Glaucine

• Catalog No.: Bio-0316
• CAS Number: 475-81-0
• M. F.: C21H25NO4
• M. W.: 355.4275

SYNONYMS

• IUPAC name: (9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2,4,6,13,15-hexaene
• IUPAC Traditional name: (9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2,4,6,13,15-hexaene
• Synonyms: 1,2,9,10-Tetramethoxyaporphine

DATABASE IDS

• CAS Number: 475-81-0

PROPERTIES

• Application(s): Shows antithrombotic, analgesic and antiinflammatory activity
• Application(s): Antifungal agent
• Application(s): Antitussive agent with similar potency to Codeine.
• Biological Source: Alkaloid from a wide variety of genera in the Annonaceae ( Alphonsea, Annona, Polyalthia, Schefferomitra, Uvaria ), Berberidaceae ( Berberis, Mahonia ), Euphorbiaceae ( Croton ), Fumariaceae ( Corydalis, Dicentra ), Lauraceae ( Beilschmiedia, Ocotea, Litsea ), Magnoliaceae ( Liriodendron, Magnolia ), Menispermaceae ( Chasmanthera ), Papaveraceae ( Glaucium, Papaver ), Ranunculaceae ( Thalictrum, Aconitum ), Rhamnaceae ( Colubrina ) and Monimiaceae ( Hedycaria )
• Mechanism of Action: PDE4 inhibitor

REFERENCES

• Go, J., Yakugaku Zasshi, 1930, 50, 933, (isol)
• Corrodi, H. et al., Helv. Chim. Acta, 1956, 39, 889, (abs config)
• Baarschers, W.H. et al., J.C.S., 1964, 4478, (pmr, ms)
• Jackson, A.H. et al., J.C.S.(C), 1966, 2061, (synth, pmr, uv)
• Shamma, M. et al., J. Pharm. Sci., 1968, 57, 262, (isol, ir)
• Kametani, T. et al., Tetrahedron, 1969, 25, 3667, (synth, ir, uv)
• Guinaudeau, H. et al., J. Nat. Prod., 1975, 38, 275; 290; 1979, 42, 325; 329, (cmr, uv, rev)
• Premila, M.S. et al., Indian J. Chem., Sect. B, 1976, 14, 134, (synth)
• Aleshinskaya, E.E., Khim.-Farm. Zh., 1976, 10, 144, (pharmacol)
• Hartenstein, J. et al., Angew. Chem., 1977, 89, 739, (synth)
• Davis, P.J. et al., J.C.S. Perkin 1, 1977, 1, (synth, ms)
• Ricca, G. et al., Gazz. Chim. Ital., 1979, 109, 1, (cmr)
• Kase, Y. et al., Arzneim.-Forsch., 1983, 33, 936; 947, (pharmacol)
• Kerr, K.M. et al., J. Nat. Prod., 1986, 49, 576, (pmr)
• Czarnocki, Z. et al., Can. J. Chem., 1987, 65, 2356, (synth)
• Gupta, S. et al., Synth. Commun., 1989, 19, 393, (synth)
• Gottlieb, L. et al., J.O.C., 1990, 55, 5659, (synth)
• Ivorra, M.D. et al., Br. J. Pharmacol., 1992, 106, 387, (pharmacol)
• Oralla, F. et al., Br. J. Pharmacol., 1993, 110, 943; 1995, 114, 1419, (pharmacol)
• Ozaki, Y. et al., Chem. Pharm. Bull., 1993, 41, 481, (synth)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 747
• Estvez, J.C. et al., Tetrahedron, 1994, 50, 2107, (synth)
• Comins, D.L. et al., Tetrahedron, 1997, 48, 16327-16340, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TDI475