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
StatusDetected and Quantified
Creation Date2006-05-18 09:17:15 UTC
Update Date2021-09-14 15:45:02 UTC
HMDB IDHMDB0001943
Secondary Accession Numbers
  • HMDB01943
Metabolite Identification
Common NamePseudoephedrine
DescriptionPseudoephedrine is a member of the class of phenylethanolamines that is (1S)-2-(methylamino)-1-phenylethan-1-ol in which the pro-S hydrogen at position 2 is replaced by a methyl group. It has a role as a sympathomimetic agent, an anti-asthmatic drug, a bronchodilator agent, a vasoconstrictor agent, a central nervous system drug, a nasal decongestant, a xenobiotic and a plant metabolite. It is a secondary alcohol, a secondary amino compound and a member of phenylethanolamines. It is a conjugate base of a pseudoephedrine(1+). Pseudoephedrine is a sympathomimetic drug of the phenethylamine and amphetamine chemical classes. It may be used as a nasal/sinus decongestant, as a stimulant, or as a wakefulness-promoting agent in higher doses. It was first characterized in 1889, by the German chemists Ladenburg and Oelschlägel, who used a sample that had been isolated from Ephedra vulgaris by the Merck pharmaceutical corporation of Darmstadt, Germany. The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many over-the-counter preparations, either as a single ingredient or (more commonly) in a fixed-dose combination with one or more additional active ingredients such as antihistamines, guaifenesin, dextromethorphan, paracetamol (acetaminophen) or an NSAID (such as aspirin or ibuprofen). At first, pseudoephedrine was known as a natural substance that occurs in shrubs of the Ephedra genus, which grow worldwide. Almost all commercial pseudoephedrine, however, is produced by fermenting dextrose in the presence of benzaldehyde. The primary product, (R)-phenylacetylcarbinol, is aminated to make pseudoephedrine. Pseudoephedrine acts on α- and β2-adrenergic receptors, to cause vasoconstriction and relaxation of smooth muscle in the bronchi, respectively. α-Adrenergic receptors are located on the muscles lining the walls of blood vessels. When these receptors are activated, the muscles contract, causing the blood vessels to constrict (vasoconstriction). The constricted blood vessels now allow less fluid to leave the blood vessels and enter the nose, throat and sinus linings, which results in decreased inflammation of nasal membranes, as well as decreased mucus production. Thus, by constriction of blood vessels, mainly those located in the nasal passages, pseudoephedrine causes a decrease in the symptoms of nasal congestion. Activation of β2-adrenergic receptors produces relaxation of smooth muscle of the bronchi, causing bronchial dilation and in turn decreasing congestion (although not fluid) and difficulty breathing.
Structure
Data?1582752219
Synonyms
ValueSource
(+) Threo-2-(methylamino)-1-phenyl-1-propanolChEBI
(+)-(1S,2S)-PseudoephedrineChEBI
(+)-PseudoephedrineChEBI
(+)-Psi-ephedrineChEBI
(+)-Threo-ephedrineChEBI
(1S,2S)-(+)-PseudoephedrineChEBI
(1S,2S)-PseudoephedrineChEBI
2-(Methylamino)-1-phenyl-1-propanolChEBI
D-IsoephedrineChEBI
D-PseudoephedrineChEBI
D-Psi-2-methylamino-1-phenyl-1-propanolChEBI
D-Psi-ephedrineChEBI
IsoephedrineChEBI
L(+)-Psi-ephedrineChEBI
L-(+)-PseudoephedrineChEBI
PseudoefedrinaChEBI
Pseudoephedrine D-formChEBI
PseudoephedrinumChEBI
Psi-ephedrinChEBI
Psi-ephedrineChEBI
trans-EphedrineChEBI
NeodurasinaKegg
AcunasoKegg
1-EphedrineHMDB
BesanHMDB
D-Pseudoephedrine baseHMDB
NovafedHMDB
Pseudoephedrine ephedrineHMDB
SudafedHMDB
Ephedrine threo isomerHMDB
Pseudoephedrine HCLHMDB
Threo isomer OF ephedrineHMDB
Pseudoephedrine hydrochlorideHMDB
Chemical FormulaC10H15NO
Average Molecular Weight165.2322
Monoisotopic Molecular Weight165.115364107
IUPAC Name(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol
Traditional Namepseudoephedrine
CAS Registry Number90-82-4
SMILES
CN[C@@H](C)[C@@H](O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1
InChI KeyKWGRBVOPPLSCSI-WCBMZHEXSA-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
  • Secondary aliphatic amine
  • Secondary amine
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point119 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.89KRIL,MB & FUNG,HL (1990)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.26 g/LALOGPS
logP10(1) g/LALOGPS
logP10(1.32) g/LChemAxon
logS10(-1.3) g/LALOGPS
pKa (Strongest Acidic)13.89ChemAxon
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.69 m³·mol⁻¹ChemAxon
Polarizability18.83 ųChemAxon
Number of Rings1ChemAxon
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]+138.33231661259
DarkChem[M-H]-136.2131661259
