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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:46:28 UTC
HMDB IDHMDB0015049
Secondary Accession Numbers
  • HMDB15049
Metabolite Identification
Common NameAnileridine
DescriptionAnileridine, also known as sulfathalidine, belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group. Anileridine is a drug which is used for treatment and management of pain (systemic) and for use as an anesthesia adjunct. Anileridine is a very strong basic compound (based on its pKa). In humans, anileridine is involved in anileridine action pathway. Anileridine is a potentially toxic compound. A piperidinecarboxylate ester that is the ethyl ester of isonipecotic acid in which the hydrogen alpha- to the carboxyl group is substituted by a phenyl group, and the hydrogen attached to the nitrogen is substituted by a 2-(4-aminophenyl)ethyl group.
Structure
Data?1582753251
Synonyms
ValueSource
1-[2-(4-Aminophenyl)ethyl]-4-phenyl-4-piperidinecarboxlic acid ethyl esterChEBI
AnileridinaChEBI
AnileridinumChEBI
Ethyl 1-(2-(4-aminophenyl)ethyl)-4-phenyl-4-piperidinecarboxylateChEBI
Ethyl 1-(4-aminophenethyl)-4-phenylisonipecotateChEBI
Ethyl 1-(p-aminophenethyl)-4-phenylisonipecotateChEBI
N-(beta-(p-Aminophenyl)ethyl)-4-phenyl-4-carbethoxypiperidineChEBI
N-beta-(p-Aminophenyl)ethylnormeperidineChEBI
1-[2-(4-Aminophenyl)ethyl]-4-phenyl-4-piperidinecarboxlate ethyl esterGenerator
Ethyl 1-(2-(4-aminophenyl)ethyl)-4-phenyl-4-piperidinecarboxylic acidGenerator
Ethyl 1-(4-aminophenethyl)-4-phenylisonipecotic acidGenerator
Ethyl 1-(p-aminophenethyl)-4-phenylisonipecotic acidGenerator
N-(b-(p-Aminophenyl)ethyl)-4-phenyl-4-carbethoxypiperidineGenerator
N-(Β-(p-aminophenyl)ethyl)-4-phenyl-4-carbethoxypiperidineGenerator
N-b-(p-Aminophenyl)ethylnormeperidineGenerator
N-Β-(p-aminophenyl)ethylnormeperidineGenerator
PhthalylsulfathiazoleHMDB
SulfathalidineHMDB
Anileridine monohydrochlorideHMDB
Anileridine hydrochlorideHMDB
Anileridine phosphateHMDB
Anileridine phosphate (1:1)HMDB
Anileridine dihydrochlorideHMDB
Chemical FormulaC22H28N2O2
Average Molecular Weight352.4699
Monoisotopic Molecular Weight352.21507815
IUPAC Nameethyl 1-[2-(4-aminophenyl)ethyl]-4-phenylpiperidine-4-carboxylate
Traditional Nameanileridine
CAS Registry Number144-14-9
SMILES
CCOC(=O)C1(CCN(CCC2=CC=C(N)C=C2)CC1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C22H28N2O2/c1-2-26-21(25)22(19-6-4-3-5-7-19)13-16-24(17-14-22)15-12-18-8-10-20(23)11-9-18/h3-11H,2,12-17,23H2,1H3
InChI KeyLKYQLAWMNBFNJT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassPhenylpiperidines
Direct ParentPhenylpiperidines
Alternative Parents
Substituents
  • Phenylpiperidine
  • Phenethylamine
  • Piperidinecarboxylic acid
  • Aniline or substituted anilines
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Primary amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point83 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 g/LNot Available
LogP3.7Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP10(4.05) g/LALOGPS
logP10(3.64) g/LChemAxon
logS10(-4.5) g/LALOGPS
pKa (Strongest Basic)8.88ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.56 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity106.55 m³·mol⁻¹ChemAxon
Polarizability40.98 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+184.69231661259
DarkChem[M-H]-182.90631661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Anileridine EI-B (Non-derivatized)splash10-0002-4490000000-1f331ba53cfcca2955902017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Anileridine EI-B (Non-derivatized)splash10-0002-4490000000-1f331ba53cfcca2955902018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anileridine GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1290000000-5ad6d8738bbf2736cf672017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anileridine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-1290000000-ba6e571da24e144b4e132014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Anileridine LC-ESI-QTOF , positive-QTOFsplash10-0udi-0009000000-51d5aa3665f0620557742017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anileridine LC-ESI-QTOF , positive-QTOFsplash10-0uk9-0509000000-da80cc1781c8dd21ddf02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anileridine LC-ESI-QTOF , positive-QTOFsplash10-00di-0900000000-4c29e57b70578de9cb542017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anileridine LC-ESI-QTOF , positive-QTOFsplash10-00di-0900000000-f69077c57a03477473bd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anileridine LC-ESI-QTOF , positive-QTOFsplash10-00di-2900000000-1a76eeca83116d6bdacd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anileridine 30V, Positive-QTOFsplash10-00di-0900000000-4c29e57b70578de9cb542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anileridine 40V, Positive-QTOFsplash10-00di-0900000000-f69077c57a03477473bd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anileridine 20V, Positive-QTOFsplash10-0uk9-0509000000-da80cc1781c8dd21ddf02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anileridine 10V, Positive-QTOFsplash10-0udi-0009000000-51d5aa3665f0620557742021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anileridine 50V, Positive-QTOFsplash10-00di-2900000000-1a76eeca83116d6bdacd2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anileridine 10V, Positive-QTOFsplash10-0udr-0019000000-6593c0e4a156a46c79562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anileridine 20V, Positive-QTOFsplash10-0zmr-1869000000-2fd6909f99655d7ca3622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anileridine 40V, Positive-QTOFsplash10-0h90-1920000000-a7fa28de2f934ebabba62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anileridine 10V, Negative-QTOFsplash10-0udi-0019000000-189435cec514e78b319c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anileridine 20V, Negative-QTOFsplash10-0zir-2359000000-5741f21c4444d4c62eff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anileridine 40V, Negative-QTOFsplash10-0r2i-3930000000-d3406654889fa6e91f612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anileridine 10V, Positive-QTOFsplash10-0udi-0039000000-6a6fad82f3da9c06e9da2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anileridine 20V, Positive-QTOFsplash10-004i-0091000000-0f04dba628619cd18fde2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anileridine 40V, Positive-QTOFsplash10-00di-0922000000-5885c5248d7877e228f42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anileridine 10V, Negative-QTOFsplash10-0udi-0009000000-eba9ed51ef3e2fac40162021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anileridine 20V, Negative-QTOFsplash10-0udi-0009000000-9ecad6ab590436544e4c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anileridine 40V, Negative-QTOFsplash10-0pk9-4898000000-7f592a843e0d378c015e2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00913 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00913 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00913
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8600
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAnileridine
METLIN IDNot Available
PubChem Compound8944
PDB IDNot Available
ChEBI ID61203
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 ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Gene Name:
OPRM1
Uniprot ID:
P35372
Molecular weight:
44778.9
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]