Narcotoline

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title: "Narcotoline" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["benzylisoquinoline-alkaloids", "hydroxyarenes", "methylenedioxyphenethylamines", "3-(5,6,7,8-tetrahydro-(1,3)dioxolo(4,5-g)isoquinolin-5-yl)-3h-2-benzofuran-1-ones", "tetrahydroisoquinoline-alkaloids"] topic_path: "general/benzylisoquinoline-alkaloids" source: "https://en.wikipedia.org/wiki/Narcotoline" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424711772 | ImageFile = Narcotoline structure.png | ImageClass = skin-invert-image | ImageSize = 200px | PIN = (3S)-3-[(5R)-4-Hydroxy-6-methyl-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-2-benzofuran-1(3H)-one | OtherNames = |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo = 521-40-4 | UNII_Ref = | UNII = M5V1K1QE3F | PubChem = 442330 | EINECS = 208-313-6 | SMILES = CN1CCC2=CC3=C(C(=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)O)OCO3 | ChemSpiderID_Ref = | ChemSpiderID = 390785 | InChI = 1/C21H21NO7/c1-22-7-6-10-8-13-20(28-9-27-13)17(23)14(10)16(22)18-11-4-5-12(25-2)19(26-3)15(11)21(24)29-18/h4-5,8,16,18,23H,6-7,9H2,1-3H3/t16-,18+/m1/s1 | InChIKey = LMGZCSKYOKDBES-AEFFLSMTBE | StdInChI_Ref = | StdInChI = 1S/C21H21NO7/c1-22-7-6-10-8-13-20(28-9-27-13)17(23)14(10)16(22)18-11-4-5-12(25-2)19(26-3)15(11)21(24)29-18/h4-5,8,16,18,23H,6-7,9H2,1-3H3/t16-,18+/m1/s1 | StdInChIKey_Ref = | StdInChIKey = LMGZCSKYOKDBES-AEFFLSMTSA-N | RTECS = | MeSHName = | ChEBI = | KEGG_Ref = | KEGG = C09593 |Section2={{Chembox Properties | C=21 | H=21 | N=1 | O=7 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }}

Narcotoline is an opiate alkaloid chemically related to noscapine. It binds to the same receptors in the brain as noscapine to act as an antitussive, and has also been used in tissue culture media.

Sources

It can be obtained from the opium poppy, Papaver somniferum. It is present at much higher levels in culinary strains (cultivars) of P. somniferum used for poppy seed production than in high-morphine pharmaceutical strains used for opium production.

References

References

  1. (1988). "Characterization of high-affinity binding sites for the antitussive 3Hnoscapine in guinea pig brain tissue". European Journal of Pharmacology.
  2. {{patent. US. 2004063205. "Composition and method for culturing potentially regenerative cells and functional tissue-organs in vitro"
  3. (2005). "Comparative qualitative and quantitative determination of alkaloids in narcotic and condiment Papaver somniferum cultivars". Journal of Natural Products.

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benzylisoquinoline-alkaloidshydroxyarenesmethylenedioxyphenethylamines3-(5,6,7,8-tetrahydro-(1,3)dioxolo(4,5-g)isoquinolin-5-yl)-3h-2-benzofuran-1-onestetrahydroisoquinoline-alkaloids