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(−)-Roemerine

Reference work entry

CAS Registry Number: 548-08-3 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Isoquinoline Alkaloids – Aporphine Alkaloids

Biological sources: Roemeria refracta

C18H17NO2: 279.1259

Mp: 102–103°C (Et2O) [1]; 87–88°C (Et2O) [2]; 95–97°C, 247–252°C (hydrochloride, H2O) [3]; 240°C (hydrochloride) [4]

[α]D −77° (EtOH) [1], −71° (EtOH) [2]

UV: 234, 264 sh, 273, 285 sh, 293 sh, 318 [3]; 234, 272, 312(4.17, 4.21, 3.52) [4]

IR: 1400, 1360, 1053, 940 [3]

MSm/z: 279(M+), 278, 264, 249, 139.5(++) [3, 4]

1H NMR: 2.46(3H, s, NCH3), 5.80, 5.95(each 1H, d, J = 1.5, CH2O2), 6.45(1H, s), 7.08–7.66(3H, m), 8.00(1H, m, H-11) [3]; 2.7(3H, s, N–CH3), 6.0, 6.04(each 1H, d, CH2O2), 6.68 (1H, H-3), 7.36(3H, m, H-8, H-9, H-10), 7.82(1H, m, H-11) [4]

Synthesis: from anonaine [4]

HPLC: [5]

Pharm./Biol.: LD505079.5, 38.8 mg/kg (s/c, i/v, mice); 26.4 mg/kg (i/v, rabbits); 114 mg/kg (s/c, frogs). Causes an increase in excitability, convulsions, vomiting. In dogs, in...

References

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    R.A. Konovalova, S.Yu. Yunusov, A.P. Orekhov, Zh. Obshch. Khim. 9(1356), 1507 (1939)Google Scholar
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    S.Yu. Yunusov, V.A. Mnatsakanyan, S.T. Akramov, DAN UzSSR (8), 43 (1961)Google Scholar
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    H. Guinaudeau, M. Leboeuf, A. Cave, Lloydia 38, 275 (1975)Google Scholar
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    D.S. Bhakuni, S. Tewari, M.M. Dhar, Phytochemistry 11, 1819 (1972)Google Scholar
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    M. Hutin, A. Oztekin, A. Cave, J.P. Foucher, J. Chromatogr. 265, 139 (1983)Google Scholar
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    F.S. Sadritdinov, A.G. Kurmukov, The Pharmacology of the Plant Alkaloids and Their Use in Medicine [in Russian] (UzSSR, Tashkent, 1980), p. 223Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

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