CAS Registry Number: 115-53-7
Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Isoquinoline Alkaloids
Biological sources: Menispermum dayricum
C19H23NO4: 329.1627
Mp: 161–162°C (Et2O), 180–181°C (EtOH) [1], 231°C (hydrochloride), 231°C (hydrobromide), 218°C (nitrate), 233°C (hydroiodide), 217°C (perchlorate), 162°C (picrate) [1]
[α]D −79° (EtOH)
Solubility: very sol. CHCl3, MeOH; spar. sol. H2O, pet. ether [1]
UV(hydrochloride): 262(3.69) [2]
IR(hydrochloride): 3370, 1700, 1642, 1496, 1283, 1205, 1150, 1056, 1000, 893, 792 [2]
13 C NMR: [3]
Table 1
C-1 |
117.9 |
C-7 |
152.3 |
C-13 |
40.5 |
2 |
109.1 |
8 |
115.3 |
14 |
45.7 |
3 |
145.2 |
9 |
56.6 |
15 |
35.8 |
4 |
144.8 |
10 |
24.4 |
16 |
47.1 |
5 |
49.1 |
11 |
130.3 |
NCH3 |
42.5 |
6 |
193.4 |
12 |
122.7 |
3-OCH3 |
55.8 |
7-OCH3 |
54.6 |
Pharm./Biol.: Hypotensive and weak ganglioblocking action [1]
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References
T.N. Il’inskaya, Trudy VILAR [Proceedings of the All-Union Scientific Research Institute of Drugs], Drugs [in Russian], 11, 51 (1959)
J. Holubek, O. Strouf, Spectral Data and Physical Constants of Alkaloids, vol. 2 (Prague Publishing House, Czechoslovak Academy of Sciences/Heyden & Son, London, 1966), No. 251
V. Terui, K. Tori, S. Maeda, K. Sawa, Tetrahedron Lett. 16, 2853 (1975)
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(2013). Sinomenine. In: Azimova, S.S., Yunusov, M.S. (eds) Natural Compounds. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-0560-3_915
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