N-desethylamiodarone (CHEM022580)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:40:09 UTC
Update Date2016-11-09 01:17:32 UTC
Accession NumberCHEM022580
Identification
Common NameN-desethylamiodarone
ClassSmall Molecule
DescriptionN-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 TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DeethylamiodaroneHMDB
N-DesethylamiodaroneMeSH
Chemical FormulaC23H25I2NO3
Average Molecular Mass617.258 g/mol
Monoisotopic Mass616.992 g/mol
CAS Registry Number83409-32-9
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
SMILESCCCCC1=C(C(=O)C2=CC(I)=C(OCCNCC)C(I)=C2)C2=CC=CC=C2O1
InChI IdentifierInChI=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 KeyVXOKDLACQICQFA-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl-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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.005 g/LALOGPS
logP6.27ALOGPS
logP6.9ChemAxon
logS-5.1ALOGPS
pKa (Strongest Basic)9.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area51.47 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity135.01 m³·mol⁻¹ChemAxon
Polarizability53.08 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000031000-c61fb1c3ee3bfb39d746Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3100549000-59ef59884d93b25637e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9010321000-a9aa3fff76e60e62099dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9107200000-d113c86be188909a7a1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2000049000-5f355505168fca4dfbfbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00r6-3102293000-9b3cc6c66ccca7b31317Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-7902160000-9919a963f9be6f25cbf7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2000009000-19bcc15b6f6434fa1725Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3000069000-36f7d0bbcad7fe88da8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9101010000-cf6787f4f3877563cd3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000009000-6e83756760649809fe32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0400249000-5646f91168685b7da23eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-590206bcf5f65e62fb79Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0060528
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID104774
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.