Description
Protopine is a benzylisoquinoline alkaloid occurring in opium poppy, Corydalis tubers and other plants of the family papaveraceae, like Fumaria officinalis. It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an analgesic..
Synonyms
Protopine (hydrochloride); Protopine HCl; 7,13a-Secoberbin-13a-one, 7-methyl-2,3:9,10-bis(methylenedioxy)-, hydrochloride
IUPAC Name
15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.04,12.06,10.018,22]tetracosa-1(17),4,6(10),11,18(22),23-hexaen-3-one; hydrochloride
Molecular Formula
C20H20ClNO5
Canonical SMILES
CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3.Cl
InChI
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
InChIKey
NWNVDSJZGYDVQW-UHFFFAOYSA-N
Solubility
Slightly in water, practically not in alcohol
Storage
Store at +4 °C, in dark place.
Safety Statements
36/37/39-45
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.