5884-22-0

Basic information

• Product Name: 1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium chloride
• Synonyms: 1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium chloride;DIHYDROALKALI HYDROCHLORIDE;1-[(3,4-diMethoxyphenyl)Methyl]-6,7-diMethoxy-3,4-dihydroisoquinoline hydrochloride;LRUSBWIBSILYNE-UHFFFAOYSA-N
• CAS NO: 5884-22-0
• Molecular Formula: C₂₀H₂₃NO₄*ClH
• Molecular Weight: 377.86186
• EINECS: 227-560-0
• Mol File: 5884-22-0.mol

Chemical Properties

• Melting Point: 202℃
• Boiling Point: 482.6°Cat760mmHg
• Flash Point: 196.9°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 5.28E-09mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: 1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium chloride(5884-22-0)
• EPA Substance Registry System: 1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium chloride(5884-22-0)

Safety Data

• Hazardous Substances Data: 5884-22-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium chloride is utilized as an antiarrhythmic agent in pharmaceutical development, due to its effects on cardiac ion channels. It is being studied for its potential to treat heart rhythm disorders, offering a novel approach to managing such conditions.
Used in Chemical Research:
In the realm of chemical research, 1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium chloride serves as a subject of study for its potential biological activity. Researchers are exploring its properties and interactions to understand its implications in the development of new drugs for a variety of medical conditions, highlighting its versatility and potential in advancing medicinal chemistry.

InChI:InChI=1/C20H23NO4/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16/h5-6,10-12H,7-9H2,1-4H3

Upstream product

• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 139-76-4 N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide 
• 102011-15-4 N-<2-(3,4-dimethoxyphenyl)ethyl>-3,4-dimethoxyphenylacetamide 

Downstream Products

• 1354039-86-3 (R)-2-[(S)-(1-3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-isopropyl-2-phenylacetamide 
• 54417-52-6 (S)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3.4-tetrahydroisoquinoline hydrochloride 
• 6429-04-5 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride 
• 522-57-6 papaveraldine 
• 1075726-79-2 (1R)-1-[(3,4-dimethoxyphenyl)-methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-benzyloxycarbonylethyl-isoquinoline oxalate 
• 50896-90-7 (-) N-norlaudanosine 
• 64228-81-5 cisatracurium besylate 
• 64228-84-8 N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(R)-(-)-tetrahydropapaverine 
• 181423-71-2 14-(3,4-dimethoxyphenyl)-2,3,11,12-tetramethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 

Relevant articles and documents

Preparation of powder injection pharmaceutical composition from high-purity papaverine hydrochloride

The invention relates to preparation of a powder injection pharmaceutical composition from high-purity papaverine hydrochloride, in particular to a preparation method of papaverine hydrochloride. Themethod comprises the following steps of: heating 3, 4-dimethoxy-beta-phenyl-ethylamine and 3, 4-dimethoxy-phenyl-acetic acid to melting, and then carrying out reaction in a mixture of benzene and chlorethoxyfos to obtain 6, 7, 3', 4'-tetramethoxy-1-benzyl-dihydro-isoquinoline hydrochloride; then dissolving the wet product in tetrahydronaphthalene after the wet product becomes free alkali, and carrying out dehydrogenation reaction at 180DEG C in the presence of a Raney nickel catalyst; after dehydrogenation is finished, directly filtering the tetrahydronaphthalene reaction mixture from the Raney nickel catalyst into a mixture of a hydrochloric acid aqueous solution and methanol; filtering out precipitates, and performing recrystallizing from the ethanol-water solution in an inert gas environment to obtain off-white 6, 7, 3', 4'-tetramethoxy-1-benzyl isoquinoline hydrochloride, namely papaverine hydrochloride. The invention also relates to a papaverine hydrochloride powder injection pharmaceutical composition, and a preparation method and a quality detection method thereof. The invention achieves excellent technical effects as described in the specification.

A xylochemically inspired synthesis of lamellarin G trimethyl ether via an enaminone intermediate

A concise high yielding synthesis of lamellarin G trimethyl ether has been achieved from precursors and solvents that can in principle be derived from xylochemical (woody biomass) sources. The route is comparatively green in that some reactions are performed without solvent or with relatively benign solvents. In addition, chromatographic purification of products is avoided, and only a single aqueous workup is performed. The novelty of the synthesis lies in the intermediacy of an enaminone for the construction of the central pyrrole ring. The overall yield of the product is among the highest reported to date.

