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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:12:09 UTC
Update Date2019-07-23 07:15:33 UTC
HMDB IDHMDB0061006
Secondary Accession Numbers
  • HMDB61006
Metabolite Identification
Common Namenorfentanyl
Descriptionnorfentanyl is a metabolite of fentanyl. Fentanyl (also known as fentanil, brand names Sublimaze, Actiq, Durogesic, Duragesic, Fentora, Matrifen, Haldid, Onsolis, Instanyl, Abstral, Lazanda and others) is a potent, synthetic narcotic analgesic with a rapid onset and short duration of action. It is a strong agonist at the μ-opioid receptors. Historically it has been used to treat breakthrough pain and is commonly used in pre-procedures as a pain reliever as well as an anesthetic in combination with a benzodiazepine. (Wikipedia)
Structure
Data?1563866133
Synonyms
ValueSource
4-(N'-phenyl-n'-propionyl)aminopiperidineChEBI
4-(N-Propionylanilino)piperidineChEBI
N-Phenyl-N-(piperidin-4-yl)propionamideChEBI
N-Phenyl-N-4-piperidinylpropanamideChEBI
N-Phenyl-N-4-piperidinylpropionamideChEBI
Norfentanyl monohydrochlorideHMDB
Chemical FormulaC14H20N2O
Average Molecular Weight232.3214
Monoisotopic Molecular Weight232.157563272
IUPAC NameN-phenyl-N-(piperidin-4-yl)propanamide
Traditional Namenorfentanyl
CAS Registry NumberNot Available
SMILES
CCC(=O)N(C1CCNCC1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C14H20N2O/c1-2-14(17)16(12-6-4-3-5-7-12)13-8-10-15-11-9-13/h3-7,13,15H,2,8-11H2,1H3
InChI KeyPMCBDBWCQQBSRJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAnilides
Alternative Parents
Substituents
  • Anilide
  • Piperidine
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

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 Solubility0.95 g/LALOGPS
logP2ALOGPS
logP1.42ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)10.03ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.34 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.82 m³·mol⁻¹ChemAxon
Polarizability26.46 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]+154.56231661259
DarkChem[M-H]-154.03331661259
DeepCCS[M+H]+152.90530932474
DeepCCS[M-H]-150.54730932474
DeepCCS[M-2H]-184.04930932474
DeepCCS[M+Na]+158.99930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
norfentanylCCC(=O)N(C1CCNCC1)C1=CC=CC=C12957.6Standard polar33892256
norfentanylCCC(=O)N(C1CCNCC1)C1=CC=CC=C12028.9Standard non polar33892256
norfentanylCCC(=O)N(C1CCNCC1)C1=CC=CC=C11996.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
norfentanyl,1TMS,isomer #1CCC(=O)N(C1=CC=CC=C1)C1CCN([Si](C)(C)C)CC12051.8Semi standard non polar33892256
norfentanyl,1TMS,isomer #1CCC(=O)N(C1=CC=CC=C1)C1CCN([Si](C)(C)C)CC11997.0Standard non polar33892256
norfentanyl,1TMS,isomer #1CCC(=O)N(C1=CC=CC=C1)C1CCN([Si](C)(C)C)CC12661.7Standard polar33892256
norfentanyl,1TBDMS,isomer #1CCC(=O)N(C1=CC=CC=C1)C1CCN([Si](C)(C)C(C)(C)C)CC12283.8Semi standard non polar33892256
norfentanyl,1TBDMS,isomer #1CCC(=O)N(C1=CC=CC=C1)C1CCN([Si](C)(C)C(C)(C)C)CC12193.4Standard non polar33892256
norfentanyl,1TBDMS,isomer #1CCC(=O)N(C1=CC=CC=C1)C1CCN([Si](C)(C)C(C)(C)C)CC12799.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - norfentanyl GC-MS (Non-derivatized) - 70eV, Positivesplash10-005c-9810000000-3caed077ea7a0ee21ff12017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - norfentanyl GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl LC-ESI-QTOF , positive-QTOFsplash10-001i-0090000000-30023a9a668dad77c1712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl LC-ESI-QTOF , positive-QTOFsplash10-001i-0490000000-67cd08c1a84bf833feb62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl LC-ESI-QTOF , positive-QTOFsplash10-0udi-0910000000-a687d66216f3f0f2a5422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl LC-ESI-QTOF , positive-QTOFsplash10-0ue9-0900000000-172bf948c02a137b45d82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl LC-ESI-QTOF , positive-QTOFsplash10-0f89-0900000000-4dbe3aa7aa26725f23842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOFsplash10-001i-1090000000-0a49897fffa5fde5c2252017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOFsplash10-001i-9170000000-bfce9be1027a8de7e1e82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOFsplash10-001i-9000000000-850655b66d289ffd449c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOFsplash10-001i-9000000000-ad4c9ad4e989e47126dd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOFsplash10-0a59-9000000000-0f96dbb8a332c80da86d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOFsplash10-0a4i-9000000000-8bb94389e58a6b848a312017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOFsplash10-0a4i-9000000000-8de4a5f24b02ee65a5842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOFsplash10-0a4i-9000000000-3728a8f7f46a40ff76ec2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl LC-ESI-QFT , positive-QTOFsplash10-0a4i-9000000000-6d3cc832e8a6d431c3b82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl 50V, Positive-QTOFsplash10-0f89-0900000000-4dbe3aa7aa26725f23842021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl 40V, Positive-QTOFsplash10-0ue9-0900000000-d764b890a85df217086c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl 15V, Positive-QTOFsplash10-001i-1090000000-fad8ab78c63174bbb4df2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl 30V, Positive-QTOFsplash10-0udi-0910000000-a687d66216f3f0f2a5422021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - norfentanyl 40V, Positive-QTOFsplash10-0ue9-0900000000-172bf948c02a137b45d82021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - norfentanyl 10V, Positive-QTOFsplash10-001i-1290000000-2e8cba986c947fbed4552016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - norfentanyl 20V, Positive-QTOFsplash10-003r-9440000000-7f5a511cb9530706b2ee2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - norfentanyl 40V, Positive-QTOFsplash10-001i-9100000000-1134c041265e979217df2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - norfentanyl 10V, Negative-QTOFsplash10-001i-0090000000-43b32b3b4df368ab59042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - norfentanyl 20V, Negative-QTOFsplash10-003r-4690000000-47ce59bca6771457156a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - norfentanyl 40V, Negative-QTOFsplash10-054p-9500000000-f60fe31246330ad46c992016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound259381
PDB IDNot Available
ChEBI ID62685
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