Title: Sanguinarine
CAS Registry Number: 2447-54-3
CAS Name: 13-Methyl[1,3]benzodioxolo[5,6-
c]-1,3-dioxolo[4,5-
i]phenanthridinium
Synonyms: pseudochelerythrine; y-chelerythrine
Molecular Formula: [C20H14NO4]+
Literature References: Principal alkaloid in sanguinaria extract. Isolated from the root of
Sanguinaria canadensis L., and other
Papaveraceae: Schmidt
et al., Arch. Pharm. 231, 145 (1893). Widely distributed in poppy-fumaria species; constituent of argemone oil: S. A. E. Hakim
et al., Nature 189, 198 (1961). Identity with pseudochelerythrine: Gadamer, Stichel,
ibid. 262, 488 (1924). Structure: Sp?th, Kuffner,
Ber. 64, 370, 2034 (1931); Beke,
Acta Chim. Acad. Sci. Hung. 17, 463 (1958). Biosynthesis: Leete,
J. Am. Chem. Soc. 85, 473 (1963). Synthesis: Dyke
et al., Tetrahedron Lett. 1968, 3933; Sainsbury
et al., J. Chem. Soc. C 1970, 1797; Onda
et al., Chem. Pharm. Bull. 17, 404 (1969);
19, 31 (1971); M. Hanaoka
et al., Chem. Lett. 22, 739 (1986). Purification procedure: Stipanovic
et al., J. Heterocycl. Chem. 9, 1453 (1972). Studies of effect of sanguinarine and argemone oil on intraocular pressure: S. A. E. Hakim,
Br. J. Ophthalmol. 38, 193 (1954); G. C. Dobbie, M. E. Langham,
ibid. 45, 81 (1961). Anti-inflammatory activity in rats: J. Lenfeld
et al., Planta Med. 43, 161 (1981). Clinical study of sanguinarine oral rinse as antiplaque agent: G. L. Southard
et al., J. Am. Dent. Assoc. 108, 338 (1984). Acute toxicity study: P. J. Becci
et al., J. Toxicol. Environ. Health 20, 199 (1987).
Review: M. Shamma,
The Isoquinoline Alkaloids (Academic Press, New York, 1972) pp 315-343. Symposium on chemistry, antimicrobial effects, clinical studies and toxicology:
J. Can. Dent. Assoc. 56, Suppl 7, 5-47 (1990).
Derivative Type: Monohydrate
Molecular Formula: C20H13NO4.H2O
Molecular Weight: 349.34
Percent Composition: C 68.76%, H 4.33%, N 4.01%, O 22.90%
Properties: Crystals from water, mp 278-280° (Stipanovic). Soluble in alcohol, chloroform, acetone, ethyl acetate.
Melting point: mp 278-280° (Stipanovic)
Derivative Type: Chloride
Trademarks: Viadent (Vipont)
Molecular Formula: C20H14ClNO4
Molecular Weight: 367.78
Percent Composition: C 65.31%, H 3.84%, Cl 9.64%, N 3.81%, O 17.40%
Properties: LD50 in male mice (mg/kg): 15.9 i.v.; in female mice (mg/kg): 102.0 s.c. (Lenfeld). LD50 in rats (mg/kg): 29 i.v.; 1658 orally (Becci).
Toxicity data: LD50 in male mice (mg/kg): 15.9 i.v.; in female mice (mg/kg): 102.0 s.c. (Lenfeld); LD50 in rats (mg/kg): 29 i.v.; 1658 orally (Becci)
Derivative Type: Chloride dihydrate
Molecular Formula: C20H14ClNO4.2H2O
Molecular Weight: 403.81
Percent Composition: C 59.49%, H 4.49%, Cl 8.78%, N 3.47%, O 23.77%
Properties: Fine orange needles, mp 273-274° (dec). uv max (methanol): 234, 283, 325 nm (log e 4.50, 4.52, 4.18).
Melting point: mp 273-274° (dec)
Absorption maximum: uv max (methanol): 234, 283, 325 nm (log e 4.50, 4.52, 4.18)
Use: In mouthwash and toothpaste.
