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(−)-Lupanine

Reference work entry

CAS Registry Number: 486-88-4 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinolizidine Alkaloids

Biological sources: Ammodendron argenteum, A. eichwaldii, A. karelinii, A. longiracemosum, Leontice darwasica, L. smirnowii, Maackia amurensis

C15H24N2O: 248.1889

Mp: 44°C, 163°C (hydrochloride), 211°C (perchlorate), 190°C (hydroiodide), 178°C (picrate) [1]

[α]D −75° [1]

UV: 215(3.80) [2]

IR: 1635 [2]

MSm/z: 248(M+), 219, 150, 149, 136(100), 110, 98, 97, 84 [2]

1H NMR: 1.45(1H, H-9), 1.75(1H, H-7), 1.85(1H, J = 11.8, 3.5, Ha-17), 1.87(1H, J = 12, Ha-15), 2.10(1H, J = 11.5, He-8), 2.27(1H, J = 12.9, 2.5, Ha-10), 2.61(1H, J = 12, He-15), 2.65(1H, J = 11.8, 11.2, He-17), 3.14(1H, H-6), 4.32(1H, J = 12.9, 2.1, 2.0, He-10) [3]

13 C NMR(75.5 MHz, CD 3OD): [ 4, 5]

Table 1

C-2

174.1

C-7

33.3

C-12

34.0

 3

33.7

 8

27.1

 13

25.4

 4

20.2

 9

36.1

 14

25.6

 5

28.1

 10

47.9

 15

56.7

 6

62.2

 11

65.7

 17

53.7

References

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  3. 3.
    M. Shamma, D.M. Hindenlang, Carbon-13 NMR Shift Assignments of Amines and Alkaloids (Plenum Press, NewYork/London, 1979). No. 209CrossRefGoogle Scholar
  4. 4.
    A.S. Sadykov, Kh.A. Aslanov, Yu.K. Kushmuradov, Alkaloids of the Quinolizidine Series [in Russian] (Nauka, Moscow, 1975), p. 217Google Scholar
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    A.-L. Sagen, J. Gertsch, R. Becker, J. Heilmann, O. Sticher, Phytochemistry 61, 975 (2002)CrossRefGoogle Scholar
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    S. Okuda, K. Tsuda, H. Kataoke, Chem. Ind. 1115 (1961)Google Scholar

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