(-)-Bicuculline methiodide

Specifications

Purity

≥95% (NMR)

Identity

1H-NMR

Appearance

White to off-white powder

Properties

Melting Point

236°C

Solvents

water (10 mg/ml) or DMSO (30 mg/ml).

Handling Advice

Protect from light and moisture.

Use / Stability

Stable for at least 2 years after receipt when stored at +4°C.

Long Term Storage

+4°C

Short Term Storage

RT

Shipping

AMBIENT

Transportation

Packing Group II

RIDADR

UN1544

Signal word

Danger

GHS Symbol

GHS06+GHS09

Precautionary statements

P260, P264, P273, P280, P301+P310, P302+P352, P304+P340

Hazard statements

H300, H311, H331, H400

Description

(-)-Bicuculline methiodide is the N-methylated water-soluble derivative of the widely-employed ionotropic GABAA receptor antagonist (+)-Bicuculline. This prototypic, competitive GABAA receptor antagonist displaces GABA from the agonist binding site to prevent receptor activation. It also acts as a negative allosteric inhibitor of channel opening to inhibit GABAA receptor activation by anaesthetic agents. Additionally it shows activity at SK calcium-activated potassium channels, nicotinic acetylcholine receptors and acetylcholinesterase. This compound reversibly and competitively blocks GABAA receptor mediated currents and is widely used to isolate glutamate receptor mediated EPSCs (excitatory postsynaptic potentials).

InChi

InChI=1S/C21H20NO6.HI/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

References

(1) R.W. Olsen, et al., Brain Res. 102, 283 (1976) , (2) V. Seutin & S.W. Johnson, TiPS 20, 268 (1999) , (3) O. Chan, et al., Diabetes 55, 1080 (2006) , (4) S. Kurt, et al., Hear Res. 212, 224 (2006) , (5) G.A. Johnston, Br. J. Pharmacol. 169, 328 (2013) , (6) R.W. Olsen, Neuropharmacol. 136, 10 (2018)

InChi Key

HKJKCPKPSSVUHY-GRTNUQQKSA-M

Smiles

C[N+]1(C)[C@@]([C@@]2([H])C(C=CC3=C4OCO3)=C4C(O2)=O)([H])C5=CC6=C(OCO6)C=C5CC1.[I-]