2-Isopropylphenyl-N-methylcarbamat

Isoprocarb

HCID 17517CAS 2631-40-5

Grundinformationen

Standard-SMILES
CNC(=O)Oc1ccccc1C(C)C
InChIKey
QBSJMKIUCUGGNG-UHFFFAOYSA-N
Summenformel
C11H15NO2
Durchschnittliche Molmasse
193,24 g/mol
Monoisotopische Masse
193,11027872

Überblick

Isoprocarb 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 2-isopropylphenol and a methylcarbamic acid.

Namen und Bezeichner

Bevorzugter Name
Isoprocarb
IUPAC
(2-propan-2-ylphenyl) N-methylcarbamate
Lokaler Name
2-Isopropylphenyl-N-methylcarbamat
Englischer Name
Isoprocarb
Summenformel
C11H15NO2
Molmasse
193.24

Namen und Synonyme

Isoprocarb2631-40-52-Isopropylphenyl methylcarbamateEtrofolanMipcineo-Cumenyl methylcarbamateMIPCHytox2-Isopropylphenyl N-methylcarbamateo-Cumenyl N-methylcarbamateMipsino-Isopropylphenol methylcarbamate
Weitere Namen anzeigen
mipc (jmaf)ppc3Ppc 3Oms 32oms-32
o-Isopropylphenyl methylcarbamateo-Isopropylphenyl N-methylcarbamateIsopropylphenol methylcarbamateRo 7-5050Carbamic acid, methyl-, o-cumenyl esterPhenol, 2-(1-methylethyl)-, methylcarbamatePhenol, 2-(1-methylethyl)-, 1-(N-methylcarbamate)2-(1-Methylethyl)phenol methylcarbamate

Datenbank-Bezeichner

CAS
2631-40-5
PubChem CID
17517
DTXSID
DTXSID6042072
ChEMBL
CHEMBL2251586
ChEBI
CHEBI:38505
UNII
714I55QH9K
EC Number
220-114-6
Nikkaji
J3.712E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,3
Polarare Oberfläche (TPSA)
38,3 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
3
Schwere Atome
14

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesFusion temperature
Pesticides · 3 Einträge

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

Pesticide (Isoprocarb) -> USDA PDB

LogP · 2 Einträge

2.31

2.31

Solubility0.4 mg/mL at 25 °C
Melting Point88 - 93 °C
Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt
92.4 °C · 92.4°C
Siedepunkt
329.46 °C · 329.46°C (rough estimate)
Dichte
1.0945 · 1.0945 (rough estimate)
Brechungsindex
1.508 · 1.5080 (estimate)
Flammpunkt
-18 °C · -18 °C
storage temp.
2 · Sealed in dry,2-8°C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

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)

Gefahrenhinweise

DOT Hazard Classification · 2 Einträge

Isoprocarb

Marine pollutant

Hazard Classes and Categories · 4 Einträge

Acute Tox. 4 (100%)

Acute toxicity - category 4

Acute toxicity (Oral) - Category 3

Acute Tox. 4 *

Toxikologische Informationen

Treatment · 1 Eintrag

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 Eintrag

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 RoutesInhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 Eintrag

2-Isopropylphenyl 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 Eintrag

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).

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
UN 3077 9/PG 3
hs_code
29224999
RTECS-Nr.
FB7880000
risk_code
22-50/53-67-65-38-11-20

Chemie und Industrie

Pharmakologische Informationen

Metabolism/MetabolitesThe carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)
MeSH Pharmacological ClassificationPesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses2-Isopropylphenyl methylcarbamate is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.
General Manufacturing InformationPhenol, 2-(1-methylethyl)-, 1-(N-methylcarbamate): INACTIVE
Anwendungen · 2 Einträge

BeschreibungIsoprocarb, o-cumenyl methylcarbamate (IUPAC), consists of colorless crystals, which are sparingly soluble in water and are readily soluble in acetone and methanol. Isoprocarb is produced by reaction of 2-isopropylphenol with methylisocyanate. Isoprocarb is used for control of rice, cacao, sugarcane, and vegetable pests.

VerwendenIsoprocarb is a non-systematic carbamate insecticide. Isoprocarb functions by reversibly inactivating the enzyme acetylcholinesterase in insects.

Anbieter50 Anbieter

阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北威德利化学试剂有限公司181-6332-1995 18062128043 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
山东海舟生物工程有限公司130-0567-0367 13006570367 · [email protected]

Zugehörige Reaktionen

2

Verknüpfte Notizen

Wird geladen…