Reticuline

Reticuline

Names
IUPAC name (1S)-1-[(3-Hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
Identifiers
CAS Number	485-19-8 Y
3D model (Jmol)	Interactive image
ChemSpider	388724 N
ECHA InfoCard	100.006.920
PubChem CID	439653
InChI InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1 N Key: BHLYRWXGMIUIHG-HNNXBMFYSA-N N InChI=1/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1 Key: BHLYRWXGMIUIHG-HNNXBMFYBI
SMILES CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)O)O)OC
Properties
Chemical formula	C19H23NO4
Molar mass	329.40 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Reticuline is a chemical compound found in a variety of plants including Lindera aggregata,Annona squamosa, and Ocotea fasciculata (also known as Ocotea duckei). It is based on the benzylisoquinoline structure.

Reticuline is one of the alkaloids found in opium, and experiments in rodents suggest it possesses potent central nervous system depressing effects. It is the precursor of morphine and many other alkaloids.

3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase uses S-adenosyl methionine and 3'-hydroxy-N-methyl-(S)-coclaurine to produce S-adenosylhomocysteine and (S)-reticuline.

Reticuline oxidase uses (S)-reticuline and O₂ to produce (S)-scoulerine and H₂O₂.

Salutaridine synthase uses (R)-reticuline, NADPH, H⁺, and O₂ to produce salutaridine, NADP⁺, and H₂O. Salutaridine can then be transformed progressively to thebaine, oripavine, and morphine.

1,2-dehydroreticulinium reductase (NADPH) uses (R)-reticuline and NADP⁺ to produce 1,2-dehydroreticulinium, NADPH, and H⁺.