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7-Oxoisothebaine (Alkaloid PO-3)

Reference work entry

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Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Isoquinoline Alkaloids – Aporphine Alkaloids

Biological sources: Papaver pseudo-orientale

C19H15NO4: 321.1001

Mp: amorph.

UV: 293, 297, 505 [1]

IR: 1620, 1580 [1]

MSm/z: 321(M+) [1]

1H NMR(DMSO-d6): 3.85, 3.95(each 3H, s, 2 × OCH3), 4.65(3H, s, NCH3), 7.15(1H, s), 7.20–7.90(4H, m), 8.40(1H, d, J = 5)

1H NMR(CDCl3/TFA, 250 MHz): 4.17, 4.22(each 3H, s, 2 × OCH3), 4.71(3H, s, NCH3), 7.50(1H, s, H-3), 7.57(1H, d, J = 7.9, H-10), 7.72(1H, m, H-9), 8.13(1H,d, J = 7.9, H-8), 8.41(1H, d, J = 6.1, H-4), 8.61(1H, d, J = 6.1, H-5) [2]

References

  1. 1.
    R. Shakirov, M.V. Telezhenetskaya, I.A. Bessonova, S.F. Aripova, I.A. Israilov, M.N. Sultankhodzhaev, V.I. Vinogradova, V.I. Akhmedzhanova, T.S. Tulyaganov, B.T. Salimov, V.A. Tel’nov, Chem. Nat. Comp. 32, 737 (1996)Google Scholar
  2. 2.
    C. Saa, E. Guitian, L. Castedo, J.M. Saa, Tetrahedron Lett. 26, 4559 (1985)Google Scholar

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© Springer Science+Business Media New York 2013

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