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General Compound Information

Noscapine

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Description

(-)-noscapine is 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. It has a role as an antitussive, an antineoplastic agent, an apoptosis inducer and a plant metabolite. It is a benzylisoquinoline alkaloid, a tertiary amino compound, a cyclic acetal, an isobenzofuranone, an organic heterobicyclic compound, an organic heterotricyclic compound and an aromatic ether. It derives from a (-)-noscapine hemiacetal.

Synonyms

noscapine; 128-62-1; NARCOTINE; Tusscapine; Methoxyhydrastine;

Terbenol;Capval;Coscopin;Narcompren;Narcosine;Vadebex;(-)-Narcotine;Narcotin;Narkotin;Noscapalin;Noscapin;Opianine;Opianin;Narcotussin;Longatin;Nectadon;Nicolane;Nipaxon;Lyobex;Opian;alpha-Narcotine;O-Methylnarcotoline;Coscotabs;Noscapinum;Key-tusscapine;Longactin;Noscapal;Noscapina;Hederix (free base);(-)-alpha-narcotine;L-alpha-Narcotine;Gnoscopine;Narcotinum;Noscopine;(-)-.alpha.-Narcotine;NSC 5366;NSC-5366;.alpha.-Narcotine;dl-Narcotine;(+/-)-Noscapine;L-.alpha.-Narcotine;(S,R)-Noscapine;A4C6WE7BZN;8V32U4AOQU;alpha-Gnoscopine;(S)-6,7-dimethoxy-3-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one;DTXSID4023385;CHEBI:73237;NSC5366;(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;(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one;(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-one;1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-((5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (3S)-rel-;1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)-isoquinolin-5-yl), (S-(R,S))-;1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (R,S)-;DTXCID303385;6035-40-1;Narcotine alkaloid;Noskapin;.alpha.-Gnoscopine;Noscapine dl-form;L-alpha-Noscapine;8-Methoxyhydrastin;Coscopin (VAN);SMR000059119;(+-)-Noscapine;(-)-.alpha.-Norcotine;(-)-alpha-Norcotine;(+-)-alpha-Narcotine;1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (S-(R,S))-;1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [S-(R,S)]-;Noscapinum [INN-Latin];Noscapina [INN-Spanish];UNII-A4C6WE7BZN;UNII-8V32U4AOQU;CCRIS 9304;NSC-96350;HSDB 3372;Noscapine [USP:INN:BAN:JAN];.beta.-Narcotine;Noscapine (TN);(-)-noscapine;NCGC00016388-01;[S-(R,S)]-6,7-Dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-1(3H)-Isobenzofuranone;08N;CAS-128-62-1;Prestwick_959;(-)-a-Narcotine;EINECS 204-899-2;NSC 96350;Noscapine (narcotine);1-.alpha.-Narcotine;BRN 0099933;Tocris-1697;Narcotine, (+-)-;NOSCAPINE [INN];NOSCAPINE [JAN];NOSCAPINE [MI];NOSCAPINE [HSDB];Prestwick0_000563;Prestwick1_000563;Prestwick2_000563;Prestwick3_000563;NARCOTINUM [HPUS];CBMicro_048259;NOSCAPINE [MART.];NOSCAPINE [USP-RS];NOSCAPINE [WHO-DD];NOSCAPINE [WHO-IP];SCHEMBL4559;(S,R)-Noscapine, 97%;Lopac0_000840;BSPBio_000346;4-27-00-06838 (Beilstein Handbook Reference);MLS000069475;MLS001060855;SPBio_002565;Noscapine (JP15/USP/INN);Noscapine (JP17/USP/INN);BPBio1_000382;CHEMBL364713;NOSCAPINE DL-FORM [MI];NOSCAPINE [EP MONOGRAPH];NOSCAPINE, (+/-)-;GTPL10212;NOSCAPINE [USP MONOGRAPH];NOSCAPINUM [WHO-IP LATIN];DTXSID901032089;HMS1569B08;HMS2096B08;HMS2269P05;1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-((5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (3S)-;6,7-Dimethoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-2-benzofuran-1(3H)-one, (S-(R,S))- #;Phthalide, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-;(+/-)-.ALPHA.-NARCOTINE;Tox21_110413;BBL012344;BDBM50424716;MFCD00069316;NSC121869;STK054401;ZINC19418974;Noscapine 1.0 mg/ml in Acetonitrile;AKOS000278036;Tox21_110413_1;CCG-204096;CS-5115;DB06174;NSC-121869;SDCCGSBI-0048054.P004;(-)-3-(2-Methyl-6,7-methylendioxy-8-methoxy-1-isochinolyl)-6,7-dimethoxyphthalid;NCGC00023230-02;NCGC00023230-04;NCGC00023230-05;NCGC00023230-07;NCGC00023230-08;NCGC00023230-10;NCGC00023230-14;(3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranone;5-(6,7-Dimethoxyphthalidyl)-5,6,7,8-tetrahydro-4-methoxy-8-methyl-1,3-dioxolo(4,5-g)isoquinoline;AC-20272;AC-33191;HY-13716;L-alpha-2-Methyl-8-methoxy-6,7-methylenedioxy-1-(6,7-dimethoxy-3-phthalidyl)-1,2,3,4-tetrahydroisoquinaline;NCI60_004322;VS-03291;BIM-0048054.P001;C09592;D01036;EN300-24402818;SR-01000075529-6;W-201012;BRD-K89237706-001-03-8;Q60998699;Noscapine, European Pharmacopoeia (EP) Reference Standard;Noscapine, United States Pharmacopeia (USP) Reference Standard;WLN: T C566 DO FO KN EH & & TJ HO1 K1 J-DT56 BVO DHJ HO1 IO1;(3S)-3-[(5R)-6-methyl-4-(methyloxy)-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-bis(methyloxy)-2-benzofuran-1(3H)-one;(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-isobenzofuran-1-one;1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (R,S)-(+-)-;1(3H)-Isobenzofuranone,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [S-(R,S)]-;Phthalide,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-;

FlavorDB ID

85

PUBCHEM ID

275196

Molecular Weight

413.4

Molecular Formula

C22H23NO7

Openeye Can Smiles

CN1CCC2=CC3=C(C(=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3

IUPAC Inchikey

AKNNEGZIBPJZJG-MSOLQXFVSA-N

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Compound Classification

Classification (Parent Nodes)

ClassyFire Ontology

Compound Quality

Quality information of this compound is not available!

Compound Toxicity and Food Additive Safety (OFAS)

Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database

Receptors

Receptor	REFERENCE	EC50 [µM]	Effective Concentration [µM]
TAS2R14	details	Activated	10.00

Consensus Spectra

Spectrum Type	Spectrum View	Description	Polarity
Experimental GCMS	view	GCMS	positive
Experimental LCMS	view	LCMS_Positive	positive
Experimental LCMS	view	LCMS_Negative	negative