Thebaine

Reference work entry

CAS Registry Number: 115-37-7 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Isoquinoline Alkaloids

Biological sources: Papaver bracteatum, P. orientale, P. somniferum

C19H21NO3: 311.1521

Mp: 192–193°C (EtOH) [1]

[α]D −217° (CHCl3) [1]

UV: 285 [2]

MSm/z: 311(M+, 100), 310, 296, 280, 268, 255, 155.5 (++) [2]

1H NMR: 2.39(3H, s, NCH3), 3.52, 3.76(each 3H, s, 2 × OCH3), 4.96, 5.48(each 1H, d, J = 8), 5.20(1H, s), 6.48, 6.60(each 1H, d, J = 9, o–H–Ar) [2]

13 C NMR: [ 2, 3]

Table 1

C-1

119.1

C-8

111.3

C-14

132.3

2

112.9

9

60.7

15

37.0

3

142.7

10

29.5

16

46.0

4

144.6

11

127.6

NCH3

42.3

5

89.0

12

133.1

3-OCH3

56.2

6

152.3

13

46.0

OCH3

54.7

7

95.8

       

References

  1. 1.
    R.A. Konovalova, S.Yu. Yunusov, A.P. Orekhov, Zh. Obshch. Khim. 7, 1791 (1937)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
  4. 4.
    J. Milo, A. Levy, D. Palevitch, G. Ladizinsky, J. Chromatogr. 452, 563 (1988)Google Scholar
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    T. Kametani, M. Ihara, K. Fukumoto, H. Yagi, J. Chem. Soc. 2030 (1969)Google Scholar

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