# Salutaridine

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Salutaridine
> Markdown URL: https://mediated.wiki/source/Salutaridine.md
> Source: https://en.wikipedia.org/wiki/Salutaridine
> Source revision: 1336734751
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{chembox
|ImageFile=Salutaridine.svg
| ImageClass = skin-invert-image
|ImageSize=200
|ImageFile2=Salutaridine 3D BS.png
| ImageClass2 = bg-transparent
|ImageSize2=200
|IUPACName=4-Hydroxy-3,6-dimethoxy-17-methyl-5,6,8,14-tetradehydromorphinan-7-one
|SystematicName=(4a''S'',10''R'')-5-Hydroxy-3,6-dimethoxy-11-methyl-9,10-dihydro-2''H''-10,4a-(azanoethano)phenanthren-2-one
|OtherNames=
|Section1={{Chembox Identifiers
|  CASNo_Ref = {{cascite|correct|??}}
| CASNo=1936-18-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7X10PRH74D
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C05179
|  PubChem=5408233
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17225
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 404097
|  ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16736005
|  StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
|  StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GVTRUVGBZQJVTF-YJYMSZOUSA-N
|  SMILES=CN1CC[C@]23C=C(C(=O)C=C2[C@H]1CC4=C3C(=C(C=C4)OC)O)OC
  }}
|Section2={{Chembox Properties
|  C=19 | H=21 | N=1 | O=4
|  Appearance=
|  Density=
|  MeltingPt=
|  BoilingPt=
|  Solubility=
  }}
}}

'''Salutaridine''', also known as '''floripavine''', is an [alkaloid](/source/alkaloid) that is present in the [morphinan](/source/morphinan) alkaloid pathway of opium poppy, ''[Papaver somniferum](/source/Papaver_somniferum)''.

==Biosynthesis==
It is produced by the enzyme [salutaridine synthase](/source/salutaridine_synthase) that [catalyzes](/source/catalysis) the [chemical reaction](/source/chemical_reaction) from its precursor (''R'')-reticuline:<ref>{{KEGG enzyme|1.14.19.67}}</ref><ref>{{cite journal | vauthors = Gerady R, Zenk MH | date = 1993 | title = Formation of salutaridine from (R)-reticuline by a membrane-bound cytochrome P-450 enzyme from Papaver somniferum | journal = [Phytochemistry](/source/Phytochemistry_(journal))  | volume = 32 | pages = 79–86 | doi = 10.1016/0031-9422(92)80111-Q }}</ref>

{{chemrxn|width=55%|
{{chemrxn/cpd|qid=Q82096614|caption=[(''R'')-reticuline](/source/Reticuline)|upright=1.2 }}
{{chemrxn/txt|+ [NADPH](/source/NADPH) }}
{{chemrxn/arw||fwd_in={{chem2|O2}}|fwd_out={{chem2|2 H2O}} }}
{{chemrxn/cpd|salutaridine }}
{{chemrxn/txt|+ [NADP<sup>+</sup>](/source/NADP%2B)}}
}}

The enzyme uses reduced [nicotinamide adenine dinucleotide phosphate](/source/nicotinamide_adenine_dinucleotide_phosphate) (NADPH) as its [cofactor](/source/cofactor_(biochemistry)).

Salutaridine is converted to salutaridinol by the enzyme [salutaridine reductase (NADPH)](/source/salutaridine_reductase_(NADPH)).<ref>{{cite journal | vauthors = Gerady R, Zenk MH | date = 1993 | title = Purification and characterization of salutaridine:NADPH 7-oxidoreductase from ''Papaver somniferum'' | journal = [Phytochemistry](/source/Phytochemistry_(journal)) | volume = 34 | issue = 1 | pages = 125&ndash;132 | doi = 10.1016/S0031-9422(00)90793-3 | bibcode = 1993PChem..34..125G }}</ref>

{{chemrxn|width=50%|
{{chemrxn/cpd|salutaridine }}
{{chemrxn/txt|+ [NADPH](/source/NADPH) }}
{{chemrxn/arw|fwd_out={{chem2|H+}} }}
{{chemrxn/cpd|salutaridinol }}
{{chemrxn/txt|+ [NADP<sup>+</sup>](/source/NADP%2B)}}
}}

== References ==
{{Reflist}}

Category:Morphinans
Category:Hydroxyarenes
Category:Enones
Category:Phenol ethers

{{alkaloid-stub}}

---
Adapted from the Wikipedia article [Salutaridine](https://en.wikipedia.org/wiki/Salutaridine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Salutaridine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.