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(+)-Lupanine

Reference work entry

CAS Registry Number: 550-90-3 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinolizidine Alkaloids

Biological sources: Ammopiptanthus mongolicus, Cytisus caucasicus, C. ratisbonensis, Leontice ewersmannii, L. smirnowii, Piptanthus nanus

C15H24N2O: 248.1889

Mp: 44°C (Et2O), 213°C (perchlorate), 180°C (picrate), 190°C (hydroiodide), 163°C (hydrochloride), 164°C (hydrobromide), 240°C (methiodide) [1]

[α]D +85° (EtOH) [1]

UV: 215(3.80) [2]

IR(hydrochloride): 3670, 3410, 3010, 2960, 2870, 1646, 1636, 1464, 1450, 1420, 1363, 1351, 1332, 1312, 1295, 1275, 1244, 1191, 1167, 1148, 1131, 1102, 1081, 1068, 1047, 1018, 1008, 991, 965, 951, 935, 923 [3]

MSm/z: 248(M+, 39), 247(21), 150(37), 149(49), 136(100), 110(24), 98(30), 97(28), 84(19), 41(40) [4]

1H NMR: 1.10(J = 11.5, 2.2, 2.2, Ha-8), 1.45(J = 10, H-9), 1.76(H-7), 1.85(J = 11.8, 3.5, H-17a), 1.87(J = 12, Ha-15), 2.10(J = 11.5, He-8), 2.27(J = 12.9, 2.5, Ha-10), 2.61(J = 12, He-15), 2.65(J...

References

  1. 1.
    S.Yu. Yunusov, The Alkaloids [in Russian] (Fan, Tashkent, 1981), p. 222Google Scholar
  2. 2.
    A.W. Sangster, K.L. Stuart, Chem. Rev. 65, 69 (1965)CrossRefGoogle Scholar
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    J. Holubek, O. Strouf, Spectral Data and Physical Constants of Alkaloids (Prague Publishing House, Czechoslovak Academy of Sciences, Heyden & Son Ltd, London, 1965), 1, No. 163Google Scholar
  4. 4.
    S.W. Pelletier (ed.), Alkaloids, Chemical and Biological Perspectives, vol. 2 (Wiley, New York, 1984), p. 105Google Scholar
  5. 5.
    A.S. Sadykov, Kh.A. Aslanov, Yu.K. Kushmuradov, Alkaloids of the Quinolizidine Series [in Russian] (Nauka, Moscow, 1975), p. 217Google Scholar
  6. 6.
    M. Shamma, D.M. Hindenlang, Carbon-13 NMR Shift Assignments of Amines and Alkaloids (Plenum Press, NewYork/London, 1979), No. 209CrossRefGoogle Scholar
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    S. Takamatsu, K. Saito, S. Ohmiya, N. Ruangrungsi, I. Murakoshi, Phytochemistry 30, 3793 (1991)CrossRefGoogle Scholar
  8. 8.
    F.S. Sadritdinov, A.G. Kurmukov, The Pharmacology of the Plant Alkaloids and Their Use in Medicine [in Russian] (UzSSR, Tashkent, 1980), p. 140Google Scholar

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© Springer Science+Business Media New York 2013

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