B7561

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)
• 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

Properties

• 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

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.

Safety Information

• Pictograms: GHS06,GHS09
• Signal Word: Danger
• Hazard Statements: H300,H311 + H331,H410
• Precautionary Statements: 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 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