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	1936-18-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17225 Y
ChEMBL	ChEMBL404097 Y
ChemSpider	16736005 Y
KEGG	C05179 Y
PubChem CID	5408233
UNII	7X10PRH74D Y
CompTox Dashboard (EPA)	DTXSID60941041
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 Y Key: GVTRUVGBZQJVTF-YJYMSZOUSA-N Y
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). Infobox references

Salutaridine, also known as floripavine, is an alkaloid that is present in the morphinan alkaloid pathway of opium poppy, Papaver somniferum.

Biosynthesis

It is produced by the enzyme salutaridine synthase that catalyzes the chemical reaction from its precursor (R)-reticuline:^[1][2]

(R)-reticuline

+ NADPH

 

 

O₂

2 H₂O

 

 

 

salutaridine

+ NADP⁺

 

The enzyme uses reduced nicotinamide adenine dinucleotide phosphate (NADPH) as its cofactor.

Salutaridine is converted to salutaridinol by the enzyme salutaridine reductase (NADPH).^[3]

salutaridine

+ NADPH

 

 

 

H⁺

 

 

 

salutaridinol

+ NADP⁺

 

References

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