131-28-2

Basic information

• Product Name: CI 15511
• Synonyms: CI 15511;NARCEIN;NARCEINE;4-(methylenedioxy)phenyl)acetyl)-6-((6-(2-(dimethylamino)ethyl)-2-methoxy-;henyl)acetyl)-;o-veratricacid,6-((6-(2-(dimethylamino)ethyl)-2-methoxy-3,4-(methylenedioxy)p;6-((6-(2-(Dimethylamino)ethyl)-2-methoxy-3,4-(methylenedioxy)phenyl)ac etyl)-o-veratric acid;Narceine (base and/or unspecified salts)
• CAS NO: 131-28-2
• Molecular Formula: C₂₃H₂₇NO₈
• Molecular Weight: 445.46
• EINECS: 205-021-0
• Mol File: 131-28-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 138°; mp 176°
• Boiling Point: 555.14°C (rough estimate)
• Flash Point: 316.3 °C
• Appearance: /
• Density: 1.3285 (rough estimate)
• Vapor Pressure: 3.26E-15mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• PKA: pKb (20°) = 10.7, pKa = 9.3
• Water Solubility: 579.1mg/L(15 oC)
• CAS DataBase Reference: CI 15511(CAS DataBase Reference)
• NIST Chemistry Reference: CI 15511(131-28-2)
• EPA Substance Registry System: CI 15511(131-28-2)

Safety Data

• Hazardous Substances Data: 131-28-2(Hazardous Substances Data)

Usage

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.

Purification Methods

Recrystallise Narcein from water (as trihydrate). The styphnate has m 185-189o (from EtOH), and the picrate has m 200o (from EtOH). [Beilstein 19 H 370, 19 I 797, 19 II 386, 19 IV 4382.]

References

Couerbe., Annalen, 17,171 (1836)Anderson., ibid, 86, 182 (1853)Roser., ibid, 247, 167 (1888)Freund, Frankforter., ibid, 277,20 (1893)Freund, Oppenheimer., Ber., 42, 1084 (1909)

InChI:InChI=1/C23H27NO8/c1-24(2)9-8-13-10-18-22(32-12-31-18)20(29-4)15(13)11-16(25)14-6-7-17(28-3)21(30-5)19(14)23(26)27/h6-7,10H,8-9,11-12H2,1-5H3,(H,26,27)

Upstream product

• 80-48-8 methyl p-toluene sulfonate 
• 10421-76-8 noscapine 
• 51606-51-0 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 
• 77-78-1 dimethyl sulfate 
• 7732-18-5 water 
• 62777-53-1 3-[6-(2-dimethylamino-ethyl)-4-methoxy-benzo[1,3]dioxol-5-ylmethylene]-6,7-dimethoxy-phthalide 

Downstream Products

• 518-90-1 3,4-dimethoxy-phthalic acid 
• 12246-80-9 6-{[6-(2-dimethylamino-ethyl)-4-methoxy-benzo[1,3]dioxol-5-yl]-acetyl}-2,3-dimethoxy-benzoic acid ethyl ester; hydrochloride 
• 125187-48-6 oxonarceine 
• 7664-41-7 ammonia 
• 124-40-3 dimethyl amine 
• 75-50-3 trimethylamine 
• 74-89-5 methylamine 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 64401-51-0 narceine amide 
• 55968-77-9 (Z)-Narceine imide 
• 71695-19-7 isonitrosonarceine 

Relevant articles and documents

Secophthalideisoquinolines

The secophthalideisoquinolines can be subdivided into enol lactones, keto acids, diketo acids, and ene lactams.The diastereomeric β- and α-hydrastine methiodides (8 and 9) supply stereoselectively Z and E enol lactones 11 and 12, respectively, in a syn β-elimination process.N-Methylhydrastine (11) reacts under mild conditions with methanol, water, or ammonia to produce keto ester 18, keto acid 17, or hydroxy lactam 36, respectively.Treatment of hydroxy lactam 36 with acid results in rapid loss of water and formation of the Z ene lactam 33.Photoequilibration of 33gives rise to a mixture of Z and E ene lactams 33 and 34.A biogenetic scheme is proposed for the secophthalideisoquinolines which includes the following sequence: classical phthalideisoquinoline -> phthalideisoquinoline N-metho salt -> secophthalide enol lactone -> secophthalide keto acid -> secophthalide diketo acid -> fumariflorine-type alkaloid.Ene lactams 30-33, as well as the hydroxy lactam fumschleicherine (35), are most probably artifacts of isolation.