-carbamat
3,5-Dimethyl-4-methylmercaptophenyl-N-methyl-carbamate
3,5-Dimethyl-4-methylthiophenyl N-methylcarbamate
3,5-Xylenol, 4-(methylthio)-, methylcarbamate
4-(Methylthio)-3,5-dimethylphenyl methylcarbamate
4-(Methylthio)-3,5-xylyl methylcarbamate
4-Methylmercapto-3,5-dimethylphenyl N-methylcarbamate
4-Methylmercapto-3,5-xylyl methylcarbamate
4-Methylthio-3,5-dimethylphenyl methylcarbamate
4-Methylthio-3,5-xylyl methylcarbamate
Borderland black
Carbamic acid, methyl-, 4-(methylthio)-3,5-xylyl ester
Carbamic acid, N-methyl-, 4-(methylthio)-3,5-xylyl ester
Caswell No. 578B
Certan
CLUB
Draza
Esurol
Grandslam
Lizetan
Mercaptodimethur
Mesurol
Mesurol phenol
Methiocarbe
Methyl carbamic acid 4-(methylthio)-3,5-xylyl ester
Metmercapturan
Metmercapturon
Phenol, 3,5-dimethyl-4-(methylthio)-, methylcarbamate
Phenol, 3,5-dimethyl-4-(methylthio)-, methylcarbamate (9CI)
Phenyl-3,5-dimethyl-4-(methylthio)-, methylcarbamate
Chemical FormulaC11H15NO2S
Average Molecular Mass225.307 g/mol
Monoisotopic Mass225.082 g/mol
CAS Registry Number2032-65-7
IUPAC Name3,5-dimethyl-4-(methylsulfanyl)phenyl N-methylcarbamate
Traditional Namegrandslam
SMILESCNC(=O)OC1=CC(C)=C(SC)C(C)=C1
InChI IdentifierInChI=1S/C11H15NO2S/c1-7-5-9(14-11(13)12-3)6-8(2)10(7)15-4/h5-6H,1-4H3,(H,12,13)
InChI KeyInChIKey=YFBPRJGDJKVWAH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenoxy compounds
Direct ParentPhenoxy compounds
Alternative Parents
Substituents
  • Phenoxy compound
  • Aryl thioether
  • Thiophenol ether
  • M-xylene
  • Xylene
  • Alkylarylthioether
  • Carboximidic acid derivative
  • Thioether
  • Sulfenyl compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point120°C
Boiling PointNot Available
Solubility0.027 mg/mL at 20°C [TOMLIN,C (1994)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
logP2.54ALOGPS
logP3.13ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)14.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity63.61 m³·mol⁻¹ChemAxon
Polarizability24.54 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 15V, positivesplash10-014i-0900000000-33b55c00563f4fde0d21JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 6V, positivesplash10-014i-0900000000-cbb70974a5ac2b3cde11JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 13V, positivesplash10-014i-0900000000-08421f61964dd9e84834JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 20V, positivesplash10-00di-0900000000-a0f4d48b95ddadeacde1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 27V, positivesplash10-00di-1900000000-26fa3656076d4f5b9747JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 33V, positivesplash10-00di-3900000000-a8337c362cccf713ee24JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 40V, positivesplash10-05fu-5900000000-ef61497e358941667a73JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 24V, positivesplash10-00di-1900000000-4c82adbc8ab4b22f9b4aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 36V, positivesplash10-00dl-6900000000-7aa3b43100afab8265c7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 15V, positivesplash10-014i-0900000000-1b7534b20d53f4066cb4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 15V, positivesplash10-00xr-0900000000-1bbf96f1b84a957d673eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-014i-0900000000-52ef47c24c6e0d16c087JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-00xr-0900000000-72b2adbcb90625250a39JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-00di-0900000000-b01752c6694d8522c4f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-00di-0900000000-992aabf50eee221378d3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, positivesplash10-00di-0900000000-ec0a5e900489da8e3792JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 23V, positivesplash10-00di-0900000000-9efcdf3176ca194fcc9aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-4960000000-635ef42cebb6ce89fcedJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3900000000-553d3e6018ccd842273dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-7900000000-9bc5a478d8c63d8e076dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0adi-9720000000-5f99e2506eb6bc178befJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adi-6910000000-9be024895baf51f0aa7fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k95-9300000000-bd3c2f1d97cdd4525f80JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0gb9-7900000000-82567d636378adabb1e1JSpectraViewer | MoNA
Toxicity Profile
Route of ExposureInhalation (3) ; oral (3); dermal (3)
Mechanism of ToxicityMethiocarb is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. 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.
MetabolismThe carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (3)
Toxicity ValuesLD50: 52-58 mg/kg (Oral, Mouse) LD50: 350 mg/kg (Dermal, Rat) (2) LD50: 16 mg/kg (Intraperitoneal, Mouse) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMethiocarb is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.
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. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (1).
SymptomsAs with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (4)
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.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID16248
ChEMBL IDCHEMBL1076495
ChemSpider ID15417
KEGG IDC18651
UniProt IDNot Available
OMIM ID
ChEBI ID38508
BioCyc IDNot Available
CTD IDD008714
Stitch IDMethiocarb
PDB IDNot Available
ACToR ID10917
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D0981.pdf
General References
  1. Roldan-Tapia L, Nieto-Escamez FA, del Aguila EM, Laynez F, Parron T, Sanchez-Santed F: Neuropsychological sequelae from acute poisoning and long-term exposure to carbamate and organophosphate pesticides. Neurotoxicol Teratol. 2006 Nov-Dec;28(6):694-703. Epub 2006 Aug 30. [17029710 ]
  2. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  3. IPCS Intox Database (1987). Antimony pentoxide. [Link]
  4. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. [Link]
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. [Link]