An enantiomer of (+)-bicuculline methochloride
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(−)-Bicuculline methochloride

Item No. 27802

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5R)-5-[(6S)-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, monochloride
CAS Number
53552-05-9
Molecular Formula
C21H20NO6 • Cl
Formula Weight
417.8
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
223, 296, 326 nm
SMILES
O=C(O1)C2=C(C=CC3=C2OCO3)[C@@]1([H])[C@@]4([H])C5=CC6=C(OCO6)C=C5CC[N+]4(C)C.[Cl-]
InChi Code
InChI=1S/C21H20NO6.ClH/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+;/m1./s1
InChi Key
RLJKFAMYSYWMND-VOMIJIAVSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    10 mg

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    25 mg

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    Product Description

    (–)-Bicuculline methochloride is an enantiomer of the GABA antagonist (+)-bicuculline methochloride.1 It increases the firing rate in rat cortical neurons similar to the (+) isomer but lacks GABA antagonist activity. (–)-Bicuculline methochloride inhibits sodium-independent GABA receptor binding with an IC50 value of 500 μM, which is approximately 100-fold less potent than (+)-bicuculline methochloride, but there is no stereoselectivity for sodium-dependent GABA receptor binding.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Collins, J.F., and Hill, R.G. (+) and (−)-bicuculline methochloride as optical isomers of a GABA antagonist. Nature 249(460), 845-847 (1974).

    2. Enna, S.J., Collins, J.F., and Snyder, S.H. Stereospecificity and structure-activity requirements of GABA receptor binding in rat brain. Brain Res. 124(1), 185-190 (1977).