ContaminantDB: Carbofuran

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-06-17 23:53:02 UTC

Update Date

2026-03-31 19:17:06 UTC

Accession Number

CHEM000806

Identification

Common Name

Carbofuran

Class

Small Molecule

Description

Carbofuran 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.

Contaminant Sources

Clean Air Act Chemicals
EPA Endocrine Screening
FooDB Chemicals
HPV EPA Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Carbamate
Ester
Ether
Food Toxin
Insecticide
Metabolite
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2,2-Dimethyl-2,3-dihydro-7-benzofuranyl N-methylcarbamate	ChEBI
2,3-Dihydro-2,2-dimethylbenzofuran-7-yl methylcarbamate	ChEBI
Furadan	ChEBI
2,2-Dimethyl-2,3-dihydro-7-benzofuranyl N-methylcarbamic acid	Generator
2,3-Dihydro-2,2-dimethylbenzofuran-7-yl methylcarbamic acid	Generator
2, 3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate	HMDB
2, 3-Dihydro-2,2-dimethylbenzofuranyl-7-N-methylcarbamate	HMDB
2,2-Dimethyl-2,2-dihydrobenzofuranyl-7 N-methylcarbamate	HMDB
2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl methylcarbamate	HMDB
2,2-Dimethyl-2,3-dihydrobenzoduranyl-7-N-methylcarbamate	HMDB
2,2-Dimethyl-7-coumaranyl N-methylcarbamate	HMDB
2,3-Dihydro-2,2-dimethyl-7-benzofuranol methylcarbamate	HMDB
2,3-Dihydro-2,2-dimethyl-7-benzofuranol N-methylcarbamate	HMDB
2,3-Dihydro-2,2-dimethyl-7-benzofuranol, methylcarbamATE	HMDB
2,3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate	HMDB
2,3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate, 9ci	HMDB
2,3-Dihydro-2,2-dimethylbenzofuranyl-7-N-methylcarbamate	HMDB
7-Benzofurano, 2,3-dihydro-2,2-dimethyl, methylcarbamate	HMDB
7-Benzofuranol, 2,3-dihydro-2,2-dimethyl-, methylcarbamate	HMDB
Bay 70143	HMDB
Brifur	HMDB
Carbodan	HMDB
Carbofuran (pesticide/fertilizer mixture)	HMDB
Carbofuran mixture	HMDB
Carbofurane	HMDB
Chinufur	HMDB
Crisfuran	HMDB
Curaterr	HMDB
FMC 10242	HMDB
Furacarb	HMDB
Furadan 3g	HMDB
Furadan 4F	HMDB
Furadan 75 WP	HMDB
Furadan g	HMDB
Furadane	HMDB
Furodan	HMDB
Karbofuranu	HMDB
Kenofuran	HMDB
NEX	HMDB
Niagaral 242	HMDB
Pillarfuran	HMDB
Rampart	HMDB
Sipcam uk carbosip 5g	HMDB
Tripart nex	HMDB
Yaltox	HMDB
Bayer 70143	HMDB
70143, Bayer	HMDB

Chemical Formula

C₁₂H₁₅NO₃

Average Molecular Mass

221.252 g/mol

Monoisotopic Mass

221.105 g/mol

CAS Registry Number

1563-66-2

IUPAC Name

1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]-N-methylmethanimidic acid

Traditional Name

furadan 4F

SMILES

CN=C(O)OC1=CC=CC2=C1OC(C)(C)C2

InChI Identifier

InChI=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 Key

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Coumarans

Sub Class

Not Available

Direct Parent

Coumarans

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbamate ester (CHEBI:34611 )
1-benzofurans (CHEBI:34611 )
Carbamate insecticides (C14291 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	150 - 152°C
Boiling Point	Not Available
Solubility	0.32 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	2.78	ALOGPS
logP	2.62	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	2.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	60.12 m³·mol⁻¹	ChemAxon
Polarizability	23.28 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-3900000000-18e09d501d9575f88e4e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-000i-9520000000-e9e198ba719d3f5dc563	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0910000000-2fbd40352781317815d9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-59bdc6f8164dc530582d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-0900000000-fb307ce637826c8f8ed1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-0900000000-6d70f3e6615ca3686a4e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-1900000000-5cd3bdfd63ba91812779	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-3900000000-836e257234a48d1bc272	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0a59-8900000000-e99bd7ae3048b468c23c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00di-1900000000-1acb80f84e36fe7b149f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-00di-3900000000-993600c646f3ecc6c643	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-053r-9600000000-ffaac10216c3e978e720	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-00di-0900000000-82d243e5f4ef1e57e1c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00di-0900000000-e09faae86eec0ada8a58	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-001i-9220000000-215a7d34050ab8609854	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-ee37c4736032ce3f85b5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-0910000000-dca45cb0650cddbf0214	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-001i-9300000000-7f4d7dd8103e89572bd1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-00di-8900000000-406c420c0a6271199e35	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00di-4900000000-6920a76171115fc9a01c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-5ffd383910826520b469	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ab9-9450000000-041464b0cff1914c2a37	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-7920000000-d29a536c8b5558db559f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052b-5900000000-d628afbe5626eb5f362b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01b9-5960000000-5285d2526b8167ac57cb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0600-3900000000-024fea1de94271528a38	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-7900000000-c27e125887753684946f	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03dj-4900000000-3a22bac014009deaedf1	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (3) ; oral (3); dermal (3)

Mechanism of Toxicity

Carbofuran 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.

Metabolism

The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (3)

Toxicity Values

LD50: 5 mg/kg (Oral, Rat) LD50: 120 mg/kg (Dermal, Rat) LD50: 450 ug/kg (Intravenous, Mouse)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Carbofuran is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

Minimum Risk Level

Not Available

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 (2).

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. (4)

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.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0031770

FooDB ID

FDB008443

Phenol Explorer ID

Not Available

KNApSAcK ID