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Isothebaine

Reference work entry

CAS Registry Number: 568-21-8 Open image in new window

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

Biological sources: Papaver bracteatum, P. orientale, P. pseudo-orientale

C19H21NO3: 311.1521

Mp: 203–204°C (EtOH) [1], 214°C (hydrochloride) [1]

[α]D +276° (abs. EtOH) [1]

UV: 207, 273, 287 [1]

MSm/z: 311(M+), 310, 296, 294, 280, 268, 155.5(++) [1]

1H NMR: 2.46(3H, s, NCH3), 3.83, 3.89(each 3H, s, 2×OCH3), 6.61(1H, s), 6.70–7.30(3H, m) [1]

13 C NMR: [ 2]

Table 1

C-1

141.4

C-4

28.4

C-9

127.8

1a

119.1

5

52.4

10

111.2

1b

127.6

6a

62.0

11

153.3

2

148.4

7

35.6

11a

121.5

3

110.5

7a

139.2

NCH3

43.4

3a

123.6

8

121.8

2-OCH3

55.5

       

11-OCH3

56.4

References

  1. 1.
    R. Shakirov, M.V. Telezhenetskaya, I.A. Bessonova, S.F. Aripova, I.A. Israilov, M.N. Sultankhodzhaev, V.I. Vinogradova, V.I. Akhmedzhanova, T.S. Tulyaganov, B.T. Salimov, V.A. Tel’nov, Chem. Nat. Comp. 32, 386 (1996)Google Scholar
  2. 2.
    H.G. Theuns, R.H.A.M. Janssen, H.W.A. Biessels, C.A. Salemink, Phytochemistry 24, 163 (1985)Google Scholar
  3. 3.
    J. Milo, A. Levy, D. Palevitch, G. Ladizinsky, J. Chromatogr. 452, 563 (1988)Google Scholar
  4. 4.
    F.S. Sadritdinov, A.G. Kurmukov, The Pharmacology of the Plant Alkaloids and Their Use Medicine [in Russian] (UzSSR, Tashkent, 1980), p. 210Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

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