Page last updated: 2024-11-07

bicuculline methiodide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Bicuculline methiodide is a potent and selective antagonist of GABAu003csubu003eAu003c/subu003e receptors. It is a quaternary ammonium derivative of bicuculline, a natural alkaloid isolated from the plant *Dicentra cucullaria*. Bicuculline methiodide is often used in research to study the role of GABAergic neurotransmission in the brain. It blocks the binding of GABA to the GABAu003csubu003eAu003c/subu003e receptor, preventing the opening of chloride channels and the hyperpolarization of neurons. Bicuculline methiodide is a valuable tool for investigating the role of GABAergic neurotransmission in a variety of physiological and pathological processes, including anxiety, epilepsy, and sleep. The synthesis of bicuculline methiodide involves the methylation of bicuculline with methyl iodide. Bicuculline methiodide is a non-permeable compound, meaning it cannot cross the blood-brain barrier. Therefore, it is typically administered directly into the brain or cerebrospinal fluid to study its effects on neural activity.'

Cross-References

ID SourceID
PubMed CID104871
CHEMBL ID556604
SCHEMBL ID20915028
MeSH IDM0067517

Synonyms (33)

Synonym
MLS001148459 ,
HMS3269M03
smr000058804
bicuculline methiodide
1,3-dioxolo(4,5-g)isoquinolinium, 5-((6r)-6,8-dihydro-8-oxofuro(3,4-e)-1,3-benzodioxol-6-yl)-5,6,7,8-tetrahydro-6,6-dimethyl-, iodide, (5s)-
1,3-dioxolo(4,5-g)isoquinolinium, 5-(6,8-dihydro-8-oxofuro(3,4-e)-1,3-benzodioxol-6-yl)-5,6,7,8-tetrahydro-6,6-dimethyl-, iodide, (r-(r*,s*))-
MLS000069548 ,
(-)-bicuculline methiodide
CHEMBL556604
40709-69-1
HMS2235E04
1(s),9(r)-(-)-bicuculline methiodide
J-100046
[r-(r*,s*)]-5-(6,8-dihydro-8-oxofuro[3,4-e]-1,3-benzodioxol-6-yl)-5,6,7,8-tetrahydro-6,6-dimethyl-1,3-dioxolo[4,5-g]isoquinolinium iodide
(6r)-6-[(5s)-6,6-dimethyl-7,8-dihydro-5h-[1,3]dioxolo[4,5-g]isoquinolin-6-ium-5-yl]-6h-furo[3,4-g][1,3]benzodioxol-8-one;iodide
HB0893
c21h20ino6
AKOS024457137
OPERA_ID_515
1(s),9(r)-(-)-bicuculline methiodide, >=95.0% (hpce)
DTXSID60873651
(+)-bicuculline methiodide
Q60688946
(-)-bicucullinemethiodide
HMS3678P09
(s)-6,6-dimethyl-5-((r)-8-oxo-6,8-dihydroisobenzofuro[5,4-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide
SCHEMBL20915028
HMS3414P11
B-136
(6r)-6-[(5s)-6,6-dimethyl-7,8-dihydro-5h-[1,3]dioxolo[4,5-g]isoquinolin-6-ium-5-yl]-6h-furo[3,4-g][1,3]benzodioxol-8-one;iodide.
BB162664
HY-103474
CS-0027978

Research Excerpts

Effects

ExcerptReferenceRelevance
"Bicuculline methiodide has been shown to block mutual inhibition between these interneurons and to cause them to spike tonically while recorded intracellularly (Schmidt and Calabrese, 1992)."( Bursting in leech heart interneurons: cell-autonomous and network-based mechanisms.
Calabrese, RL; Cymbalyuk, GS; Gaudry, Q; Masino, MA, 2002
)
1.04

