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Pseudoephedrine

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Pseudoephedrine Basic information
Pseudoephedrine Chemical Properties
  • Melting point:118-120 °C
  • alpha 52 º (c=0.6, EtOH)
  • Boiling point:293.09°C (rough estimate)
  • Density 1.0203 (rough estimate)
  • refractive index 1.5200 (estimate)
  • Flash point:9℃
  • storage temp. ?20°C
  • pkapKa 9.73(H2O,t=25±0.5,I=0.01)(Approximate)
  • optical activity[α]20/D +52°, c = 0.6 in ethanol
  • Water Solubility <0.5g/L(er)
  • Merck 13,8007
  • BRN 2414132
  • Stability:Stable. Combustible. Incompatible with strong oxidizing agents. May discolour upon exposure to light.
  • CAS DataBase Reference90-82-4(CAS DataBase Reference)
  • NIST Chemistry ReferencePseudoephedrine, (+)-(90-82-4)
  • EPA Substance Registry SystemBenzenemethanol, .alpha.-[(1S)-1-(methylamino)ethyl]-, (.alpha.S)- (90-82-4)
Safety Information
MSDS
Pseudoephedrine Usage And Synthesis
  • Chemical Propertieswhite crystals
  • UsesDecongestant.
  • DefinitionChEBI: A member of the class of the class of phenylethanolamines that is (1S)-2-(methylamino)-1-phenylethan-1-ol in which the pro-S hydrogen at position 2 is replaced by a methyl group.
  • brand nameEfidac (ALZA); Novafed (Sanofi Aventis); Sudafed (GlaxoSmithKline); Sudafed (Warner Lambert).
  • General Description(Sudafed, Afrinol, Drixoral) isthe (S,S) diastereoisomer of ephedrine. Whereas ephedrinehas a mixed mechanism of action, L-(+)-pseudoephedrineacts mostly by an indirect mechanism and has virtually nodirect activity. The structural basis for this difference inmechanism is the stereochemistry of the carbon atom possessingthe β-OH group. In pseudoephedrine, this carbon atompossesses the (S) configuration, the wrong stereochemistryat this center for a direct-acting effect at adrenoceptors.Although it crosses the BBB (log P=1.05, pKa=9.38),L-(+)-pseudoephedrine’s lack of direct activity affords fewerCNS effects than does ephedrine. It is a naturally occurringalkaloid from the Ephedra species. This agent is found inmany OTC nasal decongestant and cold medications.Although it is less prone to increase blood pressure thanephedrine, it should be used with caution in hypertensiveindividuals, and it should not be used in combination withMAO inhibitors.
  • Contact allergensThis sympathomimetic a-adrenergic agonist is found in plants of the genus Ephedra (Ephedraceae) and is systemically used as a nasal decongestant. It can induce drug skin reactions such as acute generalized exanthematic pustulosis or generalized eczema.
  • Purification MethodsCrystallise the amine from dry diethyl ether, or from water and dry it in a vacuum desiccator. [Beilstein 13 IV 1878.]
Pseudoephedrine Preparation Products And Raw materials
Pseudoephedrine(90-82-4)Related Product Information
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