ContaminantDB: Methiocarb

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-06-17 23:53:04 UTC

Update Date

2026-03-26 18:31:44 UTC

Accession Number

CHEM000841

Identification

Common Name

Methiocarb

Class

Small Molecule

Description

Methiocarb 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. (3)

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Carbamate
Ester
Ether
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,5-Dimethyl-4-(methylthio)phenol methylcarbamate	ChEBI
3,5-Dimethyl-4-(methylthio)phenyl methylcarbamate	ChEBI
3,5-Dimethyl-4-methylthiophenyl N-methylcarbamate	ChEBI
4-Methylmercapto-3,5-dimethylphenyl N-methylcarbamate	ChEBI
4-Methylmercapto-3,5-xylyl methylcarbamate	ChEBI
4-Methylthio-3,5-dimethylphenyl methylcarbamate	ChEBI
4-Methylthio-3,5-xylyl methylcarbamate	ChEBI
Mesurol	ChEBI
3,5-Dimethyl-4-(methylthio)phenol methylcarbamic acid	Generator
3,5-Dimethyl-4-(methylthio)phenyl methylcarbamic acid	Generator
3,5-Dimethyl-4-methylthiophenyl N-methylcarbamic acid	Generator
4-Methylmercapto-3,5-dimethylphenyl N-methylcarbamic acid	Generator
4-Methylmercapto-3,5-xylyl methylcarbamic acid	Generator
4-Methylthio-3,5-dimethylphenyl methylcarbamic acid	Generator
4-Methylthio-3,5-xylyl methylcarbamic acid	Generator

Chemical Formula

C₁₁H₁₅NO₂S

Average Molecular Mass

225.307 g/mol

Monoisotopic Mass

225.082 g/mol

CAS Registry Number

2032-65-7

IUPAC Name

3,5-dimethyl-4-(methylsulfanyl)phenyl N-methylcarbamate

Traditional Name

grandslam

SMILES

CNC(=O)OC1=CC(C)=C(SC)C(C)=C1

InChI Identifier

InChI=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 Key

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxy compounds

Direct Parent

Phenoxy 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

carbamate ester (CHEBI:38508 )
aryl sulfide (CHEBI:38508 )
Carbamate insecticides (C18651 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	120°C
Boiling Point	Not Available
Solubility	0.027 mg/mL at 20°C [TOMLIN,C (1994)]

Predicted Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	2.54	ALOGPS
logP	3.13	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	14.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.61 m³·mol⁻¹	ChemAxon
Polarizability	24.54 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 15V, positive	splash10-014i-0900000000-33b55c00563f4fde0d21	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 6V, positive	splash10-014i-0900000000-cbb70974a5ac2b3cde11	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 13V, positive	splash10-014i-0900000000-08421f61964dd9e84834	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 20V, positive	splash10-00di-0900000000-a0f4d48b95ddadeacde1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 27V, positive	splash10-00di-1900000000-26fa3656076d4f5b9747	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 33V, positive	splash10-00di-3900000000-a8337c362cccf713ee24	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 40V, positive	splash10-05fu-5900000000-ef61497e358941667a73	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 24V, positive	splash10-00di-1900000000-4c82adbc8ab4b22f9b4a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 36V, positive	splash10-00dl-6900000000-7aa3b43100afab8265c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 15V, positive	splash10-014i-0900000000-1b7534b20d53f4066cb4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 15V, positive	splash10-00xr-0900000000-1bbf96f1b84a957d673e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-014i-0900000000-52ef47c24c6e0d16c087	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-00xr-0900000000-72b2adbcb90625250a39	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive	splash10-00di-0900000000-b01752c6694d8522c4f7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive	splash10-00di-0900000000-992aabf50eee221378d3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 50V, positive	splash10-00di-0900000000-ec0a5e900489da8e3792	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 23V, positive	splash10-00di-0900000000-9efcdf3176ca194fcc9a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0900000000-992aabf50eee221378d3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-165018e065d9e9ff5583	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00or-4960000000-635ef42cebb6ce89fced	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-3900000000-553d3e6018ccd842273d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-7900000000-9bc5a478d8c63d8e076d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0adi-9720000000-5f99e2506eb6bc178bef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0adi-6910000000-9be024895baf51f0aa7f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0k95-9300000000-bd3c2f1d97cdd4525f80	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0gb9-7900000000-82567d636378adabb1e1	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (2) ; oral (2); dermal (2)

Mechanism of Toxicity

Methiocarb 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.

Metabolism

The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (2)

Toxicity Values

LD50: 52-58 mg/kg (Oral, Mouse) LD50: 350 mg/kg (Dermal, Rat) (4) LD50: 16 mg/kg (Intraperitoneal, Mouse) (4)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Methiocarb is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

Minimum Risk Level

Not Available

Health Effects

Acute 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).

Symptoms

As 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. (3)

Treatment

If 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

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID