Protopine

Protopine
Names
	IUPAC name 7-Methyl-2′H,2′′H-7,13a-secobis([1,3]dioxolo)[4′,5′:2,3;4′′,5′′:9,10]berbin-13a-one
	Systematic IUPAC name 5-Methyl-4,6,7,14-tetrahydro-2H,10H-bis([1,3]benzodioxolo)[4,5-c:5′,6′-g]azecin-13(5H)-one
Identifiers
CAS Number	130-86-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16415 ;
ChEMBL	ChEMBL486179 ;
ChemSpider	4799 ;
ECHA InfoCard	100.004.546
EC Number	204-999-6;
KEGG	C05189 ;
PubChem CID	4970;
UNII	UIW569HT35 ;
CompTox Dashboard (EPA)	DTXSID90156282 ;
	InChI InChI=1S/C20H19NO5/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 Key: GPTFURBXHJWNHR-UHFFFAOYSA-N ; InChI=1/C20H19NO5/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 Key: GPTFURBXHJWNHR-UHFFFAOYAW;
	SMILES c15cc3OCOc3cc5CCN(C)Cc2c(CC1=O)ccc4c2OCO4;
Properties
Chemical formula	C20H19NO5
Molar mass	353.369 g/mol
Appearance	white crystals
Density	1.399 g/cm3
Melting point	208 °C (406 °F; 481 K)
Solubility in water	practically insoluble
Solubility in chloroform	1:15
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Protopine is an alkaloid occurring in opium poppy, Corydalis tubers and other plants of the family papaveraceae, like Fumaria officinalis. Protopine is metabolically derived from the benzylisoquinoline alkaloid (S)-Reticuline through a progressive series of five enzymatic transformations: 1) berberine bridge enzyme to (S)-Scoulerine; 2) (S)-cheilanthifoline synthase/CYP719A25 to (S)-Cheilanthifoline; 3) (S)-stylopine synthase/CYP719A20 to (S)-Stylopine; 4) (S)-tetrahydroprotoberberine N-methyltransferase to (S)-cis-N-Methylstylopine; and ultimately, 5) N-methylstylopine hydroxylase to protopine.

It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an analgesic.