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A8423 Sigma-Aldrich

Amiodarone hydrochloride

≥98%

Synonym: (2-Butyl-3-benzofuranyl)[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]methanone hydrochloride, 2-Butyl-3-benzofuranyl-4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl ketone hydrochloride

  • CAS Number 19774-82-4

  • Empirical Formula (Hill Notation) C25H29I2NO3 · HCl

  • Molecular Weight 681.77

  •  EC Number 243-293-2

  •  MDL number MFCD00069204

  •  PubChem Substance ID 24277818

  •  NACRES NA.77

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Properties

Related Categories A-AM, Application Index, Approved Therapeutics/Drug Candidates, Autophagy, Autophagy Activators,
assay   ≥98%
originator   Wyeth
storage temp.   2-8°C
SMILES string   Cl[H].CCCCCc1oc2ccccc2c1C(=O)c3cc(I)c(OCCN(CC)CC)c(I)c3
InChI   1S/C26H31I2NO3.ClH/c1-4-7-8-13-23-24(19-11-9-10-12-22(19)32-23)25(30)18-16-20(27)26(21(28)17-18)31-15-14-29(5-2)6-3;/h9-12,16-17H,4-8,13-15H2,1-3H3;1H
InChI key   DBZSHZLTNYTZJM-UHFFFAOYSA-N

Description

Application

Amiodarone hydrochloride has been used to study its interaction with cysteamine to stimulate autophagy in cultured biosensor cell lines. It has also been used in larval and adult organ toxicogenomic screening to analyze the transcriptional effects of pharmaceuticals.

Amiodarone hydrochloride is a non-selective ion channel blocker with broad fungicidal activity. Amiodarone induces an immediate influx of Ca2+ in Saccharomyces cerevisiae, followed by mitochondrial fragmentation and cell death. Amiodarone hydrochloride has also been used in a study to determine concentrations of thyroid disrupting substances in effluents from wastewater treatment plants.

Packaging

1, 5, 10 g in poly bottle

Biochem/physiol Actions

Non-selective ion channel blocker with broad fungicidal activity. Amiodarone induces an immediate influx of Ca2+ in Saccharomyces cerevisiae, followed by mitochondrial fragmentation and cell death.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

This compound was developed by Wyeth. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Substrates

CYP2C8/9 and CYP3A family (minor pathway) inhibitor and substrate; CYP2D6, CYP3A family, CYP2D6, CYP2A6, CYP2B6 desethyl-form inhibitor

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Personal Protective Equipment 
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
WGK 3
RTECS 
OB1361000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
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What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
What is the solubility of Product A8423, Amiodarone hydrochloride, and in which solvents may it be reconstituted?
Sigma-Aldrich tests the solubility of Product A8423, Amiodarone hydrochloride in water at a concentration of 50 mg/ml. This requires heating at 105 °C for 10 minutes. This concentration is above the solubility maximum at room temperature. As per the chemicals encyclopedia published by the Royal Society of Chemistry 13th Ed., Entry #482, solubility at 25 °C, (g/100mL):Water (0.07), Ethanol (1.28), Methanol (9.98), Chloroform (44.51), Methylene Chloride (19.2), and Hexane (0.03).Reportedly, the solubility of the product is 10 mg/ml each in DMSO and in dimethylformamide.
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Protocols & Articles

Articles

Discover Bioactive Small Molecules for Ion Channels Research

Ion transport across the relatively impermeable lipid bilayer of the cell membrane is accomplished via membrane proteins known as ion channels, pumps and transporters. Ion channels are gated pores an...
Keywords: Biological processes, Cell signaling, Diseases, Hormones, Ligands, Neurotransmitters

Peer-Reviewed Papers
15

References

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