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4-Amino-3,5-xylyl N-methylcarbamate

HCID 13252
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
831-76-5
Standard SMILES
CNC(=O)Oc1cc(C)c(N)c(C)c1
InChIKey
WUCVFDPUWPSAKL-UHFFFAOYSA-N
Molecular formula
C10H14N2O2
Average molar mass
194.23 g/mol
Monoisotopic mass
194.10552769

Overview

4-Amino-3,5-xylyl methylcarbamate 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. (L795)

Names & identifiers

Preferred name
4-Amino-3,5-xylyl N-methylcarbamate
IUPAC
(4-amino-3,5-dimethylphenyl) N-methylcarbamate

Names & synonyms

Aminozectran831-76-54-Amino-3,5-dimethylphenol methylcarbamate (ester)59H35M76HJPhenol, 4-amino-3,5-dimethyl-, methylcarbamate (ester)Methylcarbamic acid 4-amino-3,5-xylyl esterDTXSID2041599RefChem:1070250DTXCID00215994-Amino-3,5-xylyl N-methylcarbamateBRN 2215243(4-amino-3,5-dimethylphenyl) N-methylcarbamate
Show more names
UNII-59H35M76HJCARBAMIC ACID, METHYL-, 4-AMINO-3,5-XYLYL ESTERSCHEMBL11725210WUCVFDPUWPSAKL-UHFFFAOYSA-N4-amino-3,5-xylyl methylcarbamate4-Amino-3,5-dimethylphenyl methylcarbamateNS001264623,5-Dimethyl-4-aminophenyl N-methylcarbamate

Database identifiers

CAS
831-76-5
PubChem CID
13252
DTXSID
DTXSID2041599
UNII
59H35M76HJ
Nikkaji
J596.120C

Properties

Computed structural properties

XLogP
1.7
Topological polar surface area
64.4 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
14
Formal charge
0
Complexity
196

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

Uses4-Amino-3,5-xylyl methylcarbamate is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

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Related reactions

3 records
New reaction record
HRID 106210 reaction equation
HRID 106210As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 2072437 reaction equation
HRID 2072437As reactantuspto-grants-1977_09
HRID 2072438 reaction equation
HRID 2072438As reactantuspto-grants-1977_09

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Inhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 item

4-Amino-3,5-xylyl methylcarbamate 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).