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Merck
CN

B6889

1(S),9(R)-(−)-Bicuculline methiodide

solid

Synonym(s):

(5S)-5-[(6R)-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

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About This Item

Empirical Formula (Hill Notation):
C21H20INO6
CAS Number:
40709-69-1
Molecular Weight:
509.29
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
5419649
MDL number:
MFCD00078966

Key Documents

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Product Name

1(S),9(R)-(−)-Bicuculline methiodide, solid

InChI key

HKJKCPKPSSVUHY-GRTNUQQKSA-M

SMILES string

[I-].[H][C@]1(OC(=O)c2c3OCOc3ccc12)[C@]4([H])c5cc6OCOc6cc5CC[N+]4(C)C

InChI

1S/C21H20NO6.HI/c1-22(2)6-5-11-7-15-16(26-9-25-15)8-13(11)18(22)19-12-3-4-14-20(27-10-24-14)17(12)21(23)28-19;/h3-4,7-8,18-19H,5-6,9-10H2,1-2H3;1H/q+1;/p-1/t18-,19+;/m0./s1

form

solid

color

white to tan

solubility

H2O: 10 mg/mL

storage temp.

2-8°C

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Biochem/physiol Actions

GABAA receptor antagonist; blocks Ca2+-activated potassium (SK) channels. Water soluble derivative of (+)-bicuculline

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
061H3904
044K3775
036H3897
022K37762
020K3851

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S W Johnson et al.
Neuroscience letters, 231(1), 13-16 (1997-08-01)
Apamin, a bee venom toxin which blocks a Ca2+-dependent K+ current, potentiates N-methyl-D-aspartate (NMDA)-induced burst firing in dopamine neurons. We now report that burst firing is also potentiated by an apamin-like effect of bicuculline methiodide (BMI) at the same concentration
M Avoli et al.
Canadian journal of physiology and pharmacology, 75(5), 526-534 (1997-05-01)
This paper describes some functional and pharmacological properties of GABA-mediated mechanisms in the human neocortex maintained in vitro in a slice preparation. Neocortical neurons recorded intracellularly under normal conditions generate stimulus-induced and spontaneous potentials that are mediated by the activation
M Chebib et al.
Clinical and experimental pharmacology & physiology, 26(11), 937-940 (1999-11-24)
1. In the mammalian central nervous system, GABA is the main inhibitory neurotransmitter. GABA is a highly flexible molecule and, thus, can exist in many low-energy conformations. Conformationally restricted analogues of GABA have been used to help identify three major
D Strøbaek et al.
British journal of pharmacology, 129(5), 991-999 (2000-03-01)
Three genes encode the small-conductance Ca(2+)-activated K(+) channels (SK channels). We have stably expressed hSK1 and rSK2 in HEK 293 cells and addressed the pharmacology of these subtypes using whole-cell patch clamp recordings. The bee venom peptide apamin blocked hSK1

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