<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:07:27 UTC</creation_date>
  <update_date>2025-11-18 23:03:56 UTC</update_date>
  <accession>FDB007119</accession>
  <name>Lormetazepam</name>
  <description>Lormetazepam, also known as methyllorazepam or (+-)-lorazepam, is a member of the class of compounds known as 1,4-benzodiazepines. 1,4-benzodiazepines are organic compounds containing a benzene ring fused to a 1,4-azepine. Lormetazepam is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Lormetazepam can be found in potato, which makes lormetazepam a potential biomarker for the consumption of this food product. Lormetazepam is a non-carcinogenic (not listed by IARC) potentially toxic compound. Lormetazepam is a drug which is used for the treatment of short-term insomnia [l927. The Dutch, British, and French system called the System of Objectified Judgement Analysis for assessing whether drugs should be included in drug formularies based on clinical efficacy, adverse effects, pharmacokinetic properties, toxicity, and drug interactions was used to assess lormetazepam. A Dutch analysis using the system found that lormetazepam could be suitable to be included in drug prescribing formularies, although zolpidem, zopiclone, and temazepam had higher scores and thus can be seen as relatively favorable . The primary manifestation of overdosage ranges from drowsiness to coma and symptoms may include ataxia, hypotension, hypotonia, respiratory depression which may lead to death [L927].</description>
  <synonyms>
    <synonym>(+-)-lorazepam</synonym>
    <synonym>Ergocalm</synonym>
    <synonym>Loramet</synonym>
    <synonym>Loramet (TN)</synonym>
    <synonym>Lorazepam</synonym>
    <synonym>Loretam</synonym>
    <synonym>Lormetazepam (jan/usan/inn)</synonym>
    <synonym>Lormetazepam [usan:inn:ban:jan]</synonym>
    <synonym>Lormetazepamum</synonym>
    <synonym>Methyllorazepam</synonym>
    <synonym>N-methyllorazepam</synonym>
    <synonym>Noctamid</synonym>
    <synonym>O-chlorooxazepam</synonym>
    <synonym>O-chloroxazepam</synonym>
  </synonyms>
  <chemical_formula>C16H12Cl2N2O2</chemical_formula>
  <average_molecular_weight>335.185</average_molecular_weight>
  <monisotopic_moleculate_weight>334.027583052</monisotopic_moleculate_weight>
  <iupac_name>7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one</iupac_name>
  <traditional_iupac>lormetazepam</traditional_iupac>
  <cas_registry_number>848-75-9</cas_registry_number>
  <smiles>CN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C1=CC=CC=C1Cl</smiles>
  <inchi>InChI=1S/C16H12Cl2N2O2/c1-20-13-7-6-9(17)8-11(13)14(19-15(21)16(20)22)10-4-2-3-5-12(10)18/h2-8,15,21H,1H3</inchi>
  <inchikey>FJIKWRGCXUCUIG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.</description>
    <direct_parent>1,4-benzodiazepines</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Benzodiazepines</class>
    <sub_class>1,4-benzodiazepines</sub_class>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Alkanolamines</alternative_parent>
      <alternative_parent>Alpha amino acids and derivatives</alternative_parent>
      <alternative_parent>Aryl chlorides</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Chlorobenzenes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketimines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,4-benzodiazepine</substituent>
      <substituent>Alkanolamine</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Aryl chloride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Chlorobenzene</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Ketimine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>1,4-benzodiazepinone</external_descriptor>
      <external_descriptor>organochlorine compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.64e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>206 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>3.39</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>10.68</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-2.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>335.185</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>334.027583052</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C1=CC=CC=C1Cl</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C16H12Cl2N2O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C16H12Cl2N2O2/c1-20-13-7-6-9(17)8-11(13)14(19-15(21)16(20)22)10-4-2-3-5-12(10)18/h2-8,15,21H,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>FJIKWRGCXUCUIG-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>52.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>85.82</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>32.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>49233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>49234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>49235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>152181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>152182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>152183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2658532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2658533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2658534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3050243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3050244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3050245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>47614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>130892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>138626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>44</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB0041919</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>52993</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Potato</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Solanum tuberosum</name_scientific>
      <ncbi_taxonomy_id>4113</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Sedative</name>
      <id>1311</id>
      <definition>A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.</definition>
    </health_effect>
  </health_effects>
</compound>
