Protopine

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Protopine is an alkaloid occurring in opium poppy, Corydalis tubers and other plants of the family papaveraceae, like Fumaria officinalis.

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Column 1Column 2
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
CAS Number.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}130-86-9 Y
3D model (JSmol)Interactive image
ChEBICHEBI:16415 Y
ChEMBLChEMBL453019 Y
ChemSpider4799 Y
ECHA InfoCard100.004.546
EC Number204-999-6
KEGGC05189 Y
PubChem CID4970
UNIIUIW569HT35 Y
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 YKey: GPTFURBXHJWNHR-UHFFFAOYSA-N Y
SMILES
c15cc3OCOc3cc5CCN(C)Cc2c(CC1=O)ccc4c2OCO4
Chemical formulaC20H19NO5
Molar mass353.369 g/mol
Appearancewhite crystals
Density1.399 g/cm3
Melting point208 °C (406 °F; 481 K)
Solubility in waterpractically insoluble
Solubility in chloroform1:15
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references | |

Protopine is an 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.

Protopine is derived in the plants such as the opium poppy, Papaver somniferum, 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.

The final step is oxidation by the enzyme methyltetrahydroprotoberberine 14-monooxygenase:

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The enzyme protopine 6-monooxygenase converts protopine into dihydrosanguinarine. NADP+ and water are the by-products.

The enzyme uses reduced nicotinamide adenine dinucleotide phosphate (NADPH), and oxygen, with the initial product being 6-hydroxyprotopine, which spontaneously forms dihydrosanguinarine, found in plants such as Sanguinaria canadensis.

  • Cryptopine
  • Bürgi-Dunitz angle

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