Vincamine

• Catalog No.: Bio-0225
• CAS Number: 1617-90-9
• M. F.: C21H26N2O3
• M. W.: 354.44274

SYNONYMS

• IUPAC name: methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0^2,^7.0^8,^1^8.0^1^5,^1^9]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
• IUPAC Traditional name: methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0^2,^7.0^8,^1^8.0^1^5,^1^9]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
• Synonyms: Vincamarine; Pervincamine; Vincafor; Minorine

DATABASE IDS

• CAS Number: 1617-90-9

PROPERTIES

• Application(s): Hypotensive
• Application(s): Vasodilator increasing blood flow to the brain
• Biological Source: Alkaloid from Tabernaemontana rigida (Apocynaceae)
• Mechanism of Action: Potent blockers of voltage-gated Na[+] channels

REFERENCES

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 942A, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1066D, (ir)
• Schlittler, E. et al., Helv. Chim. Acta, 1953, 36, 2017, (isol, uv, ir)
• Trojnek, J. et al., Tet. Lett., 1961, 702, (uv, ir, struct)
• Plat, M. et al., Bull. Soc. Chim. Fr., 1962, 1082, (ms, uv)
• Mokry, J. et al., Tet. Lett., 1963, 999; 1917, (pmr, abs config, epimer)
• Hugel, G. et al., C. R. Hebd. Seances Acad. Sci. Ser. C, 1972, 274, 1350, (synth)
• Neuss, N. et al., Helv. Chim. Acta, 1973, 56, 2660, (cmr)
• Taylor, W.I. et al., The Vinca Alkaloids, M. Dekker, 1973, (pharmacol)
• Pfffli, P. et al., Helv. Chim. Acta, 1975, 58, 1131, (synth, pmr, uv, ir)
• Oppolzer, W. et al., Helv. Chim. Acta, 1977, 60, 1801, (synth)
• Gibson, K.H. et al., Tetrahedron, 1977, 33, 833, (synth)
• Rossey, G. et al., J.O.C., 1982, 47, 4745, (synth)
• Govindachari, T.R. et al., Indian J. Chem., Sect. B, 1983, 22, 531, (synth)
• Szabo, L. et al., Tetrahedron, 1983, 39, 3737, (synth)
• Vereczkey, L., Eur. J. Drug Metab. Pharmacokinet., 1985, 10, 89, (rev)
• Takano, S. et al., Chem. Comm., 1986, 156, (synth)
• Lounasmaa, M. et al., Heterocycles, 1986, 24, 1663, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6203, (synonyms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1427
• Nagy, T. et al., Heterocycles, 1997, 45, 2007-2013, (synth)
• Martin, G.E. et al., J. Het. Chem., 1997, 34, 695-699, (pmr, N-15 nmr)
• Schultz, A.G. et al., J.O.C., 1997, 62, 1223, (synth)
• Desmaele, D. et al., J.O.C., 1997, 62, 3890, (synth)
• Alves, J.C.F. et al., Tetrahedron: Asymmetry, 1999, 10, 297-306, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, VLF000