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(+) – Bicuculline

Reference work entry

CAS Registry Number: 485-49-4 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Isoquinoline Alkaloids

Biological sources: Corydalis alpestris, C. caucasica, C. emanuelii, C. gigantea, C. gortschakovii, C. marschalliana, C. paniculigera, C. pseudoadunca, C. remota, C. stricta, C. vaginans, Dicentra peregrina, Fumaria capreolata, F. parviflora, F. vaillantii

C20H17NO6: 367.1056

Mp: 194–195°C (MeOH–CHCl3) [1]

[α]D +112° (CHCl3) [1]

UV: 222, 298, 324 [1]

IR: 1750 [1]

MSm/z: 190 [2]

1H NMR: 2.50(3H, s, NCH3), 3.97, 5.62(each 1H, d, J = 4), 5.83, 6.08(each 2H, s, 2 × CH2O2), 6.32, 6.49(each 1H, s, p–H–Ar), 6.21, 6.85(each 1H, d, J = 8, o–H–Ar) [2]

13 C NMR: [ 3]

Table 1

C-1

66.0

C-8

107.8

C-4′

149.1

3

49.5

8a

130.7

5′

144.5

4

27.0

9

85.0

6′

110.3

4a

124.8

10

167.2

6,7-OCH2O

101.0

5

108.5

1′

140.5

4′,5′-OCH2O

103.3

6

146.8

2′

115.6

NCH3

45.3

7

146.0

3′

113.1

   

References

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    M.S. Yunusov, S.T. Akramov, S.Yu. Yunusov, DAN SSSR [in Russian] 162, 607 (1965)Google Scholar
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  3. 3.
    R.H.F. Manske (ed.), The Alkaloids, Chemistry and Physiology, vol. 18 (Academic, New York, 1981), p. 217Google Scholar
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    F.S. Sadritdinov, A.G. Kurmukov, The Pharmacology of the Plant Alkaloids and Their Use in Medicine [in Russian] (UzSSR, Tashkent, 1980), p. 204Google Scholar
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    I. Khamdamov, F.S. Sadritdinov, Dokl. AN UzSSR (2), 58 (1972)Google Scholar
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