Phellodendrine

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

Phellodendrine
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
  • 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).
Infobox references

See also

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.


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