AllCCS[M+H]+138.3232859911
AllCCS[M-H]-139.18432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PseudoephedrineCN[C@@H](C)[C@@H](O)C1=CC=CC=C12130.9Standard polar33892256
PseudoephedrineCN[C@@H](C)[C@@H](O)C1=CC=CC=C11344.6Standard non polar33892256
PseudoephedrineCN[C@@H](C)[C@@H](O)C1=CC=CC=C11380.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pseudoephedrine,1TMS,isomer #1CN[C@@H](C)[C@@H](O[Si](C)(C)C)C1=CC=CC=C11413.7Semi standard non polar33892256
Pseudoephedrine,1TMS,isomer #2C[C@@H]([C@@H](O)C1=CC=CC=C1)N(C)[Si](C)(C)C1524.2Semi standard non polar33892256
Pseudoephedrine,2TMS,isomer #1C[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C1572.6Semi standard non polar33892256
Pseudoephedrine,2TMS,isomer #1C[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C1556.8Standard non polar33892256
Pseudoephedrine,2TMS,isomer #1C[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C1691.1Standard polar33892256
Pseudoephedrine,1TBDMS,isomer #1CN[C@@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C11643.6Semi standard non polar33892256
Pseudoephedrine,1TBDMS,isomer #2C[C@@H]([C@@H](O)C1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C1754.6Semi standard non polar33892256
Pseudoephedrine,2TBDMS,isomer #1C[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C2047.3Semi standard non polar33892256
Pseudoephedrine,2TBDMS,isomer #1C[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C1989.4Standard non polar33892256
Pseudoephedrine,2TBDMS,isomer #1C[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C2002.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pseudoephedrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9200000000-0c3fe6959703a851b9cc2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pseudoephedrine GC-MS (1 TMS) - 70eV, Positivesplash10-05cr-4900000000-d9ac11e33b32a9e427ad2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pseudoephedrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9000000000-8f0484f72b48017f1f2e2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Pseudoephedrine Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-016s-3900000000-868bf4bba93d8b4be6962012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pseudoephedrine Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-0159-2900000000-6c55fc67b7576cb42a8a2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pseudoephedrine Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-0006-9700000000-459686cbaf7d3b59c2022012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoephedrine 10V, Positive-QTOFsplash10-00kb-0900000000-677d622716b4c2545f162017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoephedrine 20V, Positive-QTOFsplash10-00kb-2900000000-416def0e527ddf116a392017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoephedrine 40V, Positive-QTOFsplash10-0aou-9500000000-155625a572f19610e1382017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoephedrine 10V, Negative-QTOFsplash10-03di-0900000000-ea7e1b550b5dc0d6d41d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoephedrine 20V, Negative-QTOFsplash10-03dj-2900000000-f4de25860574bb60daf12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoephedrine 40V, Negative-QTOFsplash10-0a6r-9600000000-62e375458e5f83795e902017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoephedrine 10V, Negative-QTOFsplash10-0297-3900000000-4496fbcd8548f7ccc58a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoephedrine 20V, Negative-QTOFsplash10-014i-1900000000-03e637debccd8d202e3c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoephedrine 40V, Negative-QTOFsplash10-004i-9100000000-7ead088c2f003219a1cf2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoephedrine 10V, Positive-QTOFsplash10-0002-0900000000-0282f3e8fc4bf9296a382021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoephedrine 20V, Positive-QTOFsplash10-014m-3900000000-8ee8987e88c6a5601ef72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoephedrine 40V, Positive-QTOFsplash10-0006-9300000000-e3932e53d7936649b8db2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.02 (0.012-6.05) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
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 References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB00852
Phenol Explorer Compound IDNot Available
FooDB IDFDB022758
KNApSAcK IDC00031097
Chemspider ID6761
KEGG Compound IDC02765
BioCyc IDCPD-9954
BiGG IDNot Available
Wikipedia LinkPseudoephedrine
METLIN ID2189
PubChem Compound7028
PDB IDNot Available
ChEBI ID51209
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular weight:
46458.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0