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Merck

B7561

Sigma-Aldrich

1(S),9(R)-(−)-Bicuculline methbromide

≥98% (HPLC), GABA receptor antagonist, 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
PubChem Substance ID:
329773298
NACRES:
NA.77

Key Documents

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Product Name

1(S),9(R)-(−)-Bicuculline methbromide, ≥98% (HPLC), solid

Quality Level

100

Assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

H2O: >10 mg/mL

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

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Application

1(S),9(R)-(-)-Bicuculline methbromide has been used:
  • as a γ-aminobutyric acid (GABAA) receptor A antagonist: in cortical neuron culture
  • in artificial cerebrospinal fluid (ACSF) formature dentate granule neurons
  • in hypothalamic explant cultures

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.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H300,H311 + H331,H410

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
102M4621V
038K46044
038K46043
038K46042
038K46041

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Amar Sahay et al.
Nature, 472(7344), 466-470 (2011-04-05)
Adult hippocampal neurogenesis is a unique form of neural circuit plasticity that results in the generation of new neurons in the dentate gyrus throughout life. Neurons that arise in adults (adult-born neurons) show heightened synaptic plasticity during their maturation and
Estefanía Estévez-Priego et al.
Network neuroscience (Cambridge, Mass.), 4(4), 1160-1180 (2021-01-08)
An elusive phenomenon in network neuroscience is the extent of neuronal activity remodeling upon damage. Here, we investigate the action of gradual synaptic blockade on the effective connectivity in cortical networks in vitro. We use two neuronal cultures configurations-one formed
S I Itazawa et al.
Journal of neurophysiology, 78(5), 2592-2601 (1997-11-14)
Inwardly rectifying and Ca2+-permeable AMPA-type glutamate receptor channels in rat neocortical neurons. J. Neurophysiol. 78: 2592-2605, 1997. Current-voltage (I-V) relations and Ca2+ permeability of alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA)type glutamate receptor channels were investigated in neurons of rat neocortex by using the
Alfredo Gonzalez-Sulser et al.
Neuropharmacology, 60(7-8), 1142-1153 (2010-10-20)
Epileptiform discharges recorded in the 4-aminopyridine (4-AP) in vitro epilepsy model are mediated by glutamatergic and GABAergic signaling. Using a 60-channel perforated multi-electrode array (pMEA) on corticohippocampal slices from 2 to 3 week old mice we recorded interictal- and ictal-like
Qing Hui Chen et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 285(5), R1231-R1239 (2003-07-26)
Blockade of GABA-A receptors in the hypothalamic paraventricular nucleus (PVN) has been repeatedly shown to increase arterial blood pressure (ABP), heart rate (HR), and sympathetic nerve activity (SNA), but the mechanism(s) that underlies this response has not been determined. Here
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