<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 18:11:01 UTC</creation_date>
  <update_date>2026-05-14 18:59:01 UTC</update_date>
  <accession/>
  <common_name>Tryptamine</common_name>
  <class>SmallMolecule</class>
  <description>Tryptamine (C10H12N2) is an organic compound with an average molecular weight of 160.22 g/mol. Tryptamine belongs to the tryptamines and derivatives, a subclass of indoles and derivatives within the organic compounds. Biologically, it serves as a neurotransmitter (PMC8213022). It acts as an inhibitor for five recorded protein targets, including Aralkylamine dehydrogenase light chain (aauA), Aralkylamine dehydrogenase heavy chain (aauB), Amine oxidase [flavin-containing] B (MAOB), and 5-hydroxytryptamine receptor 2A (HTR2A).

The compound is found in or released from 36 recorded sources across various sectors. These include Electrical &amp; Electronic Equipment such as cell phones, capacitors, wires and cables, batteries, and printed circuit boards; Household cleaning &amp; consumer products including perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and pipe accessories; Food, food processing &amp; cookware including food packaging, food contact materials, food preservation, preparation of vinegar, and fermentation processes for beer; Textiles, leather &amp; furnishings such as synthetic textiles, carpets and rugs; Healthcare, pharmaceuticals &amp; veterinary products via medical devices; and Energy, oil &amp; gas through lubricants. Recorded exposure routes include oral, inhalation, and touch.

Tryptamine is a biomarker of hypothyroidism (PMC7009407). Blood levels are elevated in cases of obesity (PMC10372128), thyroid cancer (PMC7998837), and hypothyroidism (PMC6915086, PMC7009407). It is further associated with vomiting (PMC9775352), nausea (PMC9775352), hyperthyroidism (increase) (PMC10593800), thyroid cancer (decrease) (PMC10593800), and hypothyroidism (PMC2592280, PMC10593800, PMC12695664, PMC13024578). Conversely, blood levels are decreased in hyperthyroidism (PMC1492602, PMC6915086).</description>
  <categories/>
  <types>
    <type>PFAS</type>
    <type>Phytotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C10H12N2</chemical_formula>
  <average_molecular_weight>160.2157</average_molecular_weight>
  <monisotopic_moleculate_weight>160.100048394</monisotopic_moleculate_weight>
  <iupac_name>2-(1H-indol-3-yl)ethan-1-amine</iupac_name>
  <traditional_iupac>tryptamine</traditional_iupac>
  <cas_registry_number>61-54-1</cas_registry_number>
  <smiles>NCCC1=CNC2=CC=CC=C12</smiles>
  <inchi>InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2</inchi>
  <inchikey>APJYDQYYACXCRM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Tryptamines and derivatives</sub_class>
    <direct_parent>Tryptamines and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>2-arylethylamines</alternative_parent>
      <alternative_parent>3-alkylindoles</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>2-arylethylamine</substituent>
      <substituent>3-alkylindole</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Indole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
      <substituent>Tryptamine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>Indole alkaloids</descriptor>
      <descriptor>aminoalkylindole</descriptor>
      <descriptor>aralkylamino compound</descriptor>
      <descriptor>indole alkaloid</descriptor>
      <descriptor>tryptamines</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0000063</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>1.49</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.34e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>17.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(1H-indol-3-yl)ethan-1-amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>160.2157</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>160.100048394</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCC1=CNC2=CC=CC=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>APJYDQYYACXCRM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>41.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</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:0x00007f3baf14dc18&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB08653</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>1150</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>1118</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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</compound>
