Protopine

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 373460923

| ImageFile = Protopine structure.svg

| ImageSize =

| ImageFile1 = Protopine-from-xtal-Mercury-3D-balls.png

| IUPACName = 7-Methyl-2′H,2′′H-7,13a-secobis([1,3]dioxolo)[4′,5′:2,3;4′′,5′′:9,10]berbin-13a-one

| SystematicName = 5-Methyl-4,6,7,14-tetrahydro-2H,10H-bis([1,3]benzodioxolo)[4,5-c:5′,6′-g]azecin-13(5H)-one

| Reference = {{cite book|title=The Merck Index|publisher=Merck & Co|location=New Jersey|year=1976|edition=9|page=1023}}

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 130-86-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = UIW569HT35

| PubChem = 4970

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 486179

| SMILES = c15cc3OCOc3cc5CCN(C)Cc2c(CC1=O)ccc4c2OCO4

| EINECS = 204-999-6

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4799

| 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

| InChIKey = GPTFURBXHJWNHR-UHFFFAOYAW

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = GPTFURBXHJWNHR-UHFFFAOYSA-N

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 16415

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C05189

}}

|Section2={{Chembox Properties

| Formula = C₂₀H₁₉NO₅

| MolarMass = 353.369 g/mol

| Appearance = white crystals

| Density = 1.399 g/cm³

| MeltingPtC = 208

| BoilingPt =

| Solubility = practically insoluble

| SolubleOther = 1:15

| Solvent = chloroform

}}

}}

Protopine is an alkaloid occurring in opium poppy,[http://www.thefreedictionary.com/Protopine The Free Dictionary: Protopine] Corydalis tubers{{cite journal|doi=10.1016/j.ejphar.2004.11.004|pmid=15588728|year=2004|last1=Jiang|first1=B|last2=Cao|first2=K|last3=Wang|first3=R|title=Inhibitory effect of protopine on K(ATP) channel subunits expressed in HEK-293 cells.|volume=506|issue=2|pages=93–100|journal=European Journal of Pharmacology}} and other plants of the family papaveraceae, like Fumaria officinalis.{{Cite journal

| last1 = Vrba | first1 = J.

| last2 = Vrublova | first2 = E.

| last3 = Modriansky | first3 = M.

| last4 = Ulrichova | first4 = J.

| title = Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR

| doi = 10.1016/j.toxlet.2011.03.015

| journal = Toxicology Letters

| volume = 203

| issue = 2

| pages = 135–141

| year = 2011

| pmid = 21419197

}} 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.{{Cite journal|last=Hagel|first=Jillian M|last2=Morris|first2=Jeremy S|last3=Lee|first3=Eun-Jeong|last4=Desgagne-Penix|first4=Isabel|last5=Bross|first5=Crystal D|last6=Chang|first6=Limei|last7=Chen|first7=Xue|last8=Farrow|first8=Scott C|last9=Zhang|first9=Ye|date=2015|title=Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants|url=http://openlib.tugraz.at/download.php?id=564f2fa60a35b&location=browse|journal=BMC Plant Biology|volume=15|pages=227|doi=10.1186/s12870-015-0596-0| pmc=4575454 |pmid=26384972|doi-access=free}}

It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an analgesic.{{cite journal|pmid=9368908|year=1997|last1=Saeed|first1=SA|last2=Gilani|last3=Majoo|last4=Shah|title=Anti-thrombotic and anti-inflammatory activities of protopine.|volume=36|issue=1|pages=1–7|doi=10.1006/phrs.1997.0195|journal=Pharmacological Research|first2=AH|first3=RU|first4=BH}}{{MeshName|Protopine}}