Available from stock

(-)-Bicuculline methiodide

SKU: B0240

Category: API's & Intermediates

Synonyms: N-Methylbicuculline iodide , 55950-07-7; 40709-69-1
CAS-Number: C₂₁H₂₀INO₆
Molecular Formula: 509.29
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥95% (NMR)
Appearance: White to off-white powder
Identity: 1H-NMR

Properties

Solvents: water (10 mg/ml) or DMSO (30 mg/ml).
Melting Point: 236°C

Shipping: AMBIENT
Short Term Storage: RT
Long Term Storage: +4°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at +4°C.

Hazard statements: H300, H311, H331, H400
Precautionary statements: P260, P264, P273, P280, P301+P310, P302+P352, P304+P340
GHS Symbol: GHS06+GHS09
Signal word: Danger
RIDADR: UN1544
Transportation: Packing Group II

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).
Smiles: C[N+]1(C)[C@@]([C@@]2([H])C(C=CC3=C4OCO3)=C4C(O2)=O)([H])C5=CC6=C(OCO6)C=C5CC1.[I-]
InChi Key: HKJKCPKPSSVUHY-GRTNUQQKSA-M
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: 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

(-)-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).

SKU: B0240 Category: API's & Intermediates

Additional information

Additional information

Synonyms	N-Methylbicuculline iodide, 55950-07-7
Purity	≥95% (NMR)
Appearance	White to off-white powder
CAS-Number	40709-69-1
Molecular Formula	C21H20INO6
Molecular Weight	509.29
Identity	1H-NMR
Solvents	water (10 mg/ml) or DMSO (30 mg/ml).
Melting Point	236°C
Smiles	C[N+]1(C)[C@@]([C@@]2([H])C(C=CC3=C4OCO3)=C4C(O2)=O)([H])C5=CC6=C(OCO6)C=C5CC1.[I-]
InChi Key	HKJKCPKPSSVUHY-GRTNUQQKSA-M
Shipping	AMBIENT
Short Term Storage	RT
Long Term Storage	+4°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at +4°C.
Hazard statements	H300, H311, H331, H400
Precautionary statements	P260, P264, P273, P280, P301+P310, P302+P352, P304+P340
GHS Symbol	GHS06+GHS09
Signal word	Danger
RIDADR	UN1544
Transportation	Packing Group II
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	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
Quantity	25 mg, 100 mg, Bulk