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    (-)-Bicuculline methiodide

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      (-)-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

      • Product Data
      • Handling
      • Safety Information
      • Details

      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-]

      (-)-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).

      Artikelnummer: B0240 Kategorie: API's & Intermediates
      • Zusätzliche Information

      Zusätzliche 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

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