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Lupinine

Reference work entry

CAS Registry Number: 486-70-4 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinolizidine Alkaloids

Biological sources: Anabasis aphylla, Genista transcaucasica

C10H19NO: 169.1467

Mp: 68–69°C (pet. ether), 212°C (hydrochloride) [1]

[α]D −24° (H2O)

Solubility: very sol. H2O, EtOH, Et2O; spar. sol. pet. ether [1]

IR: 3250, 3010, 2945, 2900, 2860, 2815, 2770, 2700, 2680, 1484, 1459, 1407, 1365, 1345, 1303, 1278, 1264, 1193, 1155, 1134, 1118, 1112, 1091, 1070, 1058, 1021, 1013, 940, 891, 878, 870, 857, 823, 815 [2]

MSm/z: 169(M+, 32), 168(28), 152(54), 138(52), 97(66), 96(51), 83(100), 82(43), 55(57), 41(57) [3,4]

1H NMR: 2.82, 3.65(J = 11.6, 3), 4.00(J = 11.6, 6), 4.65(OH) [4]

13 C NMR: [ 5]

Table 1

C-1

38.5

C-6

56.9

C-9

29.5

 2

30.8

 7

25.5

10

65.0

 3

22.7

 8

24.6

CH2OH

65.0

 4

56.9

       

References

  1. 1.
    A.P. Orekhov, G.P. Men’shikov, Byull. NIKhFI (1), 1 (1931)Google Scholar
  2. 2.
    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. 164Google Scholar
  3. 3.
    S.W. Pelletier (ed.), Alkaloids, Chemical and Biological Perspectives, vol. 2 (Wiley, New York, 1984), p. 105Google Scholar
  4. 4.
    T.K. Yunusov, A.I. Ishbaev, V.B. Leont’ev, A.S. Sadykov, Chem. Nat. Comp. 7, 44 (1971)CrossRefGoogle Scholar
  5. 5.
    M. Shamma, D.M. Hindenlang, Carbon-13 NMR Shift Assignments of Amines and Alkaloids (Plenum Press, NewYork/London, 1979), No. 168CrossRefGoogle Scholar
  6. 6.
    F.S. Sadritdinov, A.G. Kurmukov, The Pharmacology of the Plant Alkaloids and Their Use in Medicine [in Russian] (UzSSR, Tashkent, 1980), p. 103Google Scholar
  7. 7.
    V.P. Ryabchenko, S.S. Kolesnikova, The Pharmacology of Plant Substances [in Russian] (Fan, Tashkent, 1973), p. 41Google Scholar

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© Springer Science+Business Media New York 2013

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