title: Tetrahydroberberine, a pharmacologically active naturally occurring alkaloid.
abstract: Tetrahydroberberine (systematic name: 9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-benzo[g][1,3]benzodioxolo[5,6-a]quinolizine), C20H21NO4, a widely distributed naturally occurring alkaloid, has been crystallized as a racemic mixture about an inversion center. A bent conformation of the molecule is observed, with an angle of 24.72 (5)° between the arene rings at the two ends of the reduced quinolizinium core. The intermolecular hydrogen bonds that play an apparent role in crystal packing are 1,3-benzodioxole -CH2···OCH3 and -OCH3···OCH3 interactions between neighboring molecules.
authors.affiliation: Department of Chemistry, Xavier University of New Orleans, 1 Drexel Drive, Box 114, New Orleans, Louisiana 70125, USA.
authors.forename: Subramanya
authors.initials: S
authors.lastname: Pingali
authors.affiliation: Department of Chemistry, Tulane University, 6400 Freret Street, New Orleans, Louisiana 70118-5698, USA.
authors.forename: James P
authors.initials: JP
authors.lastname: Donahue
authors.affiliation: Department of Chemistry, Xavier University of New Orleans, 1 Drexel Drive, Box 114, New Orleans, Louisiana 70125, USA.
authors.forename: Florastina
authors.initials: F
authors.lastname: Payton-Stewart
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000494:pharmacology*; D001600:Berberine Alkaloids / Q000737:chemistry* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure
chemical_list: D000470:Alkaloids; D001600:Berberine Alkaloids
keywords: C—H...O hydrogen bonding; alkaloid; berberine derivative; biological activity; canadine; crystal structure; quinolizidine core; tetrahydroberberine
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