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Thalicmine (Ocoteine)

Reference work entry

CAS Registry Number: 3246-21-7 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Isoquinoline Alkaloids – Aporphine Alkaloids

Biological sources: Thalictrum isopyroides, T. minus, T.simplex, T. strictum

C21H23NO5: 369.1576

Mp: 137–138°C (MeOH) [1], 270°C (hydrochloride), 224°C (dec., hydroiodide), 260°C (hydrobromide), 237°C (methiodide)

[α]D +60° (CHCl3) [2]

UV: 220, 282, 304, 315(4.46, 4.22, 4.22, 4.18) [3]

IR: 1627, 1608, 1510, 935 [4]

MSm/z: 369(M+, 100), 368(94), 354(22), 338(21), 326(15), 311(16), 295(21) [5]

1H NMR: 2.42(3H, s, NCH3), 3.79, 3.82(each 3H, s, 10-OCH3, 9-OCH3), 3.90(3H, s, 3-OCH3), 5.90(2H, d, J = 2, CH2O2), 6.70(1H, s, H-8), 7.53(1H, s, H-11) [6]

13 C NMR: [ 7]

Table 1

C-1

143.2

C-4

23.6

C-10

147.5

1a

110.4

5

53.2

11

110.0

1b

127.4

6a

62.3

11a

123.5

2

134.8

7

34.1

CH2O2

100.4

3

139.1

7a

127.4

3-OCH3

59.3

3a

119.1

8

111.1

9-OCH3

56.0

   

9

147.5

10-OCH3

55.8

References

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    Z.F. Ismailov, M.R. Yagudaev, S.Yu. Yunusov, Chem. Nat. Comp. 4, 175 (1968)Google Scholar
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    A.J. Marsaioli, F.A.M. Ries, A.F. Magalhaes, E.A. Ruveda, A.M. Kuck, Phytochemistry 18, 165 (1979)Google 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. 250Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

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