Reticuline

Reticuline
(S)-(+)-reticuline
Names
IUPAC name
3,10-Dimethoxy-8,8a-secoberbine-2,9-diol
Systematic IUPAC name
(1S)-1-[(3-Hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
Identifiers
3D model (JSmol)
95671
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.920
EC Number
  • (S): 207-611-3
KEGG
UNII
  • 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 Y
    Key: BHLYRWXGMIUIHG-HNNXBMFYSA-N Y
  • (S): CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)O)O)OC
Properties
C19H23NO4
Molar mass 329.396 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

Reticuline is a tetrahydroisoquinoline alkaloid. It is also classified as a benzylisoquinoline alkaloid. It is produced in the opium poppy from the amino acid tyrosine, initially as (S)-reticuline, which is a precursor to alkaloids including papaverine and stylopine. Another large group of alkaloids including morphine are made after (S)-reticuline has been converted in the poppy to its enantiomer, (R)-reticuline.