Dosage Studied

ExcerptRelevanceReference
" Flumazenil (Ro 15-1788) administration caused a parallel shift to the right of the dose-response curve for midazolam spinal analgesia."( On the mechanism by which midazolam causes spinally mediated analgesia.
Edwards, M; Gent, JP; Goodchild, CS; Serrao, JM, 1990
)
0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (15)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency25.11890.631035.7641100.0000AID504339
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency28.18380.177814.390939.8107AID2147
acid sphingomyelinaseHomo sapiens (human)Potency31.622814.125424.061339.8107AID504937
TDP1 proteinHomo sapiens (human)Potency7.30780.000811.382244.6684AID686979
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency35.48130.011212.4002100.0000AID1030
hypothetical protein, conservedTrypanosoma bruceiPotency35.48130.223911.245135.4813AID624173
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency89.12510.707936.904389.1251AID504333
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency22.38720.035520.977089.1251AID504332
lysosomal alpha-glucosidase preproproteinHomo sapiens (human)Potency3.16230.036619.637650.1187AID1466; AID2242
chromobox protein homolog 1Homo sapiens (human)Potency56.23410.006026.168889.1251AID540317
serine/threonine-protein kinase PLK1Homo sapiens (human)Potency3.35870.168316.404067.0158AID720504
gemininHomo sapiens (human)Potency12.99530.004611.374133.4983AID624297
Neuronal acetylcholine receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency3.16233.548118.039535.4813AID1466
Neuronal acetylcholine receptor subunit beta-2Rattus norvegicus (Norway rat)Potency3.16233.548118.039535.4813AID1466
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1 isoform 1Homo sapiens (human)IC50 (µMol)3.48402.05808.205241.3880AID540297
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID72134Binding affinity, determined by its ability to displace the [3H]GABA from Gamma-aminobutyric acid A (GABA-A) receptor site of rat brain membranes1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
Synthesis and structure-activity relationships of a series of aminopyridazine derivatives of gamma-aminobutyric acid acting as selective GABA-A antagonists.
AID1847952Induction of cell proliferation of mouse CD4+ve Th cells at 100 uM measured after 48 hrs in presence of alprazolam by flow cytometry analysis relative to control2021Journal of medicinal chemistry, 12-23, Volume: 64, Issue:24
Structure-Activity Studies of 3,9-Diazaspiro[5.5]undecane-Based γ-Aminobutyric Acid Type A Receptor Antagonists with Immunomodulatory Effect.
AID1847945Induction of cell proliferation of human CD8-positive T cells at 100 uM measured after 96 hrs by flow cytometry analysis relative to control2021Journal of medicinal chemistry, 12-23, Volume: 64, Issue:24
Structure-Activity Studies of 3,9-Diazaspiro[5.5]undecane-Based γ-Aminobutyric Acid Type A Receptor Antagonists with Immunomodulatory Effect.
AID1847951Induction of cell proliferation of mouse CD8-positive T cells at 100 uM measured after 48 hrs in presence of alprazolam by flow cytometry analysis relative to control2021Journal of medicinal chemistry, 12-23, Volume: 64, Issue:24
Structure-Activity Studies of 3,9-Diazaspiro[5.5]undecane-Based γ-Aminobutyric Acid Type A Receptor Antagonists with Immunomodulatory Effect.
AID1847946Induction of cell proliferation of human CD4+ve Th cells at 100 uM measured after 96 hrs by flow cytometry analysis relative to control2021Journal of medicinal chemistry, 12-23, Volume: 64, Issue:24
Structure-Activity Studies of 3,9-Diazaspiro[5.5]undecane-Based γ-Aminobutyric Acid Type A Receptor Antagonists with Immunomodulatory Effect.
AID1224864HCS microscopy assay (F508del-CFTR)2016PloS one, , Volume: 11, Issue:10
Increasing the Endoplasmic Reticulum Pool of the F508del Allele of the Cystic Fibrosis Transmembrane Conductance Regulator Leads to Greater Folding Correction by Small Molecule Therapeutics.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (472)

TimeframeStudies, This Drug (%)All Drugs %
pre-199085 (18.01)18.7374
1990's175 (37.08)18.2507
2000's131 (27.75)29.6817
2010's77 (16.31)24.3611
2020's4 (0.85)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.69

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.69 (24.57)
Research Supply Index6.18 (2.92)
Research Growth Index4.54 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.69)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (0.62%)6.00%
Case Studies1 (0.21%)4.05%
Observational0 (0.00%)0.25%
Other477 (99.17%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]