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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-10-23 19:06:26 UTC
HMDB IDHMDB0015049
Secondary Accession Numbers
  • HMDB15049
Metabolite Identification
Common NameAnileridine
DescriptionAnileridine is a synthetic opioid and strong analgesic medication. It is a narcotic pain reliever used to treat moderate to severe pain. Narcotic analgesics act in the central nervous system (CNS) to relieve pain. Some of their side effects are also caused by actions in the CNS.
Structure
Thumb
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 monohydrochlorideMeSH
Anileridine hydrochlorideMeSH
Anileridine phosphateMeSH
Anileridine phosphate (1:1)MeSH
Anileridine dihydrochlorideMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPiperidines
Direct ParentPhenylpiperidines
Alternative Parents
Substituents
  • Phenylpiperidine
  • Phenethylamine
  • Piperidinecarboxylic acid
  • Aniline or substituted anilines
  • Aralkylamine
  • Monocyclic benzene moiety
  • Primary aromatic amine
  • Benzenoid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Azacycle
  • Primary amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Observation:

  Health condition:

    Blood and lymphatic system disorders:

    Gastrointestinal disorders:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point83 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 g/LNot Available
LogP3.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP4.05ALOGPS
logP3.64ChemAxon
logS-4.5ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-4490000000-1f331ba53cfcca295590View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1290000000-5ad6d8738bbf2736cf67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-51d5aa3665f062055774View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0uk9-0509000000-da80cc1781c8dd21ddf0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-4c29e57b70578de9cb54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-f69077c57a03477473bdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-2900000000-1a76eeca83116d6bdacdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0019000000-6593c0e4a156a46c7956View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zmr-1869000000-2fd6909f99655d7ca362View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h90-1920000000-a7fa28de2f934ebabba6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-189435cec514e78b319cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zir-2359000000-5741f21c4444d4c62effView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0r2i-3930000000-d3406654889fa6e91f61View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0002-1290000000-ba6e571da24e144b4e13View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Anileridine Action PathwayPw000651Pw000651 greyscalePw000651 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00913 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00913 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00913
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
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 ]