<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:15 UTC</creation_date>
  <update_date>2020-09-17 15:42:23 UTC</update_date>
  <accession>FDB012589</accession>
  <name>Dimethylamine</name>
  <description>Dimethylamine, also known as DMA or (CH3)2NH, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Dimethylamine is a very strong basic compound (based on its pKa). Dimethylamine (DMA) is also classified as a secondary amine. It is a colorless, liquefied and flammable gas with an ammonia and fish-like odor. Dimethylamine is abundantly present in human urine. The main sources of urinary DMA have been reported to include trimethylamine N-oxide, a common food component found in cold-water fish, and asymmetric dimethylarginine (ADMA), an endogenous inhibitor of nitric oxide (NO) synthesis. ADMA is excreted in the urine in part unmetabolized and in part after hydrolysis to DMA by dimethylarginine dimethylaminohydrolase (DDAH). Statistically significant increases in urinary DMA have been found in individuals after the consumption of fish and seafoods. The highest values were obtained for individuals that consumed coley, squid, whitting, cod, haddock, sardine, skate and swordfish (PMID: 18282650). DMA has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Industrially, DMA is used as dehairing agent in tanning, in dyes, in rubber polymerization accelerators, in soaps and cleaning compounds and as an agricultural fungicide. In the body, DMA also undergoes nitrosation under weak acid conditions to give dimethlynitrosamine. Recent studies have shown that DMA is a metabolite produced by several species of bacteria including Arthrobacter and Micrococcus (PMID: 11422368). Dimethylamine is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2).</description>
  <synonyms>
    <synonym>(CH3)2NH</synonym>
    <synonym>Dimethylamine (anhydrous)</synonym>
    <synonym>Dimethylamine anhydrous</synonym>
    <synonym>Dimethylamine anhydrous (dot)</synonym>
    <synonym>Dimethylamine aqueous solution</synonym>
    <synonym>Dimethylamine hydrobromide</synonym>
    <synonym>Dimethylamine solution</synonym>
    <synonym>Dimethylamine, anhydrous [UN1032] [Flammable gas]</synonym>
    <synonym>Dimethylammonium bromide</synonym>
    <synonym>HNMe2</synonym>
    <synonym>Me2NH</synonym>
    <synonym>Methanamine, n-methyl-</synonym>
    <synonym>Methanamine, n-methyl-, hydrobromide</synonym>
    <synonym>N-methyl-methanamine</synonym>
    <synonym>N-methylmethanamine</synonym>
    <synonym>N-Methylmethanamine (acd/name 4.0)</synonym>
    <synonym>N-Methylmethanamine, 9CI</synonym>
    <synonym>N,n-dimethylamine</synonym>
    <synonym>nchem.125-comp12</synonym>
  </synonyms>
  <chemical_formula>C2H7N</chemical_formula>
  <average_molecular_weight>45.0837</average_molecular_weight>
  <monisotopic_moleculate_weight>45.057849229</monisotopic_moleculate_weight>
  <iupac_name>dimethylamine</iupac_name>
  <traditional_iupac>dimethylamine</traditional_iupac>
  <cas_registry_number>124-40-3</cas_registry_number>
  <smiles>CNC</smiles>
  <inchi>InChI=1S/C2H7N/c1-3-2/h3H,1-2H3</inchi>
  <inchikey>ROSDSFDQCJNGOL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.</description>
    <direct_parent>Dialkylamines</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary aliphatic amine</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>methylamines</external_descriptor>
      <external_descriptor>secondary aliphatic amine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Liquid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>1.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.16e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp -96°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-0.19</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>10.52</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>dimethylamine</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>45.0837</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>45.057849229</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CNC</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C2H7N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C2H7N/c1-3-2/h3H,1-2H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>ROSDSFDQCJNGOL-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>14.69</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>5.75</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</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>
  <pathways>
  </pathways>
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      <type>Specdb::CMs</type>
      <spectrum_id>20008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>137140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>144874</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1135</spectrum_id>
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      <spectrum_id>1138</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>142090</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>142091</spectrum_id>
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      <type>Specdb::NmrOneD</type>
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      <spectrum_id>142098</spectrum_id>
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      <spectrum_id>142099</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>142100</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>142101</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142102</spectrum_id>
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      <spectrum_id>142103</spectrum_id>
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      <type>Specdb::NmrOneD</type>
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      <spectrum_id>166489</spectrum_id>
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      <spectrum_id>6127</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>6128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310543</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>310544</spectrum_id>
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      <spectrum_id>310545</spectrum_id>
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      <spectrum_id>355297</spectrum_id>
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      <spectrum_id>355298</spectrum_id>
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      <spectrum_id>355299</spectrum_id>
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      <spectrum_id>446053</spectrum_id>
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      <spectrum_id>446055</spectrum_id>
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  </spectra>
  <hmdb_id>HMDB00087</hmdb_id>
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  <kegg_id/>
  <chebi_id>17170</chebi_id>
  <biocyc_id/>
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  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
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  <foods>
    <food>
      <name>Anatidae</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anatidae</name_scientific>
      <ncbi_taxonomy_id>8830</ncbi_taxonomy_id>
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    <food>
      <name>Barley</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Hordeum vulgare</name_scientific>
      <ncbi_taxonomy_id>4513</ncbi_taxonomy_id>
      <average_value>0.16</average_value>
      <max_value>0.16</max_value>
      <min_value>0.16</min_value>
      <unit>mg/100 g</unit>
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    <food>
      <name>Beefalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus X Bison bison</name_scientific>
      <ncbi_taxonomy_id>297284</ncbi_taxonomy_id>
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    <food>
