Basic information
- CAS
1099738-80-3- Standard SMILES
C[n+]1cc2c3c(ccc2c2ccc4cc5c(cc4c21)OCO5)OCO3.[Cl-]- InChIKey
GIZKAXHWLRYMLE-UHFFFAOYSA-M- Molecular formula
- C20H14NO4.Cl
- Average molar mass
- 367.8 g/mol
- Monoisotopic mass
- 367.0611356
Overview
Sanguinarine is found in opium poppy. Consumption of Sanguinarine, present in poppy seeds and in the oil of <i>Argemone mexicana</i> which has been used as an adulterant for mustard oil in India, has been linked to development of glaucoma. Sanguinarine is banned by FDA. Sanguinarine is a quaternary ammonium salt from the group of benzylisoquinoline alkaloids. It is extracted from some plants, including bloodroot (Sanguinaria canadensis), Mexican prickly poppy Argemone mexicana, Chelidonium majus and Macleaya cordata. It is also found in the root, stem and leaves of the opium poppy but not in the capsule. 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. Sanguinarine has been shown to exhibit antibiotic, anti-apoptotic, anti-fungal, anti-inflammatory and anti-angiogenic functions Sanguinarine belongs to the family of Benzoquinolines. These are organic compounds containing a benzene fused to a quinoline ring system. (A3208, A3209, A3208, A3208, A3208).
Names & identifiers
- Preferred name
- Sanguinarine chloride
- IUPAC
- 24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene chloride
- English name
- SANGUINARINE CHLORIDE
- Molecular formula
- C20H14ClNO4
- Molecular weight
- 367.78
Names & synonyms
SANGUINARINE CHLORIDERefChem:884540621-641-85578-73-4Sanguinarium ChlorideSanguinarine hydrochlorideViadentSanguinarine chloride hydrateSanguinarine (chloride)MFCD0001212613-methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium chloride[1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium,13-methyl-, chloride (1:1)
Show more names
SanguinariumSANGUINARINE HCLSANGUINARINE(SH)PSEUDOCHELERYTHRINESPECIOCILIATINE(SH)sanguinariumchlorideSANGUINARINE HCl hplcSanguinarine Choloride
CHEMBL490129B8Z8J4400HPseudochelerythrine chloride;Sanguinarium chloride(1,3)Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridinium, 13-methyl-, chloride13-Methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i] phenanthridinium chloride24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene;chlorideSanguinarine, chlorideSanguinarium chloride [USAN:INN]
Properties
Computed structural properties
- Topological polar surface area
- 40.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 530
Physicochemical properties
- Melting point
- 281 · 281-285°C
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- 20 mg/mL, · methanol: 20 mg/mL, clear, orange
- form
- Orange solid.
- color
- Orange to Dark Orange
- Water Solubility
- 2 O: · H2O: slightly soluble methanol: 3.8mg/mL
- Stability
- Hygroscopic, Light Sensitive
- InChI
- InChI=1S/C20H14NO4.ClH/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;1H/q+1;/p-1
- InChIKey
- GIZKAXHWLRYMLE-UHFFFAOYSA-M
- SMILES
- C12[N+](C)=CC3=C4OCOC4=CC=C3C1=CC=C1C=C3OCOC3=CC=21.[Cl-]
- FDA UNII
- 8 Z8J4400H · B8Z8J4400H
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 2 notifications to the ECHA C&L Inventory.
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Hazard information
Regulatory InformationChemical: [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, 13-methyl-, chloride
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazard Classes and Categories
Acute Tox. 4 (97.6%)
Acute Tox. 4 (100%)
Toxicology
Toxicity Summary
Sanguinarine, at micromolar concentrations, imparts cell growth inhibitory response in human squamous carcinoma (A431) cells via an induction of apoptosis. This is while sanguinarine treatment did not result in apoptosis of the normal human epidermal keratinocytes at similar dose. Sanguinarine [0.1 (M-2 (M)] treatment to HaCaT cells was found to inhibit in a dose-dependent manner the cell proliferation and induce apoptosis, as measured by 3-(4,5 dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay and ELISA, respectively. Sanguinarine treatment also resulted in a significant cleavage of poly(ADP-ribose) polymerase in HaCaT cells. Sanguinarine treatment to HaCaT cells resulted in a dose-dependent (a) increase in the level of Bax with a concomitant decrease in Bcl-2 levels and (b) increase in Bax/Bcl-2 ratio. Sanguinarine also resulted in significant increases in the proapoptotic members of Bcl-2 family proteins, i.e., Bak and Bid. This was accompanied by increase in (a) protein expression of cytochrome c and apoptotic protease-activating factor-1 and (b) activity and protein expression of caspase-3, caspase-7, caspase-8, and caspase-9. This indicates the involvement of mitochondrial pathway and Bcl-2 family proteins during sanguinarine-mediated apoptosis of immortalized keratinocytes. (A15415)
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).
Uses & manufacturing
Uses
Sanguinarine is found in opium poppy. Consumption of Sanguinarine, present in poppy seeds and in the oil of <i>Argemone mexicana</i> which has been used as an adulterant for mustard oil in India, has been linked to development of glaucoma. It is also found in the root, stem and leaves of the opium poppy but not in the capsule. Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. These are organic compounds containing a benzene fused to a quinoline ring system.
Applications
UsesSanguinarium Chloride is a natural product with antimicrobial, anti-inflammatory, and anti-oxidant properties. Sanguinarium Chloride has antiproliferative, pro-apoptosis effects in some cancer cell lines.
Usesantineoplastic, antiplaque agent
UsesSanguinarine chloride hydrate was tested for anti-schistosomal activities against Schistosoma mansoni.9 It was tested for anti-lipase activity against Candida rugosa lipase.10
General DescriptionThis substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
Upstream & downstream products
Related reactions
0 records
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Compound notes
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