Gnoscopine

Base Information

• Chemical Name: Gnoscopine
• CAS No.: 10421-76-8
• Molecular Formula: C₂₂H₂₃NO₇
• Molecular Weight: 413.427
• DSSTox Substance ID: DTXSID20859254
• Nikkaji Number: J1.359.361B
• Wikidata: Q96631984
• Metabolomics Workbench ID: 133685
• ChEMBL ID: CHEMBL402487

Synonyms:Gnoscopine;10421-76-8;dl-Narcotine;( -)-Noscapine;( -)-alpha-Narcotine;6,7-Dimethoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3h-isobenzofuran-1-one;alpha-Gnoscopine;Noscapine dl-form;6035-40-1;(S,R)-Noscapine;6,7-dimethoxy-3-(4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-2-benzofuran-1-one;6,7-dimethoxy-3-{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;6,7-dimethoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one;Narcotine alkaloid;NSC 96350;Noscapine (narcotine);Narcotine, (+-)-;Narcotine, (.+.)-;(-)-.alpha.-Norcotine;a-Gnoscopine;C22-H23-N-O7;Anarcotine (TN);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*)]-;(.+-.)-Narcotine;(+/-) a-Narcotine;(+/-)-alpha-Narcotine;(.+-.)-alpha-narcotine;D04TDQ;MLS000104989;CHEMBL402487;SCHEMBL2494164;ACon1_001760;DTXSID20859254;AKNNEGZIBPJZJG-UHFFFAOYSA-N;CHEBI:110185;HMS2268L14;[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;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*)-(.+.)-;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)-;AKOS000264931;NCGC00015757-04;NCGC00015757-05;NCGC00015757-07;NCGC00015757-09;6,7-dimethoxy-3-(4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-isobenzofuran-1-one;LS-96013;SMR000054918;CS-0206804;AB00642499_13;Q415619;SR-01000003078;SR-01000003078-2;BRD-A77907596-001-01-9;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-Alpha-2-methyl-8-methoxy-6,7-methylenedioxy-1-(6,7-dimethoxy-3-phthalidyl)-1,2,3,4-tetrahydroisoquinoline;3-(4-Methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinoline-5-yl)-6,7-dimethoxyisobenzofuran-1(3H)-one;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

Chemical Property of Gnoscopine

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 413.14745207
• Heavy Atom Count: 30
• Complexity: 647

Purity/Quality:

99% ^*data from raw suppliers

Nascopine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C(=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3

Technology Process of Gnoscopine

There total 59 articles about Gnoscopine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

(+/-)-α-3-(9-bromo-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-6,7-dimethoxy-1(3H)-isobenzofuranone → (±)-α-noscapine (128-62-1,3860-46-6,6035-40-1,10421-76-8,35933-62-1,35933-63-2,35933-64-3,85280-20-2)

Guidance literature:

With hydrogen; triethylamine; for 30h;

DOI:10.1016/j.tet.2011.05.060

Reference yield: 46.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (+/-)-erythro-1-<1'-(4',5'-dimethoxyphthalidyl)>-8-methoxy-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (36017-64-8) → (±)-α-noscapine (128-62-1,3860-46-6,6035-40-1,10421-76-8,35933-62-1,35933-63-2,35933-64-3,85280-20-2)

Guidance literature:

With formic acid; In water; at 100 ℃; for 0.166667h;

Reference yield: 42.0%

4-methoxy-6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide (30936-27-7) + 6,7-dimethoxy-3-(trimethylsilyl)isobenzofuran-1(3H)-one (133932-07-7) → (±)-α-noscapine (128-62-1,3860-46-6,6035-40-1,10421-76-8,35933-62-1,35933-63-2,35933-64-3,85280-20-2)

Guidance literature:

With potassium hydrogen difluoride; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.3987/COM-13-12843

upstream raw materials:

4-methoxy-6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide

3-bromo-6,7-dimethoxyphthalide

benzophenone

(-)-α-narcotinediol

Downstream raw materials:

meconin

Narcein

3,4-dimethoxy-phthalic acid

4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-ol

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