Application of differential reactivity towards synthesis of lamellarin and 8-oxoprotoberberine derivatives: Study of photochemical properties of aryl-substituted benzofuran-8-oxoprotoberberines

A unique differential reactivity between dihydroisoquinolines and 3-nitrocoumarins was observed and was exploited for the efficient construction of lamellarins and their isomeric benzofuran-8-oxoprotoberberine derivatives under acid-catalyzed or base-promoted conditions. Further, these prepared aryl-substituted benzofuran-8-oxoprotoberberine derivatives bearing electron-donating substituents on benzofuran moiety are found to be benchtop stable but light-sensitive, and can undergo oxidative ring-opening reaction to give the corresponding keto products when exposed to visible light under aerobic conditions.

Total synthesis of 8-epi-javaberine A and javaberine A

The total synthesis of berberine alkaloid javaberine A was examined. The B/C ring of berberine was successfully constructed by sequential Bischler-Napieralski cyclization-reduction protocols, and final demethylation afforded both javaberine A and its epimer.

Discovery and Characterization of ACT-335827, an Orally Available, Brain Penetrant Orexin Receptor Type1 Selective Antagonist

Stress relief: Orexin neuropeptides regulate arousal and stress processing through orexin receptor type1 (OXR-1) and 2 (OXR-2) signaling. A selective OXR-1 antagonist, represented by a phenylglycine-amide substituted tetrahydropapaverine derivative (ACT-335827), is described that is orally available, penetrates the brain, and decreases fear, compulsive behaviors and autonomic stress reactions in rats. Copyright

1,2,3,4-tetrahydroisoquinoline derivative and its use as orexin receptor antagonist

The invention relates to the compound (R)-2-[(S)-1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-isopropyl-2-phenyl-acetamide; and to its use as active ingredient in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compound, pharmaceutical compositions containing the compound and methods of treatment comprising administration of said compound to a human being.

Novel hybrids from lamellarin D and combretastatin A 4 as cytotoxic agents

A new series of hybrids of lamellarin D and combretastatin A 4, 1,2-diphenyl-5,6-dihydropyrrolo [2,1-a] isoquinolines, were designed as cytotoxic agents based on principles of combination in medicinal chemistry and taking the parent compounds' different anti-proliferative mechanisms into consideration. Twenty-two novel hybrids were synthesized through a convenient route, with a key step of core pyrrole formation and evaluated for their anti-proliferative activities in vitro against K-562, A-549, SMMC-7721, SGC-7901 and HCT-116 cancer cell lines. The results showed that some hybrids had good anti-proliferative activities in low IC50 ranges.

Piperazine derivatives

A compound represented by formula (I): STR1 wherein Q represents an aryl group, a heterocyclic group, a diarylmethyl group, an aralkyl group composed of an aryl group and an alkylene group, an alkyl group or a cycloalkyl group, in which the aryl group, heterocyclic group, and the aryl moiety of the diarylmethyl group and aralkyl group may be substituted with one or more substituents; R represents a bicyclic, substituted, nitrogen-containing heterocyclic group or a substituted phenyl group, in which the nitrogen-containing heterocyclic group is composed of a 5-membered, substituted, aromatic or saturated ring containing one or two nitrogen atoms and a 6-membered ring; and Z represents an alkylene group, an alkenylene group, an alkylene group, a carbonyl group, an alkylene group containing a carbonyl group or an oxalyl group, or a salt thereof. The compound has calmodulin inhibitory activity and is useful as a treating agent for diseases in the circulatory organs or in the cerebral region which are caused by excessive activation of calmodulin.

Piperazine derivatives useful as calmodolin inhibitors

A compound represented by formula (I): wherein Q represents an aryl group, a heterocyclic group, a diarylmethyl group, an aralkyl group composed of an aryl group and an alkylene group, an alkyl group or a cycloalkyl group, in which the aryl group, heterocyclic group, and the aryl moiety of the diarylmethyl group and aralkyl group may be substituted with one or more substituents; R represents a bicyclic, substituted, nitrogen-containing heterocyclic group or a substituted phenyl group, in which the nitrogen-containing heterocyclic group is composed of a 5-membered, substituted, aromatic or saturated ring containing one or two nitrogen atoms and a 6-membered ring; and Z represents an alkylene group, an alkenylene group, an alkylene group, a carbonyl group, an alkylene group containing a carbonyl group or an oxalyl group,or a salt thereof. The compound has calmodulin inhibitory activity and is useful as a treating agent for diseases in the circulatory organs or in the cerebral region which are caused by excessive activation of calmodulin.