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Sophoramine

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Natural Compounds
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CAS Registry Number: 6882-66-2

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinolizidine Alkaloids

Biological sources: Leptorhabdos parviflora, Sophora alopecuroides, S. griffithii, S. pachycarpa

C15H20N2O: 244.1576

Mp: 164–165°C (pet. ether), 231°C (picrate), 248°C (dec., hydrochloride), 175°C (picrolonate), 247°C (chloroplatinate), 296°C (hydroiodide) [1]

[α]D −91° (EtOH)

Solubility: very sol. EtOH, C6H6, CHCl3; sol. Et2O, pet. ether; spar. sol. H2O [1]

UV: 234, 310(3.80, 3.90) [2]

IR: 2800–2700, 1645, 1580, 1560 [2]

MS m/z: 244(M+, 94), 243(100), 229(3), 215(14), 201(13), 186(12), 159(8), 149(8), 136(21), 122(5), 110(8), 98(3), 97(4), 96(8), 82(7), 55(11) [3, 4]

HPLC. GC: [5]

Pharm./Biol.: Tranquilizing action. Prolongs sleep induced by hexenal and barbital sodium [6]

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References

  1. A.P. Orekhov, Chem. Pharm. Prom. (5), 10 (1934)

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  2. W. Comin, V. Deulofeu, Aust. J. Chem. 12, 462 (1959)

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  3. T.E. Monakhova, O.N. Tolkachev, V.S. Kabanov, M.E. Perel’son, N.F. Proskurnina, Chem. Nat. Comp. 10, 477 (1974)

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  4. Yu.K. Kushmuradov, F.Sh. Eshbaev, A.K. Kasymov, S. Kuchkarov, Chem. Nat. Comp. 15, 306 (1979)

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  5. X. Chen, C.Q. Yi, X.Q. Yang, X. Wang, J. Chromatogr. B 812, 149 (2004)

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  6. M.P. Bichkhanov, B.-D.V. Badyaraev, T.E. Monakhova, E.A. Trutneva, O.N. Tolkachev, Rast. Res. 26, 387 (1990)

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(2013). Sophoramine. In: Azimova, S.S., Yunusov, M.S. (eds) Natural Compounds. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-0560-3_1258

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