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Codeine

Reference work entry

CAS Registry Number: 76-57-3 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Isoquinoline Alkaloids

Biological sources: Papaver somniferum

C18H21NO3: 299.1521

Mp: 155–156°C (C6H6)

[α]D −134° (MeOH)

UV: 211, 239 sh, 286 [1]

IR: 3400, 1698, 1641, 1618, 1593, 1496, 1323, 1283, 1247, 1238, 1206, 1173, 1151, 1132, 1114, 1095, 1076, 1028, 1000, 968, 950, 914, 894, 882, 861, 834, 807, 793, 776, 745, 730, 705 [2]

MSm/z: 299(M+), 282, 229, 214, 188, 162 [3]

1H NMR: 2.41(3H, s, NCH3), 2.48(1H, d, J = 6, H-10α), 2.63(1H, dd, J = 3; 3.5, H-14), 3.06(1H, d, J = 1, H-10β), 3.34(1H, dd, J = 6; 1, H-9), 3.82(3H, s, OCH3), 4.16(1H, dd, J = 6.4; 2.9, H-6), 4.91(1H, dd, J = 6.4; 1.3, H-5), 5.32(1H, dd, J = 10; 2.9, H-8), 5.72(1H, dd, J = 10; 3, H-7), 6.68(2H, s) [4]

13 C NMR: [ 5]

Table 1

C-1

119.4

C-7

133.4

C-13

42.9

2

112.8

8

127.8

14

40.3

3

142.1

9

58.8

15

35.4

4

146.9

10

20.4

16

46.3

5

91.1

11

126.7

NCH3

42.8

6

66.9

12

131.1

3-OCH3

56.2

References

  1. 1.
    A.W. Sangster, K.L. Stuart, Chem. Rev. 65, 69 (1965)Google Scholar
  2. 2.
    J. Holubek, O. Strouf, Spectral Data and Physical Constants of Alkaloids, vol. 1 (Prague Publishing House, Czechoslovak Academy of Sciences/Heyden & Son, London, 1965), No. 59Google Scholar
  3. 3.
    R.H.F. Manske (ed.), The Alkaloids, Chemistry and Physiology (Academic, New York, 1971). 13, 3Google Scholar
  4. 4.
    T.J. Batterham, K.H. Bell, U. Weiss, Aust. J. Chem. 18, 1799 (1965)Google Scholar
  5. 5.
    F.I. Carroll, C.G. Moreland, G.A. Brine, J.A. Kepler, J. Org. Chem. 41, 996 (1976)Google Scholar
  6. 6.
    H. Corrodi, E. Hardegger, Helv. Chim. Acta 38, 2038 (1955)Google Scholar
  7. 7.
    J.M. Lindsey, W.H. Barnes, Acta Cryst. 8, 227 (1955)Google Scholar
  8. 8.
    G. Chari, A. Gulati, R. Bhat, I.R. Tebbett, J. Chromatogr. 571, 263 (1991)Google Scholar
  9. 9.
    M.D. Mashkovskii, Drugs [in Russian], vol. 1 (Meditsina, Moscow, 1984), p. 171Google Scholar

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© Springer Science+Business Media New York 2013

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