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Salutaridine

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Salutaridine
Names
IUPAC name 4-Hydroxy-3,6-dimethoxy-17-methyl-5,6,8,14-tetradehydromorphinan-7-one
Systematic IUPAC name (4aS,10R)-5-Hydroxy-3,6-dimethoxy-11-methyl-9,10-dihydro-2H-10,4a-(azanoethano)phenanthren-2-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
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InChI
  • InChI=1S/C19H21NO4/c1-20-7-6-19-10-16(24-3)14(21)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9-10,13,22H,6-8H2,1-3H3/t13-,19+/m1/s1Key: GVTRUVGBZQJVTF-YJYMSZOUSA-N
  • InChI=1/C19H21NO4/c1-20-7-6-19-10-16(24-3)14(21)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9-10,13,22H,6-8H2,1-3H3/t13-,19+/m1/s1Key: GVTRUVGBZQJVTF-YJYMSZOUBK
SMILES
  • CN1CC23C=C(C(=O)C=C21CC4=C3C(=C(C=C4)OC)O)OC
Properties
Chemical formula C19H21NO4
Molar mass 327.380 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Salutaridine, also known as floripavine, is an alkaloid that is present in the morphinian alkaloid pathway of opium poppy. Its biosynthetic precursor is the alkaloid (R)-reticuline. (R)-Reticuline is converted to salutaridine by the enzyme salutaridine synthase. Salutaridine is converted to salutaridinol by the enzyme salutaridine reductase (SalR), with the reduction of NADPH to NADP.

References

  1. "Floripavine ChemicalBook".
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