<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4609</id>
  <title>T3D4555</title>
  <common-name>Pseudoephedrine</common-name>
  <description>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. [PubChem]</description>
  <cas>90-82-4</cas>
  <pubchem-id>7028</pubchem-id>
  <chemical-formula>C10H15NO</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>119 °C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>7 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Pseudoephedrine is readily and almost completely absorbed from the GI tract and there is no evidence of first-pass metabolism.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Pseudoephedrine acts directly on both alpha- and, to a lesser degree, beta-adrenergic receptors. Through direct action on alpha-adrenergic receptors in the mucosa of the respiratory tract, pseudoephedrine produces vasoconstriction. Pseudoephedrine relaxes bronchial smooth muscle by stimulating beta2-adrenergic receptors. Like ephedrine, pseudoephedrine releasing norepinephrine from its storage sites, an indirect effect. This is its main and direct mechanism of action. The displaced noradrenaline is released into the neuronal synapse where it is free to activate the postsynaptic adrenergic receptors.</mechanism-of-toxicity>
  <metabolism>Hepatic.Half Life: 9-16 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of nasal congestion, sinus congestion, Eustachian tube congestion, and vasomotor rhinitis, and as an adjunct to other agents in the optimum treatment of allergic rhinitis, croup, sinusitis, otitis media, and tracheobronchitis. Also used as first-line therapy of priapism.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Common adverse reactions include nervousness, restlessness, and insomnia. Rare adverse reactions include difficult/painful urination, dizziness/lightheadedness, heart palpitations, headache, increased sweating, nausea/vomiting, trembling, troubled breathing, unusual paleness, and weakness.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-30T21:03:50Z</created-at>
  <updated-at type="dateTime">2026-04-05T10:43:27Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Pseudoephedrine</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C02765</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>51209</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB00852</drugbank-id>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CN[C@@H](C)[C@@H](O)C1=CC=CC=C1</moldb-smiles>
  <moldb-formula>C10H15NO</moldb-formula>
  <moldb-inchi>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</moldb-inchi>
  <moldb-inchikey>KWGRBVOPPLSCSI-WCBMZHEXSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">165.2322</moldb-average-mass>
  <moldb-mono-mass type="decimal">165.115364107</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>0.89</logp>
  <hmdb-id nil="true"/>
  <chembl-id>CHEMBL1590</chembl-id>
  <chemspider-id>6761</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Andrew G. Myers, &amp;#8220;Synthesis of l-azatyrosine using pseudoephedrine as a chiral auxiliary.&amp;#8221; U.S. Patent US5760237, issued June, 1991.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003515</chemdb-id>
  <dsstox-id>DTXSID0023537</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00067939</susdat-id>
  <iupac>(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol</iupac>
</compound>
