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(−) –Argemonine

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Taxonomy:Physicochemical and Pharmacological Properties of Alkaloids – Isoquinoline Alkaloids

Biological sources: Argemone platyceras, Thalictrum minus, T. strictum

C21H25NO4: 355.1783

Mp: 147–148°C [1], 154–155°C [2]

[α]D −208° (CHCl3) [2]

UV: 223, 287(4.20, 4.00) [2]

MSm/z: 355(M+, 30), 354, 204(100) [3]

1H NMR: 2.57(3H, s, NCH3), 2.62(2H, d, J = 17, H-5, H-11), 3.42, 3.53(2H, dd, J = 6; 17, H-5, H-11), 3.84, 3.92(each 6H, s, 4 × OCH3), 4.08(2H, d, J = 6, H-6, H-12), 6.59, 6.76(each 2H, s, p–H–Ar) [3]

13 C NMR: [ 4]

Table 1

C-1

C-10

109.9

C-4

C-7

111.4

C-6

C-12

66.2

2

9

147.3

4a

10a

123.7

6a

12a

129.7

3

8

147.7

5

11

33.3

 

NCH3

40.6

References

  1. 1.
    P.G. Gorovoi, A.A. Ibragimov, S.Kh. Maekh, S.Yu. Yunusov, Chem. Nat. Comp. 11, 568 (1975)Google Scholar
  2. 2.
    V.A. Chelombitґko, L.E. Nazarova, Khim. Farm. Zh. 580 (1988)Google Scholar
  3. 3.
    R.H.F. Manske, K.H. Shin, A.R. Battersby, D.E. Shaw, Can. J. Chem. 43, 2183 (1965)Google Scholar
  4. 4.
    R. Shamma, J.L. Moniot, Isoquinoline Alkaloids Research (Plenum Press, New York/London, 1978), p. 69Google Scholar

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