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Apoglaziovine (1,10-Dihydroxy-2-methoxyaporphine)

Reference work entry

CAS Registry Number: 18058-59-8 Open image in new window

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

Biological sources: Liriodendron tulipiferum

C18H19NO3: 297.1365

Mp: 249°C (dec.) [2], 256°C (hydrochloride, Me2CO–EtOH) [1]

[α]D (hydrochloride) +165° (CHCl3) [2]

UV: 218, 266, 275, 307 [3]

IR: 3460, 3300, 1600, 1302, 1136 [3]

1H NMR: 2.57(3H, s, NCH3), 3.92(3H, s, OCH3), 6.62(1H, q, J = 7.8, 2.5), 6.77(1H, s), 7.18(1H, d, J = 7.8), 8.08(1H, d, J = 2.5) [3]

13 C NMR(25,2MHz, DMSO-d 6): [ 4]

Table 1

C-1

141.6

C-4

28.4

C-9

113.2*

2

146.5

5

52.8

10

155.3

3

110.2

6a

62.5

11

115.4*

3a

122.9

7

33.6

11a

133.0

1a

119.4

7a

126.0

N-CH3

43.5

1b

127.5

8

127.9

2-OCH3

55.7

References

  1. 1.
    R. Ziyaev, K. Ikramov, Kh.A. Kadyrov, A. Abdusamatov, Chem. Nat. Comp. 27, 516 (1991)Google Scholar
  2. 2.
    M.P. Cava, M. Behforouz, M.J. Mitchell, Tetrahedron Lett. 13, 4647 (1972)Google Scholar
  3. 3.
    B. Gilbert, M.E.A. Gilbert, M.M. De Oliveira, O. Ribeiro, E. Wenkert, B. Wickberg, U. Hollstein, H. Rapoport, J. Am. Chem. Soc. 86, 694 (1964)Google Scholar
  4. 4.
    B.K. Cassels, A. Cave, M. Leboeuf, J. Nat. Prod. 50, 297 (1987)Google Scholar

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© Springer Science+Business Media New York 2013

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