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(-)-noscapine

Go to external page http://purl.obolibrary.org/obo/CHEBI_73237

A benzylisoquinoline alkaloid that is 1,2,3,4-tetrahydroisoquinoline which is substituted by a 4,5-dimethoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl group at position 1, a methylenedioxy group at positions 6-7 and a methoxy group at position 8. Obtained from plants of the Papaveraceae family, it lacks significant painkilling properties and is primarily used for its antitussive (cough-suppressing) effects.

Term info

Label

(-)-noscapine

Synonyms
  • (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2-benzofuran-1(3H)-one
database cross reference
Subsets

3_STAR

INN
noscapinum [ ChemIDplus ]

INN
noscapine [ ChemIDplus ]

INN
noscapina [ ChemIDplus ]

INN
noscapine [ WHO_MedNet ]

IUPAC NAME
(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2-benzofuran-1(3H)-one [ IUPAC ]

charge

0

formula

C22H23NO7

has alternative id

CHEBI:10321

has obo namespace

chebi_ontology

has related synonym

(-)-narcotine, noscapinum, noscapine, noscapina, (-)-alpha-narcotine, alpha-Narcotine

id

CHEBI:73237

inchi

InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1

inchikey

AKNNEGZIBPJZJG-MSOLQXFVSA-N

mass

413.421

monoisotopicmass

413.14745

smiles

C1N([C@@](C2=C(C1)C=C3OCOC3=C2OC)([H])[C@@]4(C=5C=CC(=C(C5C(O4)=O)OC)OC)[H])C