Human Metabolome Database Version 3.5

Showing metabocard for Pseudoephedrine (HMDB01943)

Record Information
Version 3.5
Creation Date 2006-05-18 03:17:15 -0600
Update Date 2013-02-08 17:11:04 -0700
HMDB ID HMDB01943
Secondary Accession Numbers None
Metabolite Identification
Common Name Pseudoephedrine
Description Pseudoephedrine (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.
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms
  1. (+)-(1S,2S)-Pseudoephedrine
  2. (+)-Pseudoephedrine
  3. (+)-psi-Ephedrine
  4. (+)-threo-Ephedrine
  5. (1S,2S)-(+)-Pseudoephedrine
  6. (1S,2S)-Pseudoephedrine
  7. 1-Ephedrine
  8. 2-(Methylamino)-1-phenyl-1-propanol
  9. Besan
  10. D-Isoephedrine
  11. D-Pseudoephedrine
  12. D-Pseudoephedrine base
  13. D-Psi-2-Methylamino-1-phenyl-1-propanol
  14. D-Psi-Ephedrine
  15. Isoephedrine
  16. L(+)-Psi-Ephedrine
  17. L-(+)-Pseudoephedrine
  18. Novafed
  19. Pseudoefedrina
  20. Pseudoephedrine
  21. Pseudoephedrine D-form
  22. Pseudoephedrine Ephedrine
  23. Pseudoephedrinum
  24. Psi-ephedrin
  25. Sudafed
  26. trans-Ephedrine
Chemical Formula C10H15NO
Average Molecular Weight 165.2322
Monoisotopic Molecular Weight 165.115364107
IUPAC Name (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol
Traditional IUPAC Name pseudoephedrine
CAS Registry Number 90-82-4
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 Key KWGRBVOPPLSCSI-WCBMZHEXSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenethylamines
Sub Class Amphetamines and Derivatives
Other Descriptors
  • Alkaloids(KEGG)
  • Organic Compounds
  • Phenylalanine derived alkaloids(KEGG)
  • phenethylamine alkaloid(ChEBI)
  • phenylethanolamines(ChEBI)
Substituents
  • 1,2 Aminoalcohol
  • Benzyl Alcohol Derivative
  • Secondary Alcohol
  • Secondary Aliphatic Amine (Dialkylamine)
Direct Parent Amphetamines and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Drug
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 119 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 0.89 KRIL,MB & FUNG,HL (1990)
Predicted Properties
Property Value Source
Water Solubility 8.26 g/L ALOGPS
LogP 1.00 ALOGPS
LogP 1.32 ChemAxon
LogS -1.30 ALOGPS
pKa (strongest acidic) 13.89 ChemAxon
pKa (strongest basic) 9.52 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 32.26 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 49.69 ChemAxon
Polarizability 18.83 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
3.02 (0.012-6.05) uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022758
KNApSAcK ID Not Available
Chemspider ID 6761 Link_out
KEGG Compound ID C02765 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Pseudoephedrine Link_out
NuGOwiki Link HMDB01943 Link_out
Metagene Link HMDB01943 Link_out
METLIN ID 2189 Link_out
PubChem Compound 7028 Link_out
PDB ID Not Available
ChEBI ID 51209 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available

Enzymes
Name: Amine oxidase [flavin-containing] A
Reactions: Not Available
Gene Name: MAOA
Uniprot ID: P21397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-2A adrenergic receptor
Reactions: Not Available
Gene Name: ADRA2A
Uniprot ID: P08913 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-2 adrenergic receptor
Reactions: Not Available
Gene Name: ADRB2
Uniprot ID: P07550 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-1A adrenergic receptor
Reactions: Not Available
Gene Name: ADRA1A
Uniprot ID: P35348 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA