Reticuline
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| Names | |
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| IUPAC name
(1S)-1-[(3-Hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
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| Identifiers | |
485-19-8  |
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| ChEMBL | ChEMBL401501  |
| ChemSpider | 388724 |
| Jmol 3D model | Interactive image |
| PubChem | 439653 |
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| Properties | |
| C19H23NO4 | |
| Molar mass | 329.40 g·mol−1 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |
Reticuline is a chemical compound found in a variety of plants including Lindera aggregata,[1] Annona squamosa,[2] and Ocotea fasciculata (also known as Ocotea duckei).[3] It is based on the benzylisoquinoline structure.
Reticuline is one of the alkaloids found in opium, and experiments in rodents suggest it possesses potent central nervous system depressing effects.[3] It is the precursor of morphine and many other alkaloids.
Metabolism
3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase uses S-adenosyl methionine and 3'-hydroxy-N-methyl-(S)-coclaurine to produce S-adenosylhomocysteine and (S)-reticuline.
Reticuline oxidase uses (S)-reticuline and O2 to produce (S)-scoulerine and H2O2.
Salutaridine synthase uses (R)-reticuline, NADPH, H+, and O2 to produce salutaridine, NADP+, and H2O. Salutaridine can then be transformed progressively to thebaine, oripavine, and morphine.
1,2-dehydroreticulinium reductase (NADPH) uses (R)-reticuline and NADP+ to produce 1,2-dehydroreticulinium, NADPH, and H+.
