Narcotoline

Narcotoline
Names

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^Y
ChemSpider	390785^N
EC Number	208-313-6
Jmol interactive 3D	Image
KEGG	C09593^N
PubChem	442330
InChI 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
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
Chemical formula	C₂₁H₂₁NO₇
Molar mass	399.40 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
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

↑ 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.
↑ US 2004063205 "Composition and method for culturing potentially regenerative cells and functional tissue-organs in vitro"
↑ 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

Opium components

Alkaloids	16-Hydroxythebaine Berberine Canadine Codamine Coptisine Coreximine Cycloartenol Cycloartenone Cyclolaudenol Dehydroreticuline Dihydrosanguinarine Glaucine Isoboldine Isocorypalmine Laudanidine Magnoflorine Narceine Narceinone Norlaudanosoline Norsanguinarine Oripavine Oxysanguinarine Palaudine Papaverrubine B (O-methyl-porphyroxine) Papaverrubine C (epiporphyroxine) Reticuline Salutaridine (sinoacutine) Sanguinarine Scoulerine Somniferine Stepholidine

Morphine group (Phenanthrenes. Includes opioids)	Codeine Morphine Narcotoline Neopine Perparin Papaverrubine D (porphyroxine) Pseudocodeine Pseudomorphine Thebaine

Isoquinolines	Cotarnine Eupaverine Hydrocotarnine Laudanosine Laudanine Noscapine (narcotine) Papaverine Papaveraldine Xanthaline

Protopine group	α-Allocryptopine α-Fagarine Corycavamine Corycavine Cryptopine Protopine

Tetrahydroprotoberberine group	Corydaline Corybulbine Isocorybulbine Capaurine

Aporphine group	Dicentrine Glaucine Corytuberine Cularine Corydine Isocorydine Bulbocapnine

Phtalide-isoquinolines	Adulmine Bicuculline Bicucine Corlumine

α-Naphthaphenanthridines	Chelidonine β-Homochelidonoine Chelerythrine Sanguinarine

Other components	Meconic acid

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