147030-50-0

Basic information

• Product Name: 3-(4-HYDROXY-3-IODOBENZOYL)-2-BUTYLBENZOFURAN
• Synonyms: 3-(4-HYDROXY-3-IODOBENZOYL)-2-BUTYLBENZOFURAN;De(diethylaMinoethyl-5-iodo) AMiodarone;(2-Butyl-3-benzofuranyl)(4-hydroxy-3-iodophenyl)Methanone;L 6424;AMiodarone EP IMpurity F
• CAS NO: 147030-50-0
• Molecular Formula: C19H17IO3
• Molecular Weight: 420.24
• Product Categories: Heterocycles;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 147030-50-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 3-(4-HYDROXY-3-IODOBENZOYL)-2-BUTYLBENZOFURAN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-HYDROXY-3-IODOBENZOYL)-2-BUTYLBENZOFURAN(147030-50-0)
• EPA Substance Registry System: 3-(4-HYDROXY-3-IODOBENZOYL)-2-BUTYLBENZOFURAN(147030-50-0)

Safety Data

• Hazardous Substances Data: 147030-50-0(Hazardous Substances Data)

Usage

Description

3-(4-HYDROXY-3-IODOBENZOYL)-2-BUTYLBENZOFURAN is a complex organic compound characterized by its unique molecular structure, which features a benzofuran core with a hydroxy-iodobenzoyl group attached to the third position and a butyl group at the second position. 3-(4-HYDROXY-3-IODOBENZOYL)-2-BUTYLBENZOFURAN exhibits an off-white solid appearance and is known for its potential applications in various industries due to its chemical properties.

Uses

Used in Pharmaceutical Industry:
3-(4-HYDROXY-3-IODOBENZOYL)-2-BUTYLBENZOFURAN is used as an intermediate for the synthesis of Amiodarone (A632950), a non-selective ion channel blocker and an antiarrhythmic agent classified under class III. Amiodarone is widely utilized in the treatment of various cardiac arrhythmias, including atrial fibrillation and ventricular tachycardia, due to its ability to stabilize the heart's electrical activity.
As an intermediate, 3-(4-HYDROXY-3-IODOBENZOYL)-2-BUTYLBENZOFURAN plays a crucial role in the production process of Amiodarone, contributing to the development of this essential medication for cardiac patients.

Upstream product

• 1951-25-3 Amiodarone 
• 52490-15-0 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran 

Downstream Products

• 85642-08-6 Deiodoamiodarone 

Relevant articles and documents

Structure effect relationships of amiodarone analogues on the inhibition of thyroxine deiodination

Objectives: Amiodarone (AMI) has proven to be a potent anti-arrhythmic compound. Due to the structural similarity between AMI and thyroid hormone, it is possible that the drug could inhibit the activity of the 5'-thyroxine- deiodinase. Methods: AMI analogues resulting from (1) dealkylation, (2) deiodination and (3) deamination were synthesised and used as inhibitors in an in vitro biotransformation reaction of thyroxine (T4) to 3,3',5'- triiodothyronine (T3). Using high-performance liquid chromatography and ultraviolet detection for quantifying T3, it was found that the 5'-T4 deiodinase type I was involved in the reaction. On separate occasions, AMI or an AMI analogue was added to the reaction as an inhibitor. Results: All studied AMI analogues inhibited 5'-T4 deiodination competitively (K(i) value range 25-360 μM). In the concentration range of 1-1000 μM, AMI and its N- desethylated, deiodinated analogues inhibited 5'-T4 deiodination very weakly. AMI analogues with a hydroxyl group at the 4-position were strong inhibitors. Moreover, diiodo-AMI analogues inhibited 5'-T4 deiodination more strongly than their corresponding monoiodo- or deiodinated derivatives. Conclusion: It is likely that the degraded products of AMI could be responsible for thyroid dysfunction toxicosis in AMI therapy.

Trace amine-associated receptor 1 (TAAR1) is activated by amiodarone metabolites

Amiodarone (Cordarone, Wyeth-Ayerst Pharmaceuticals) is a clinically available drug used to treat a wide variety of cardiac arrhythmias. We report here the synthesis and characterization of a panel of potential amiodarone metabolites that have significant structural similarity to thyroid hormone and its metabolites the iodothyronamines. Several of these amiodarone derivatives act as specific agonists of the G protein-coupled receptor (GPCR) trace amine-associated receptor 1 (TAAR1). This result demonstrates a novel molecular target for amiodarone derivatives with potential clinical significance.