<?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 23:03:57 UTC</update_date>
  <accession>FDB007124</accession>
  <name>N-Demethyldiazepam</name>
  <description>N-demethyldiazepam, also known as nordiazepam or calmday, 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. N-demethyldiazepam is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). N-demethyldiazepam can be found in common wheat, corn, and potato, which makes N-demethyldiazepam a potential biomarker for the consumption of these food products. N-demethyldiazepam can be found primarily in blood and urine, as well as in human kidney and liver tissues. N-demethyldiazepam is a non-carcinogenic (not listed by IARC) potentially toxic compound. General supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained. Hypotension may be combated by the use of norepinephrine or metaraminol. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Its use, however, is controversial as it has numerous contraindications. It is contraindicated in patients who are on long-term benzodiazepines, those who have ingested a substance that lowers the seizure threshold, or in patients who have tachycardia or a history of seizures. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. Although benzodiazepines are absorbed by activated charcoal, gastric decontamination with activated charcoal is not beneficial in pure benzodiazepine overdose as the risk of adverse effects often outweigh any potential benefit from the procedure. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. Gastric lavage (stomach pumping) or whole bowel irrigation are also not recommended (T3DB).</description>
  <synonyms>
    <synonym>1-Demethyldiazepam</synonym>
    <synonym>2H-1,4-Benzodiazepin-2-one, 1, 3-dihydro-7-chloro-5-phenyl-</synonym>
    <synonym>2H-1,4-Benzodiazepin-2-one, 1,3-dihydro-7-chloro-5-phenyl-</synonym>
    <synonym>2H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-5-phenyl-</synonym>
    <synonym>5-phenyl-7-chloro-1,4-benzodiazepin-2-one</synonym>
    <synonym>7-Chlor-2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-on</synonym>
    <synonym>7-Chloro-1, 3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one</synonym>
    <synonym>7-Chloro-1,3-dihydro-5-phenyl-(2H)-1,4-benzodiazepin-2-one</synonym>
    <synonym>7-Chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one</synonym>
    <synonym>7-Chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one</synonym>
    <synonym>7-Chloro-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one</synonym>
    <synonym>Calmday</synonym>
    <synonym>Chlordesmethyldiazepam</synonym>
    <synonym>Clorazepate (break down)</synonym>
    <synonym>Dealkylprazepam</synonym>
    <synonym>Demadar</synonym>
    <synonym>Demethyldiazepam</synonym>
    <synonym>Deoxydemoxepam</synonym>
    <synonym>Desalkylprazepam</synonym>
    <synonym>Desmethyldiazepam</synonym>
    <synonym>DMDZ</synonym>
    <synonym>Lomax</synonym>
    <synonym>Madar</synonym>
    <synonym>N-demethyldiazepam</synonym>
    <synonym>N-deoxydemoxapam</synonym>
    <synonym>N-deoxydemoxepam</synonym>
    <synonym>N-desalkylhalazepam</synonym>
    <synonym>N-descyclopropylmethyl-prazepam</synonym>
    <synonym>N-descyclopropylmethylprazepam</synonym>
    <synonym>N-desmethyldiazepam</synonym>
    <synonym>N-destrifluoroethylhalazepam</synonym>
    <synonym>N1-Desmethyldiazepam</synonym>
    <synonym>NDD</synonym>
    <synonym>NDZ</synonym>
    <synonym>Nordaz</synonym>
    <synonym>Nordazepam</synonym>
    <synonym>Nordazepam [inn]</synonym>
    <synonym>Nordazepamum</synonym>
    <synonym>Nordiazepam</synonym>
    <synonym>Norprazepam</synonym>
    <synonym>Praxadium</synonym>
    <synonym>Sopax</synonym>
    <synonym>Stilny</synonym>
    <synonym>Vegesan</synonym>
  </synonyms>
  <chemical_formula>C15H11ClN2O</chemical_formula>
  <average_molecular_weight>270.714</average_molecular_weight>
  <monisotopic_moleculate_weight>270.055990691</monisotopic_moleculate_weight>
  <iupac_name>7-chloro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one</iupac_name>
  <traditional_iupac>nordiazepam</traditional_iupac>
  <cas_registry_number>1088-11-5</cas_registry_number>
  <smiles>ClC1=CC=C2NC(=O)CN=C(C3=CC=CC=C3)C2=C1</smiles>
  <inchi>InChI=1S/C15H11ClN2O/c16-11-6-7-13-12(8-11)15(17-9-14(19)18-13)10-4-2-1-3-5-10/h1-8H,9H2,(H,18,19)</inchi>
  <inchikey>AKPLHCDWDRPJGD-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>Aryl chlorides</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Cyclic carboximidic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketimines</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,4-benzodiazepine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Aryl chloride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Cyclic carboximidic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Ketimine</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</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>
    </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>2.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.19e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>216.5 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>3.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>12.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>2.85</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>7-chloro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>270.714</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>270.055990691</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>ClC1=CC=C2NC(=O)CN=C(C3=CC=CC=C3)C2=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C15H11ClN2O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C15H11ClN2O/c16-11-6-7-13-12(8-11)15(17-9-14(19)18-13)10-4-2-1-3-5-10/h1-8H,9H2,(H,18,19)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>AKPLHCDWDRPJGD-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>41.46</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>76.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>27.41</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>2</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::EiMs</type>
      <spectrum_id>1372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>34607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>165074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>47853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>47854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>47855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>121443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>121444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>121445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444452</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB0060538</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Common wheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Triticum aestivum</name_scientific>
      <ncbi_taxonomy_id>4565</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Corn</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zea mays</name_scientific>
      <ncbi_taxonomy_id>4577</ncbi_taxonomy_id>
    </food>
    <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>Anxiolytic</name>
      <id>698</id>
      <definition>Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.</definition>
    </health_effect>
    <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>
