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B103

Sigma-Aldrich

1(S),9(R)-(−)-Bicuculline methbromide

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 bromide (1:1)

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About This Item

Empirical Formula (Hill Notation):
C21H20BrNO6
CAS Number:
66016-70-4
Molecular Weight:
462.29
MDL number:
MFCD00055149
UNSPSC Code:
12352200

form

solid

optical activity

[α]25/D −102.7°, c = 0.9 in methanol(lit.)

color

white

solubility

aqueous base: unstable
water and ethanol: soluble (Solutions should be freshly prepared.)

storage temp.

2-8°C

SMILES string

[Br-].C[N+]1(C)CCc2cc3OCOc3cc2[C@H]1[C@@H]4OC(=O)c5c6OCOc6ccc45

InChI

1S/C21H20NO6.BrH/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

InChI key

BWXCECYGGMGBHD-GRTNUQQKSA-M

Gene Information

human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562)

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Biochem/physiol Actions

1(S),9(R)-(−)-Bicuculline methbromide is a GABAA receptor antagonist, which blocks Ca2+-activated potassium (SK) channels. It is the water-soluble derivative of (+)-bicuculline.

Caution

Light sensitive

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 1 Oral - Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
045K4623
063K4616

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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
Doris P Molina et al.
Neurobiology of aging, 33(9), 1938-1949 (2011-10-22)
Alterations in the alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionate receptor (AMPA-R) and N-methyl-D-aspartate receptor (NMDA-R) have been documented in aged animals and may contribute to changes in hippocampal-dependent memory. Growth hormone (GH) regulates AMPA-R and NMDA-R-dependent excitatory transmission and decreases with age. Chronic GH treatment
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
K J Watling et al.
Journal of neurochemistry, 46(6), 1755-1762 (1986-06-01)
Basal and vasoactive intestinal peptide (VIP)-stimulated accumulations of cyclic AMP were measured in slices of rat cerebral cortex. Neither gamma-aminobutyric acid (GABA) nor the selective GABAB receptor agonist (-)-baclofen stimulated basal cyclic AMP accumulation, whereas VIP caused a large dose-dependent
G E Cordingley et al.
British journal of pharmacology, 88(4), 847-856 (1986-08-01)
We studied the synaptic pharmacology of an excitatory pathway in the neostriatum using electrophysiological techniques in tissue slices from rats. In response to single electrical stimuli, two negative, extracellular potentials (N-1 and N-2) were recorded through micropipette electrodes within 150-450
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