<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2956</id>
  <title>T3D2914</title>
  <common-name>Levorphanol</common-name>
  <description>Levorphanol is only found in individuals that have used or taken this drug. It is a narcotic analgesic that may be habit-forming. It is nearly as effective orally as by injection. [PubChem]Like other mu-agonist opioids it is believed to act at receptors in the periventricular and periaqueductal gray matter in both the brain and spinal cord to alter the transmission and perception of pain.</description>
  <cas>77-07-6</cas>
  <pubchem-id>5359272</pubchem-id>
  <chemical-formula>C17H23NO</chemical-formula>
  <weight>257.177960</weight>
  <appearance>White powder.</appearance>
  <melting-point>198-199°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>1840 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Subcutaneous, Intravenous, or Intramuscular injection ; Oral. Levorphanol is well absorbed after PO administration with peak plasma concentrations occurring approximately 1 hour after dosing.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Like other mu-agonist opioids it is believed to act at receptors in the periventricular and periaqueductal gray matter in both the brain and spinal cord to alter the transmission and perception of pain.</mechanism-of-toxicity>
  <metabolism>Levorphanol is extensively metabolized in the liver and is eliminated as the glucuronide metabolite.Half Life: 11-16 hours</metabolism>
  <toxicity>LD50: 150 mg/kg (Oral, Rat) (A308)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the management of moderate to severe pain or as a preoperative medication where an opioid analgesic is appropriate</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Medical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose.</health-effects>
  <symptoms>Signs of overdose include nausea, emesis, dizziness, respiratory depression, hypotension, urinary retention, cardiac arrhythmias, allergic reactions, skin rash, and uticaria.</symptoms>
  <treatment>The specific treatment of suspected levorphanol tartrate overdosage is immediate establishment of an adequate airway and ventilation, followed (if necessary) by intravenous naloxone. The respiratory and cardiac status of the patient should be continuously monitored and appropriate supportive measures instituted, such as oxygen, intravenous fluids and/or vasopressors, if required. Physicians are reminded that the duration of levorphanol action far exceeds the duration of action of naloxone, and repeated dosing with naloxone may be required. Naloxone should be administered cautiously to persons known or suspected to be physically dependent on Levorphanol. In such cases an abrupt and complete reversal of opioid effects may precipitate an acute abstinence syndrome. If necessary to administer naloxone to the physically dependent patient, the antagonist should be administered with extreme care and by titration with smaller than usual doses of the antagonist. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:27:50Z</created-at>
  <updated-at type="dateTime">2026-04-05T10:43:22Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Levorphanol</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C08014</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>119572</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Levorphanol</stitch-id>
  <drugbank-id>DB00854</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(O)C=C2</moldb-smiles>
  <moldb-formula>C17H23NO</moldb-formula>
  <moldb-inchi>InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m0/s1</moldb-inchi>
  <moldb-inchikey>JAQUASYNZVUNQP-USXIJHARSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">257.3706</moldb-average-mass>
  <moldb-mono-mass type="decimal">257.177964363</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>3.11</logp>
  <hmdb-id>HMDB14992</hmdb-id>
  <chembl-id>CHEMBL592</chembl-id>
  <chemspider-id>16736212</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;Joseph P. Haar, &amp;#8220;Process for the Production of Levorphanol and Related Compounds.&amp;#8221; U.S. Patent US20080146805, issued June 19, 2008.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002290</chemdb-id>
  <dsstox-id>DTXSID3023213</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00067936</susdat-id>
  <iupac>(1R,9R,10R)-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-trien-4-ol</iupac>
</compound>
