53251-94-8

Basic information

• Product Name: Pinaverium bromide
• Synonyms: 4-[(2-Bromo-4,5-dimethoxyphenyl)methyl]-4-[2-[2-(6,6-dimethylbicyclo[3.1.1]-hept-2-yl)ethoxy]ethyl]morpholinium Bromide;Dicetel;LAT-1717;Pinaverium;4-[(2-Bromo-4,5-dimethoxyphenyl)methyl]-4-[2-[2-(7,7-dimethyl-2-bicyclo[3.1.1]heptanyl)ethoxy]ethyl]morpholin-4-ium bromide;Pinaverium bromide;4-[(2-Bromo-4,5-dimethoxyphenyl)methyl]-4-[2-[2-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethoxy]ethyl]-, bromide;4-[(2-Bromo-4,5-dimethoxy-phenyl)methyl]-4-[2-[2-(6,6-dimethylnorpinan-2-yl)ethoxy]ethyl]-1-oxa-4-azoniacyclohexane bromide
• CAS NO: 53251-94-8
• Molecular Formula: Br*C₂₆H₄₁BrNO₄
• Molecular Weight: 591.42
• EINECS: 258-450-0
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 53251-94-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 159-1640C
• Appearance: white crystalline powder
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Pinaverium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Pinaverium bromide(53251-94-8)
• EPA Substance Registry System: Pinaverium bromide(53251-94-8)

Safety Data

• Hazardous Substances Data: 53251-94-8(Hazardous Substances Data)

Usage

Description

Pinaverium bromide is a white crystalline powder that serves as a spasmolytic agent with a low incidence of anticholinergic effects. It is primarily used for its antispasmodic properties, making it a valuable compound in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
Pinaverium bromide is used as a spasmolytic agent for its antispasmodic properties, which help in reducing muscle spasms and cramps, particularly in the gastrointestinal tract. Its low incidence of anticholinergic effects makes it a preferred choice for patients who are sensitive to such side effects.
Used in Gastrointestinal Treatment:
Pinaverium bromide is used as an antispasmodic in the treatment of gastrointestinal disorders, such as irritable bowel syndrome (IBS) and other conditions characterized by excessive smooth muscle contractions. Its ability to alleviate spasms and cramps without causing significant anticholinergic side effects makes it an effective and safe option for patients suffering from these conditions.

InChI:InChI=1/C26H41BrNO4.BrH/c1-26(2)21-6-5-19(22(26)16-21)7-11-31-12-8-28(9-13-32-14-10-28)18-20-15-24(29-3)25(30-4)17-23(20)27;/h15,17,19,21-22H,5-14,16,18H2,1-4H3;1H/q+1;/p-1

Synthetic route

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + 4-{2-[2-(6,6-dimethyl-norpinan-2-yl)-ethoxy]-ethyl}-morpholine (38284-47-8) → Pinaverium bromide (53251-94-8)

Conditions	Yield
In butanone Solvent; Reflux;	92.1%

N-chloroacetylmorpholine (1440-61-5) → Pinaverium bromide (53251-94-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0 - 20 °C 2: sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex / tetrahydrofuran / 0 °C 3: butanone / Reflux View Scheme

nopol (128-50-7) → Pinaverium bromide (53251-94-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: palladium on activated charcoal; hydrogen / ethanol / 20 °C 2: sodium hydride / tetrahydrofuran / 0 - 20 °C 3: sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex / tetrahydrofuran / 0 °C 4: butanone / Reflux View Scheme

dihydronopol (4747-61-9) → Pinaverium bromide (53251-94-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0 - 20 °C 2: sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex / tetrahydrofuran / 0 °C 3: butanone / Reflux View Scheme

Upstream product

• 53207-00-4 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene 
• 38284-47-8 4-{2-[2-(6,6-dimethyl-norpinan-2-yl)-ethoxy]-ethyl}-morpholine 
• 1440-61-5 N-chloroacetylmorpholine 
• 128-50-7 nopol 
• 4747-61-9 dihydronopol 

Relevant articles and documents

A synthesis method of pinaverium bromide

The invention relates to a pinaverium bromide synthesis method. Cheap and easily available morpholine as a raw material and an acylating agent undergo a reaction to produce a novel intermediate and pinaverium bromide is synthesized from the intermediate under mild conditions. Raw material reaction is complete, side reaction is less, the pinaverium bromide has treatment cis-isomeride content greater than or equal to 99% and trans-isomer content less than or equal to 1%, and product cis-isomer content is greatly improved.