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Carbofuran (T3D0944)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (2)XML
Targets (2)
Record Information
Version2.0
Creation Date2009-06-17 23:53:02 UTC
Update Date2014-12-24 20:22:58 UTC
Accession NumberT3D0944
Identification
Common NameCarbofuran
ClassSmall Molecule
DescriptionCarbofuran is a carbamate pesticide. It is used as systemic agricultural insecticide, acaricide and nematocide. Carbofuran has been shown to exhibit neuroprotectant and neuroprotective functions (1, 1). Carbofuran belongs to the family of Benzofurans. These are organic compounds containing a benzene ring fused to a furan.
Compound Type
  • Amine
  • Carbamate
  • Ester
  • Ether
  • Food Toxin
  • Insecticide
  • Metabolite
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
2, 3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate
2, 3-Dihydro-2,2-dimethylbenzofuranyl-7-N-methylcarbamate
2,2-Dimethyl-2,2-dihydrobenzofuranyl-7 N-methylcarbamate
2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl methylcarbamate
2,2-Dimethyl-2,3-dihydro-7-benzofuranyl N-methylcarbamate
2,2-Dimethyl-2,3-dihydrobenzoduranyl-7-N-methylcarbamate
2,2-Dimethyl-7-coumaranyl N-methylcarbamate
2,3-Dihydro-2,2-dimethyl-7-benzofuranol methylcarbamate
2,3-Dihydro-2,2-dimethyl-7-benzofuranol N-methylcarbamate
2,3-DIHYDRO-2,2-DIMETHYL-7-BENZOFURANOL, METHYLCARBAMATE
2,3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate
2,3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate, 9CI
2,3-Dihydro-2,2-dimethylbenzofuran-7-yl methylcarbamate
2,3-Dihydro-2,2-dimethylbenzofuranyl-7-N-methylcarbamate
7-Benzofurano, 2,3-dihydro-2,2-dimethyl, methylcarbamate
7-Benzofuranol, 2,3-dihydro-2,2-dimethyl-, methylcarbamate
Bay 70143
Brifur
Carbodan
Carbofuran (pesticide/fertilizer mixture)
Carbofuran mixture
Carbofurane
Chinufur
Crisfuran
Curaterr
FMC 10242
Furacarb
Furadan
Furadan 3G
Furadan 4f
Furadan 75 WP
Furadan g
Furadane
Furodan
Karbofuranu
Kenofuran
NEX
Niagaral 242
Pillarfuran
Rampart
Sipcam UK carbosip 5G
Tripart nex
Yaltox
Chemical FormulaC12H15NO3
Average Molecular Mass221.252 g/mol
Monoisotopic Mass221.105 g/mol
CAS Registry Number1563-66-2
IUPAC Name1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]-N-methylmethanimidic acid
Traditional Namefuradan 4F
SMILESCN=C(O)OC1=CC=CC2=C1OC(C)(C)C2
InChI IdentifierInChI=1S/C12H15NO3/c1-12(2)7-8-5-4-6-9(10(8)16-12)15-11(14)13-3/h4-6H,7H2,1-3H3,(H,13,14)
InChI KeyInChIKey=DUEPRVBVGDRKAG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassCoumarans
Sub ClassNot Available
Direct ParentCoumarans
Alternative Parents
Substituents
  • Coumaran
  • Alkyl aryl ether
  • Benzenoid
  • Carboximidic acid derivative
  • Ether
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Imine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Point150 - 152°C
Boiling PointNot Available
Solubility0.32 mg/mL at 25°C
LogP2.32
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP2.78ALOGPS
logP2.62ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.78ChemAxon
pKa (Strongest Basic)2.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area51.05 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity60.12 m³·mol⁻¹ChemAxon
Polarizability23.28 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-3900000000-18e09d501d9575f88e4e2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-9520000000-e9e198ba719d3f5dc5632017-10-06View 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 - LC-ESI-QFT , positivesplash10-014i-0910000000-2fbd40352781317815d92017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-59bdc6f8164dc530582d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0900000000-fb307ce637826c8f8ed12017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0900000000-6d70f3e6615ca3686a4e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-1900000000-5cd3bdfd63ba918127792017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-3900000000-836e257234a48d1bc2722017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0a59-8900000000-e99bd7ae3048b468c23c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-00di-1900000000-1acb80f84e36fe7b149f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-00di-3900000000-993600c646f3ecc6c6432021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-053r-9600000000-ffaac10216c3e978e7202021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-00di-0900000000-82d243e5f4ef1e57e1c72021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00di-0900000000-e09faae86eec0ada8a582021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-001i-9220000000-215a7d34050ab86098542021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-ee37c4736032ce3f85b52021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014i-0910000000-dca45cb0650cddbf02142021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-001i-9300000000-7f4d7dd8103e89572bd12021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-00di-8900000000-406c420c0a6271199e352021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-00di-4900000000-6920a76171115fc9a01c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-5ffd383910826520b4692021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-9450000000-041464b0cff1914c2a372016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-7920000000-d29a536c8b5558db559f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-5900000000-d628afbe5626eb5f362b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-5960000000-5285d2526b8167ac57cb2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0600-3900000000-024fea1de94271528a382017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-7900000000-c27e125887753684946f2017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03dj-4900000000-3a22bac014009deaedf12014-09-20View Spectrum
Toxicity Profile
Route of ExposureInhalation (4) ; oral (4); dermal (4)
Mechanism of ToxicityCarbofuran 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. (4)
Toxicity ValuesLD50: 5 mg/kg (Oral, Rat) LD50: 120 mg/kg (Dermal, Rat) LD50: 450 ug/kg (Intravenous, Mouse)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesCarbofuran 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 (2).
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. (5)
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 IDHMDB31770
PubChem Compound ID2566
ChEMBL IDCHEMBL416081
ChemSpider ID2468
KEGG IDC14291
UniProt IDNot Available
OMIM ID
ChEBI ID34611
BioCyc IDNot Available
CTD IDD002235
Stitch IDCarbofuran
PDB IDNot Available
ACToR ID252
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D0944.pdf
General References
  1. Kamboj A, Kiran R, Sandhir R: Carbofuran-induced neurochemical and neurobehavioral alterations in rats: attenuation by N-acetylcysteine. Exp Brain Res. 2006 Apr;170(4):567-75. Epub 2005 Nov 24. [16307259 ]
  2. 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 ]
  3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  4. IPCS Intox Database (1987). Antimony pentoxide. [Link]
  5. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

Target Details
1. 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]
Target Details
2. 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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.42 uMNVS_ENZ_hAChENovascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]