139-76-4

Basic information

• Product Name: N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide
• Synonyms: N-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-dimethoxyphenylacetam;N-(3,4-Dimethoxyphenethyl)-3,4-dimethoxybenzeneacetamide;N-[2-(3,4-Dimethoxyphenyl)ethyl]-3,4-dimethoxybenzeneacetamide;2-(3,4-dimethoxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide
• CAS NO: 139-76-4
• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.4162
• EINECS: 205-374-0
• Mol File: 139-76-4.mol

Chemical Properties

• Boiling Point: 559.3 °C at 760 mmHg
• Flash Point: 292 °C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 1.54E-12mmHg at 25°C
• Refractive Index: 1.54
• CAS DataBase Reference: N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide(139-76-4)
• EPA Substance Registry System: N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide(139-76-4)

Safety Data

• Hazardous Substances Data: 139-76-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-(3,4-Dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide is used as an impurity in the production of Papaverine (P190500), a smooth muscle relaxant. Its presence is significant due to its potential effects on the overall pharmacological activity and safety profile of the final product. As a vasodilator, it may contribute to the drug's ability to relax smooth muscles and dilate blood vessels, particularly in the cerebral circulation.
In the context of its use as an impurity in Papaverine, the compound may also be relevant for research and development purposes. Understanding its properties and interactions with Papaverine can help in optimizing the manufacturing process, ensuring the quality and efficacy of the final drug product, and potentially discovering new therapeutic applications or mechanisms of action.

InChI:InChI=1/C20H25NO5/c1-23-16-7-5-14(11-18(16)25-3)9-10-21-20(22)13-15-6-8-17(24-2)19(12-15)26-4/h5-8,11-12H,9-10,13H2,1-4H3,(H,21,22)

Upstream product

• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 7647-01-0 hydrogenchloride 
• 854391-46-1 bis-[(3,4-dimethoxy-phenyl)-acetyl]-amine 
• 64-19-7 acetic acid 
• 861597-70-8 (3,4-dimethoxy-phenyl)-acetic acid-(3,4-dimethoxy-phenacylamide) 
• 76579-53-8 2-(3,4-dimethoxyphenyl)-N,N-dimethylethanethioamide 
• 85621-43-8 3,4-dihydroxyphenylacetic acid diacetate 
• 14773-41-2 3-(3,4-dimethoxyphenyl)propionic acid amide 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 73663-56-6 (3,4-Dimethoxy-phenyl)-[5-(3,4-dimethoxy-phenyl)-oxazol-2-yl]-methanol 
• 73663-61-3 5-(3,4-Dimethoxyphenyl)oxazole 
• 7306-46-9 4-chloromethyl-1,2-dimethoxy-benzene 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 

Downstream Products

• 5884-22-0 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3.4-dihydroisoquinoline hydrochloride 
• 54417-52-6 (S)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3.4-tetrahydroisoquinoline hydrochloride 
• 1354039-86-3 (R)-2-[(S)-(1-3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-isopropyl-2-phenylacetamide 
• 64228-80-4 C₅₃H₇₂N₂O₁₂⁽²⁺⁾*2CH₃O₃S^(1-) 
• 64229-25-0 C₅₀H₆₆N₂O₁₂⁽²⁺⁾*2CH₃O₃S^(1-) 
• 64228-78-0 pentamethylene bis(1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate) dioxalate 
• 81165-35-7 3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 2-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-ethyl ester; compound with oxalic acid 
• 81182-07-2 3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 4-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-butyl ester; compound with oxalic acid 
• 81165-42-6 3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 3-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-propyl ester; compound with oxalic acid 
• 64264-79-5 C₅₆H₇₈N₂O₁₂⁽²⁺⁾*2I^(1-) 
• 64229-15-8 C₅₅H₇₆N₂O₁₂⁽²⁺⁾*2I^(1-) 
• 81182-09-4 C₅₂H₇₀N₂O₁₃⁽²⁺⁾*2I^(1-) 
• 64229-02-3 C₅₄H₇₄N₂O₁₂⁽²⁺⁾*2I^(1-) 
• 64493-21-6 C₅₃H₇₂N₂O₁₂⁽²⁺⁾*2I^(1-) 

Relevant articles and documents

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.

