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B7561

1(S),9(R)-(−)-Bicuculline methbromide

Name: 1(S),9(R)-(&#8722;)-Bicuculline methbromide
Brand: SIGMA

≥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

UNSPSC Code:

12352200

PubChem Substance ID:

329773298

NACRES:

NA.77

MDL number:

MFCD00055149

Assay:

≥98% (HPLC)

Form:

solid

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Properties

Product Name

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

Quality Segment

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

Description

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 GABA_A 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

GHS06,GHS09

signalword

Danger

hcodes

H300,H311 + H331,H410

pcodes

P261 - P273 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311

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

WGK 3

flash_point_f

Not applicable

flash_point_c