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Graveoline (Foliosine)

Reference work entry

CAS Registry Number: 485-61-0 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinoline Alkaloids

Biological sources: Haplophyllum dubium, H. foliosum, H. perforatum, Ruta graveolens

C17H13NO3: 279.0895

Mp: 188°C (hydrated form, EtOH–H2O), 204–205°C (anhydrous form, EtOH), 254°C (hydrochloride), 250°C (hydrobromide), 226°C (hydroiodide), 171°C (nitrate), 211°C (methiodide), 231°C (perchlorate) [1]

Solubility: spar. sol. MeOH, Me2CO, EtOH; insol. Et2O, CHCl3 [1]

UV: 214, 244, 275, 294 sh, 326, 338 (4.30, 4.28, 3.77, 3.78, 4.03, 4.04) [2]

IR: 1623, 1602, 1574, 1492, 1250, 927, 885, 841, 819, 730 [3]

MSm/z: 279(M+, 100), 278(8), 251(58), 220, 192, 165 [3]

1H NMR(CF3COOH): 3.83(3H, s, NCH3), 5.67(2H, s, CH2O2), 6.60–6.63(3H, m, H–Ar), 6.86(1H, s, H-3), 7.52(1H, m, H-8), 7.76(2H, m, H-7, H-6), 8.22(1H, d, J = 9, H-5) [2]

Pharm./Biol.: LD50 363.5, 410 mg/kg (i/p., oral, mice). Respiratory analeptic. Tones the cardiovascular system [4, 5]

References

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    G.P. Sidyakin, M. Eskairov, S.Yu. Yunusov, Zh. Obshch. Khim. 30, 338 (1960)Google Scholar
  2. 2.
    D.M. Razakova, I.A. Bessonova, S.Yu. Yunusov, Chem. Nat. Comp. 8, 737 (1972)Google Scholar
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    R. Shakirov, M.V. Telezhenetskaya, I.A. Bessonova, S.F. Aripova, I.A. Israilov, M.N. Sultankhodzhaev, V.I. Vinogradova, V.I. Akhmedzhanova, T.S. Tulyaganov, B.T. Salimov, V.A. Tel’nov, Chem. Nat. Comp. 32, 216 (1996)Google Scholar
  4. 4.
    S.F. Fakhrutdinov, The Pharmacology of Alkaloids and Their Derivatives [in Russian] (FAN, Tashkent, 1972), p. 64Google Scholar
  5. 5.
    M.B. Sultanov, The Pharmacology of Plant Substances [in Russian] (FAN, Tashkent, 1976), p. 3Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

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