Noscapine

Base Information

• Chemical Name: Noscapine
• CAS No.: 128-62-1
• Deprecated CAS: 8055-18-3,8057-19-0,567-86-2,1368-39-4
• Molecular Formula: C22H23NO7
• Molecular Weight: 413.427
• Hs Code.: 29329990
• European Community (EC) Number: 204-899-2
• NSC Number: 121869,5366
• UNII: 8V32U4AOQU,A4C6WE7BZN
• DSSTox Substance ID: DTXSID4023385,DTXSID901032089
• Nikkaji Number: J9.283E
• Wikipedia: Noscapine
• Wikidata: Q415619
• NCI Thesaurus Code: C80589
• Pharos Ligand ID: Z9WGQBHQ8UVV
• Metabolomics Workbench ID: 46045
• ChEMBL ID: CHEMBL364713
• Mol file: 128-62-1.mol

Synonyms:Capval;Capval Tropfen;Embonate, Noscapine Hydrogen;Hydrochloride, Noscapine;Hydrogen Embonate, Noscapine;Librochin prikkelhoest;Narcotine;Noscapect;Noscapine;Noscapine Hydrochloride;Noscapine Hydrogen Embonate;prikkelhoest, Librochin;Tropfen, Capval;Tuscalman

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Chemical Property of Noscapine

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 4.83E-14mmHg at 25°C
• Melting Point: 174-176 °C(lit.)
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 565.316 °C at 760 mmHg
• PKA: 7.8(at 25℃)
• Flash Point: 295.692 °C
• PSA: 84.48000
• Density: 1.333 g/cm³
• LogP: 2.86840
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Practically insoluble in water, soluble in acetone, slightly soluble in ethanol (96 per cent). It dissolves in strong acids; on dilution of the solution with water, the base may be precipitated.
• Water Solubility.: 302.9mg/L(25 oC)
• 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:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C(=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3
• Isomeric SMILES: CN1CCC2=CC3=C(C(=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3
• Recent ClinicalTrials: Study of Noscapine for Patients With Low Grade Non Hodgkin's Lymphoma or Chronic Lymphocytic Leukemia Refractory to Chemotherapy
• Recent EU Clinical Trials: A randomised, two-period two-stage cross-over study on the relative bioavailability of two different liquid formulations of single noscapine doses (phase I/IV, open-label) in healthy volunteers (fasted state)
• Description: A major constituent of opium (Papaver sornni!erurn), this phthalideisolquinoline base was probably first discovered by Derosne, but initially characterized by Robiquet who gave it the formula C23H3S0 7N, changed to that now accepted by Matthiesen and Foster. It crystallizes in colourless needles from EtOH and has [α]D - 198° (c 1.0, CHC13); - 146° (c 2.0, toluene); - 147° (c 1.59, C6H6) and + 50° (1 % HCl). The alkaloid is a weak, monoacidic, tertiary base, forming unstable salts with acids which are dissociated with H20. The hydrochloride crystallizes with varying amounts of H20, is very soluble in water, readily decomposing into basic salts on standing. The platinichloride is amorphous; the oxalate has m.p. 174°C;[α]20D + 39.5° (H20); the phthalate, m.p. 160°C; [α]22D + 115° (CHC13); sesquisulphate, colourless crystals of the hexahydrate and the picrate, m.p. 1 74-S°C. The (+)-bromocamphorsulphonate has m.p. 110- 120°C; [α]D + 100.7° (CHC13) and the corresponding (-)-bromocamphorsul_x0002_phonate, m.p. l80.SoC; [α]D + 29° (CHC13). The alkaloid yields an N-oxide which is a hygroscopic solid; [α]D + 135° (CHC13) furnishing a crystalline hydrochloride, m.p. 193°C; platinichloride, m.p. 175°C and a picrate, m.p. 130°C.The base is unstable to heat and when heated in a sealed tube yields a mixture of dimethylnornarcotine, methylnornarcotine and nornarcotine. On heating with H20 and 150°C, or on boiling with dilute acids, it is hydrolyzed to opianic acid and hydrocotarnine. Similar degradations are brought about by acid oxidation orreduction, e.g. Zn and dilute HCl gives hydrocotarnine and meconin while dilute HN03 yields cotarnine and opianic acid. Pharmacologically, narcotine resembles thebaine (q.v.) in its action, being a reflex stimulant rather than a narcotic.
• Uses: Antitussive. Antitussive
• Biological Functions: Noscapine is a naturally occurring product of the opium poppy. It is a benzylisoquinoline with no analgesic or other CNS effects. Its antitussive effects are weak, but it is used in combination with other agents in mixtures for cough relief.

Technology Process of Noscapine

There total 66 articles about Noscapine 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: 80.0%

9-bromonoscapine (488721-01-3) + phenylboronic acid (98-80-6) → (3S)-6,7-dimethoxy-3-((5R)-4-methoxy-6-methyl-9-phenyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one (946068-65-1) + noscapine (128-62-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate; In ethanol; toluene; at 120 ℃; for 48h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

DOI:10.1016/j.bmcl.2014.10.046

Reference yield: 62.0%

9-bromonoscapine (488721-01-3) → [(S)-3-((R)-9-amino-4-methoxy-6-methyl-5,6,7 ,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6,7-dimethoxyisobenzofuran-(3H)-one] (1214255-25-0) + noscapine (128-62-1)

Guidance literature:

With copper(l) iodide; sodium azide; L-proline; In dimethyl sulfoxide; at 130 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.02.033

upstream raw materials:

diazomethane

(S)-7-hydroxy-6-methoxy-3-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo-[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one

(-)-N-cyano-1(S)-hydroxy-1,2-seco-1'(S)-narcotine

(S)-7-tert-butoxy-6-methoxy-3-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-isobenzofuran-1-one

Downstream raw materials:

meconin

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

2,3-dimethoxy-6-{[4-methoxy-6-(2-methylamino-ethyl)-benzo[1,3]dioxol-5-yl]-acetyl}-benzoic acid

hydrocotarnine

Refernces

• 1、 Battersby,Spencer. "-". . p. 1087,1091. Retrieved 1965.
• 2、 Li, Jihui,Liu, Yongxiang,Song, Xinjing,Wu, Tianxiao,Meng, Jiaxin,Zheng, Yang,Qin, Qiaohua,Zhao, Dongmei,Cheng, Maosheng. "An Acid-Catalyzed Epoxide Ring-Opening/Transesterification Cascade Cyclization to Diastereoselective Syntheses of (±)-β-Noscapine and (±)-β-Hydrastine". . p. 7149 - 7153. Retrieved 2019/09/30.
• 3、 -. "COMPOSITIONS AND METHODS FOR MAKING NOSCAPINE AND SYNTHESIS INTERMEDIATES THEREOF". Paragraph 000216-000217. . Retrieved 2015/02/25.