Chelerythrine

Title: Chelerythrine
CAS Registry Number: 34316-15-9
CAS Name: 1,2-Dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridinium
Additional Names: toddaline
Molecular Formula: [C21H18NO4]+
Literature References: From root of Chelidonium majus L., Papaveraceae: Kratzmann, Pharm. Monatsh. 5, 161 (1924), C.A. 18, 34062 (1924); Platonova et al., J. Gen. Chem. USSR 26, 181 (1956). Structure: Späth, Kuffner, Ber. 64, 1123 (1931); N. Decaudain et al., Ann. Pharm. Fr. 35, 521 (1977). Identity with toddaline: Govindachari, Thyagarajan, J. Chem. Soc. 1956, 769. Synthesis of chelerythrine chloride: Bailey, Worthing, ibid. 4535; S. V. Kessar et al., J. Org. Chem. 53, 1708 (1988). Pharmacology: Chelombit'o, Murav'eva, Aktual. Probl. Farmakol. Farm. Vses. Nauchn. Konf. 1971, 183, C.A. 76, 112g (1972).
Properties: Crystals from chloroform + methanol, mp 207° [Manske, Can. J. Res. 21B, 140 (1943)]. The free base is colorless, but its quaternary salts are yellow. Aq solns of base and salts show violet fluorescence. uv spectrum of chelerythrine chloride: Hruban et al., Collect. Czech. Chem. Commun. 35, 3420 (1970).
Melting point: mp 207° [Manske, Can. J. Res. 21B, 140 (1943)]
Chelidonic Acid Chelidonine CHES Chimaphilin Chimonanthine

Chelerythrine
Chelerythrine.png
Identifiers
CAS number 34316-15-9 N
PubChem 2703
ChemSpider 2602 YesY
UNII E3B045W6X0 YesY
ChEMBL CHEMBL258893 N
Jmol-3D images Image 1
Properties
Molecular formula C21H18NO4
Molar mass 348.37 g mol−1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Chelerythrine is a benzophenanthridine alkaloid extracted from the plant Greater celandine (Chelidonium majus). It is a potent, selective, and cell-permeable protein kinase C inhibitor.[1] It is also the major active natural product found in the plant Zanthoxylum clava-herculis, exhibiting anti-bacterial activity against Staphylococcus aureus.[2]