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55950-07-7 molecular structure
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(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 and InChIs

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

Cite this record

CBID:156006 http://www.chembase.cn/molecule-156006.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(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
(5S)-6,6-dimethyl-5-[(10R)-12-oxo-3,5,11-trioxatricyclo[7.3.0.02,6]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[7.3.0.02,6]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[7.3.0.02,6]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
CAS Number
55950-07-7
40709-69-1
MDL Number
MFCD00078966
Beilstein Number
5419649
PubChem SID
162250144
PubChem CID
104871

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 104871 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 14.270657  H Acceptors
H Donor LogD (pH = 5.5) -1.4853793 
LogD (pH = 7.4) -1.4853792  Log P -1.4853793 
Molar Refractivity 109.367 cm3 Polarizability 38.44413 Å3
Polar Surface Area 63.22 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
H2O: soluble10 mg/mL, almost clear, greenish-yellow expand Show data source
Methanol expand Show data source
Water expand Show data source
Apperance
Off-White to Pale Yellow Solid expand Show data source
Melting Point
175-177°C expand Show data source
Optical Rotation
[α]/D -116±6°, c = 1 in chloroform expand Show data source
Storage Condition
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥95.0% (HPCE) expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C21H20INO6 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - 14343 external link
Preparation Note
prepared from (+)-bicuculline
Toronto Research Chemicals - B382505 external link
GABA receptor antagonist.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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