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Ergotamine

Reference work entry

CAS Registry Number: 113-15-5 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Miscellaneous Alkaloids

Biological sources: Claviceps purpurea

C33H35N5O5: 581.2638

Mp: 184°C (dec., Me2CO) [1], 212–214°C [2]; 184°C (dec., sulfate), 203°C (dec., hydrochloride), 204°C (dec., hydrobromide), 193°C (dec., tartrate) [1]; 194.5°C (dec., sulfate) [3]

[α]D −160° (CHCl3) [2]

Solubility: very sol. CHCl3, EtOH, MeOH, Me2CO; insol. H2O [1]

UV: 240, 312(4.33, 3.99) [2]

IR: 1732, 1647, 1609, 1570, 1558, 1538, 1518, 1485, 1316, 1306, 1294, 1283, 1266, 1250, 1228, 1197, 1181, 1160, 1141, 1123, 1100, 1082, 1068, 1048, 1030, 996, 979, 954, 922, 915, 890, 877, 867, 850, 818, 807, 794, 762, 752, 745 [2]

IR(LiF): 3520, 3375, 3230 [2]

13 C NMR (DMSO-d 6): [ 4]

Table 1

C-2

119.4

C-13

122.2

C-10′

25.9

 3

108.8

 14

110.2

 11′

63.9

 4

26.6

 15

133.8

 12′

102.8

 5

62.4

 16

174.3

 13′

23.8

 7

55.1

  2′

85.9

  1″

38.7

 8

42.5

  3′

165.8

  2″

138.7

 9

118.3

  5′

56.1

3″, 7″

References

  1. 1.
    A.N. Ban’kovskaya, A.I. Ban’kovskii, Trudy VILAR, Lekarstvennye rasteniya 15, 368 (1969)Google Scholar
  2. 2.
    J. Holubek, O. Strouf, Spectral Data and Physical Constants of Alkaloids, (Prague Publishing House, Czechoslovak Academy of Sciences/Heyden & Son, London, 1965), 1, No. 111Google Scholar
  3. 3.
    A.N. Ban’kovskaya, A.I. Ban’kovskii, A.I. Shalagina, N.I. Ostrovskii, Med. Prom. SSSR (11), 18 (1964)Google Scholar
  4. 4.
    M. Shamma, D.M. Hindenlang, Carbon- 13 NMR Shift Assignments of Amines and Alkaloids (Plenum Press, New York/London, 1979). No. 245CrossRefGoogle Scholar
  5. 5.
    H. Potter, M. Hulm, S. Schumann, J. Chromatogr. 319, 440 (1985)CrossRefGoogle Scholar
  6. 6.
    F.S. Sadritdinov, A.G. Kurmukov, The Pharmacology of the Plant Alkaloids and Their Use in Medicine [in Russian] (UzSSR, Tashkent, 1980), p. 111Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

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