Narcotoline

Last updated
Narcotoline
Narcotoline structure.png
Names
Preferred IUPAC name
(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
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.559 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-313-6
KEGG
PubChem CID
UNII
  • InChI=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 X mark.svgN
    Key: LMGZCSKYOKDBES-AEFFLSMTSA-N X mark.svgN
  • 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
    Key: LMGZCSKYOKDBES-AEFFLSMTBE
  • CN1CCC2=CC3=C(C(=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)O)OCO3
Properties
C21H21NO7
Molar mass 399.399 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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, [1] and has also been used in tissue culture media. [2]

Contents

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. [3]

References

  1. ↑ Karlsson, MO; Dahlström, B; Neil, A (1988). "Characterization of high-affinity binding sites for the antitussive 3Hnoscapine in guinea pig brain tissue". European Journal of Pharmacology. 145 (2): 195–203. doi:10.1016/0014-2999(88)90230-0. PMID   3350041.
  2. ↑ US 2004063205 "Composition and method for culturing potentially regenerative cells and functional tissue-organs in vitro"
  3. ↑ Frick, S; Kramell, R; Schmidt, J; Fist, AJ; Kutchan, TM (2005). "Comparative qualitative and quantitative determination of alkaloids in narcotic and condiment Papaver somniferum cultivars". Journal of Natural Products. 68 (5): 666–73. doi:10.1021/np0496643. PMID   15921406.
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