(10R)-10-[(5S)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.02,6]dodeca-1(9),2(6),7-trien-12-one

• ChemBase ID: 130533
• Molecular Formular: C20H17NO6
• Molecular Mass: 367.35208
• Monoisotopic Mass: 367.10558727
• SMILES: O=C1O[C@H](c2c1c1OCOc1cc2)[C@@H]1c2cc3OCOc3cc2CCN1C
• Canonical SMILES: CN1CCc2c([C@H]1[C@@H]1OC(=O)c3c1ccc1c3OCO1)cc1c(c2)OCO1
• InChI: InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18+/m0/s1
• InChIKey: IYGYMKDQCDOMRE-ZWKOTPCHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10R)-10-[(5S)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.0^2,^6]dodeca-1(9),2(6),7-trien-12-one
• IUPAC Traditional name: bicuculline; (10R)-10-[(5S)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.0^2,^6]dodeca-1(9),2(6),7-trien-12-one
• Synonyms: Bicuculline; (6R)-6-[(5S)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-g]lisoquinolin-5-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one; (+)-Bicuculline; d-Bicuculline; NSC 32192; d-Bicuculline

Database IDs

• CAS Number: 485-49-4
• PubChem SID: 162224812
• PubChem CID: 10237
• CHEBI ID: 3092
• CHEMBL: 417990
• Chemspider ID: 9820
• IUPHAR ligand ID: 2312
• Unique Ingredient Identifier: Y37615DVKC
• Wikipedia Title: Bicuculline

CALCULATED PROPERTIES

• Acid pKa: 14.719359
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 0.7533164
• LogD (pH = 7.4): 2.3607793
• Log P: 2.6769574
• Molar Refractivity: 93.4534 cm^3
• Polarizability: 36.674076 Å^3
• Polar Surface Area: 66.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Benzene; Chloroform; Ethyl Acetate
• Apperance: Pale Yellow Solid
• Melting Point: 193-197°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Mechanism of Action: GABA(A)-receptor antagonist

Product Information

• Biological Source: Alkaloid from many Corydalis spp. and several Fumaria spp. (opt. rotn. of isolates not recorded in some cases). Also isol. from Adlumia fungosa (Adlumia cirrhosa) (Fumariaceae, Papaveraceae)
• Application(s): Mimics epilepsy.; Utilised in the in vitro study of epilepsy.

DETAILS

Toronto Research Chemicals - B382500

Alkaloid naturally occurring in the d-form. Shows GABA antagonist activity.

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)
• 1. Manske, Can. J. Res. 7:265, 1932
• 2. Khawaled R, Bruening-Wright A, Adelman JP, Maylie J (1999) Bicuculline block of small-conductance calcium-activated potassium channels. Pflugers Arch 438: 314-321