(5S)-6,6-dimethyl-5-[(10R)-12-oxo-3,5,11-trioxatricyclo[7.3.0.02,6]dodeca-1,6,8-trien-10-yl]-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide

• ChemBase ID: 156006
• Molecular Formular: C21H20INO6
• Molecular Mass: 509.29107
• Monoisotopic Mass: 509.03353537
• SMILES: C[N+]1(CCc2cc3c(cc2[C@H]1[C@H]1c2ccc4c(c2C(=O)O1)OCO4)OCO3)C.[I-]
• Canonical SMILES: O=C1O[C@H](c2c1c1OCOc1cc2)[C@@H]1c2cc3OCOc3cc2CC[N+]1(C)C.[I-]
• 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
• InChIKey: HKJKCPKPSSVUHY-GRTNUQQKSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-6,6-dimethyl-5-[(10R)-12-oxo-3,5,11-trioxatricyclo[7.3.0.0^2,^6]dodeca-1,6,8-trien-10-yl]-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide; (5S)-6,6-dimethyl-5-[(10R)-12-oxo-3,5,11-trioxatricyclo[7.3.0.0^2,^6]dodeca-1(9),2(6),7-trien-10-yl]-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide
• IUPAC Traditional name: (5S)-6,6-dimethyl-5-[(10R)-12-oxo-3,5,11-trioxatricyclo[7.3.0.0^2,^6]dodeca-1,6,8-trien-10-yl]-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide; (5S)-6,6-dimethyl-5-[(10R)-12-oxo-3,5,11-trioxatricyclo[7.3.0.0^2,^6]dodeca-1(9),2(6),7-trien-10-yl]-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide
• Synonyms: (5S)-5-[(6R)-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 iodide; 1(S),9(R)-(-)-Bicuculline methiodide; (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 Iodide; (-)-Bicuculline Methiodide; Bicuculline Methiodide

Database IDs

• CAS Number: 40709-69-1; 55950-07-7
• MDL Number: MFCD00078966
• Beilstein Number: 5419649
• PubChem SID: 162250144
• PubChem CID: 104871

CALCULATED PROPERTIES

• Acid pKa: 14.270657
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -1.4853793
• LogD (pH = 7.4): -1.4853792
• Log P: -1.4853793
• Molar Refractivity: 109.367 cm^3
• Polarizability: 38.44413 Å^3
• Polar Surface Area: 63.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble10 mg/mL, almost clear, greenish-yellow; Methanol; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 175-177°C
• Optical Rotation: [α]/D -116±6°, c = 1 in chloroform

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (HPCE)
• Empirical Formula (Hill Notation): C21H20INO6

DETAILS

Sigma Aldrich - 14343

Preparation Note
prepared from (+)-bicuculline

Toronto Research Chemicals - B382505

GABA receptor antagonist.

REFERENCES

• Curtis, et al.: Nature, 226, 1222 (1970)
• Avoli, M., et al.: J. Physiol. Pharmacol., 75, 526 (1970)
• Chebib, M., et al.: Clin. Exp. Pharmacol. Physiol., 26, 927 (1970)