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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 20:46:15 UTC
Update Date2021-09-26 22:50:36 UTC
HMDB IDHMDB0243518
Secondary Accession NumbersNone
Metabolite Identification
Common Name(-)-Norephedrine
Description(-)-Norephedrine, also known as triaminic DM or prolamine, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Based on a literature review a significant number of articles have been published on (-)-Norephedrine. This compound has been identified in human blood as reported by (PMID: 31557052 ). (-)-norephedrine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (-)-Norephedrine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
Triaminic DMHMDB
NorephedrineHMDB
Phenylpropanolamine hydrochlorideHMDB
ProlamineHMDB
DexatrimHMDB
Hydrochloride, phenylpropanolamineHMDB
PropagestHMDB
Chemical FormulaC9H13NO
Average Molecular Weight151.209
Monoisotopic Molecular Weight151.099714043
IUPAC Name2-amino-1-phenylpropan-1-ol
Traditional Namedl-norephedrine
CAS Registry NumberNot Available
SMILES
CC(N)C(O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3
InChI KeyDLNKOYKMWOXYQA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Aralkylamine
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organopnictogen compound
  • Primary amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP0.57ALOGPS
logP0.89ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)13.9ChemAxon
pKa (Strongest Basic)9.37ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.91 m³·mol⁻¹ChemAxon
Polarizability16.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+133.79430932474
DeepCCS[M-H]-130.57130932474
DeepCCS[M-2H]-167.58430932474
DeepCCS[M+Na]+143.11130932474
AllCCS[M+H]+136.532859911
AllCCS[M+H-H2O]+132.232859911
AllCCS[M+NH4]+140.532859911
AllCCS[M+Na]+141.732859911
AllCCS[M-H]-133.132859911
AllCCS[M+Na-2H]-134.732859911
AllCCS[M+HCOO]-136.532859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(-)-Norephedrine,1TMS,isomer #1CC(N)C(O[Si](C)(C)C)C1=CC=CC=C11365.6Semi standard non polar33892256
(-)-Norephedrine,1TMS,isomer #1CC(N)C(O[Si](C)(C)C)C1=CC=CC=C11497.1Standard non polar33892256
(-)-Norephedrine,1TMS,isomer #1CC(N)C(O[Si](C)(C)C)C1=CC=CC=C11833.1Standard polar33892256
(-)-Norephedrine,1TMS,isomer #2CC(N[Si](C)(C)C)C(O)C1=CC=CC=C11430.4Semi standard non polar33892256
(-)-Norephedrine,1TMS,isomer #2CC(N[Si](C)(C)C)C(O)C1=CC=CC=C11434.3Standard non polar33892256
(-)-Norephedrine,1TMS,isomer #2CC(N[Si](C)(C)C)C(O)C1=CC=CC=C11869.9Standard polar33892256
(-)-Norephedrine,2TMS,isomer #1CC(N[Si](C)(C)C)C(O[Si](C)(C)C)C1=CC=CC=C11431.8Semi standard non polar33892256
(-)-Norephedrine,2TMS,isomer #1CC(N[Si](C)(C)C)C(O[Si](C)(C)C)C1=CC=CC=C11519.6Standard non polar33892256
(-)-Norephedrine,2TMS,isomer #1CC(N[Si](C)(C)C)C(O[Si](C)(C)C)C1=CC=CC=C11698.5Standard polar33892256
(-)-Norephedrine,2TMS,isomer #2CC(C(O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1607.0Semi standard non polar33892256
(-)-Norephedrine,2TMS,isomer #2CC(C(O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1655.1Standard non polar33892256
(-)-Norephedrine,2TMS,isomer #2CC(C(O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1910.2Standard polar33892256
(-)-Norephedrine,3TMS,isomer #1CC(C(O[Si](C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1695.4Semi standard non polar33892256
(-)-Norephedrine,3TMS,isomer #1CC(C(O[Si](C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1653.4Standard non polar33892256
(-)-Norephedrine,3TMS,isomer #1CC(C(O[Si](C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1744.1Standard polar33892256
(-)-Norephedrine,1TBDMS,isomer #1CC(N)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C11595.6Semi standard non polar33892256
(-)-Norephedrine,1TBDMS,isomer #1CC(N)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C11691.9Standard non polar33892256
(-)-Norephedrine,1TBDMS,isomer #1CC(N)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C11988.0Standard polar33892256
(-)-Norephedrine,1TBDMS,isomer #2CC(N[Si](C)(C)C(C)(C)C)C(O)C1=CC=CC=C11673.6Semi standard non polar33892256