      <name>Beer</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
      <average_value>0.575</average_value>
      <max_value>0.575</max_value>
      <min_value>0.575</min_value>
      <unit>mg/100 g</unit>
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    <food>
      <name>Bison</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bison bison</name_scientific>
      <ncbi_taxonomy_id>9901</ncbi_taxonomy_id>
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    <food>
      <name>Buffalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bubalus bubalis</name_scientific>
      <ncbi_taxonomy_id>89462</ncbi_taxonomy_id>
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    <food>
      <name>Cabbage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Brassica oleracea var. capitata</name_scientific>
      <ncbi_taxonomy_id>3716</ncbi_taxonomy_id>
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      <max_value>0.24</max_value>
      <min_value>0.24</min_value>
      <unit>mg/100 g</unit>
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    <food>
      <name>Cattle (Beef, Veal)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus</name_scientific>
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      <category>specific</category>
      <name_scientific>Gallus gallus</name_scientific>
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    <food>
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      <category>specific</category>
      <name_scientific>Columbidae</name_scientific>
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      <category>specific</category>
      <name_scientific>Vitis vinifera</name_scientific>
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      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zea mays</name_scientific>
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      <average_value>0.23</average_value>
      <max_value>0.23</max_value>
      <min_value>0.23</min_value>
      <unit>mg/100 g</unit>
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    <food>
      <name>Deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervidae</name_scientific>
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      <name>Domestic goat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
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    </food>
    <food>
      <name>Domestic pig</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
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    </food>
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      <food_type>Type 1</food_type>
      <category>specific</category>
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    </food>
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      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Dromaius novaehollandiae</name_scientific>
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      <food_type>Type 1</food_type>
      <category>specific</category>
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      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Musa X paradisiaca</name_scientific>
      <ncbi_taxonomy_id>89151</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Grape wine</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
      <average_value>0.4</average_value>
      <max_value>0.4</max_value>
      <min_value>0.4</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Greylag goose</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anser anser</name_scientific>
      <ncbi_taxonomy_id>8843</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Guinea hen</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Numida meleagris</name_scientific>
      <ncbi_taxonomy_id>8996</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Horse</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Equus caballus</name_scientific>
      <ncbi_taxonomy_id>9796</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mallard duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anas platyrhynchos</name_scientific>
      <ncbi_taxonomy_id>8839</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Milk (Cow)</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>14.278571</average_value>
      <max_value>17.0</max_value>
      <min_value>9.4</min_value>
      <unit>uM</unit>
    </food>
    <food>
      <name>Mountain hare</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lepus timidus</name_scientific>
      <ncbi_taxonomy_id>62621</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mule deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Odocoileus</name_scientific>
      <ncbi_taxonomy_id>9871</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Ostrich</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Struthio camelus</name_scientific>
      <ncbi_taxonomy_id>8801</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pheasant</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianus colchicus</name_scientific>
      <ncbi_taxonomy_id>9054</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Quail</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianidae</name_scientific>
      <ncbi_taxonomy_id>9005</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Leporidae</name_scientific>
      <ncbi_taxonomy_id>9979</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rice</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryza sativa</name_scientific>
      <ncbi_taxonomy_id>4530</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rock ptarmigan</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lagopus muta</name_scientific>
      <ncbi_taxonomy_id>64668</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sheep (Mutton, Lamb)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ovis aries</name_scientific>
      <ncbi_taxonomy_id>9940</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Soy bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Glycine max</name_scientific>
      <ncbi_taxonomy_id>3847</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Squab</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columba</name_scientific>
      <ncbi_taxonomy_id>8931</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Turkey</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Meleagris gallopavo</name_scientific>
      <ncbi_taxonomy_id>9103</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Velvet duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Melanitta fusca</name_scientific>
      <ncbi_taxonomy_id>371864</ncbi_taxonomy_id>
    </food>
    <food>
      <name>White cabbage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Brassica oleracea L. var. capitata L. f. alba DC.</name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>0.24</average_value>
      <max_value>0.24</max_value>
      <min_value>0.24</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Wild boar</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa</name_scientific>
      <ncbi_taxonomy_id>9823</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild celery</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Apium graveolens</name_scientific>
      <ncbi_taxonomy_id>4045</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>N(G),N(G)-dimethylarginine dimethylaminohydrolase 2</name>
      <uniprot_id>O95865</uniprot_id>
      <uniprot_name/>
      <gene_name>DDAH2</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Coleoptophile</name>
      <id>821</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Pesticide</name>
      <id>1210</id>
      <definition>Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.</definition>
    </health_effect>
  </health_effects>
</compound>
