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bicuculline
Bicuculline 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.


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08. Chemical Category: main group molecular entity [CHEBI:33579] > p-block molecular entity [CHEBI:33675]
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05. Industrial Uses: agrochemical [CHEBI:33286]
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more general categories    information about this item
03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biophysical uses [CHEBI:52208] (136) 
 membrane transport modulator [CHEBI:38632] (122) 
 GABA-gated chloride channel antagonist [CHEBI:38999] (6) 
 bicuculline [CHEBI:3092] (1)
 aetiopathogenetic uses [CHEBI:52209] (178) 
 neurotoxin [CHEBI:50910] (26) 
 bicuculline [CHEBI:3092] (1)
 pharmacological uses [CHEBI:52210] (736) 
 neurotransmitter agent [CHEBI:35942] (471) 
 GABA agent [CHEBI:51374] (7) 
 GABA antagonist [CHEBI:65259] (3) 
 bicuculline [CHEBI:3092] (1)
05. Industrial Uses 
05. Industrial Uses
 pharmaceutical [CHEBI:52217] (1978) 
 drug [CHEBI:23888] (1930) 
 central nervous system drug [CHEBI:35470] (217) 
 central nervous system stimulant [CHEBI:35337] (15) 
 bicuculline [CHEBI:3092] (1)
 agrochemical [CHEBI:33286] (142) 
 bicuculline [CHEBI:3092] (1)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 p-block molecular entity [CHEBI:33675] (25343) 
 pnictogen molecular entity [CHEBI:33302] (10027) 
 nitrogen molecular entity [CHEBI:51143] (7930) 
 organonitrogen compound [CHEBI:35352] (6705) 
 alkaloid [CHEBI:22315] (473) 
 isoquinoline alkaloid [CHEBI:24921] (120) 
 bicuculline [CHEBI:3092] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 isoquinolines [CHEBI:24922] (86) 
 bicuculline [CHEBI:3092] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 isoquinolines [CHEBI:24922] (86) 
 bicuculline [CHEBI:3092] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 isoquinolines [CHEBI:24922] (86) 
 bicuculline [CHEBI:3092] (1)
 organonitrogen compound [CHEBI:35352] (6705) 
 alkaloid [CHEBI:22315] (473) 
 isoquinoline alkaloid [CHEBI:24921] (120) 
 bicuculline [CHEBI:3092] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 isoquinolines [CHEBI:24922] (86) 
 bicuculline [CHEBI:3092] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 isoquinolines [CHEBI:24922] (86) 
 bicuculline [CHEBI:3092] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 isoquinolines [CHEBI:24922] (86) 
 bicuculline [CHEBI:3092] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 polycyclic compound [CHEBI:33635] (4078) 
 heteropolycyclic compound [CHEBI:33671] (2613) 
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 isoquinolines [CHEBI:24922] (86) 
 bicuculline [CHEBI:3092] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 isoquinolines [CHEBI:24922] (86) 
 bicuculline [CHEBI:3092] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 isoquinolines [CHEBI:24922] (86) 
 bicuculline [CHEBI:3092] (1)
 heterocyclic compound [CHEBI:5686] (5275) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 isoquinolines [CHEBI:24922] (86) 
 bicuculline [CHEBI:3092] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 isoquinolines [CHEBI:24922] (86) 
 bicuculline [CHEBI:3092] (1)
 heteropolycyclic compound [CHEBI:33671] (2613) 
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 isoquinolines [CHEBI:24922] (86) 
 bicuculline [CHEBI:3092] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 isoquinolines [CHEBI:24922] (86) 
 bicuculline [CHEBI:3092] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 isoquinolines [CHEBI:24922] (86) 
 bicuculline [CHEBI:3092] (1)
ChEBI Compound Accession Identifier  [CHEBI:3092]
ChEBI Compound Description  Bicuculline 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.
ChEBI Compound Identification Number  3092
ChEBI InChI Value  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
ChEBI InChIKey Value  IYGYMKDQCDOMRE-ZWKOTPCHSA-N
ChEBI Compound Name  bicuculline
ChEBI SMILES Value  [H][C@]1(OC(=O)c2c3OCOc3ccc12)[C@@]1([H])N(C)CCc2cc3OCOc3cc12
ChEBI Substance ID  85305365
ChEBI URL  ChEBI:3092
ChemSpider ID  9820
Ontomatica Chemical Accession Key (OnChAKey)  IYGYMKDQCDOMRE_ZWKOTPCHSA_N_000_000000
PubChem Compound ID  10237