Narcotoline

Narcotoline
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 Edit this at Wikidata
EC Number
  • 208-313-6
KEGG
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 ☒N
    Key: LMGZCSKYOKDBES-AEFFLSMTSA-N ☒N
  • 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]

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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