Salutaridine

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

1. Enzyme 1.14.19.67 at KEGG Pathway Database.
2. Gerady R, Zenk MH (1993). "Formation of salutaridine from (R)-reticuline by a membrane-bound cytochrome P-450 enzyme from Papaver somniferum". Phytochemistry . 32: 79–86. doi:10.1016/0031-9422(92)80111-Q.
3. Gerady R, Zenk MH (1993). "Purification and characterization of salutaridine:NADPH 7-oxidoreductase from Papaver somniferum". Phytochemistry . 34 (1): 125–132. Bibcode:1993PChem..34..125G. doi:10.1016/S0031-9422(00)90793-3.