Carbon-13 NMR Spectra of Tembamide, Aegeline and Related Amides

Carbon-13 NMR spectral studies of tembamide (1) and aegeline (2), constituents of Fagara hyemalis and Aegle marmelos respectively, and a series of their structurally related amides (3-13) have been carried out.The assignment of the resonances of two related dimers are also reported.The assignment of the various resonances were made by considering the changes in chemical shifts produced by the change of substituents and also by using 1, 13 and a related compound as model compounds.

COMPOUNDS, COMPOSITIONS AND METHODS FOR TREATING NASH, NAFLD, AND OBESITY

The present technology relates to methods of treating NASH, NAFLD and/or obesity using compounds of Formulas I, II, III, IV, V, and/or VI. The methods include administering to a subject suffering from one or more of non-alcoholic steatohepatitis (NASH), non- alcoholic fatty liver disease (NAFLD) and/or obesity a therapeutically effective amount of such a compound

Preparation method of papaverine

The invention discloses a preparation method of papaverine. The invention provides a preparation method of papaverine, which comprises the following steps: (1) in a solvent, in the presence of a cyclization agent, carrying out cyclization reaction as shown in the specification on a compound as shown in a formula I to obtain a compound as shown in a formula II; and (2) in a solvent, in the presence of a dehydrogenation catalyst, carrying out dehydrogenation reaction as shown in the specification on the compound as shown in the formula II to obtain papaverine. The compound as shown in the formula II prepared in the step (1) is directly used in the step (2) without being purified. The method is simple in process, easy to operate, low in cost and suitable for industrial production, and the product is high in yield and purity.

Synthesis and SARs of dopamine derivatives as potential inhibitors of influenza virus PAN endonuclease

Currently, influenza PAN endonuclease has become an attractive target for development of new drugs to treat influenza infections. Herein we report the discovery of new PAN endonuclease inhibitors derived from a chelating agent dopamine moiety. A series of dopamine amide derivatives and their conformationally constrained 1,2,3,4-tetrahydroisoquinoline-6,7-diol-based analogs were elaborated and assayed against influenza virus A/WSN/33 (H1N1). Most compounds exhibited moderate to excellent antiviral activities, generating a preliminary SARs. Among them, compounds 14 and 19 showed stronger anti-IAV activity compared with the reference Peramivir. Moreover, 14 and 19 demonstrated a concentration-dependent inhibition of PAN endonuclease based on both FRET assay and SPR assay. Docking studies were also performed to elucidate the binding mode of 14 and 19 with the PAN protein and to identify amino acids involved in their mechanism of action, which were well consistent with the biological data. This finding was beneficial to laying the foundation for the rational development of more effective PAN endonuclease inhibitors.

One-Pot Synthesis of Papaverine Hydrochloride and Identification of Impurities

Abstract: A one-pot synthesis of papaverine hydrochloride with 99.6% purity was performed using xylene as solvent for the entire process. The critical parameters of each step, as well as the impurities generated, were identified. The overall yield was improved to 63%. The proposed synthetic procedure is suitable for industrial production.

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.

Oxidative route to pyrroloisoquinoline-2,3-dione

We herein report an efficient constructive method for synthesis of structurally important Pyrroloisoquinoline-2,3-dione from dihydroisoquinoline through oxidative cyclisation. Process is optimised to give best efficiency at gram scale and laborious purification techniques such as column chromatography or recrystallisation were avoided in all steps further featuring uniqueness of this method as compared to the available literature.

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.

A facile synthesis of 1-oxo-pyrrolo[2,1-a]isoquinolines

The facile synthesis of 1-oxo-pyrrolo[2,1-a]isoquinolines from the reaction of 1-aroyl-3,4-dihydroisoquinolines and symmetrical alkynes in toluene is described. The novel compounds contain functional groups that are suitable for further modification.