Reticuline

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title: "Reticuline" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["hydroxyarenes", "natural-opium-alkaloids", "phenols", "phenol-ethers", "tetrahydroisoquinoline-alkaloids"] topic_path: "general/hydroxyarenes" source: "https://en.wikipedia.org/wiki/Reticuline" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 398757401 | Name = Reticuline | ImageFile = Reticuline.png | ImageClass = skin-invert-image | IUPACName = 3,10-Dimethoxy-8,8a-secoberbine-2,9-diol | SystematicName = (1S)-1-[(3-Hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol | OtherNames = |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo = 485-19-8 | UNII_Ref = | UNII = X35Z551WT4 | SMILES = CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)O)O)OC | PubChem = 439653 | ChemSpiderID_Ref = | ChemSpiderID = 388724 | KEGG_Ref = | KEGG = C02105 | 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 | InChIKey = BHLYRWXGMIUIHG-HNNXBMFYBI | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = BHLYRWXGMIUIHG-HNNXBMFYSA-N | ChEMBL_Ref = | ChEMBL = 401501 |Section2={{Chembox Properties | C=19 | H=23 | N=1 | O=4

Reticuline is a tetrahydroisoquinoline alkaloid. It is also classified as a benzylisoquinoline alkaloid.

Occurrence

Reticuline is found in opium and a variety of plants including Lindera aggregata, Annona squamosa, and Ocotea fasciculata.

Physiological effects

In rodents reticuline possesses potent central nervous system depressing effects.

Metabolism

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+.

References

References

  1. (2008). "Production of Benzylisoquinoline Alkaloids in ''Saccharomyces cerevisiae''". Nature Chemical Biology.
  2. (2008). "Simultaneous determination of four alkaloids in ''Lindera aggregata'' by ultra-high-pressure liquid chromatography–tandem mass spectrometry". Journal of Chromatography A.
  3. (2013). "Potential applications for ''Annona squamosa'' leaf extract in the treatment and prevention of foodborne bacterial disease". Natural Product Communications.
  4. (1998). "Central depressant effects of reticuline extracted from ''Ocotea duckei'' in rats and mice". Journal of Ethnopharmacology.
  5. (25 October 2015). "Bradley's neurology in clinical practice". Elsevier.

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hydroxyarenesnatural-opium-alkaloidsphenolsphenol-etherstetrahydroisoquinoline-alkaloids