Cannabis Compound Database: Showing Compound Card for Carbofuran (CDB000580)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References Show 1 protein XML

Record Information

Version

1.0

Created at

2020-03-19 00:44:48 UTC

Updated at

2020-12-07 19:07:32 UTC

CannabisDB ID

CDB000580

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Carbofuran

Description

Carbofuran, also known as furadan 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. Carbofuran is a potentially toxic compound and is, in fact, one of the most toxic carbamate pesticides. It is manufactured by the reaction of methyl isocyanate with 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran. In one study, the exposure of rats to sublethal amounts of carbofuran decreased testosterone by 88%, while the levels of progesterone, cortisol, and estradiol were significantly increased (1279%, 202%, and 150%, respectively) (PMID: 20021136 ). The use of carbofuran on human consumable crops is currently banned in the U.S.A, Canada and the European Union. Carbofuran is a structural mimic of the neurohormone melatonin and could directly bind to MT2 melatonin receptor (Ki = 1.7 uM) (PMID: 28027439 ). Disruption of melatonin signaling could impact the circadian rhythm balance and is linked to elevated risk of developing diabetes. Carbofuran has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ).

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 Weight

221.25

Monoisotopic Molecular Weight

221.1052

IUPAC Name

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

Traditional Name

furadan 4F

CAS Registry Number

1563-66-2

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 )

Ontology

Ingestion

Source:

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Indirect biological role:

Toxin

Industrial application:

Household products:

Pesticide:

Environmental role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	150 - 152°C	Not Available
Boiling Point	Not Available	Wikipedia
Water Solubility	0.32 mg/mL at 25°C	Not Available
logP	2.32	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-03dj-4900000000-3a22bac014009deaedf1	2014-09-20	View Spectrum
Predicted GC-MS	Carbofuran, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03di-3900000000-18e09d501d9575f88e4e	Spectrum
Predicted GC-MS	Carbofuran, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-9520000000-e9e198ba719d3f5dc563	Spectrum
Predicted GC-MS	Carbofuran, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Carbofuran, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0910000000-2fbd40352781317815d9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-59bdc6f8164dc530582d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-0900000000-fb307ce637826c8f8ed1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-0900000000-6d70f3e6615ca3686a4e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-1900000000-5cd3bdfd63ba91812779	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-3900000000-836e257234a48d1bc272	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0a59-8900000000-e99bd7ae3048b468c23c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00di-1900000000-1acb80f84e36fe7b149f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-00di-3900000000-993600c646f3ecc6c643	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-053r-9600000000-ffaac10216c3e978e720	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-00di-0900000000-82d243e5f4ef1e57e1c7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00di-0900000000-e09faae86eec0ada8a58	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-001i-9220000000-215a7d34050ab8609854	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-ee37c4736032ce3f85b5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-0910000000-dca45cb0650cddbf0214	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-001i-9300000000-7f4d7dd8103e89572bd1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-00di-8900000000-406c420c0a6271199e35	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00di-4900000000-6920a76171115fc9a01c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-5ffd383910826520b469	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ab9-9450000000-041464b0cff1914c2a37	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-7920000000-d29a536c8b5558db559f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052b-5900000000-d628afbe5626eb5f362b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01b9-5960000000-5285d2526b8167ac57cb	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0600-3900000000-024fea1de94271528a38	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-7900000000-c27e125887753684946f	2017-09-01	View Spectrum

NMR

Type	Description		View

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Melatonin receptor type 1B	MTNR1B	11q21-q22	P49286	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0031770

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008443

KNApSAcK ID

Not Available

Chemspider ID

2468

KEGG Compound ID

C14291

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carbofuran

METLIN ID

Not Available

PubChem Compound

2566

PDB ID

Not Available

ChEBI ID

34611

References

General References

Popovska-Gorevski M, Dubocovich ML, Rajnarayanan RV: Carbamate Insecticides Target Human Melatonin Receptors. Chem Res Toxicol. 2017 Feb 20;30(2):574-582. doi: 10.1021/acs.chemrestox.6b00301. Epub 2017 Jan 11. [PubMed:28027439 ]
Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
Moulins JR, Blais M, Montsion K, Tully J, Mohan W, Gagnon M, McRitchie T, Kwong K, Snider N, Blais DR: Multiresidue Method of Analysis of Pesticides in Medical Cannabis. J AOAC Int. 2018 Nov 1;101(6):1948-1960. doi: 10.5740/jaoacint.17-0495. Epub 2018 May 29. [PubMed:29843862 ]
Goad RT, Goad JT, Atieh BH, Gupta RC: Carbofuran-induced endocrine disruption in adult male rats. Toxicol Mech Methods. 2004;14(4):233-9. doi: 10.1080/15376520490434476. [PubMed:20021136 ]

Showing Compound Card for Carbofuran (CDB000580)

Structure for CDB000580 (Carbofuran)