<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2009-08-05 16:56:17 UTC</creation_date>
  <update_date>2026-08-20 04:54:32 UTC</update_date>
  <accession>T3D3558</accession>
  <common_name>Cellulose nitrate</common_name>
  <class>SmallMolecule</class>
  <description>Cellulose nitrate is an exogenous organic compound with the formula C20H16N4 and an average molecular weight of 312.37 g/mol. It exists as a solid at room temperature. Cellulose nitrate belongs to the triazoles, a subclass of azoles within the organic compounds.

This compound serves several roles across different fields, acting as a chemical explosive, an industrial film former, and a biological tissue adhesive. It has been recorded in sources such as tents or canopies used in building and construction, as well as electrical and electronic equipment, specifically within antennas and superconductive or hyperconductive conductors cables or transmission lines.

Two protein targets are recorded for this substance: hemoglobin subunit alpha (HBA1) and hemoglobin subunit beta (HBB). Nitrite causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, which is characterized by tissue hypoxia because methemoglobin cannot bind oxygen.</description>
  <categories>
    <category>Household Toxin</category>
    <category>Industrial/Workplace Toxin</category>
    <category>Synthetic Toxin</category>
  </categories>
  <types>
    <type>Inorganic Compound</type>
    <type>Organic Compound</type>
    <type>Explosive Agent</type>
    <type>Nitrate</type>
    <type>Household Toxin</type>
    <type>Industrial/Workplace Toxin</type>
    <type>Synthetic Compound</type>
  </types>
  <synonyms>
    <synonym>CELLOIDIN</synonym>
    <synonym>Cellulose nitric acid</synonym>
    <synonym>Collodion</synonym>
  </synonyms>
  <chemical_formula>C20H16N4</chemical_formula>
  <average_molecular_weight>312.3678</average_molecular_weight>
  <monisotopic_moleculate_weight>312.137496532</monisotopic_moleculate_weight>
  <iupac_name>1,4-diphenyl-3-(phenylazanidyl)-1H-1,2,4λ⁵-triazol-4-ylium</iupac_name>
  <traditional_iupac>1,4-diphenyl-3-(phenylazanidyl)-1,2,4λ⁵-triazol-4-ylium</traditional_iupac>
  <cas_registry_number>9004-70-0</cas_registry_number>
  <smiles>[N-](C1=NN(C=[N+]1C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C20H16N4/c1-4-10-17(11-5-1)21-20-22-24(19-14-8-3-9-15-19)16-23(20)18-12-6-2-7-13-18/h1-16H</inchi>
  <inchikey>CWGBFIRHYJNILV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Azoles</class>
    <sub_class>Triazoles</sub_class>
    <direct_parent>Phenyl-1,2,4-triazoles</direct_parent>
    <alternate_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenyl-1,2,4-triazole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin>Exogenous</origin>
  <cellular_locations>
    <cellular_location>Membrane</cellular_location>
  </cellular_locations>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state>Solid</state>
  <appearance>White powder.</appearance>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>160-170°C (ignites)</value>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.4</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.57e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1,4-diphenyl-3-(phenylazanidyl)-1H-1,2,4λ⁵-triazol-4-ylium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>312.3678</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>312.137496532</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[N-](C1=NN(C=[N+]1C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H16N4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H16N4/c1-4-10-17(11-5-1)21-20-22-24(19-14-8-3-9-15-19)16-23(20)18-12-6-2-7-13-18/h1-16H</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CWGBFIRHYJNILV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>30.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>103.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</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>
  </predicted_properties>
  <route_of_exposure>Oral (L1137)  ;inhalation  (L1137)</route_of_exposure>
  <mechanism_of_toxicity>Nitrate's toxicity is a result of it's conversion to nitrite once in the body. Nitrite causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen. (A2450, L1613)</mechanism_of_toxicity>
  <metabolism>Intake of some amount of nitrates and nitrites is a normal part of the nitrogen cycle in humans. In vivo conversion of nitrates to nitrites can occur in the gastrointestional tract under the right conditions, significantly enhancing nitrates' toxic potency. The major metabolic pathway for nitrate is conversion to nitrite, and then to ammonia. Nitrites, nitrates, and their metabolites are excreted in the urine. (L1137)</metabolism>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity>Ingested nitrate or nitrite under conditions that result in endogenous nitrosation is probably carcinogenic to humans (Group 2A). (L135)</carcinogenicity>
  <use_source>It can be used as a propellant, low-order explosive, film base, laquer, wound dressing, and carrier of topical medications.</use_source>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3baf146c38&gt;</health_effects>
  <symptoms>Nitrate and nitrite poisoning causes methemoglobinemia. Symptoms include cyanosis, cardiac dysrhythmias and circulatory failure, and progressive central nervous system (CNS) effects. CNS effects can range from mild dizziness and lethargy to coma and convulsions. (L1137)</symptoms>
  <treatment>Methemoglobinemia can be treated with supplemental oxygen and methylene blue 1% solution administered intravenously slowly over five minutes followed by IV flush with normal saline. Methylene blue restores the iron in hemoglobin to its normal (reduced) oxygen-carrying state. (L1613)</treatment>
  <drugbank_id/>
  <hmdb_id/>
  <pubchem_compound_id>44135439</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id/>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id>Cellulose nitrate</stitch_id>
  <actor_id>12323</actor_id>
  <pdb_id/>
  <wikipidia>http://en.wikipedia.org/wiki/Nitrocellulose</wikipidia>
  <general_references>
    <reference>
      <pubmed_id>18203719</pubmed_id>
    </reference>
    <reference>
      <reference_text>International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. : http://monographs.iarc.fr/index.php</reference_text>
    </reference>
    <reference>
      <reference_text>International Programme on Chemical Safety (IPCS) INCHEM (1996). Poison Information Monograph for Dieldrin. : http://www.inchem.org/documents/pims/chemical/pim575.htm</reference_text>
    </reference>
    <reference>
      <reference_text>ATSDR - Agency for Toxic Substances and Disease Registry (2007). Case Studies in Environmental Medicine. Nitrate/Nitrite Toxicity. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/csem/nitrate/nitrate.html</reference_text>
    </reference>
    <reference>
      <reference_text>Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. : http://en.wikipedia.org/wiki/Methemoglobinemia</reference_text>
    </reference>
    <reference>
      <reference_text>Wikipedia. Nitrocellulose. Last Updated 13 July 2009.: http://en.wikipedia.org/wiki/Nitrocellulose</reference_text>
    </reference>
  </general_references>
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        <reference>
          <reference_text>Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. : http://en.wikipedia.org/wiki/Methemoglobinemia</reference_text>
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</compound>
