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Lirinine (3-Hydroxynuciferine)

Reference work entry

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

Biological sources: Liriodendron tulipiferum

C19H21NO3: 311.1521

Mp: 152–154°C (EtOH), 255°C (dec., hydrochloride) [1]

[α]D −55° (CHCl3) [1]

Solubility: spar. sol. C6H6, EtOH, Me2CO; very sol. CHCl3, MeOH [1]

UV: 223, 284(4.42, 4.17) [1]

IR: 3400–3100, 2850, 1590, 1290 [1]

MSm/z: 311(M+, 100), 310, 296, 294, 280, 253, 237, 155.5(++) [1]

1H NMR: 2.45(3H, s, NCH3), 3.63, 3.81(each 3H, s, 2×OCH3), 7.22–7.28(3H, m, H-8, H-9, H-10), 8.15(1H, dd, J = 7.5; 0.8, H-11) [1]

Pharm./Biol.: LD50 28.105 mg/kg (i/v, s/c). Relaxes the smooth musculature. Exerts a hypotensive and spasmolytic action. Enhances the action of caffeine and arecoline on combined use [2]

References

  1. 1.
    R. Ziyaev, A. Abdusamatov, S.Yu. Yunusov, Chem. Nat. Comp. 9, 59 (1973)Google Scholar
  2. 2.
    Kh.U. Aliev, The Pharmacology of Plant Substances [in Russian] (Fan, Tashkent, 1976), p. 111Google Scholar

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© Springer Science+Business Media New York 2013

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