550-10-7

Basic information

• Product Name: hydrocotarnine
• Synonyms: 1,2,3,4-Tetrahydro-2-methyl-6,7-(methylenebisoxy)-8-methoxyisoquinoline;4-Methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinoline;5,6,7,8-Tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinoline;8-Methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline;Hydrocotarnine Hydrochloride;4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline hydrate hydrochloride
• CAS NO: 550-10-7
• Molecular Formula: C₁₂H₁₅NO₃
• Molecular Weight: 302.1643
• EINECS: 208-978-2
• Mol File: 550-10-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 56°C
• Boiling Point: 362.31°C (rough estimate)
• Flash Point: 106.7°C
• Appearance: /
• Density: 1.1514 (rough estimate)
• Vapor Pressure: 7.56E-05mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• PKA: 7.75±0.20(Predicted)
• CAS DataBase Reference: hydrocotarnine(CAS DataBase Reference)
• NIST Chemistry Reference: hydrocotarnine(550-10-7)
• EPA Substance Registry System: hydrocotarnine(550-10-7)

Safety Data

• Hazardous Substances Data: 550-10-7(Hazardous Substances Data)

Usage

Uses

Hydrocotarnine Hydrochloride, is an oxidative degradation product of the drug Noscapine (128-62-1).

InChI:InChI=1/C12H15NO3.BrH/c1-13-4-3-8-5-10-12(16-7-15-10)11(14-2)9(8)6-13;/h5H,3-4,6-7H2,1-2H3;1H

Upstream product

• 5263-81-0 4-Methoxy-6-methyl-1,3-dioxolo<4,5-g>isochinolinium-methoiodid 
• 75-16-1 methylmagnesium bromide 
• 128-62-1 noscapine 
• 1589-82-8 phenylmagnesium bromide 
• 186581-53-3 diazomethane 
• 5890-61-9 6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-4-ol 
• 108434-79-3 5,6,7,8-Tetrahydro-8-acetoxy-4-methoxy-6-methyl-1,3-dioxolo<4,5-g>isoquinoline 
• 912-60-7 (-)-α-Narcotine hydrochloride 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 7647-01-0 hydrogenchloride 
• 7664-93-9 sulfuric acid 
• 128-62-1 (±)-α-noscapine 
• 769-42-6 1,3-dimethylbarbituric acid 

Downstream Products

• 30936-27-7 4-methoxy-6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide 
• 494-55-3 N-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline 
• 88493-58-7 1,2,3,4-tetrahydro-2-methylisoquinolin-7-ol 
• 128-62-1 (±)-α-noscapine 
• 5985-55-7 Hydrocotarnine hydrochloride 
• 14097-39-3 N-methyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline 
• 5263-81-0 4-Methoxy-6-methyl-1,3-dioxolo<4,5-g>isochinolinium-methoiodid 
• 82-54-2 4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-ol 
• 569-31-3 meconin 

Relevant articles and documents

New Structural Modifications of Cotarnine Alkaloid Derivatives: Cotarnone and Dihydrocotarnine

Abstract: Simplest derivatives of the cotarnine alkaloid, like cotarnone and 1,2-dihydrocotarnine, undergo electrophilic Einhorn acylamidomethylation (with 60–95% yield) and sulfochlorination with chlorosulfonic acid at position 5. At the same time cotarnone and its derivatives undergo additional O-protodemethylation. Using these and some other reactions, we synthesized a number of previously unknown derivatives of two substrates with 5-chloroacetamidomethyl, 5-arylaminomethyl, 5-aminomethyl and 5-sulfamide groups.

Reactions of 5-dihydrocotarnyl-1,3-dimethylbarbituric acid and other cotarnine derivatives with 1,3-dimethylbarbituric acid. X-ray diffraction analysis of a 5,5-spiro derivative of 1,3-dimethylbarbituric acid

6-Methyl-4-methoxy-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g] isoquinolin-5-ol (cotarnine) and its derivatives, namely, 5-dihydrocotarnyl-1,3-dimethylbarbituric acid, dihydrocotarnylnitromethane, and dihydrocotarnylphenylacetonitrile, react with an excess

Practical Synthesis of 5,6,7,8-Tetrahydro-4-methoxy-6-methyl-1,3-dioxoloisoquinolin-5-ol (Cotarnine)

5,6,7,8-Tetrahydro-4-methoxy-6-methyl-1,3-dioxoloisoquinolin-5-ol (cotarnine, 1), an oxidative degradation product of (3S)-6,7-dimethoxy-3-isoquinolin-5-yl>phthalide (noscapine), has efficiently been synthesized from 2-methoxy-3,4-(methylenedioxy)benzaldehyde (7) in 66percent overall yield. -N-methylamino>acetaldehyde dimethyl acetal, obtained by reductive amination of 7 with aminoacetaldehyde dimethyl acetal followed by N-methylation, was cylized in acid to 5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxoloisoquinolin-8-ol (12).The major byproduct of the cyclization was C-8 methoxy derivative of 12, and the amount of this byproduct was decreased by removal of MeOH formed in the reaction mixture.Acetylation of the hydroxyl group in 12 and hydrogenolysis gave 5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxoloisoquinoline (hydrocotarnine), which was oxidized with I2 followed by basification to afford 1.