Bicuculline information

Bicuculline
Clinical data
ATC code	none;
Identifiers
	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(6H)-one;
CAS Number	485-49-4 ;
PubChem CID	10237;
IUPHAR/BPS	2312;
ChemSpider	9820 ;
UNII	Y37615DVKC;
ChEBI	CHEBI:3092 ;
ChEMBL	ChEMBL417990 ;
PDB ligand	H0Z (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID3042687 ;
ECHA InfoCard	100.006.927
Chemical and physical data
Formula	C20H17NO6
Molar mass	367.357 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	215 °C (419 °F)
	SMILES O=C1O[C@H](c3c1c2OCOc2cc3)[C@@H]5c4cc6OCOc6cc4CCN5C;
	InChI InChI=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 ; Key:IYGYMKDQCDOMRE-ZWKOTPCHSA-N ;
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Bicuculline is a phthalide-isoquinoline compound that is a light-sensitive competitive antagonist of GABA_A receptors.^[1] It was originally identified in 1932 in plant alkaloid extracts^[2] and has been isolated from Dicentra cucullaria, Adlumia fungosa, and several Corydalis species (all in subfamily Fumarioideae, previously known as family Fumariaceae). Since it blocks the inhibitory action of GABA receptors, the action of bicuculline mimics epilepsy; it also causes convulsions. This property is utilized in laboratories around 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 GABA_A 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, z-drugs, and related anxiolytic drugs.

The half-maximal inhibitory concentration (IC₅₀) of bicuculline on GABA_A receptors is 3 μM.^{[citation needed]}

In addition to being a potent GABA_A receptor antagonist, bicuculline can be used to block Ca²⁺-activated potassium channels.^[3]

Sensitivity to bicuculline is defined by IUPHAR as a major criterion in the definition of GABA_A receptors

^ Johnston, Graham AR (2013). "Advantages of an antagonist: bicuculline and other GABA antagonists". British Journal of Pharmacology. 169 (2): 328–336. doi:10.1111/bph.12127. ISSN 1476-5381. PMC 3651659. PMID 23425285.
^ Manske RH (1932). "The Alkaloids of Fumaraceous Plants. II. Dicentra cucullaria (L.) Bernh". Canadian Journal of Research. 7 (3): 265–269. Bibcode:1932CJRes...7..265M. doi:10.1139/cjr32-078.
^ Khawaled R, Bruening-Wright A, Adelman JP, Maylie J (August 1999). "Bicuculline block of small-conductance calcium-activated potassium channels". Pflügers Archiv. 438 (3): 314–21. doi:10.1007/s004240050915. PMID 10398861. S2CID 7033568.

[1] Johnston, Graham AR (2013). "Advantages of an antagonist: bicuculline and other GABA antagonists". British Journal of Pharmacology. 169 (2): 328–336. doi:10.1111/bph.12127. ISSN 1476-5381. PMC 3651659. PMID 23425285.

[2] Manske RH (1932). "The Alkaloids of Fumaraceous Plants. II. Dicentra cucullaria (L.) Bernh". Canadian Journal of Research. 7 (3): 265–269. Bibcode:1932CJRes...7..265M. doi:10.1139/cjr32-078.

[3] Khawaled R, Bruening-Wright A, Adelman JP, Maylie J (August 1999). "Bicuculline block of small-conductance calcium-activated potassium channels". Pflügers Archiv. 438 (3): 314–21. doi:10.1007/s004240050915. PMID 10398861. S2CID 7033568.

Bicuculline information

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Clinical data

ATC code	none
Identifiers
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(6H)-one
CAS Number	485-49-4^Y
PubChem CID	10237
IUPHAR/BPS	2312
ChemSpider	9820^Y
UNII	Y37615DVKC
ChEBI	CHEBI:3092^N
ChEMBL	ChEMBL417990^N
PDB ligand	H0Z (PDBe, RCSB PDB)
CompTox Dashboard (EPA)	DTXSID3042687
ECHA InfoCard	100.006.927
Chemical and physical data
Formula	C₂₀H₁₇NO₆
Molar mass	367.357 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	215 °C (419 °F)
SMILES O=C1O[C@H](c3c1c2OCOc2cc3)[C@@H]5c4cc6OCOc6cc4CCN5C
InChI InChI=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^Y Key:IYGYMKDQCDOMRE-ZWKOTPCHSA-N^Y
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