Narcotoline

Narcotoline
IUPAC name (3S)-3-[(5R)-4-hydroxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-3H-2-benzofuran-1-one
Identifiers
CAS number	521-40-4
PubChem	442330
EC number	208-313-6
Jmol-3D images	Image 1
SMILES CN1CCC2=CC3=C(C(=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)O)OCO3
Properties
Molecular formula	C21H21NO7
Molar mass	399.39 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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]

Source

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. 

External links

• KEGG compound C09593