Phellodendrine

Last updated
Phellodendrine
Phellodendrine.png
Names
IUPAC name
2,11-Dihydroxy-3,10-dimethoxyberbin-7α-ium
Systematic IUPAC name
(7S,13aS)-2,11-Dihydroxy-3,10-dimethoxy-7-methyl-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-7-ium
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1/C20H23NO4/c1-21-5-4-12-8-19(24-2)18(23)10-15(12)16(21)6-13-7-17(22)20(25-3)9-14(13)11-21/h7-10,16H,4-6,11H2,1-3H3,(H-,22,23)/p+1/t16-,21-/m0/s1
    Key: RBBVPNQTBKHOEQ-ZJYUTNJKBY
  • O(c1cc3c(cc1O)C[C@H]4c2c(cc(OC)c(O)c2)CC[N@+]4(C3)C)C
Properties
C20H24NO4
Molar mass 342.4083 g/mol
Melting point 258 °C (496 °F; 531 K) (as iodide)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Phellodendrine is an alkaloid isolated originally from Phellodendron amurense (Rutaceae). [1] [2]

See also

Related Research Articles

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Phellodendron, or cork-tree, is a genus of deciduous, dioecious trees in the family Rutaceae, native to east and northeast Asia. It has leathery, pinnate leaves and yellow, clumped flowers. The name refers to the thick and corky bark of some species in the genus.

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<i>Phellodendron amurense</i> Species of tree

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<span class="mw-page-title-main">Apparicine</span> Chemical compound

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References

  1. SHIMAMOTO K, JUJIHARA M, TORII H (March 1962). "[Pharmacological studies on phellodendrine, the quaternary ammonium alkaloid isolated from Phellodendron amurense, a type of Rutaceae.]". Nippon Yakurigaku Zasshi. Folia Pharmacologica Japonica (in Japanese). 58: 138–49. doi: 10.1254/fpj.58.138 . PMID   13911932.
  2. Mori H, Fuchigami M, Inoue N, Nagai H, Koda A, Nishioka I, Meguro K (February 1995). "Principle of the bark of Phellodendron amurense to suppress the cellular immune response: effect of phellodendrine on cellular and humoral immune responses". Planta Medica. 61 (1): 45–9. doi:10.1055/s-2006-957997. PMID   7700991.