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Showing Compound Pseudoephedrine (FDB022758)

Record Information
Version1.0
Creation date2011-09-21 00:19:09 UTC
Update date2015-10-09 22:31:18 UTC
Primary IDFDB022758
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePseudoephedrine
DescriptionPseudoephedrine (commonly abbreviated as PSE) is a sympathomimetic amine commonly used as a decongestant. The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many over-the-counter preparations either as single ingredient preparations, or more commonly in combination with antihistamines, paracetamol and/or ibuprofen. Consumers often refer to it by a product which contains pseudoephedrine, such as Sudafed, the trademark for a common brand of pseudoephedrine hydrochloride in North America; Pseudoephedrine is a phenethylamine, and an isomer of ephedrine. Pseudoephedrine is the International Nonproprietary Name (INN) of the (1S,2S)- diastereomer of ephedrine (which has 1R,2S- configuration). Other names are (+)-pseudoephedrine and D-pseudoephedrine. (Reynolds, 1989) (-)-(1R,2R)-Pseudoephedrine is not used clinically, since it is associated with greater central nervous system (CNS) stimulatory effects. (+)-(1S,2S)-Pseudoephedrine is a less-potent CNS stimulant, yet it retains its efficacy as a decongestant. -- Wikipedia; Pseudoephedrine is a sympathomimetic amine - that is, its principal mechanism of action relies on its indirect action on the adrenergic receptor system. While it may have weak agonist activity at adrenergic receptors, the principal mechanism is to displace noradrenaline from storage vesicles in presynaptic neurons. The displaced noradrenaline is released into the neuronal synapse where it is free to activate the aforementioned postsynaptic adrenergic receptors. -- Wikipedia; Pseudoephedrine is a phenethylamine, and an isomer of ephedrine. Pseudoephedrine is the International Nonproprietary Name (INN) of the (1S,2S)- diastereomer of ephedrine (which has 1R,2S- configuration). Other names are (+)-pseudoephedrine and D-pseudoephedrine (Reynolds, 1989). The enantiomer (-)-(1R,2R)-Pseudoephedrine has fewer side-effects, fewer central nervous system (CNS) stimulatory effects, does not reduce to d-methamphetamine, yet retains its efficacy as a decongestant.[citation needed] However, the patent holder for (-)-Pseudoephedrine (Pfizer/Warner-Lambert) has not yet sought or received government approval for its sale to the public.(US Patent 6,495,529); Treatment for urinary incontinence is an unlabeled use for these medications. Unlabeled use means doctors can use the medication to treat a condition other than that for which it was first approved by the U.S. Food and Drug Administration (FDA). These medications are approved by the FDA for the treatment of nasal congestion caused by colds or allergies. However it has also been succesful in treating stress incontinence by increasing the pressure (tension) exerted by the muscles of the bladder neck and the urethra, which helps retain the urine within the bladder; An alpha and beta adrenergic agonist that may also enhance release of norepinephrine. It has been used in the treatment of several disorders including asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists; Pseudoephedrine is a sympathomimetic amine commonly used as a decongestant. The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many over-the-counter preparations either as single-ingredient preparations, or more commonly in combination with antihistamines, paracetamol and/or ibuprofen. It is often referred to by consumers as Sudafed, which is the trademark for a common brand of pseudoephedrine hydrochloride. -- Wikipedia; Pseudoephedrine is a sympathomimetic amine - that is, its principal mechanism of action relies on its indirect action on the adrenergic receptor system. While it may have weak agonist activity at alpha and beta adrenergic receptors, the principal mechanism is to displace noradrenaline from storage vesicles in presynaptic neurons. The displaced noradrenaline is released into the neuronal synapse where it is free to activate the aforementioned postsynaptic adrenergic receptors. [HMDB]
CAS Number90-82-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(+) 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
(+)-psi-Ephedrinehmdb
(+)-threo-Ephedrinehmdb
1-ephedrinehmdb
D-isoephedrinehmdb
D-pseudoephedrinehmdb
d-Pseudoephedrine basehmdb
d-psi-2-Methylamino-1-phenyl-1-propanolhmdb
D-psi-Ephedrinehmdb
L(+)-psi-Ephedrinehmdb
Pseudoephedrinehmdb
Pseudoephedrine d-formhmdb
Pseudoephedrine Ephedrinehmdb
Predicted Properties
PropertyValueSource
Water Solubility8.26 g/LALOGPS
logP1ALOGPS
logP1.32ChemAxon
logS-1.3ALOGPS
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
Chemical FormulaC10H15NO
IUPAC name(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol
InChI IdentifierInChI=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
Isomeric SMILESCN[C@@H](C)[C@@H](O)C1=CC=CC=C1
Average Molecular Weight165.2322
Monoisotopic Molecular Weight165.115364107
Classification
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
Physiological effect

Health effect:

Disposition

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-9000000000-8f0484f72b48017f1f2e2014-09-20View Spectrum
Predicted GC-MSPseudoephedrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9200000000-0c3fe6959703a851b9ccSpectrum
Predicted GC-MSPseudoephedrine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05cr-4900000000-d9ac11e33b32a9e427adSpectrum
Predicted GC-MSPseudoephedrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-016s-3900000000-868bf4bba93d8b4be6962012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0159-2900000000-6c55fc67b7576cb42a8a2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0006-9700000000-459686cbaf7d3b59c2022012-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0900000000-677d622716b4c2545f162017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-2900000000-416def0e527ddf116a392017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9500000000-155625a572f19610e1382017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ea7e1b550b5dc0d6d41d2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-2900000000-f4de25860574bb60daf12017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9600000000-62e375458e5f83795e902017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0297-3900000000-4496fbcd8548f7ccc58a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-03e637debccd8d202e3c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-7ead088c2f003219a1cf2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-0282f3e8fc4bf9296a382021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014m-3900000000-8ee8987e88c6a5601ef72021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-e3932e53d7936649b8db2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID6761
ChEMBL IDCHEMBL1590
KEGG Compound IDC02765
Pubchem Compound ID7028
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00852
HMDB IDHMDB01943
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPseudoephedrine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Alpha-2A adrenergic receptorADRA2AP08913
Beta-2 adrenergic receptorADRB2P07550
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
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References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference