<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:42:55 UTC</creation_date>
  <update_date>2026-08-18 13:16:42 UTC</update_date>
  <accession/>
  <common_name>Mecamylamine</common_name>
  <class>SmallMolecule</class>
  <description>Mecamylamine is an organic compound with the chemical formula C11H21N and an average molecular weight of 167.29 g/mol. Mecamylamine belongs to the monoterpenoids, a subclass of prenol lipids within the organic compounds.

This compound is found in or released from 13 recorded sources. These include healthcare, pharmaceuticals, and veterinary products, specifically antihypertensives. It is also associated with household cleaning and consumer products, including cigar cigarettes, non-electric simulated smoking devices, other smoking requisites, pipe accessories, and perfumes within detergents and soaps. Additionally, it is found in electrical and electronic equipment, such as antennas, conductors or conductive bodies characterised by the conductive materials, electrically stimulated smoking devices, electrodes, fixed capacitors and their manufacture, and one other source. The recorded route of exposure for this substance is oral.

At the molecular level, mecamylamine interacts with four recorded protein targets. It functions as an antagonist of the neuronal acetylcholine receptor subunit alpha-2 (CHRNA2), neuronal acetylcholine receptor subunit alpha-7 (CHRNA7), neuronal acetylcholine receptor subunit alpha-4 (CHRNA4), and neuronal acetylcholine receptor subunit beta-2 (CHRNB2).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C11H21N</chemical_formula>
  <average_molecular_weight>167.2911</average_molecular_weight>
  <monisotopic_moleculate_weight>167.167399677</monisotopic_moleculate_weight>
  <iupac_name>N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine</iupac_name>
  <traditional_iupac>mecamylamine</traditional_iupac>
  <cas_registry_number>60-40-2</cas_registry_number>
  <smiles>CNC1(C)C2CCC(C2)C1(C)C</smiles>
  <inchi>InChI=1S/C11H21N/c1-10(2)8-5-6-9(7-8)11(10,3)12-4/h8-9,12H,5-7H2,1-4H3</inchi>
  <inchikey>IMYZQPCYWPFTAG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Monoterpenoids</sub_class>
    <direct_parent>Bicyclic monoterpenoids</direct_parent>
    <alternate_parents>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Bicyclic monoterpenoid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>primary aliphatic amine</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Mecamylamine Drug Metabolism</name>
      <smpdb_id>SMP0130861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mecamylamine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143102</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>2.37</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.24e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>167.2911</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>167.167399677</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CNC1(C)C2CCC(C2)C1(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H21N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H21N/c1-10(2)8-5-6-9(7-8)11(10,3)12-4/h8-9,12H,5-7H2,1-4H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IMYZQPCYWPFTAG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>12.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</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:0x00007f726c4028c0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00657</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>4032</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>5036243</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
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  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
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  <wikipidia/>
  <general_references/>
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</compound>
