CAS Registry Number: 113-15-5
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-d6): [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″ |
129.9 |
10 |
136.0 |
6′ |
164.2... |
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References
A.N. Ban’kovskaya, A.I. Ban’kovskii, Trudy VILAR, Lekarstvennye rasteniya 15, 368 (1969)
J. Holubek, O. Strouf, Spectral Data and Physical Constants of Alkaloids, (Prague Publishing House, Czechoslovak Academy of Sciences/Heyden & Son, London, 1965), 1, No. 111
A.N. Ban’kovskaya, A.I. Ban’kovskii, A.I. Shalagina, N.I. Ostrovskii, Med. Prom. SSSR (11), 18 (1964)
M. Shamma, D.M. Hindenlang, Carbon- 13 NMR Shift Assignments of Amines and Alkaloids (Plenum Press, New York/London, 1979). No. 245
H. Potter, M. Hulm, S. Schumann, J. Chromatogr. 319, 440 (1985)
F.S. Sadritdinov, A.G. Kurmukov, The Pharmacology of the Plant Alkaloids and Their Use in Medicine [in Russian] (UzSSR, Tashkent, 1980), p. 111
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(2013). Ergotamine. In: Azimova, S.S., Yunusov, M.S. (eds) Natural Compounds. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-0560-3_938
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