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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 12:16:16 UTC
Update Date2021-09-26 23:06:52 UTC
HMDB IDHMDB0253568
Secondary Accession NumbersNone
Metabolite Identification
Common NameIprindole
DescriptionIprindole belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position. Iprindole is a very strong basic compound (based on its pKa). The CAS Registry Number of the free base is 5560-72-5 and of the hydrochloride is 20432-64-8. Anticholinergic side effects such as dry mouth and constipation are either greatly reduced in comparison to imipramine and most other TCAs or fully lacking with iprindole. Iprindole has been shown to be a potent inhibitor of the aromatic hydroxylation and/or N-dealkylation-mediated metabolism of many substances including, but not limited to octopamine, amphetamine, methamphetamine, fenfluramine, phenelzine, tranylcypromine, trimipramine, and fluoxetine, likely via inactivating cytochrome P450 enzymes. This compound has been identified in human blood as reported by (PMID: 31557052 ). Iprindole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Iprindole 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
PramindoleChEMBL
TertranChEMBL
GalaturChEMBL
ProndolChEMBL
Chemical FormulaC19H28N2
Average Molecular Weight284.447
Monoisotopic Molecular Weight284.22524891
IUPAC Name(3-{5H,6H,7H,8H,9H,10H,11H-cycloocta[b]indol-5-yl}propyl)dimethylamine
Traditional Nameiprindole
CAS Registry NumberNot Available
SMILES
CN(C)CCCN1C2=C(CCCCCC2)C2=CC=CC=C12
InChI Identifier
InChI=1S/C19H28N2/c1-20(2)14-9-15-21-18-12-6-4-3-5-10-16(18)17-11-7-8-13-19(17)21/h7-8,11,13H,3-6,9-10,12,14-15H2,1-2H3
InChI KeyPLIGPBGDXASWPX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassN-alkylindoles
Direct ParentN-alkylindoles
Alternative Parents
Substituents
  • N-alkylindole
  • 3-alkylindole
  • Indole
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP4.98ALOGPS
logP4.48ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)9.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area8.17 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity91.64 m³·mol⁻¹ChemAxon
Polarizability35.6 ųChemAxon
Number of Rings3ChemAxon
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-2H]-199.97930932474
DeepCCS[M+Na]+175.54430932474
AllCCS[M+H]+171.032859911
AllCCS[M+H-H2O]+167.732859911
AllCCS[M+NH4]+174.132859911
AllCCS[M+Na]+175.032859911
AllCCS[M-H]-178.332859911
AllCCS[M+Na-2H]-178.632859911
AllCCS[M+HCOO]-179.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IprindoleCN(C)CCCN1C2=C(CCCCCC2)C2=CC=CC=C123139.3Standard polar33892256
IprindoleCN(C)CCCN1C2=C(CCCCCC2)C2=CC=CC=C122343.1Standard non polar33892256
IprindoleCN(C)CCCN1C2=C(CCCCCC2)C2=CC=CC=C122315.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Iprindole GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-8190000000-a111eca0cbeca1854fe32021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iprindole 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 - Iprindole 10V, Positive-QTOFsplash10-000i-1090000000-cf49b97702c0cfd743e62017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iprindole 20V, Positive-QTOFsplash10-000l-5090000000-c71b7498a941c31420c02017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iprindole 40V, Positive-QTOFsplash10-000l-9120000000-fad42419a35441f332dd2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iprindole 10V, Negative-QTOFsplash10-001i-0090000000-a6527ac12efe4f13230d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iprindole 20V, Negative-QTOFsplash10-001j-1590000000-ce16a019c13297cb00e92017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iprindole 40V, Negative-QTOFsplash10-006t-1910000000-4d6542e23f7fda1df47c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iprindole 10V, Positive-QTOFsplash10-000i-0090000000-9577a96176594ed2d28c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iprindole 20V, Positive-QTOFsplash10-000i-1090000000-d7578a1f0c9a2a4fb91c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iprindole 40V, Positive-QTOFsplash10-0bt9-9680000000-455a308ac7041becc4dc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iprindole 10V, Negative-QTOFsplash10-001i-0090000000-f5334bfa95dd6629fe732021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iprindole 20V, Negative-QTOFsplash10-001i-0390000000-d8fc4c4fb53b2bfa4b632021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iprindole 40V, Negative-QTOFsplash10-0002-0920000000-66d4098541e8690b99ea2021-10-12Wishart 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 IDDB13496
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIprindole
METLIN IDNot Available
PubChem Compound21722
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 ]