Structure via PubChem · Public domain (PubChem)
(±)-norephedrine
Sign in to savePhenylpropanolamine (PPA), sold under many brand names, is a sympathomimetic agent used as a decongestant and appetite suppressant. It was once common in prescription and over-the-counter cough and cold preparations. The medication is taken orally.
Key facts
- Drug.Watchedfields
- verified
- Drug.verifiedrevid
- 464201364
- Drug.image
- Phenylpropanolamine structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200px
- Drug.alt
- RS-Norephedrin
- Drug.image2
- Phenylpropanolamine molecule ball.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 215px
- Drug.alt2
- Ball-and-stick model of the phenylpropanolamine molecule
- Drug.pregnancy_AU
- B2
- Drug.legal_AU
- S4
- Drug.legal_BR
- F3
- Drug.legal_CA
- Schedule VI
- Drug.legal_US
- Rx-only
- Drug.routes_of_administration
- By mouth
- Drug.bioavailability
- High
- Drug.protein_bound
- 20%
via Wikipedia infobox
Chemical data
- Formula
- C9H13NO
- Molecular weight
- 151.21 g/mol
- IUPAC name
- 2-amino-1-phenylpropan-1-ol
- SMILES
- CC(C(C1=CC=CC=C1)O)N
- InChIKey
- DLNKOYKMWOXYQA-UHFFFAOYSA-N
- XLogP
- 0.8
- Polar surface area
- 46.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
~19 min read
Encyclopedic overview
23 sectionsContents
- Medical uses
- Available forms
- Side effects
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Absorption
- Distribution
- Metabolism
- Elimination
- Miscellaneous
- Chemistry
- History
- Society and culture
- Names
- Availability
- Exercise and sports
- Legal status
- Veterinary use
- Notes
- Reference notes
- References
Phenylpropanolamine (PPA), sold under many brand names, is a sympathomimetic agent used as a decongestant and appetite suppressant. It was once common in prescription and over-the-counter cough and cold preparations. The medication is taken orally.
Side effects of phenylpropanolamine include increased heart rate and blood pressure. Rarely, PPA has been associated with hemorrhagic stroke. PPA acts as a norepinephrine releasing agent, indirectly activating adrenergic receptors. As such, it is an indirectly acting sympathomimetic. It was once thought to act as a sympathomimetic with additional direct agonist action on adrenergic receptors, but this proved wrong. Chemically, phenylpropanolamine is a substituted amphetamine and is closely related to ephedrine, pseudoephedrine, amphetamine, and cathinone. It is usually a racemic mixture of the (1R,2S)- and (1S,2R)-enantiomers of β-hydroxyamphetamine and is also known as dl-norephedrine.
Excerpted from Wikipedia’s “(±)-norephedrine” article, available under the CC BY-SA 4.0 licence.