File:Pseudoephedrine.svg · Wikimedia Commons · See Wikimedia Commons
(+)-pseudoephedrine
Sign in to saveAlso known as (+) threo-2-(methylamino)-1-phenyl-1-propanol, ψ-ephedrine, (+)-(1S,2S)-pseudoephedrine, trans-ephedrine, d-psi-ephedrine, d-psi-2-methylamino-1-phenyl-1-propanol, d-pseudoephedrine, d-isoephedrine
Key facts
- Drug.synonyms
- PSE; PDE; (+)-ψ-Ephedrine; ψ-Ephedrine; d-Isoephedrine; (1S,2S)-Pseudoephedrine; d-Pseudoephedrine; (+)-Pseudoephedrine; L(+)-Pseudoephedrine; Isoephedrine; (1S,2S)-α,N-Dimethyl-β-hydroxyphenethylamine; (1S,2S)-N-Methyl-β-hydroxyamphetamine
- Drug.IUPAC_name
- (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol
- Drug.C
- 10
- Drug.H
- 15
- Drug.N
- 1
- Drug.O
- 1
- Drug.SMILES
- O[C@@H](c1ccccc1)[C@@H](NC)C
- Drug.StdInChI
- 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
- Drug.StdInChIKey
- KWGRBVOPPLSCSI-WCBMZHEXSA-N
- Drug.legal_EU
- OTC
- Drug.width
- 200px
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 464375838
- Drug.image
- Pseudoephedrine.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- (1S,2S)-Pseudoephedrine molecule ball.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 225px
via Wikipedia infobox
Chemical data
- Formula
- C10H15NO
- Molecular weight
- 165.23 g/mol
- IUPAC name
- (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol
- SMILES
- C[C@@H]([C@H](C1=CC=CC=C1)O)NC
- InChIKey
- KWGRBVOPPLSCSI-WCBMZHEXSA-N
- XLogP
- 0.9
- Polar surface area
- 32.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
1,734 papersvia PubMed
~54 min read
Encyclopedic overview
48 sectionsContents
- Medical uses
- Nasal congestion
- Other uses
- Available forms
- Contraindications
- Side effects
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Absorption
- Distribution
- Metabolism
- Elimination
- Chemistry
- Nomenclatures
- Detection in body fluids
- Manufacturing
- History
- Society and culture
- Generic names
- Brand names
- Recreational use
- Use in exercise and sports
- List of doping cases
- Manufacture of amphetamines
- Legal status
- Australia
- Belgium
- Canada
- Colombia
- Estonia
- Finland
- France
- Germany
- Japan
- Mexico
- Netherlands
- New Zealand
- Switzerland
- Turkey
- United Kingdom
- United States
- Federal
- State
- Research
- References
Pseudoephedrine, sold under the brand name Sudafed among others, is a sympathomimetic medication which is used as a decongestant to treat nasal congestion. It has also been used off-label for certain other indications, like treatment of low blood pressure. At higher doses, it may produce various additional effects including stimulant, appetite suppressant, and performance-enhancing effects. In relation to this, non-medical use of pseudoephedrine has been encountered. The medication is taken by mouth.
Side effects of pseudoephedrine include insomnia, elevated heart rate, increased blood pressure, restlessness, dizziness, anxiety, and dry mouth, among others. Rarely, pseudoephedrine has been associated with serious cardiovascular complications like heart attack and hemorrhagic stroke. Some people may be more sensitive to its cardiovascular effects. Pseudoephedrine acts as a norepinephrine releasing agent, thereby indirectly activating adrenergic receptors. As such, it is an indirectly acting sympathomimetic. Pseudoephedrine significantly crosses into the brain, but has some peripheral selectivity due to its hydrophilicity. Chemically, pseudoephedrine is a substituted amphetamine and is closely related to ephedrine, phenylpropanolamine, and amphetamine. It is the (1S,2S)-enantiomer of β-hydroxy-N-methylamphetamine.
Excerpted from Wikipedia’s “(+)-pseudoephedrine” article, available under the CC BY-SA 4.0 licence.