MedKoo Cat#: 574050 | Name: (−)-Bicuculline methochloride
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

(−)-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.

Chemical Structure

(−)-Bicuculline methochloride
(−)-Bicuculline methochloride
CAS#53552-05-9 (methochloride)

Theoretical Analysis

MedKoo Cat#: 574050

Name: (−)-Bicuculline methochloride

CAS#: 53552-05-9 (methochloride)

Chemical Formula: C21H20ClNO6

Exact Mass: 0.0000

Molecular Weight: 417.84

Elemental Analysis: C, 60.37; H, 4.82; Cl, 8.48; N, 3.35; O, 22.97

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 Weeks
50mg USD 1,100.00 2 Weeks
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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

Preparing Stock Solutions

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.

Recalculate based on batch purity %
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
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).