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sanguinarine

Chemical Structure

General Material Information

Preferred name sanguinarine
Trivial Name Sanguinarine
Short Description [1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, 13-methyl-
Formula C20 H14 N O4
CAS Number 2447-54-3
FDA UNII AV9VK043SS
Nikkaji Number J7.576K
Beilstein Number 3915507
MDL MFCD00064925
xLogP3-AA 4.40 (est)
Bio Activity Summary External link
NMR Predictor External link
Applications
  • pharmaceuticals / chemical synthisis
Synonyms
  • (1,3)- benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridinium, 13-methyl-
  • [1,3] benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, 13-methyl-
  • dimethylenedioxy benzphenanthridine
  • 13- methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium
  • 13- methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium
  • 13- methyl[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium
  • sanguinarin
  • sanguiritrin
  • sangvinarin
  • veadent
  • viadent
  • [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, 13-methyl-
  • 13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium
  • Pseudochelerythrine
  • Sanguinarium
  • Sangrovit
  • UI5

Occurrences

argemone mexicana
poppy opium poppy
sanguinaria canadensis

Potential Uses

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5154
Pubchem (sid):134981925
Publications by PubMed
Identification of sanguinarine metabolites in pig liver preparations by accurate mass measurements using electrospray ionization hybrid ion trap/time-of-flight mass spectrometry.
Inhibitory effects of sanguinarine on human liver cytochrome P450 enzymes.
Sanguinarine suppresses prostate tumor growth and inhibits survivin expression.
[Testing of the potentially probiotic lactobacilli for use in food supplements].
Phenotype of hepatic xenobiotic metabolizing enzymes and CYP450 isoforms of sanguinarine treated rats: effect of P450 inducers on its toxicity.
Effect of argemone oil and argemone alkaloid, sanguinarine on Sertoli-germ cell coculture.
Investigation of sanguinarine and chelerythrine effects on CYP1A1 expression and activity in human hepatoma cells.
In vivo DNA damaging potential of sanguinarine alkaloid, isolated from argemone oil, using alkaline Comet assay in mice.
Quaternary benzo[c]phenathridine alkaloids sanguinarine and chelerythrine do not affect transcriptional activity of aryl hydrocarbon receptor: analyses in rat hepatoma cell line H4IIE.luc.
Effect of sanguinarine on the transport of essential nutrients in an everted gut sac model: role of Na+,K(+)-ATPase.
Sanguinarine and chelerythrine: assessment of safety on pigs in ninety days feeding experiment.
Outbreak of epidemic dropsy in Ethiopia: the clinical and therapeutic observation.
Identification of new inhibitors for human hematopoietic prostaglandin D2 synthase among FDA-approved drugs and other compounds.
Skin tumor promotion by argemone oil/alkaloid in mice: evidence for enhanced cell proliferation, ornithine decarboxylase, cyclooxygenase-2 and activation of MAPK/NF-kappaB pathway.
The plant alkaloid sanguinarine is a potential inhibitor of follicular angiogenesis.
Biometabolic elimination and organ retention profile of argemone alkaloid, sanguinarine, in rats and guinea pigs.
Laboratory investigation of epidemic dropsy in Addis Ababa, Ethiopia.
Outbreak investigation of epidemic dropsy in Addis Ababa, Ethiopia:.
Interaction of sanguinarine alkaloid, isolated from argemone oil, with hepatic cytochrome p450 in rats.
Removal of sanguinarine from edible oils contaminated with argemone oil.
Sanguinarine in the blood and urine of cases of epidemic dropsy.
Protective effect of topical application of α-tocopherol and/or N-acetyl cysteine on argemone oil/alkaloid-induced skin tumorigenesis in mice.
Epidemic dropsy: case report and the morphologic features in a patient who died at Tikur Anbessa Specialized Hospital.
Special issue on epidemic dropsy.
Integration of transcriptome, proteome and metabolism data reveals the alkaloids biosynthesis in Macleaya cordata and Macleaya microcarpa.
Food contamination.
Clinicoepidemiological, toxicological, and safety evaluation studies on argemone oil.
In vitro growth-inhibitory effect of plant-derived extracts and compounds against Paenibacillus larvae and their acute oral toxicity to adult honey bees.
Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals.
Epidemic dropsy in India.
Natural feed additive of Macleaya cordata: safety assessment in rats a 90-day feeding experiment.
Epidemic dropsy in Andhra Pradesh due to contaminated ghee.
Epidemic dropsy in Trans Yamuma areas of Delhi and U.P.
Safety evaluation studies on argemone oil through dietary exposure for 90days in rats.
Epidemic dropsy in New Delhi.
Argemone oil poisoning.
Variability in the yield of benzophenanthridine alkaloids in wildcrafted vs cultivated bloodroot (Sanguinaria canadensis L.).
An out-break of epidemic dropsy in the Barabanki District of Uttar Pradesh, India: a limited trial for the scope of antioxidants in the management of symptoms.
Epidemic dropsy in the eastern region of Nepal.
Argemone oil induced cellular damage in the reproductive tissues of transgenic Drosophila melanogaster: protective role of 70 kDa heat shock protein.
The octadecanoic pathway: signal molecules for the regulation of secondary pathways.
Sodium retention from mouthwashes.
[Plaque and plaque control].
Epidemic dropsy: observations on pathophysiology and clinical features during the Delhi epidemic of 1998.
Argemone mexicana and epidemic dropsy: phytopharmacology and putative sequelae and therapy.
Epidemic dropsy: atypical presentation.
The toxicity and pharmacokinetics of dihydrosanguinarine in rat: a pilot study.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C06162
HMDB (The Human Metabolome Database):HMDB29367
FooDB:FDB000436
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 332.33538818359
Flash Point TCC Value N/a
logP (o/w) -0.653 est
Solubility
water, 3.316 mg/L @ 25 °C (est) Yes

Safety Information

Safety information

Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 18 mg/kg
"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(1), Pg. 195, 1982.

intravenous-mouse LD50 19400 ug/kg
BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Farmakologiya i Toksikologiya Vol. 29, Pg. 76, 1966.

intraperitoneal-rat LD50 18 mg/kg
Indian Journal of Cancer. Vol. 5, Pg. 183, 1968.

intravenous-rat LD50 28700 ug/kg
Toxicologist. Vol. 5, Pg. 176, 1985.

oral-rat LD50 1660 mg/kg
Toxicologist. Vol. 5, Pg. 176, 1985.

Dermal Toxicity:
subcutaneous-cat LD50 120 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.

subcutaneous-dog LD50 70 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.

subcutaneous-frog LD50 70 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.

subcutaneous-mouse LD50 80 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.

subcutaneous-rabbit LD50 125 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.

Inhalation Toxicity:
inhalation-rat LC50 2200000 mg/m3
Toxicologist. Vol. 5, Pg. 176, 1985.

Safety in use information

Category:
pharmaceuticals / chemical synthisis
Recommendation for sanguinarine usage levels up to:
not for fragrance use.
Recommendation for sanguinarine flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5154
National Institute of Allergy and Infectious Diseases:Data
Chemidplus:0002447543