<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-06-03 11:12:04 UTC</creation_date>
  <update_date>2026-05-14 17:08:21 UTC</update_date>
  <accession/>
  <common_name>dihydrocodeine</common_name>
  <class>SmallMolecule</class>
  <description>Dihydrocodeine is an organic compound with the formula C18H23NO3 and an average molecular weight of 301.38 g/mol. Dihydrocodeine belongs to the morphinans, a class of alkaloids and derivatives within the organic compounds.

This compound is found in or released from three recorded sources: drinking water and water supply (drinking water), healthcare, pharmaceuticals and veterinary products (analgesics), and household cleaning and consumer products (non electric simulated smoking devices). The recorded exposure route for dihydrocodeine is oral. Regarding its biological activity, one protein target has been recorded: it acts as an antagonist of the Mu-type opioid receptor (OPRM1).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C18H23NO3</chemical_formula>
  <average_molecular_weight>301.3801</average_molecular_weight>
  <monisotopic_moleculate_weight>301.167793607</monisotopic_moleculate_weight>
  <iupac_name>(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-ol</iupac_name>
  <traditional_iupac>dihydrocodeine</traditional_iupac>
  <cas_registry_number>125-28-0</cas_registry_number>
  <smiles>[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])CC[C@@H]2O</smiles>
  <inchi>InChI=1S/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1</inchi>
  <inchikey>RBOXVHNMENFORY-DNJOTXNNSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Alkaloids and derivatives</super_class>
    <class>Morphinans</class>
    <sub_class/>
    <direct_parent>Morphinans</direct_parent>
    <alternate_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Coumarans</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Piperidines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Amine</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Coumaran</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Morphinan</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Piperidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Dihydrocodeine Opioid Agonist Action Pathway</name>
      <smpdb_id>SMP0124998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Remifentanil Opioid Anasthetic Action Pathway</name>
      <smpdb_id>SMP0125022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dihydrocodeine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143774</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>1.55</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.38e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>301.3801</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>301.167793607</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])CC[C@@H]2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H23NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RBOXVHNMENFORY-DNJOTXNNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>41.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>83.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</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:0x00007f7221a3d0c8&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01551</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>5284543</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4447600</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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  </targets>
</compound>
