Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:40 UTC
HMDB IDHMDB0014597
Secondary Accession Numbers
  • HMDB14597
Metabolite Identification
Common NameMeperidine
DescriptionMeperidine, also known as pethidine or dolantin, 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. Meperidine is a drug which is used to control moderate to severe pain. Meperidine is a very strong basic compound (based on its pKa). Meperidine is a potentially toxic compound.
Structure
Data?1582753197
Synonyms
ValueSource
PethidineKegg
Pethidine DBLKegg
DolantinHMDB
DolcontralHMDB
Operidine epj-IHMDB
LydolHMDB
DolarganHMDB
DolinHMDB
DolosalHMDB
Operidine epj IHMDB
DemerolHMDB
DolsinHMDB
IsonipecainHMDB
LidolHMDB
Meperidine hydrochlorideHMDB
Chemical FormulaC15H21NO2
Average Molecular Weight247.3327
Monoisotopic Molecular Weight247.157228921
IUPAC Nameethyl 1-methyl-4-phenylpiperidine-4-carboxylate
Traditional Namemeperidine
CAS Registry Number57-42-1
SMILES
CCOC(=O)C1(CCN(C)CC1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C15H21NO2/c1-3-18-14(17)15(9-11-16(2)12-10-15)13-7-5-4-6-8-13/h4-8H,3,9-12H2,1-2H3
InChI KeyXADCESSVHJOZHK-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
  • Piperidinecarboxylic acid
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point186 - 189 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.11 g/LNot Available
LogP2.6Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.11 g/LALOGPS
logP2.9ALOGPS
logP2.46ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)8.16ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.48 m³·mol⁻¹ChemAxon
Polarizability28.09 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+158.42331661259
DarkChem[M-H]-156.63231661259
DeepCCS[M+H]+162.34430932474
DeepCCS[M-H]-159.98630932474
DeepCCS[M-2H]-192.87230932474
DeepCCS[M+Na]+168.43730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MeperidineCCOC(=O)C1(CCN(C)CC1)C1=CC=CC=C12296.5Standard polar33892256
MeperidineCCOC(=O)C1(CCN(C)CC1)C1=CC=CC=C11733.0Standard non polar33892256
MeperidineCCOC(=O)C1(CCN(C)CC1)C1=CC=CC=C11738.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Meperidine EI-B (Non-derivatized)splash10-00dl-9310000000-9f5598127b487d9339dc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Meperidine CI-B (Non-derivatized)splash10-0002-0090000000-bcf24d9e6302b6454d0e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Meperidine EI-B (Non-derivatized)splash10-00dl-9310000000-9f5598127b487d9339dc2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Meperidine CI-B (Non-derivatized)splash10-0002-0090000000-bcf24d9e6302b6454d0e2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Meperidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1900000000-ea19250f67bb7f6843802017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Meperidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-9620000000-7309f4ee3918ea05f00d2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Meperidine LC-ESI-QFT , positive-QTOFsplash10-0002-0090000000-2d9035995cbed82a83822017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Meperidine LC-ESI-QFT , positive-QTOFsplash10-0002-0190000000-96507adebcd15f1cb9172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Meperidine LC-ESI-QFT , positive-QTOFsplash10-00di-1490000000-d1e318ddf3f73eb8db302017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Meperidine LC-ESI-QFT , positive-QTOFsplash10-00di-7970000000-d3f460862fa9a6d8be1f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Meperidine LC-ESI-QFT , positive-QTOFsplash10-00di-8910000000-b45b71541829339425362017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Meperidine LC-ESI-QFT , positive-QTOFsplash10-00dl-9800000000-e79c047f6c6a8c9c00332017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Meperidine 90V, Positive-QTOFsplash10-00dl-9700000000-121bbb952edc449abb752021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Meperidine 75V, Positive-QTOFsplash10-00di-9810000000-1ecfa38f326384b22b6c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Meperidine 15V, Positive-QTOFsplash10-0002-0090000000-32a2416ef149cdf6e2ba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Meperidine 30V, Positive-QTOFsplash10-0002-0190000000-553d10a55d1124382fb32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Meperidine 60V, Positive-QTOFsplash10-00di-7970000000-ca6d994cd203c94bf4aa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Meperidine 45V, Positive-QTOFsplash10-00di-1490000000-d1b086505c982e77f3052021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meperidine 10V, Positive-QTOFsplash10-0002-0190000000-75ce42839d066b768d842016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meperidine 20V, Positive-QTOFsplash10-0uka-1390000000-dc66b8476b990cda1efe2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meperidine 40V, Positive-QTOFsplash10-00di-6910000000-745b390b8b1b329a92522016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meperidine 