Phenylpropanolamine
- CAS No.
- 14838-15-4
- Chemical Name:
- Phenylpropanolamine
- Synonyms
- EOS-62306;Norefedrine;Norpseudoephedrine;PHENYLPROPANOLAMINE;Phenylpropanolamine USP/EP/BP;(1S,2R)-2-amino-1-phenylpropan-1-ol;(1S,2R)-2-amino-1-phenyl-propan-1-ol;(1S,2R)-2-azanyl-1-phenyl-propan-1-ol;BenzeneMethanol, a-[(1R)-1-aMinoethyl]-, (aS)-rel-;Benzenemethanol, α-[(1R)-1-aminoethyl]-, (αS)-rel-
- CBNumber:
- CB22131029
- Molecular Formula:
- C9H13NO
- Molecular Weight:
- 151.21
- MOL File:
- 14838-15-4.mol
- Modify Date:
- 2023/5/4 17:34:33
| Melting point | 101-101.5° |
|---|---|
| Boiling point | 273.23°C (rough estimate) |
| Density | 1.0406 (rough estimate) |
| refractive index | 1.5380 (estimate) |
| pka | pKa 9.19(H2O,t =25±0.5,I=0.01)(Approximate) |
| color | Plates from H2O |
| NIST Chemistry Reference | Benzenemethanol, «alpha»-(1-aminoethyl)-, (r*,s*)-(.+/-.)-(14838-15-4) |
| EPA Substance Registry System | Phenylpropanolamine (14838-15-4) |
Phenylpropanolamine Chemical Properties,Uses,Production
Description
Phenylpropanolamine (PPA) is a mixed-acting sympathomimetic amine similar to ephedrine. Its primary mechanism of action is through direct a-adrenergic agonism, but there is also indirect stimulation of norepinephrine release. In November 2000, the US Food and Drug Administration (FDA) Nonprescription Drugs Advisory Committee determined that there is a significant association between PPA and hemorrhagic stroke and recommended that PPA not be considered safe for over-thecounter use. At this time, a letter was issued to manufacturers requesting voluntary removal of PPA from their products. Later, in 2005, the FDA published a Tentative Final Monograph for PPA-containing products proposing Category II status (not generally recognized as safe and effective). To date, no Final Monograph has been released; however, all manufacturers have removed PPA from their products.
Uses
Norephedrine, also called Phenylpropanolamine (PPA), is a synthetic form of the ephedrine alkaloid. Used in treatment of urinary incontinence in dogs and cats; decongestant nasal. After reports of the occurrence of intracranial hemorrhage and other adverse effects, including several deaths, PPA is no longer sold in USA and Canada.
World Health Organization (WHO)
Phenylpropanolamine, a symopathomimetic amine, has been widely available in over-the-counter preparations since 1941. It is one of the most frequently used nasal decongestants and it is a common ingredient in preparations for weight reduction, although doubts have been raised about its usefulness in this indication. It is also used in stress incontinence. Its use has been associated with occasional excessive elevation of blood pressure, especially in hypersensitive individuals.
General Description
Phenylpropanolamine is the N-desmethylanalog of ephedrine and thus has many similar properties.Lacking the N-methyl group, phenylpropanolamine is slightlymore polar, and therefore does not enter the CNS as well asephedrine. This modification gives an agent that has slightlyhigher vasopressive action and lower central stimulatoryaction than ephedrine. Its action as a nasal decongestant ismore prolonged than that of ephedrine. It is orally active.Phenylpropanolamine was a common active component inOTC appetite suppressants and cough and cold medicationsuntil 2001 when the Food and Drug Administration (FDA)recommended its removal from such medications, becausestudies showed an increased risk of hemorrhagic stroke inyoung women who took the drug.
Safety Profile
Moderately toxic by subcutaneousroute. When heated to decomposition it emits very toxicfumes of NOx.
Phenylpropanolamine Preparation Products And Raw materials
Raw materials
Preparation Products
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