Structure via PubChem · Public domain (PubChem)
Reticuline
Sign in to saveReticuline 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.
In the Vinony graph
Vinony's link graph records 1,141 inbound references to Reticuline, and connects out to nicotinamide adenine dinucleotide phosphate, benzylisoquinoline and International Standard Book Number.
It sits within the topics Chemical articles with multiple CAS registry numbers, Chemical articles with multiple compound IDs and Chemical articles with multiple PubChem CIDs.
Vinony links it to 9 Wikipedia language editions.
Chemical data
- Formula
- C19H23NO4
- Molecular weight
- 329.4 g/mol
- IUPAC name
- (1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
- SMILES
- CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)O)O)OC
- InChIKey
- BHLYRWXGMIUIHG-HNNXBMFYSA-N
- XLogP
- 3
- Polar surface area
- 62.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 329.16270821599994
Show 6 more facts
- found in taxon
- Thalictrum flavum
- chemical formula
- C₁₉H₂₃NO₄
- isomeric SMILES
- CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)O)O)OC
- canonical SMILES
- OC1=CC(=CC=C1OC)CC2C3=CC(O)=C(OC)C=C3CCN2C
- Commons category
- Reticuline
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
6 sectionsContents
- Occurrence
- Physiological effects
- Biosynthesis
- Metabolism
- References
- External links
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.
==Occurrence== Reticuline is found in opium and a variety of plants including Lindera aggregata, Annona squamosa, and Ocotea fasciculata.
Excerpted from Wikipedia’s “Reticuline” article, available under the CC BY-SA 4.0 licence.