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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-02 16:12:44 UTC
Update Date2021-09-26 22:50:12 UTC
HMDB IDHMDB0242620
Secondary Accession NumbersNone
Metabolite Identification
Common Name(2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine
Description(2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine, also known as iofetamine hydrochloride, I 123 or N-isopropyl-p-iodoamphetamine, belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. Based on a literature review very few articles have been published on (2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine. This compound has been identified in human blood as reported by (PMID: 31557052 ). (2r)-1-(4-iodophenyl)-n-propan-2-ylpropan-2-amine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
Hydrochloride, I-123 iofetamineHMDB
I-123 iofetamine hydrochlorideHMDB
I-123, iofetamineHMDB
Iodine 123 impHMDB
Iodine-123-impHMDB
Iofetamine hydrochloride, I 123HMDB
Iofetamine hydrochloride, I-123HMDB
Iofetamine I 123HMDB
Iofetamine I-123HMDB
N Isopropyl p iodoamphetamineHMDB
N-Isopropyl-p-(iodine-123)-iodoamphetamineHMDB
N-Isopropyl-p-iodoamphetamineHMDB
N-Isopropyl-p-iodoamphetamine (I123) hydrochlorideHMDB
Chemical FormulaC12H18IN
Average Molecular Weight303.187
Monoisotopic Molecular Weight303.04839
IUPAC Name[1-(4-iodophenyl)propan-2-yl](propan-2-yl)amine
Traditional Nameiofetamine
CAS Registry NumberNot Available
SMILES
CC(C)NC(C)CC1=CC=C(I)C=C1
InChI Identifier
InChI=1S/C12H18IN/c1-9(2)14-10(3)8-11-4-6-12(13)7-5-11/h4-7,9-10,14H,8H2,1-3H3
InChI KeyISEHJSHTIVKELA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Phenylpropane
  • Aralkylamine
  • Halobenzene
  • Iodobenzene
  • Aryl halide
  • Aryl iodide
  • Secondary aliphatic amine
  • Secondary amine
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organohalogen compound
  • Organoiodide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.58ALOGPS
logP3.94ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)10.35ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity71.01 m³·mol⁻¹ChemAxon
Polarizability27.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+161.14430932474
DeepCCS[M-H]-158.26830932474
DeepCCS[M-2H]-194.05630932474
DeepCCS[M+Na]+169.34830932474
AllCCS[M+H]+165.132859911
AllCCS[M+H-H2O]+161.732859911
AllCCS[M+NH4]+168.332859911
AllCCS[M+Na]+169.232859911
AllCCS[M-H]-161.432859911
AllCCS[M+Na-2H]-163.032859911
AllCCS[M+HCOO]-164.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amineCC(C)NC(C)CC1=CC=C(I)C=C12251.0Standard polar33892256
(2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amineCC(C)NC(C)CC1=CC=C(I)C=C11648.3Standard non polar33892256
(2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amineCC(C)NC(C)CC1=CC=C(I)C=C11650.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine,1TMS,isomer #1CC(C)N(C(C)CC1=CC=C(I)C=C1)[Si](C)(C)C1843.4Semi standard non polar33892256
(2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine,1TMS,isomer #1CC(C)N(C(C)CC1=CC=C(I)C=C1)[Si](C)(C)C1896.7Standard non polar33892256
(2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine,1TMS,isomer #1CC(C)N(C(C)CC1=CC=C(I)C=C1)[Si](C)(C)C1811.2Standard polar33892256
(2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine,1TBDMS,isomer #1CC(C)N(C(C)CC1=CC=C(I)C=C1)[Si](C)(C)C(C)(C)C2082.1Semi standard non polar33892256
(2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine,1TBDMS,isomer #1CC(C)N(C(C)CC1=CC=C(I)C=C1)[Si](C)(C)C(C)(C)C2147.6Standard non polar33892256
(2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine,1TBDMS,isomer #1CC(C)N(C(C)CC1=CC=C(I)C=C1)[Si](C)(C)C(C)(C)C1944.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9050000000-78ce43a43349b7ca19482021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine 10V, Positive-QTOFsplash10-0udi-2039000000-4ab830f2e93573d506e32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine 20V, Positive-QTOFsplash10-014i-0090000000-0e1c77b7e802f6a1e6472021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine 40V, Positive-QTOFsplash10-014i-4090000000-a147a2add5a401f58a5f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine 10V, Negative-QTOFsplash10-0udi-0019000000-0de6c42f34bce3e661a92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine 20V, Negative-QTOFsplash10-004l-0961000000-4c790822447390fbc3a12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R)-1-(4-Iodophenyl)-N-propan-2-ylpropan-2-amine 40V, Negative-QTOFsplash10-004i-1920000000-ab8d85d89765285ee6bb2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3598
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3729
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]