Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:49:59 UTC
Update Date2019-07-23 06:35:18 UTC
HMDB IDHMDB0041958
Secondary Accession Numbers
  • HMDB41958
Metabolite Identification
Common NameNormeperidine
DescriptionPethidine (INN) or meperidine hydrochloride (USAN) (commonly referred to as Demerol in the US but also referred to as: isonipecaine; lidol; pethanol; piridosal; Algil; Alodan; Centralgin; Dispadol; Dolantin; Mialgin (in Indonesia); Petidin Dolargan (in Poland); Dolestine; Dolosal; Dolsin; Mefedina) is a fast-acting opioid analgesic drug. Pethidine is quickly hydrolysed in the liver to pethidinic acid and is also demethylated to norpethidine, which has half the analgesic activity of pethidine but a longer elimination half-life (8-12 hours); accumulating with regular administration, or in renal failure. Norpethidine is toxic and has convulsant and hallucinogenic effects. The toxic effects mediated by the metabolites cannot be countered with opioid receptor antagonists such as naloxone or naltrexone and are probably primarily due to norpethidine's anticholinergic activity probably due to its structural similarity to atropine though its pharmacology has not been thoroughly explored. The neurotoxicity of pethidine's metabolites is a unique feature of pethidine compared to other opioids. Pethidine's metabolites are further conjugated with glucuronic acid and excreted into the urine.
Structure
Data?1563863718
Synonyms
ValueSource
4-(Ethoxycarbonyl)-4-phenylpiperidineHMDB
4-Carbethoxy-4-phenylpiperidineHMDB
4-Phenyl-4-carbethoxypiperidineHMDB
Ethyl 4-phenyl-4-piperidinecarboxylateHMDB
Ethyl 4-phenylisonipecotateHMDB
Ethyl 4-phenylpiperidine-4-carboxylateHMDB
Isonipecotic acid, 4-phenyl-, ethyl esterHMDB
NordolsinHMDB
NorpethidineHMDB
Normeperidine carbonate (2:1)HMDB
Normeperidine hydrochlorideHMDB
Normeperidine, 3H-labeled CPDHMDB
Ethyl 4-phenylpiperidine-4-carboxylic acidHMDB
NormeperidineMeSH
Chemical FormulaC14H19NO2
Average Molecular Weight233.3062
Monoisotopic Molecular Weight233.141578857
IUPAC Nameethyl 4-phenylpiperidine-4-carboxylate
Traditional Namenorpethidine
CAS Registry Number77-17-8
SMILES
CCOC(=O)C1(CCNCC1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C14H19NO2/c1-2-17-13(16)14(8-10-15-11-9-14)12-6-4-3-5-7-12/h3-7,15H,2,8-11H2,1H3
InChI KeyQKHMFBKXTNQCTM-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
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Azacycle
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
Water Solubility0.32 g/LALOGPS
logP1.45ALOGPS
logP2.07ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)9.33ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67.19 m³·mol⁻¹ChemAxon
Polarizability26.13 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]+154.97731661259
DarkChem[M-H]-154.73431661259
DeepCCS[M+H]+155.80430932474
DeepCCS[M-H]-153.44630932474
DeepCCS[M-2H]-186.69830932474
DeepCCS[M+Na]+161.89730932474
AllCCS[M+H]+153.332859911
AllCCS[M+H-H2O]+149.432859911
AllCCS[M+NH4]+157.032859911
AllCCS[M+Na]+158.032859911
AllCCS[M-H]-158.732859911
AllCCS[M+Na-2H]-158.932859911
AllCCS[M+HCOO]-159.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NormeperidineCCOC(=O)C1(CCNCC1)C1=CC=CC=C12334.5Standard polar33892256
NormeperidineCCOC(=O)C1(CCNCC1)C1=CC=CC=C11757.1Standard non polar33892256
NormeperidineCCOC(=O)C1(CCNCC1)C1=CC=CC=C11773.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Normeperidine,1TMS,isomer #1CCOC(=O)C1(C2=CC=CC=C2)CCN([Si](C)(C)C)CC11892.7Semi standard non polar33892256
Normeperidine,1TMS,isomer #1CCOC(=O)C1(C2=CC=CC=C2)CCN([Si](C)(C)C)CC11970.2Standard non polar33892256
Normeperidine,1TBDMS,isomer #1CCOC(=O)C1(C2=CC=CC=C2)CCN([Si](C)(C)C(C)(C)C)CC12166.9Semi standard non polar33892256
Normeperidine,1TBDMS,isomer #1CCOC(=O)C1(C2=CC=CC=C2)CCN([Si](C)(C)C(C)(C)C)CC12185.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Normeperidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1900000000-b43cba7846535ead29d32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normeperidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Normeperidine 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 - Normeperidine 10V, Positive-QTOFsplash10-001i-0390000000-a12c5e20253fed7060082017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normeperidine 20V, Positive-QTOFsplash10-0019-2950000000-a36e1982a192e3f1c1bf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normeperidine 40V, Positive-QTOFsplash10-06z9-9800000000-3668d1535fc2fd0122192017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normeperidine 10V, Negative-QTOFsplash10-001i-0190000000-80f29ac48e0d76a752652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normeperidine 20V, Negative-QTOFsplash10-001r-3790000000-ce9fd6d72143008eb0d02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normeperidine 40V, Negative-QTOFsplash10-01t9-9710000000-1ca41e452381ae5965df2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normeperidine 10V, Positive-QTOFsplash10-01q9-0790000000-a2020f59c6a5cdbc4d8b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normeperidine 20V, Positive-QTOFsplash10-03di-1920000000-5d0c5488f282a077b42b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normeperidine 40V, Positive-QTOFsplash10-01q1-2910000000-e533559084fd0b22eba32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normeperidine 10V, Negative-QTOFsplash10-001i-0090000000-116620fb1c68c13721592021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normeperidine 20V, Negative-QTOFsplash10-001r-0960000000-72346e33aa360c50adf12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normeperidine 40V, Negative-QTOFsplash10-0pb9-2900000000-bf3685fbe38972677d872021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 ID30039
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPethidine
METLIN IDNot Available
PubChem Compound32414
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 ReferencesNot Available