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3,4,5-Trimethylphenyl methylcarbamate

HCID 17592
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Basic information

CAS
2686-99-9
Standard SMILES
CNC(=O)Oc1cc(C)c(C)c(C)c1
InChIKey
AUQAUAIUNJIIEP-UHFFFAOYSA-N
Molecular formula
C11H15NO2
Average molar mass
193.24 g/mol
Monoisotopic mass
193.11027872

Overview

3,4,5-trimethylphenyl methylcarbamate is a carbamate ester that consists of 3,4,5-trimethylphenol carrying an O-(N-methylcarbamoyl) group. One of two constituents of trimethacarb. It has a role as an insecticide and an agrochemical. It is functionally related to a 3,4,5-trimethylphenol.

Names & identifiers

Preferred name
3,4,5-Trimethylphenyl methylcarbamate
IUPAC
(3,4,5-trimethylphenyl) N-methylcarbamate
English name
3,4,5-TRIMETHACARB
Molecular formula
C11H15NO2
Molecular weight
193.24

Names & synonyms

3,4,5-Trimethacarb3,4,5-Trimethylphenyl methylcarbamate3,4,5-Trimethylphenyl N-methylcarbamateShell 85303,4,5-LandrinOMS-597Phenol, 3,4,5-trimethyl-, methylcarbamateSD 8530ENT-25,843JG6XSN0Z2I(3,4,5-trimethylphenyl) N-methylcarbamate3,4,5-Trimethylfenylester kyseliny methylkarbaminove
Show more names
dimethacarbLANDRINlandrin1landrinaMPMC-XMCshell8530hunmiewei
Trimethacarb [ANSI]EINECS 220-245-9UNII-JG6XSN0Z2IBRN 2052372AI3-258433,4,5-Trimethylfenylester kyseliny methylkarbaminove [Czech]SCHEMBL119743orb1705540

Database identifiers

CAS
2686-99-9
PubChem CID
17592
DTXSID
DTXSID1040322
ChEBI
CHEBI:38894
UNII

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
38.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
14
Formal charge
0
Complexity
193

Experimental & physicochemical properties

SpringerMaterials PropertiesFusion temperature
LogP2.66

Physicochemical properties

Melting point
109 °C · 109 °C
Boiling point
329.46 °C · 329.46°C (rough estimate)
Density
1.0945 · 1.0945 (rough estimate)
refractive index
1.508 · 1.5080 (estimate)
storage temp.
0 · 0-6°C
pka
12.39 · 12.39±0.46(Predicted)
FDA UNII
6 XSN0Z2I · JG6XSN0Z2I
EPA Substance Registry System
3 · 3,4,5-Trimethylphenyl methylcarbamate (2686-99-9)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Treatment · 1 item

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.

Health Effects · 1 item

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 (A15321).

Exposure Routes

Chemistry & industry

Pharmacology

Metabolism/MetabolitesThe carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

Uses & manufacturing

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

Applications

Uses3,4,5-Trimethacarb is a pesticide metabolites/residue in foods and agricultural products.

Upstream & downstream products

Upstream raw materials

Petroleum crude oilMethylamineChloroformatePhosgeneXylenol

Additional notes

DefinitionChEBI: A carbamate ester that consists of 3,4,5-trimethylphenol carrying an O-(N-methylcarbamoyl) group. One of two constituents of trimethacarb.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
JG6XSN0Z2I
Nikkaji
J7.646E
Inhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 item

Trimethacarb 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.

Signs and Symptoms · 1 item

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. (L795)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).