10V, Negative-QTOFsplash10-0002-0090000000-1e8e811f90230b3be3762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meperidine 20V, Negative-QTOFsplash10-0f6t-3290000000-0b623b033726827aa22f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meperidine 40V, Negative-QTOFsplash10-004i-7930000000-e7e194d99480b7e534012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meperidine 10V, Positive-QTOFsplash10-0002-0190000000-690c257e3fce5319d7e42021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meperidine 20V, Positive-QTOFsplash10-007k-1980000000-582b4105598dbfb055a62021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meperidine 40V, Positive-QTOFsplash10-0fka-2930000000-1497d0c7ca0d6bc1bb682021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meperidine 10V, Negative-QTOFsplash10-00kb-0090000000-6fdb2cf7255c1034e8fc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meperidine 20V, Negative-QTOFsplash10-0f6t-0390000000-03b23664f4176b9e58472021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meperidine 40V, Negative-QTOFsplash10-00xr-2920000000-9f01b67d39967a5a12032021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00454 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00454 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 IDDB00454
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3918
KEGG Compound IDC07128
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPethidine
METLIN IDNot Available
PubChem Compound4058
PDB IDNot Available
ChEBI ID122528
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 monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Ramirez J, Innocenti F, Schuetz EG, Flockhart DA, Relling MV, Santucci R, Ratain MJ: CYP2B6, CYP3A4, and CYP2C19 are responsible for the in vitro N-demethylation of meperidine in human liver microsomes. Drug Metab Dispos. 2004 Sep;32(9):930-6. [PubMed:15319333 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Ramirez J, Innocenti F, Schuetz EG, Flockhart DA, Relling MV, Santucci R, Ratain MJ: CYP2B6, CYP3A4, and CYP2C19 are responsible for the in vitro N-demethylation of meperidine in human liver microsomes. Drug Metab Dispos. 2004 Sep;32(9):930-6. [PubMed:15319333 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Ramirez J, Innocenti F, Schuetz EG, Flockhart DA, Relling MV, Santucci R, Ratain MJ: CYP2B6, CYP3A4, and CYP2C19 are responsible for the in vitro N-demethylation of meperidine in human liver microsomes. Drug Metab Dispos. 2004 Sep;32(9):930-6. [PubMed:15319333 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Ramirez J, Innocenti F, Schuetz EG, Flockhart DA, Relling MV, Santucci R, Ratain MJ: CYP2B6, CYP3A4, and CYP2C19 are responsible for the in vitro N-demethylation of meperidine in human liver microsomes. Drug Metab Dispos. 2004 Sep;32(9):930-6. [PubMed:15319333 ]
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic plasticity, synaptogenesis, excitotoxicity, memory acquisition and learning. It mediates neuronal functions in glutamate neurotransmission. Is involved in the cell surface targeting of NMDA receptors
Gene Name:
GRIN1
Uniprot ID:
Q05586
Molecular weight:
105371.9
References
  1. Yamakura T, Sakimura K, Shimoji K: N-methyl-D-aspartate receptor channel block by meperidine is dependent on extracellular pH. Anesth Analg. 2000 Apr;90(4):928-32. [PubMed:10735801 ]
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
NMDA receptor subtype of glutamate-gated ion channels possesses high calcium permeability and voltage-dependent sensitivity to magnesium. Activation requires binding of agonist to both types of subunits
Gene Name:
GRIN2A
Uniprot ID:
Q12879
Molecular weight:
165281.2
References
  1. Yamakura T, Sakimura K, Shimoji K: N-methyl-D-aspartate receptor channel block by meperidine is dependent on extracellular pH. Anesth Analg. 2000 Apr;90(4):928-32. [PubMed:10735801 ]
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine
Gene Name:
GRIN2C
Uniprot ID:
Q14957
Molecular weight:
134531.1
References
  1. Yamakura T, Sakimura K, Shimoji K: N-methyl-D-aspartate receptor channel block by meperidine is dependent on extracellular pH. Anesth Analg. 2000 Apr;90(4):928-32. [PubMed:10735801 ]
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine
Gene Name:
GRIN2B
Uniprot ID:
Q13224
Molecular weight:
166365.9
References
  1. Yamakura T, Sakimura K, Shimoji K: N-methyl-D-aspartate receptor channel block by meperidine is dependent on extracellular pH. Anesth Analg. 2000 Apr;90(4):928-32. [PubMed:10735801 ]
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine
Gene Name:
GRIN2D
Uniprot ID:
O15399
Molecular weight:
143750.7
References
  1. Yamakura T, Sakimura K, Shimoji K: N-methyl-D-aspartate receptor channel block by meperidine is dependent on extracellular pH. Anesth Analg. 2000 Apr;90(4):928-32. [PubMed:10735801 ]
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 dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions
Gene Name:
OPRK1
Uniprot ID:
P41145
Molecular weight:
42644.7
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 ]