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P8489

Protopine hydrochloride

Name: Protopine hydrochloride
Brand: SIGMA

≥98%, solid

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₁₉NO₅·HCl

CAS Number:

6164-47-2

Molecular Weight:

389.83

NACRES:

NA.77

PubChem Substance ID:

329820328

UNSPSC Code:

51111800

EC Number:

228-196-5

MDL number:

MFCD00236406

Assay:

≥98%

Form:

solid

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Properties

Quality Segment

100

assay

≥98%

form

solid

storage temp.

2-8°C

SMILES string

Cl.CN1CCc2cc3OCOc3cc2C(=O)Cc4ccc5OCOc5c4C1

InChI

1S/C20H19NO5.ClH/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17;/h2-3,7-8H,4-6,9-11H2,1H3;1H

InChI key

NWNVDSJZGYDVQW-UHFFFAOYSA-N

Description

General description

Protopine is a celandine alkaloid and a bioactive compound associated with the plant families including fumariaceae, berberidaceae and papaveraceae. It is metabolized by demethylenation in the presence of the cytochrome enzymes cytochrome P450 family 2 subfamily d polypeptide 1 (CYP2D1) and cytochrome P450 family 2 subfamily c polypeptide 11 (CYP2C11).

Application

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.

Biochem/physiol Actions

Protopine hydrochloride is a Ca²⁺ channel blocker and antiplatelet agent.

Protopine possesses anti-parasitic, antimicrobial and anti-inflammatory property. It mediates mitotic arrest by favoring tubulin polymerization. Protopine elicits anti-invasive effects in breast cancer tumor progression.. It also provides protection against oxidative stress-induced cell death.

Disclaimer

Protect from light.

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

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