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Bicuculline: Wikis

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Bicuculline
Systematic (IUPAC) name
(6R)-​6-​[(5S)-​6-​methyl-​5,​6,​7,​8-​tetrahydro​[1,3]dioxolo​[4,5- g]​isoquinolin-​5-​yl]​furo[3,4-e]​[1,3]​benzodioxol-​8(6 H)-​one
Identifiers
CAS number 485-49-4
ATC code none
PubChem 10237
ChemSpider 9820
Chemical data
Formula C 20H17NO6  
Mol. mass 367.352 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?
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Bicuculline (BIC) is a light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts[1] 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 utilised 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.

The 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, bicuculine can be used to block Ca2+-activated potassium channels [2].

Sensitivity to bicuculline is defined by IUPHAR as a major criterion in the definition of GABAA receptors — however in recent years a new class of ionotropic GABA receptor, defined variously as GABAA or GABAC has been characterised, which is insensitive to both benzodiazepines and bicuculline.

A water soluble form of bicuculline, bicuculline methiodide, is soluble in water to a concentration of 10 mg/mL.

References

  1. ^ Manske, Can. J. Res. 7:265, 1932
  2. ^ Khawaled R, Bruening-Wright A, Adelman JP, Maylie J (1999) Bicuculline block of small-conductance calcium-activated potassium channels. Pflügers Arch 438: 314-321
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