Protopine
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| 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
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| 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 | |
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C20H19NO5 | |
| Molar mass | 353.369 g/mol |
| Appearance | white crystals |
| Density | 1.399 g/cm3 |
| Melting point | 208 °C (406 °F; 481 K) |
| 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).
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Protopine is an alkaloid occurring in opium poppy,[2] Corydalis tubers[3] and other plants of the family papaveraceae, like Fumaria officinalis.[4] 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.[5]
It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an analgesic.[6][7]
See also
[edit | edit source]References
[edit | edit source]- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ The Free Dictionary: Protopine
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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- ^ Protopine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
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