10539-19-2

Basic information

• Product Name: moxaverine
• Synonyms: Isoquinoline, 3-ethyl-6,7-dimethoxy-1-(phenylmethyl)-;Moxaverina;Moxaverina [inn-spanish];1-Benzyl-3-ethyl-6,7-dimethoxyisoquinoline hydrochloride;moxaverine;1163-37-7 (Hydrochloride);3-Ethyl-1-benzyl-6,7-dimethoxyisoquinoline;Einecs 234-117-5
• CAS NO: 10539-19-2
• Molecular Formula: C₂₀H₂₁NO₂
• Molecular Weight: 307.391
• EINECS: 234-117-5
• Mol File: 10539-19-2.mol

Chemical Properties

• Melting Point: 71-72.5°
• Boiling Point: 441.2°Cat760mmHg
• Flash Point: 158.7°C
• Appearance: /
• Density: 1.109g/cm³
• Vapor Pressure: 1.44E-07mmHg at 25°C
• Refractive Index: 1.597
• PKA: 7.12±0.50(Predicted)
• CAS DataBase Reference: moxaverine(CAS DataBase Reference)
• NIST Chemistry Reference: moxaverine(10539-19-2)
• EPA Substance Registry System: moxaverine(10539-19-2)

Safety Data

• Hazardous Substances Data: 10539-19-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Moxaverine is used as a therapeutic agent for the treatment of peripheral vascular diseases, leveraging its ability to improve blood flow and alleviate symptoms associated with poor circulation.
Used in Gastrointestinal Applications:
Moxaverine is utilized as a muscle relaxant in the gastrointestinal tract, helping to reduce contractions and provide relief for conditions such as irritable bowel syndrome.
Used in Vascular Conditions:
Moxaverine is employed as a vasodilator, particularly for conditions like Raynaud's phenomenon, where it helps to relax constricted blood vessels and improve blood flow to affected areas.
Used in Smooth Muscle Relaxation:
Moxaverine is used as a smooth muscle relaxant in various medical applications, targeting conditions characterized by muscle spasm and reduced blood flow, thereby enhancing overall patient comfort and well-being.

InChI:InChI=1/C20H21NO2/c1-4-16-11-15-12-19(22-2)20(23-3)13-17(15)18(21-16)10-14-8-6-5-7-9-14/h5-9,11-13H,4,10H2,1-3H3

Upstream product

• 103-82-2 phenylacetic acid 
• 3141-93-3 4',5'-dimethoxydeoxybenzoin 
• 103-80-0 phenylacetyl chloride 
• 95314-73-1 methyl 1-methyl-2-propynyl carbonate 
• 536-74-3 phenylacetylene 

Relevant articles and documents

Redox-Neutral Manganese(I)-Catalyzed C?H Activation: Traceless Directing Group Enabled Regioselective Annulation

A strategy is reported in which traceless directing groups (TDGs) are used to promote the redox-neutral MnI-catalyzed regioselective synthesis of N-heterocycles. Alkyne coupling partners bearing a traceless directing group, which serves as both the chelator and internal oxidant, were used to control the regioselectivity of the annulation reactions. This operationally simple approach is highly effective with previously challenging unsymmetrical alkyne systems, including unbiased dialkyl alkynes, with perfect regioselectivity. The simple conditions and the ability to carry out synthesis on a gram scale underscore the usefulness of this method. The application of this strategy in the concise synthesis of the bioactive compound PK11209 and the pharmaceutical moxaverine is also described.

Copper-Catalyzed Aza-Sonogashira Cross-Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles

Nitrogen-substituted alkynes, such as ynamines and ynamides, are versatile synthetic building blocks. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high synthetic potential. However, their chemical reactivity remains unexplored owing mainly to the lack of synthetic accessibility. We report herein a versatile copper-catalyzed synthesis of ynimines from readily available O-acetyl ketoximes and terminal alkynes. A wide range of O-acetyl ketoximes derived from diaryl ketones, aryl alkyl ketones and dialkyl ketones underwent cross-coupling with a diverse set of terminal alkynes to afford the ynimines in good to excellent yields. An unprecedented [5+1] heteroannulation reaction exploiting the reactivity of the ynimine generated in situ was subsequently developed for the synthesis of medicinally important heterocycles, including isoquinolines, azaindoles, azabenzofurans, azabenzothiophenes and carbolines.

Rh(III)-catalyzed C-H activation/cyclization of oximes with alkenes for regioselective synthesis of isoquinolines

A Rh(iii)-catalyzed C-H activation/cyclization of oximes and alkenes for facile and regioselective access to isoquinolines has been developed. This protocol features mild reaction conditions and easily accessible starting materials, and has been applied to the concise synthesis of moxaverine. A kinetic isotope effect study was conducted and a plausible mechanism was proposed.