Title: Berberine
CAS Registry Number: 2086-83-1
CAS Name: 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium
Additional Names: 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)berbinium; umbellatine
Molecular Formula: [C20H18NO4]+
Literature References: Tautomeric alkaloid widely distributed in nine or more botanical familes but occurs most frequently in Berberidaceae. A component of many traditional medicines, first isolated in 1826. Structure: Perkin, Robinson, J. Chem. Soc. 97, 305 (1910). Biosynthesis: J. R. Gear, I. D. Spenser, Can. J. Chem. 41, 783 (1963). Pharmacology: Fukuda et al., Chem. Pharm. Bull. 18, 1299 (1970). Total synthesis: Kametani et al., J. Chem. Soc. C 1969, 2036. NMR: G. Blasko et al., Heterocycles 27, 911 (1988). HPLC determn in biological fluids: C.-M. Chen, H.-C. Chang, J. Chromatogr. B 665, 117 (1995). Clinical evaluation in malaria: W. D. Sheng et al., East Afr. Med. J. 74, 283 (1997). Review of biological activities: F. E. Hahn, J. Ciak, in Antibiotics vol. 3, D. Gottlieb et al., Eds. (Springer-Verlag, New York, 1975) pp 577-584; of chemistry, distribution and use: R. S. Thakur, S. K. Srivastava, Curr. Res. Med. Aromat. Plants 4, 249-272 (1982). Review of antidiarrheal action: A. W. Baird et al., Adv. Drug Delivery Rev. 23, 111-120 (1997).
Properties: Yellow needles from ether, mp 145°: Gadamer, Arch. Pharm. 243, 33 (1905). uv max: 265, 343 nm. pK 2.47.
Melting point: mp 145°: Gadamer, Arch. Pharm. 243, 33 (1905)
pKa: pK 2.47
Absorption maximum: uv max: 265, 343 nm
Derivative Type: Acid sulfate
Additional Names: Berberine bisulfate
Molecular Formula: C20H19NO8S
Molecular Weight: 433.43
Percent Composition: C 55.42%, H 4.42%, N 3.23%, O 29.53%, S 7.40%
Properties: Yellow needles. Sol in about 100 parts water; slightly sol in alc.
Derivative Type: Chloride dihydrate
Molecular Formula: C20H18NO4.Cl.2H2O
Molecular Weight: 407.84
Percent Composition: C 58.90%, H 5.44%, N 3.43%, O 23.54%, Cl 8.69%
Properties: Yellow crystals. Slightly sol in cold, freely in boiling water. Practically insol in cold alcohol, chloroform, ether.
Derivative Type: Sulfate trihydrate
Properties: Yellow needles. Sol in about 30 parts water; sol in alcohol. Activity studies: Amin et al., Can. J. Microbiol. 15, 1067 (1969). Pharmacology: Sabir, Bhide, Indian J. Physiol. Pharmacol. 15, 111 (1971).
Therap-Cat: Antiprotozoal (Leishmania); antimalarial; antibacterial; antidiarrheal.
Keywords: Antimalarial; Antipyretic. |