Lehmanine (Lehmannine)

Reference work entry

CAS Registry Number: 58480-54-9 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinolizidine Alkaloids

Biological sources: Ammothamnus lehmannii

C15H22N2O: 246.1732

Mp: 93–94°C (pet. ether), 145°C (picrate) [1]

[α]D +37° (c 0.54, EtOH) [1]

UV: 255–260 sh [1]

IR: 2810, 2770, 2750, 2680, 1650 [1]

MSm/z: 246(M+, 100), 245(62), 231(1.5), 217(16), 203(85), 188(9), 177(12), 160(32), 150(89), 137(30), 122(34), 96(98) [2]

EI-MS: 246(M+, 100), 245(67), 217(10), 203(52), 159(13), 150(28), 136(19), 122(12), 121(19), 96(42) [3]

1H NMR: 1.00–2.10 (m), 2.60–2.85(He-2, He-10), 2.95(1H, t, J = 12, 11, Ha-17), 4.20–4.50(2H, He-17, H-11), 5.60–5.90(H-12, H-13) [1]

1H NMR(CDCl3, 400 MHz): 5.85(1H, dm, J = 10.5, H-12), 5.76(1H, dm, J = 10.5, H-13), 4.46–4.56(2H, m, H-11, Hα-17), 3.11(1H, dd, J = 12.1, 12.1, Hβ-17), 2.93(2H, m, Hα-14) [3]

13 C NMR(CDCl 3, 400 MHz): [ 3]

Table 1

C-2

57.2

C-7

44.4

C-12

122.6

 3

21.0

 8

26.7

 13

123.6

 4

27.8

 9

21.0

 14

29.7

 5

35.8...

References

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    Yu.K. Kushmuradov, Kh.A. Aslanov, S. Kuchkarov, Chem. Nat. Comp. 11, 389 (1975)CrossRefGoogle Scholar
  2. 2.
    S. Kuchkarov, Yu.K. Kushmuradov, Kh.A. Aslanov, A.S. Sadykov, Chem. Nat. Comp. 13, 451 (1977)CrossRefGoogle Scholar
  3. 3.
    P. Xiao, J. Li, H. Kubo, K. Saito, I. Murakoshi, S. Ohmiya, Chem. Pharm. Bull. 44, 1951 (1996)CrossRefGoogle Scholar
  4. 4.
    X. Chen, C.Q. Yi, X.Q. Yang, X. Wang, J. Chromatogr. B 812, 149 (2004)Google Scholar

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