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B7561

Sigma-Aldrich

1(S),9(R)-(−)-Bicuculline methbromide

≥98% (HPLC), 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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M A Castro-Alamancos
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