WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H574050
CAS#: 53552-05-9
Description: (−)-Bicuculline methochloride is an enantiomer of the GABA antagonist (+)-bicuculline methochloride. 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.
Hodoodo Cat#: H574050
Name: (−)-Bicuculline methochloride
CAS#: 53552-05-9
Chemical Formula: C21H20ClNO6
Exact Mass: 417.10
Molecular Weight: 417.840
Elemental Analysis: C, 60.37; H, 4.82; Cl, 8.48; N, 3.35; O, 22.97
Synonym: (−)-Bicuculline methochloride
IUPAC/Chemical 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
InChi Key: RLJKFAMYSYWMND-VOMIJIAVSA-M
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
SMILES Code: 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-]
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
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The following data is based on the product molecular weight 417.84 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
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| In vivo protocol: |
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).
