Salutaridine

Salutaridine
Names
IUPAC name
4-Hydroxy-3,6-dimethoxy-17-methyl-5,6,8,14-tetradehydromorphinan-7-one
Preferred 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
PubChem CID
UNII
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/s1 ☒N
    Key: GVTRUVGBZQJVTF-YJYMSZOUSA-N ☒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/s1
    Key: GVTRUVGBZQJVTF-YJYMSZOUBK
SMILES
  • CN1CC[C@]23C=C(C(=O)C=C2[C@H]1CC4=C3C(=C(C=C4)OC)O)OC
Properties
Chemical formula
 C19H21NO4
Molar mass 327.380 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Salutaridine, also known as floripavine,[1] 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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