2051. Chelerythrine

Nomenclature

CAS number: 34316-15-9
1,2-Dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridinium; toddaline.
[C21H18NO4]+.

Description and 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: Sp"ath, 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).

Chemical structure

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).