Protopine hydrochloride

Base Information

• Chemical Name: Protopine hydrochloride
• CAS No.: 6164-47-2
• Molecular Formula: C20H19 N O5 . Cl H
• Molecular Weight: 353.37
• European Community (EC) Number: 228-196-5
• NSC Number: 11440
• UNII: 96481YJ70G
• DSSTox Substance ID: DTXSID70210654
• Wikidata: Q27271857
• ChEMBL ID: CHEMBL2165579
• Mol file: 6164-47-2.mol

Synonyms:4,6,7,14-tetrahydro-5-methyl-bis(1,3)benzodioxolo(4,5-c-5',6'-g)azecin-13(5H)-one;fumarine;protopine;protopine hydrochloride;protopine mesylate

Chemical Property of Protopine hydrochloride

Chemical Property:

• Vapor Pressure: 4.86E-12mmHg at 25°C
• Melting Point: 208oC
• Boiling Point: 547.5oC at 760 mmHg
• Flash Point: 284.9oC
• PSA: 57.23000
• LogP: 3.29720
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 389.1030004
• Heavy Atom Count: 27
• Complexity: 542

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Protopine hydrochloride ≥98%, solid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3.Cl
• Description: Protopine is an alkaloid found in Berberidaceae, Ranunculaceae, Rutaceae, Fumariaceae, and Papaveraceae with diverse biological activities. It inhibits platelet aggregation induced by ADP, arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607), platelet-activating factor (PAF), and collagen in rabbit platelet-rich plasma at a concentration of 100 μM. Protopine inhibits contraction of isolated rat thoracic aorta induced by norepinephrine and is a non-selective inhibitor of ICa, IK, IK1, and INa in guinea pig ventricular myocytes. Protopine inhibits the growth of H. pylori with an MIC50 value of 100 μg/ml. It reduces growth of PC3 and DU145 prostate cancer cells in a dose-dependent manner via induction of mitotic cell cycle arrest. Protopine (0.005 mg/kg) increases latency to first seizure in a mouse model induced by pentylenetetrazole .
• Uses: Protopine hydrochloride may be used in the calibration curve preparation for the quantification of alkaloids from Fumaria capreolata using liquid chromatography coupled to diode array detection and electrospray ionization tandem mass spectrometry (LC-DAD-MS) and tandem mass spectrometry(MS/MS). It may also be used as an alkaloid in cytotoxicity and permeability studies carcinogenic cell lines.