Title: Bicuculline
CAS Registry Number: 485-49-4
CAS Name: (6R)-6-[(5S)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one
Molecular Formula: C20H17NO6
Molecular Weight: 367.35
Percent Composition: C 65.39%, H 4.66%, N 3.81%, O 26.13%
Literature References: Alkaloid naturally occurring in the d-form; found in Dicentra cucullaria (L.) Bernh., Adlumia fungosa (Ait.) Greene, Fumariaceae, and several Corydalis species: Manske, Can. J. Res. 7, 265 (1932); 8, 210, 407 (1933); 9, 436 (1933); Edwards, Handa, Can. J. Chem. 39, 1801 (1961). Synthesis of dl-form: Groenewoud, Robinson, J. Chem. Soc. 1936, 199. Resolution of isomers: Haworth et al., Nature 165, 529 (1950). Stereoisomer of adlumidine, q.v., and of capnoidine: Manske, J. Am. Chem. Soc. 72, 3207 (1950). Preliminary stereochemical studies: Safe, Moir, Can. J. Chem. 42, 160 (1964). Revised stereochemistry: Blaha et al., Collect. Czech. Chem. Commun. 29, 2328 (1964); Snatzke et al., Tetrahedron 25, 5059 (1969). Crystal and molecular structure: Gorinsky, Moss, J. Cryst. Mol. Struct. 3, 299 (1973). Shows GABA (q.v.) antagonist activity: Curtis et al., Nature 226, 1222 (1970).
Properties: Elongated plates from chloroform-methanol, mp 215°; also reported as mp 177°, solidifies and remelts 193-195°: Manske, Can. J. Res. 21B, 13 (1943). uv max (acidified ethanol): 225, 296, 324 nm (e 36700, 6390, 5870). [a]D25 +130.5° (CHCl3). pKa 4.84. Sol in benzene, chloroform, ethyl acetate. Sparingly sol in alc and ether.
Melting point: mp 215°; mp 177°
pKa: pKa 4.84
Optical Rotation: [a]D25 +130.5° (CHCl3)
Absorption maximum: uv max (acidified ethanol): 225, 296, 324 nm (e 36700, 6390, 5870) |