(-)-Norephedrine,1TBDMS,isomer #2CC(N[Si](C)(C)C(C)(C)C)C(O)C1=CC=CC=C11676.2Standard non polar33892256
(-)-Norephedrine,1TBDMS,isomer #2CC(N[Si](C)(C)C(C)(C)C)C(O)C1=CC=CC=C12028.3Standard polar33892256
(-)-Norephedrine,2TBDMS,isomer #1CC(N[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C11884.0Semi standard non polar33892256
(-)-Norephedrine,2TBDMS,isomer #1CC(N[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C11920.3Standard non polar33892256
(-)-Norephedrine,2TBDMS,isomer #1CC(N[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C12009.5Standard polar33892256
(-)-Norephedrine,2TBDMS,isomer #2CC(C(O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2042.8Semi standard non polar33892256
(-)-Norephedrine,2TBDMS,isomer #2CC(C(O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2066.4Standard non polar33892256
(-)-Norephedrine,2TBDMS,isomer #2CC(C(O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2123.4Standard polar33892256
(-)-Norephedrine,3TBDMS,isomer #1CC(C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2293.6Semi standard non polar33892256
(-)-Norephedrine,3TBDMS,isomer #1CC(C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2251.3Standard non polar33892256
(-)-Norephedrine,3TBDMS,isomer #1CC(C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2098.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Norephedrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9600000000-51d22fac659028f8b2d42021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Norephedrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Norephedrine 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 - (-)-Norephedrine 30V, Positive-QTOFsplash10-001i-0900000000-df9f77c51f7a1b0742192021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Norephedrine 45V, Positive-QTOFsplash10-001i-0900000000-3990a4fc55f9d2e73eea2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Norephedrine 90V, Positive-QTOFsplash10-014i-3900000000-102de06f1adf563ed2c82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Norephedrine 75V, Positive-QTOFsplash10-014i-2900000000-44b8a77c3d8c5a5aaf802021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Norephedrine 180V, Positive-QTOFsplash10-014l-9200000000-ef0b3527a6061b2881d92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Norephedrine 60V, Positive-QTOFsplash10-014i-0900000000-84d9734743fda2b942ea2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Norephedrine 150V, Positive-QTOFsplash10-014l-9400000000-e6e34699e96c9271d1fc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Norephedrine 120V, Positive-QTOFsplash10-014l-8900000000-bbcb812618a2ee308c622021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Norephedrine 35V, Negative-QTOFsplash10-000f-9000000000-36845e13dc4ac965df252021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Norephedrine 35V, Positive-QTOFsplash10-014i-1900000000-a8d392dcb6605888b0532021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Norephedrine 10V, Positive-QTOFsplash10-001i-0900000000-bd416c91052a9169cf442021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Norephedrine 20V, Positive-QTOFsplash10-014i-1900000000-72a0c1340e1e430183912021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Norephedrine 40V, Positive-QTOFsplash10-0006-9200000000-92f5cd8bb5a23727da792021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Norephedrine 10V, Negative-QTOFsplash10-000x-9600000000-9d8b01ad2c9953ab29392021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Norephedrine 20V, Negative-QTOFsplash10-00nf-7900000000-85ff14d88d237302bc5d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Norephedrine 40V, Negative-QTOFsplash10-004i-9000000000-7f166534dabf6f41827e2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal 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 IDC00055789
Chemspider ID4622
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4786
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 References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]