2-Isopropylphenyl methylcarbamate (T3D0977)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (2)XML
Targets (2)
Record Information
Version2.0
Creation Date2009-06-17 23:53:04 UTC
Update Date2014-12-24 20:23:00 UTC
Accession NumberT3D0977
Identification
Common Name2-Isopropylphenyl methylcarbamate
ClassSmall Molecule
Description2-Isopropylphenyl methylcarbamate is a carbamate pesticide. 2-Isopropylphenyl methylcarbamate is an agricultural insecticide used on rice, cocoa, sugar cane, vegetables and other crops. 2-isopropylphenyl methylcarbamate belongs to the family of Cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety.
Compound Type
  • Amine
  • Carbamate
  • Ester
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
2-(1-Methylethyl)phenol methylcarbamate
2-(1-Methylethyl)phenyl methylcarbamate, 9CI
2-(Propan-2-yl)phenyl methylcarbamate
2-Isopropylphenyl methylcarbamic acid
2-Isopropylphenyl N-methylcarbamate
Carbamic acid, methyl-, 2-(1-methylethyl)phenyl ester
Carbamic acid, methyl-, O-cumenyl ester
Carbamic acid, methyl-, O-isopropylphenyl ester
Cumenyl N-methylcarbamate
Etrofolan
Etrolan
Hytox
Isoprocarb, BSI, ISO
Isopropyl phenylmethyl carbamate
Isopropylphenol methylcarbamate
Methylcarbamic acid, O-cumenyl ester
MIPC, JMAF
Mipcin
Mipsin
N-Methyl-2-isopropylphenylcarbam
O-Cumenyl methylcarbamate
O-Cumenyl N-methylcarbamate
O-Isopropylphenol methylcarbamate
O-Isopropylphenyl methylcarbamate
O-Isopropylphenyl N-methylcarbamate
Phenol, 2-(1-methylethyl)-, 1-(N-methylcarbamate)
Phenol, 2-(1-methylethyl)-, methylcarbamate
Chemical FormulaC11H15NO2
Average Molecular Mass193.242 g/mol
Monoisotopic Mass193.110 g/mol
CAS Registry Number2631-40-5
IUPAC NameN-methyl-1-[2-(propan-2-yl)phenoxy]methanimidic acid
Traditional Name1-2-isopropylphenoxy-N-methylmethanimidic acid
SMILESCN=C(O)OC1=CC=CC=C1C(C)C
InChI IdentifierInChI=1S/C11H15NO2/c1-8(2)9-6-4-5-7-10(9)14-11(13)12-3/h4-8H,1-3H3,(H,12,13)
InChI KeyInChIKey=QBSJMKIUCUGGNG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassCumenes
Direct ParentCumenes
Alternative Parents
Substituents
  • Phenylpropane
  • Cumene
  • Phenoxy compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point88 - 93°C
Boiling PointNot Available
Solubility0.4 mg/mL at 25°C
LogP2.31
Predicted Properties
PropertyValueSource
Water Solubility0.09 g/LALOGPS
logP2.93ALOGPS
logP3.21ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.19ChemAxon
pKa (Strongest Basic)2.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.82 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity55.48 m³·mol⁻¹ChemAxon
Polarizability20.76 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-00di-4900000000-1dacd913ecac094384332017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-00di-4900000000-1dacd913ecac094384332018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053i-3900000000-1b743530c1e2545eb5062017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-8930000000-f72687d627daa716f2fe2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-052b-9400000000-17fce78c935b944f08f42020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-0002-9100000000-597b2a5817b85775d3e92020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-0002-9100000000-eab4986a83d98c33ead72020-08-04View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0ue9-0900000000-021b334ef8e4ef37d2fa2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0ue9-0900000000-5f18160355a18f5d267b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0006-0900000000-5e797859ecbc9b7484772021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-0900000000-612d8c623f2183411bd82021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0udi-0900000000-7a576ce9448f4635c6ee2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0gdl-0900000000-67076bb8a32722c1581c2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-3900000000-65ea5f7b4ef11453200c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-6900000000-c16ed3ee74bfb27c01822016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9500000000-f1f3811fd03d582003dc2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-7900000000-fee3dec29006039bef232016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-7900000000-c9e2381d19e62749fc8e2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9600000000-aa03c1810b479c1c91f12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-dfe56706d16703c128d32021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-5900000000-f56efb0e3f7a1e168d152021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5900000000-98adcbaf2ca7f74b59c92021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9800000000-5264f45780c84b4cab4a2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05tr-2900000000-5d1a93ddca47bb028dc72021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-9500000000-bb7ff30be5ecb234d5852021-09-23View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-4900000000-9d53647b287b561a19d72014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100.40 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureInhalation (3) ; oral (3); dermal (3)
Mechanism of Toxicity2-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.
MetabolismThe carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (3)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources2-Isopropylphenyl methylcarbamate is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.
Minimum Risk LevelNot Available
Health EffectsAcute 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 (1).
SymptomsAs 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. (4)
TreatmentIf 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.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB31797
PubChem Compound ID17517
ChEMBL IDCHEMBL2251586
ChemSpider ID16564
KEGG IDC18418
UniProt IDNot Available
OMIM ID
ChEBI ID38505
BioCyc IDCPD-10489
CTD IDC065256
Stitch IDIsoprocarb
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Roldan-Tapia L, Nieto-Escamez FA, del Aguila EM, Laynez F, Parron T, Sanchez-Santed F: Neuropsychological sequelae from acute poisoning and long-term exposure to carbamate and organophosphate pesticides. Neurotoxicol Teratol. 2006 Nov-Dec;28(6):694-703. Epub 2006 Aug 30. [17029710 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  3. IPCS Intox Database (1987). Antimony pentoxide. [Link]
  4. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Acetylcholinesterase
General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. [Link]
Target Details
2. Cholinesterase
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. [Link]