Reticuline

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.

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 Å²
H-bond donors: 2
H-bond acceptors: 5
Formal charge: 0

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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
inhibitor of: 3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase
Commons category: Reticuline

Sources (2)

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Encyclopedic overview

6 sections

Contents

Occurrence
Physiological effects
Biosynthesis
Metabolism
References
External links

==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.

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