ContaminantDB: N-desethylamiodarone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:40:09 UTC

Update Date

2026-03-27 01:35:16 UTC

Accession Number

CHEM022580

Identification

Common Name

N-desethylamiodarone

Class

Small Molecule

Description

N-Desethylamiodarone is a CYP3A4 metabolite of amiodarone. Amiodarone is recognized as an effective drug in the treatment of arrhythmias. The main in-vivo metabolite of amiodarone, N-desethylamiodarone (DEAM), possesses clinically relevant class-II antiarrhythmic and vasodilator activities. (PMID: 11138840)

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Deethylamiodarone	HMDB
N-Desethylamiodarone	MeSH

Chemical Formula

C₂₃H₂₅I₂NO₃

Average Molecular Mass

617.258 g/mol

Monoisotopic Mass

616.992 g/mol

CAS Registry Number

83409-32-9

IUPAC Name

{2-[4-(2-butyl-1-benzofuran-3-carbonyl)-2,6-diiodophenoxy]ethyl}(ethyl)amine

Traditional Name

{2-[4-(2-butyl-1-benzofuran-3-carbonyl)-2,6-diiodophenoxy]ethyl}(ethyl)amine

SMILES

CCCCC1=C(C(=O)C2=CC(I)=C(OCCNCC)C(I)=C2)C2=CC=CC=C2O1

InChI Identifier

InChI=1S/C23H25I2NO3/c1-3-5-9-20-21(16-8-6-7-10-19(16)29-20)22(27)15-13-17(24)23(18(25)14-15)28-12-11-26-4-2/h6-8,10,13-14,26H,3-5,9,11-12H2,1-2H3

InChI Key

VXOKDLACQICQFA-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl-phenylketones

Alternative Parents

Substituents

Aryl-phenylketone
Benzofuran
Phenoxy compound
Benzoyl
3-aroylfuran
Phenol ether
Alkyl aryl ether
Halobenzene
Iodobenzene
Aryl halide
Aryl iodide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Secondary aliphatic amine
Ether
Secondary amine
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organoiodide
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.005 g/L	ALOGPS
logP	6.27	ALOGPS
logP	6.9	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.47 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	135.01 m³·mol⁻¹	ChemAxon
Polarizability	53.08 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000031000-c61fb1c3ee3bfb39d746	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-3100549000-59ef59884d93b25637e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9010321000-a9aa3fff76e60e62099d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-9107200000-d113c86be188909a7a1c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2000049000-5f355505168fca4dfbfb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00r6-3102293000-9b3cc6c66ccca7b31317	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-7902160000-9919a963f9be6f25cbf7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-2000009000-19bcc15b6f6434fa1725	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-3000069000-36f7d0bbcad7fe88da8a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-9101010000-cf6787f4f3877563cd3d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000009000-6e83756760649809fe32	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0400249000-5646f91168685b7da23e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-590206bcf5f65e62fb79	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0060528

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

104774

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Himmel HM, Dobrev D, Grossmann M, Ravens U: N-desethylamiodarone modulates intracellular calcium concentration in endothelial cells. Naunyn Schmiedebergs Arch Pharmacol. 2000 Dec;362(6):489-96.

N-desethylamiodarone (CHEM022580)

Structure for CHEM022580: N-desethylamiodarone