550-10-7

Usage

Uses

Used in Pharmaceutical Applications:
Hydrocotarnine is used as an active pharmaceutical ingredient for its various pharmacological effects. It is particularly known for its potential applications in the treatment of certain medical conditions due to its ability to interact with specific biological targets.
Used in Research and Development:
In the field of research and development, Hydrocotarnine serves as a valuable compound for studying the structure-activity relationships of Noscapine and its derivatives. This helps in the design and synthesis of new drugs with improved properties and therapeutic potential.
Used in Drug Synthesis:
Hydrocotarnine can be utilized as a key intermediate in the synthesis of novel drugs with potential applications in various therapeutic areas. Its unique chemical structure allows for further modification and optimization to develop more effective and safer medications.
Used in Quality Control and Standardization:
Hydrocotarnine is used as a reference compound in the quality control and standardization of Noscapine and its related products. It helps ensure the consistency, purity, and potency of these drugs, which is crucial for their safety and efficacy.

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

• 82-54-2 4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-ol 
• 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 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 7647-01-0 hydrogenchloride 
• 128-62-1 (±)-α-noscapine 
• 5779-99-7 4-methoxybenzo[d][1,3]dioxole-5-carbaldehyde 
• 108434-81-7 5,6,7,8-Tetrahydro-8-ethoxy-4-methoxy-6-methyl-1,3-dioxolo<4,5-g>isoquinoline 
• 60-29-7 diethyl ether 

Downstream Products

• 569-31-3 meconin 
• 494-55-3 N-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline 
• 82-54-2 4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-ol 
• 5263-81-0 4-Methoxy-6-methyl-1,3-dioxolo<4,5-g>isochinolinium-methoiodid 
• 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 
• 30936-27-7 4-methoxy-6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide 

Relevant academic research and scientific papers

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.

A new total synthesis of (±)-α-noscapine

A new, convergent total synthesis of (±)-α-noscapine was developed on a grams scale through the condensation of 3-trimethylsilyl-meconin derivative 9 and the iodized salt cotarnine derivative 20 as the key step. Staring from simple 2,3-dimethoxybenzoic acid, piperonal and 2,2-dimethoxyethanamine, through the traditional chemical processes to give the final product in 11.6% yield over 14 steps.

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

THE SYNTHESIS OF 6-METHOXY-7,8-METHYLENEDIOXYISOQUINOLINE DERIVATIVES

Several new 6-methoxy-7,8-methylenedioxyisoquinolines were synthesized starting from 4-methoxy-2,3-methylenedioxybenzaldehyde.

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.

Certain 6,7-methylene dioxydihydro or tetrahydro-isoquinoline derivatives

A tetrahydroisoquinoline derivative represented by formula: STR1 wherein R1 represents hydrogen or methyl and X1, X2, Y1 and Y2 are defined as follows: (1) X1 represents --OH, STR2 or OR2 wherein R2 represents lower alkyl when X2, Y1 and Y2 represent hydrogen (2) X1 and X2 together form oxo (=O), when Y1 and Y2 represent hydrogen or (3) Y1 and Y2 together form oxo (=O), when X1 and X2 represent hydrogen which is useful as an intermediate in preparation of Cotarnine.

Benzylamine derivative

There is provided a novel benzylamine derivative of the formula I: STR1 wherein R1 represents a hydrogen atom or a methyl group, X represents a hydrogen atom, a methyl group or a tosyl group, and Y represents a hydrogen atom, a methyl group or STR2 in which R2 and R3 being identical or different from each other represent independently a lower alkyl group.