Basic information
- Standard SMILES
CNC(=O)Oc1ccc(C)c(C)c1- InChIKey
WCJYTPVNMWIZCG-UHFFFAOYSA-N- Molecular formula
- C10H13NO2
- Average molar mass
- 179.22 g/mol
- Monoisotopic mass
- 179.09462866
Overview
Xylylcarb is a carbamate ester. It has a role as an agrochemical, a carbamate insecticide and an EC 3.1.1.7 (acetylcholinesterase) inhibitor. It is functionally related to a 3,4-xylenol and a methylcarbamic acid.
Names & identifiers
- Preferred name
- Xylylcarb
- IUPAC
- (3,4-dimethylphenyl) N-methylcarbamate
- English name
- MPMC
- Molecular formula
- C10H13NO2
- Molecular weight
- 179.22
Names & synonyms
Show more names
Database identifiers
- CAS
2425-10-7- PubChem CID
- 17040
- DTXSID
DTXSID3058032- ChEBI
CHEBI:35048- UNII
- 2999840EDW
- EC Number
- 219-364-9
- Nikkaji
- J3.027I
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 38.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 182
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 79.1 °C · 79.1°C
- Boiling point
- 311.75 °C · 311.75°C (rough estimate)
- Density
- 1.1248 · 1.1248 (rough estimate)
- vapor pressure
- 70 x · 70 x 10-3 Pa (20 °C)
- refractive index
- 1.515 · 1.5150 (estimate)
- Water Solubility
- 580 mg · 580 mg l-1 (20 °C)
- pka
- 12.38 · 12.38±0.46(Predicted)
- Henry's Law Constant
- 9.1 · 9.1×101 mol/(m3Pa) at 25℃, Watanabe (1993)
- CAS DataBase Reference
- 2425 · 2425-10-7
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 2999840 EDW · 2999840EDW
- EPA Substance Registry System
- 3 · Phenol, 3,4-dimethyl-, methylcarbamate (2425-10-7)
- Symbol(GHS)
- 7 · GHS07,GHS09
- Signal word
- Warning
- Hazard statements
- 302 · H302-H410
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501-P273-P391-P501
- Hazard Codes
- Xn,N
- Risk Statements
- 22 · 22-50/53
- Safety Statements
- 60 · 60-61
- TSCA
- TSCA listed
- Toxicity
- 50 oral · LD50 oral in rat: 290mg/kg
Safety & regulation
GHS classification
GHS Classification
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)
Hazard information
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute toxicity - category 4
Acute toxicity (Oral) - Category 3
Acute Tox. 4 *
Toxicology
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.
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 (A15321).
Toxicity Summary
Xylylcarb 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
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)
Safety data
- tsca
- TSCA listed
- Toxicity
- LD50 oral in rat: 290mg/kg
- risk_code
- 22-50/53
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- hazard_code
- Xn,N
- safety_code
- 60-61
- Hazard statements
- H302-H410
- Precautionary statements
- P264-P270-P301+P312-P330-P501-P273-P391-P501
Chemistry & industry
Pharmacology
Uses & manufacturing
Applications
DescriptionXylylcarb (MPMC) is a colorless solid, which is sparingly soluble in water and is fairly soluble in acetonitrile, cyclohexane, and xylene.
UsesXylylcarb is a non-systemic insecticide. It is mainly used to control hoppers and other sucking pests on rice, and leafhoppers, planthoppers and scale insects on fruit.
Suppliers11 total
Additional notes
DefinitionChEBI: Xylylcarb is a carbamate ester. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a carbamate insecticide and an agrochemical. It is functionally related to a methylcarbamic acid and a 3,4-xylenol.
Related reactions
Linked notes
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