Narceine

Base Information

• Chemical Name: Narceine
• CAS No.: 131-28-2
• Molecular Formula: C23H27 N O8
• Molecular Weight: 445.469
• European Community (EC) Number: 205-021-0
• UNII: CTT09X2F1M
• DSSTox Substance ID: DTXSID40156833
• Nikkaji Number: J5.559J
• Wikipedia: Narceine
• Wikidata: Q907355
• NCI Thesaurus Code: C91050
• Metabolomics Workbench ID: 44277
• ChEMBL ID: CHEMBL486305
• Mol file: 131-28-2.mol

Synonyms:NARCEINE;Narcein;131-28-2;CHEBI:7480;C23H27NO8;EINECS 205-021-0;UNII-CTT09X2F1M;BRN 0371009;CTT09X2F1M;6-((6-(2-(Dimethylamino)ethyl)-2-methoxy-3,4-(methylenedioxy)phenyl)acetyl)-o-veratric acid;2,3-Dimethoxy-6-((6-(2-dimethylaminoethyl)-2-methoxy-3,4-methylendioxyphenyl)acetyl)benzosaeure;5-19-09-00051 (Beilstein Handbook Reference);6-[[6-[2-(Dimethylamino)ethyl]-4-methoxy-1,3-benzodioxol-5-yl]acetyl]-2,3-dimethoxybenzoic acid;6-[2-[6-[2-(dimethylamino)ethyl]-4-methoxy-1,3-benzodioxol-5-yl]acetyl]-2,3-dimethoxybenzoic acid;6-(2-(6-(2-(Dimethylamino)ethyl)-4-methoxybenzo[d][1,3]dioxol-5-yl)acetyl)-2,3-dimethoxybenzoic acid;Benzoic acid, 6-[[6-[2-(dimethylamino)ethyl]-4-methoxy-1,3-benzodioxol-5-yl]acetyl]-2,3-dimethoxy-;o-Veratric acid, 6-((6-(2-(dimethylamino)ethyl)-2-methoxy-3,4-(methylenedioxy)phenyl)acetyl)-;o-Veratric acid, 6-[[6-[2-(dimethylamino)ethyl]-2-methoxy-3,4-(methylenedioxy)phenyl]acetyl]-;6-((6-(2-(DIMETHYLAMINO)ETHYL)-4-METHOXY-1,3-BENZODIOXOL-5-YL)ACETYL)-2,3-DIMETHOXYBENZOIC ACID;6-[[6-[2-(dimethylamino)ethyl]-2-methoxy-3,4-(methylenedioxy)phenyl]acetyl]-o-veratric acid;Benzoic acid, 6-((6-(2-(dimethylamino)ethyl)-4-methoxy-1,3-benzodioxol-5-yl)acetyl)-2,3-dimethoxy-;NARCEINE [MI];NARCEINE [MART.];NARCEINE [WHO-DD];C09591;SCHEMBL24919;CHEMBL486305;DTXSID40156833;BDBM50480327;C23-H27-N-O8;NIH 10760;BENZOIC ACID,6-[2-[6-[2-(DIMETHYLAMINO)ETHYL]-4-METHOXY-1,3-BENZODIOXOL-5-YL]ACETYL]-2,3-DIMETHOXY-;LS-162042;FT-0631763;Q907355;6-((6-[2-(Dimethylamino)ethyl]-4-methoxy-1,3-benzodioxol-5-yl)acetyl)-2,3-dimethoxybenzoic acid #;6-(2-{6-[2-(dimethylamino)ethyl]-4-methoxy-2H-1,3-benzodioxol-5-yl}acetyl)-2,3-dimethoxybenzoic acid;6-[[6-[2-(Dimethylamino)ethyl]-4-methoxy-1,3-benzodioxol-5-yl]acetyl]-2,3-dimethoxybenzoic acid, 9CI;6-[2-[6-(2-dimethylaminoethyl)-4-methoxy-1,3-benzodioxol-5-yl]acetyl]-2,3-dimethoxy-benzoic acid

Chemical Property of Narceine

Chemical Property:

• Vapor Pressure: 3.26E-15mmHg at 25°C
• Melting Point: 138°; mp 176°
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 599.3 °C at 760 mmHg
• PKA: pKb (20°) = 10.7, pKa = 9.3
• Flash Point: 316.3 °C
• PSA: 103.76000
• Density: 1.271 g/cm³
• LogP: 2.66880
• Water Solubility.: 579.1mg/L(15 oC)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 445.17366682
• Heavy Atom Count: 32
• Complexity: 644

Purity/Quality:

99%, ^*data from raw suppliers

NARCEINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCC1=CC2=C(C(=C1CC(=O)C3=C(C(=C(C=C3)OC)OC)C(=O)O)OC)OCO2
• Description: An alkaloid of opium (Papaver somniferum) was first isolated by Pelletier in 1832 but not characterized until some years later by Couerbe and Anderson, the latter assigning to it the formula C23H2909N which was accepted until Freund showed that it contains H20 of crystallization. The base remains in the mother liquors after removal of the major alkaloids. It forms slender, colourless needles or prisms of the trihydrate, m.p. 170°C. It is optically inactive and dissolves readily in alkalies forming metallic derivatives. It behaves as a weak, monoacidic base forming well-crystallized salts. The hydrochloride crystallizes with 5.5 H20 from cold, dilute HCI, or as the trihydrate from hot solutions. From MeOH it yields crystals with 1 mole of solvent, m.p. 190-2°C. The aurichloride forms reddish-yellow needles, m.p. 130°C and the picrate has m.p. 195°C. With chlorine water, followed by the addition of ammonia, it gives a characteristic blood-red colour while with dilute iodine solution, the solid alkaloid develops a blue colour. With ethyl nitrite, narceine forms an oximino derivative which, on exhaustive methylation, furnishes trimethylamine, hemipinic acid and 2-cyano-3- methoxy-4: s-methylenedioxy-1-vinylbenzene.

Technology Process of Narceine

There total 12 articles about Narceine 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: 76.0%

5-(4,5-dimethoxy-3-oxo-1,3-dihydroisobenzofuran-1-yl)-4-methoxy-6,6-dimethyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide (51606-51-0) → Narcein (131-28-2)

Guidance literature:

With sodium hydroxide; In dichloromethane; for 0.25h;

DOI:10.1021/jo00344a025

Reference yield:

→ Narcein (131-28-2)

Guidance literature:

With pyridine; water;

DOI:10.1021/ja01332a065

Reference yield:

→ Narcein (131-28-2)

Guidance literature:

With water;

DOI:10.1021/ja01332a065

upstream raw materials:

methyl p-toluene sulfonate

noscapine

5-(4,5-dimethoxy-3-oxo-1,3-dihydroisobenzofuran-1-yl)-4-methoxy-6,6-dimethyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide

water

Downstream raw materials:

isonitrosonarceine

(Z)-Narceine imide

3,4-dimethoxy-phthalic acid

narceine amide

Refernces