Sanguinarine

Sanguinarine

Clinical data
ATC code	none
Identifiers
IUPAC name 13-Methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium
CAS Number	2447-54-3 N
PubChem CID	5154
ChemSpider	4970 Y
UNII	AV9VK043SS
ChEBI	CHEBI:17183 Y
ChEMBL	CHEMBL417799 Y
ECHA InfoCard	100.017.731
Chemical and physical data
Formula	C20H14NO4
Molar mass	332.09
3D model (Jmol)	Interactive image
SMILES O1c3c(OC1)c2c[n+](c5c(c2cc3)ccc6cc4OCOc4cc56)C
InChI InChI=1S/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1 Y Key:INVGWHRKADIJHF-UHFFFAOYSA-N Y
NY (what is this?)

Sanguinarine is a toxic polycyclic quaternary ammonium salt. It is extracted from some plants, including bloodroot (Sanguinaria canadensis), Mexican prickly poppy Argemone mexicana,Chelidonium majus and Macleaya cordata.

Sanguinarine is a toxin that kills animal cells through its action on the Na⁺-K⁺-ATPase transmembrane protein.Epidemic dropsy is a disease that results from ingesting sanguinarine.

If applied to the skin, sanguinarine may cause a massive scab of dead flesh, called an eschar. For this reason, sanguinarine is termed an escharotic.

Preliminary pre-clinical in vitro and in vivo studies have demonstrated that sanguinarine causes apoptosis in human cancer cells, and recommend study of sanguinarine as a potential cancer treatment. A study conducted by the Case Western Reserve University in 2000 found that low doses of sanguinarine caused this apoptosis in cancerous human epidermoid carcinoma cells while little reaction from normal human skin cells was observed. However, no products containing sanguinarine are currently approved by the FDA for the treatment of cancer; the FDA warns that unapproved bloodroot preparations are ineffective and dangerous.

In plants, sanguinarine is synthesized from dihydrosanguinarine through the action of dihydrobenzophenanthridine oxidase.