Bicuculline (CHEM003033)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2014-08-29 05:03:00 UTC
Update Date2016-11-09 01:09:02 UTC
Accession NumberCHEM003033
Identification
Common NameBicuculline
ClassSmall Molecule
DescriptionBicuculline is a light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species. Since it blocks the inhibitory action of GABA receptors, the action of bicuculline mimics epilepsy. This property is utilized in laboratories across the world in the in vitro study of epilepsy, generally in hippocampal or cortical neurons in prepared brain slices from rodents. This compound is also routinely used to isolate glutamatergic (excitatory amino acid) receptor function.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amine
  • Ester
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
BicculineChEBI
BicucullinChEBI
D-BicucullineChEBI
6-(5,6,7,8-tetrahydro-6-Methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)furo(3,4-e)1,3-benzodioxol-8(6H)oneMeSH
Chemical FormulaC20H17NO6
Average Molecular Mass367.352 g/mol
Monoisotopic Mass367.106 g/mol
CAS Registry Number485-49-4
IUPAC Name(10R)-10-[(5S)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-12-one
Traditional Namebicuculline
SMILES[H][C@]1(OC(=O)C2=C1C=CC1=C2OCO1)[C@@]1([H])N(C)CCC2=CC3=C(OCO3)C=C12
InChI IdentifierInChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18+/m0/s1
InChI KeyIYGYMKDQCDOMRE-ZWKOTPCHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassPhthalide isoquinolines
Sub ClassNot Available
Direct ParentPhthalide isoquinolines
Alternative Parents
Substituents
  • Phthalide isoquinoline
  • Benzofuranone
  • Phthalide
  • Isobenzofuranone
  • Tetrahydroisoquinoline
  • Benzodioxole
  • Isocoumaran
  • Aralkylamine
  • Benzenoid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Lactone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cell junction
  • Cell surface
  • Cytoskeleton
  • Endoplasmic reticulum
  • Extracellular
  • Golgi apparatus
  • Lysosome
  • Membrane
  • Membrane Fraction
  • Mitochondrion
  • Nerve Fiber
  • Nuclear Membrane
  • Plasma Membrane
  • Synaptic Vesicle
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Long-term potentiationNot Availablemap04720
Gastric acid secretionNot Availablemap04971
ProteasomeNot AvailableNot Available
AnticonvulsantsNot AvailableNot Available
Long-term depressionNot Availablemap04730
Circadian rhythmNot Availablemap04710
Opioid AnalgesicsNot AvailableNot Available
EicosanoidsNot AvailableNot Available
Renin-angiotensin systemNot Availablemap04614
Metabolic PathwaysNot AvailableNot Available
Glycerolipid MetabolismSMP00039 map00561
Gabaergic synapseNot Availablemap04727
ApoptosisNot Availablemap04210
AnxiolyticsNot AvailableNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP1.76ALOGPS
logP2.68ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)14.72ChemAxon
pKa (Strongest Basic)7.43ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity93.45 m³·mol⁻¹ChemAxon
Polarizability37.3 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-056s-2592000000-e3973ba2799d460c3b59Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0009000000-7549cdeeb71ef4470dc1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-066r-0009000000-d8e744c493912dace636Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0039000000-01b4f70e0d954ed7658eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004j-0091000000-4bda65b490b53129adf9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0aor-0109000000-40c14a57cb6620310332Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0309000000-7ca1258f5e6afe7f84cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-01p9-0906000000-4d63889ee99dca8cab11Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0039000000-b9f59e9657a74348c6a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056s-2592000000-e3973ba2799d460c3b59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-c181caec72711cdf90a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01b9-0309000000-911d653eff0bb92aaf9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0952000000-1eef2687ebf3adc6ff75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-6556b5579b30115da7f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-0019000000-577733de055f298b7deeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fu-4298000000-9af528a64d0ecefbf9abSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityThe action of bicuculline is primarily on the ionotropic GABAA receptors, which are ligand-gated ion channels concerned chiefly with the passing of chloride ions across the cell membrane, thus promoting an inhibitory influence on the target neuron. These receptors are the major targets for benzodiazepines and related anxiolytic drugs. The half-maximal inhibitory concentration (IC50) of bicuculline on GABAA receptors is 3 μM. In addition to being a potent GABAA receptor antagonist, bicuculline can be used to block Ca2+-activated potassium channels. Sensitivity to bicuculline is defined by IUPHAR as a major criterion in the definition of GABAA receptors.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIt was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species. This compound is also routinely used to isolate glutamatergic (excitatory amino acid) receptor function.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB11562
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001820
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBicuculline
Chemspider IDNot Available
ChEBI ID3092
PubChem Compound ID10237
Kegg Compound IDC09364
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available