<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 18:26:14 UTC</creation_date>
  <update_date>2026-08-20 00:48:44 UTC</update_date>
  <accession/>
  <common_name>Trimeprazine</common_name>
  <class>SmallMolecule</class>
  <description>Trimeprazine is an organic compound with the chemical formula C18H22N2S and an average molecular weight of 298.45 g/mol. Trimeprazine belongs to the phenothiazines, a subclass of benzothiazines within the organic compounds. In terms of biological activity, it is recorded as an antagonist of the Histamine H1 receptor (HRH1).

The substance is identified in nine recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used as an antihistamine. It is also found in food preservation within the food, food processing, and cookware category. Additionally, it is released from household cleaning and consumer products, including soap detergents, perfumes within detergents and soaps, and non electric simulated smoking devices. It is further associated with electrical and electronic equipment, specifically relays, electric switches, fixed capacitors and their manufacture, and electrically stimulated smoking devices. The recorded exposure route for this compound is oral.</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms>
    <synonym>alimemazine</synonym>
  </synonyms>
  <chemical_formula>C18H22N2S</chemical_formula>
  <average_molecular_weight>298.446</average_molecular_weight>
  <monisotopic_moleculate_weight>298.150369404</monisotopic_moleculate_weight>
  <iupac_name>dimethyl[2-methyl-3-(10H-phenothiazin-10-yl)propyl]amine</iupac_name>
  <traditional_iupac>trimeprazine</traditional_iupac>
  <cas_registry_number>84-96-8</cas_registry_number>
  <smiles>CC(CN(C)C)CN1C2=CC=CC=C2SC2=CC=CC=C12</smiles>
  <inchi>InChI=1S/C18H22N2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3</inchi>
  <inchikey>ZZHLYYDVIOPZBE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Benzothiazines</class>
    <sub_class>Phenothiazines</sub_class>
    <direct_parent>Phenothiazines</direct_parent>
    <alternate_parents>
      <alternative_parent>1,4-thiazines</alternative_parent>
      <alternative_parent>Alkyldiarylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Diarylthioethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alkyldiarylamine</substituent>
      <substituent>Amine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Aryl thioether</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Diarylthioether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Para-thiazine</substituent>
      <substituent>Phenothiazine</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary aliphatic/aromatic amine</substituent>
      <substituent>Tertiary amine</substituent>
      <substituent>Thioether</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>phenothiazines</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Alimemazine H1-Antihistamine Action</name>
      <smpdb_id>SMP0059689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Alimemazine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Alimemazine H1 Antihistamine Smooth Muscle Relaxation Action Pathway</name>
      <smpdb_id>SMP0174905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Alimemazine H1-Antihistamine Blood Vessel Constriction Action Pathway</name>
      <smpdb_id>SMP0174997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Alimemazine H1-Antihistamine Immune Response Action Pathway</name>
      <smpdb_id>SMP0175089</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>4.41</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.35e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>dimethyl[2-methyl-3-(10H-phenothiazin-10-yl)propyl]amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>298.446</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>298.150369404</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(CN(C)C)CN1C2=CC=CC=C2SC2=CC=CC=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H22N2S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H22N2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZZHLYYDVIOPZBE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>6.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>93.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7223b32f80&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01246</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>5574</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>5373</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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      <target_id>BE0000442</target_id>
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  </targets>
</compound>
