<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3083</id>
  <title>T3D3041</title>
  <common-name>Methotrimeprazine</common-name>
  <description>Methotrimeprazine is only found in individuals that have used or taken this drug. It is a phenothiazine with pharmacological activity similar to that of both chlorpromazine and promethazine. It has the histamine-antagonist properties of the antihistamines together with central nervous system effects resembling those of chlorpromazine. (From Martindale, The Extra Pharmacopoeia, 30th ed, p604). Methotrimeprazine's antipsychotic effect is largely due to its antagonism of dopamine receptors in the brain. In addition, its binding to 5HT2 receptors may also play a role.</description>
  <cas>60-99-1</cas>
  <pubchem-id>72287</pubchem-id>
  <chemical-formula>C19H24N2OS</chemical-formula>
  <weight>328.160930</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>20 mg/L (at 25°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral; parental (intramuscular). Methotrimeprazine has an incomplete oral bioavailability, because it undergoes considerable first-pass-metabolism in the liver. Oral bioavailability is approximately 50 to 60%.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Methotrimeprazine's antipsychotic effect is largely due to its antagonism of dopamine receptors in the brain. In addition, its binding to 5HT2 receptors may also play a role. Methotrimeprazine exerts its actions through a central adrenergic-blocking, a dopamine-blocking, a serotonin-blocking, and a anticholinergic blocking.</mechanism-of-toxicity>
  <metabolism>Hepatic. Methotrimeprazine is metabolized in the liver and degraded to a sulfoxid-, a glucuronid- and a demethyl-moiety.Half Life: Approximately 20 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 psychosis, particular those of schizophrenia, and manic phases of bipolar disorder.As a potentiator of anesthetics: In general anesthesia where it can be used as both a pre- and post-operative sedative and analgesic. (L1857)As an anti-emetic: For the treatment of nausea and vomiting of central origin.(L1857)As a sedative: For the management of insomnia. (L1857)</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Symptoms of overdose include convulsions, spastic movements, and coma.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:28:48Z</created-at>
  <updated-at type="dateTime">2026-04-05T10:50:06Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Levomepromazine</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C07192</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>6838</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Methotrimeprazine</stitch-id>
  <drugbank-id>DB01403</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>COC1=CC2=C(SC3=C(C=CC=C3)N2C[C@H](C)CN(C)C)C=C1</moldb-smiles>
  <moldb-formula>C19H24N2OS</moldb-formula>
  <moldb-inchi>InChI=1S/C19H24N2OS/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21/h5-11,14H,12-13H2,1-4H3/t14-/m1/s1</moldb-inchi>
  <moldb-inchikey>VRQVVMDWGGWHTJ-CQSZACIVSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">328.472</moldb-average-mass>
  <moldb-mono-mass type="decimal">328.16093409</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>4.68</logp>
  <hmdb-id>HMDB15474</hmdb-id>
  <chembl-id>CHEMBL1764</chembl-id>
  <chemspider-id>65239</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;Christian Berger, &amp;#8220;Process for preparing levomepromazine hydrogen maleate.&amp;#8221; U.S. Patent US4798895, issued January 17, 1989.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002393</chemdb-id>
  <dsstox-id>DTXSID1023289</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id nil="true"/>
  <iupac>[(2R)-3-(2-methoxy-10H-phenothiazin-10-yl)-2-methylpropyl]dimethylamine</iupac>
</compound>
