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
Weitere Namen anzeigen
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
- Formalladung
- 0
- Komplexität
- 192
Experimentelle und physikochemische Eigenschaften
Pesticides
Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Not approved
Pesticide (Isoprocarb) -> USDA PDB
LogP
2.31
2.31
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
- Löslichkeit
- Chloroform (Slightly), Methanol (Slightly)
- Aggregatzustand
- Crystalline
- pka
- 12.22 · 12.22±0.46(Predicted)
- Farbe
- White to off-white
- BRN
- 1875020 · 1875020
- Henry's Law Constant
- 7.4 · 7.4×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Major Application
- agricultureenvironmental
- InChI
- InChI=1S/C11H15NO2/c1-8(2)9-6-4-5-7-10(9)14-11(13)12-3/h4-8H,1-3H3,(H,12,13)
- InChIKey
- QBSJMKIUCUGGNG-UHFFFAOYSA-N
- SMILES
- C1(OC(=O)NC)=CC=CC=C1C(C)C
- CAS Datenbank
- 2631 · 2631-40-5(CAS DataBase Reference)
- NIST chemische Informationen
- 2 · 2-(1-Methylethyl)phenyl methylcarbamate(2631-40-5)
- EPA chemische Informationen
- Isoprocarb (2631-40-5)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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)
Gefahrenhinweise
DOT Hazard Classification
Isoprocarb
Marine pollutant
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute toxicity - category 4
Acute toxicity (Oral) - Category 3
Acute Tox. 4 *
Toxikologische Informationen
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
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
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)
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
- hazard_code
- Xn,N,F
- safety_code
- 60-61-62-33-16-9-25
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1
Chemie und Industrie
Pharmakologische Informationen
Verwendung und Herstellung
Anwendungen
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.
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