<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2009-07-23 18:26:15 UTC</creation_date>
  <update_date>2026-05-14 16:58:42 UTC</update_date>
  <accession>T3D3097</accession>
  <common_name>Tubocurarine</common_name>
  <class>SmallMolecule</class>
  <description>Tubocurarine belongs to the ethers, a subclass of organooxygen compounds within the organic compounds. With an average molecular weight of 609.73 g/mol, Tubocurarine is a heavy molecule. This exogenous compound has the chemical formula C37H41N2O6 and exists as a solid at room temperature. It functions as a muscle relaxant and a nicotinic antagonist. As a non-depolarizing muscle relaxant, it acts as a competitive antagonist at nicotinic acetylcholine receptors.

The compound targets several proteins, including the acetylcholine receptor subunit alpha (CHRNA1), neuronal acetylcholine receptor subunit alpha-2 (CHRNA2), neuronal acetylcholine receptor subunit alpha-3 (CHRNA3), and neuronal acetylcholine receptor subunit alpha-4 (CHRNA4), among 12 other proteins. Other recorded protein targets include acetylcholinesterase (ACHE), 5-hydroxytryptamine receptor 3A (HTR3A), solute carrier family 22 member 2 (SLC22A2), and multidrug and toxin extrusion protein 2 (SLC47A2). In terms of health effects, Tubocurarine has a therapeutic effect on inflammation (PMC12970233).

Tubocurarine is found in several recorded sources, including healthcare, pharmaceuticals, and veterinary products as a muscle relaxant, as well as in food preservation. It is also associated with household cleaning and consumer products such as cigar cigarettes, pipe accessories, other smoking requisites, tobacco smoke filters, and non-electric simulated smoking devices. Additionally, it is found in electrically stimulated smoking devices and in building and construction materials like tents or canopies. Recorded exposure routes for this compound include intravenous and intramuscular administration.</description>
  <categories>
    <category>Drug</category>
    <category>Plant Toxin</category>
    <category>Natural Toxin</category>
  </categories>
  <types>
    <type>Organic Compound</type>
    <type>Amine</type>
    <type>Ether</type>
    <type>Drug</type>
    <type>Plant Toxin</type>
    <type>Metabolite</type>
    <type>Muscle Relaxant, Skeletal</type>
    <type>Natural Compound</type>
    <type>Neuromuscular Nondepolarizing Agent</type>
    <type>Nicotinic Antagonist</type>
  </types>
  <synonyms>
    <synonym>(+)-tubocurarine</synonym>
    <synonym>7',12'-Dihydroxy-6,6'-dimethoxy-2,2',2'-trimethyltubocuraranium</synonym>
    <synonym>D-Tubocurarine</synonym>
    <synonym>D-Tubocurarine Chloride</synonym>
    <synonym>Isoquinoline Alkaloid</synonym>
    <synonym>Tubarine</synonym>
    <synonym>Tubocurarin</synonym>
    <synonym>tubocurarin</synonym>
    <synonym>Tubocurarine Chloride</synonym>
    <synonym>Tubocurarinum</synonym>
  </synonyms>
  <chemical_formula>C37H41N2O6</chemical_formula>
  <average_molecular_weight>609.7312</average_molecular_weight>
  <monisotopic_moleculate_weight>609.296462054</monisotopic_moleculate_weight>
  <iupac_name>(1S,16R)-9,21-dihydroxy-10,25-dimethoxy-15,15,30-trimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24,26,31,35-dodecaen-15-ium</iupac_name>
  <traditional_iupac>tubocurarine</traditional_iupac>
  <cas_registry_number>6989-98-6</cas_registry_number>
  <smiles>[H][C@@]12CC3=CC=C(OC4=C5C(CC[N+](C)(C)[C@]5([H])CC5=CC(OC6=C(OC)C=C(CCN1C)C2=C6)=C(O)C=C5)=CC(OC)=C4O)C=C3</smiles>
  <inchi>InChI=1S/C37H40N2O6/c1-38-14-12-24-19-32(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-37-35-25(20-34(43-5)36(37)41)13-15-39(2,3)29(35)17-23-8-11-30(40)31(18-23)45-33/h6-11,18-21,28-29H,12-17H2,1-5H3,(H-,40,41)/p+1/t28-,29+/m0/s1</inchi>
  <inchikey>JFJZZMVDLULRGK-URLMMPGGSA-O</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Ethers</sub_class>
    <direct_parent>Diarylethers</direct_parent>
    <alternate_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <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>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
      <alternative_parent>Tetrahydroisoquinolines</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</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>Diaryl ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
      <substituent>Tetrahydroisoquinoline</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>Isoquinoline alkaloids</descriptor>
      <descriptor>benzylisoquinoline alkaloid</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin>Exogenous</origin>
  <cellular_locations>
    <cellular_location>Cytoplasm</cellular_location>
    <cellular_location>Membrane</cellular_location>
  </cellular_locations>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Tubocurarine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143618</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state>Solid</state>
  <appearance>White powder.</appearance>
  <experimental_properties>
    <property>
      <kind>solubility</kind>
      <value>3.23e-04 g/L</value>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.23</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.23e-04 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>6.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,16R)-9,21-dihydroxy-10,25-dimethoxy-15,15,30-trimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24,26,31,35-dodecaen-15-ium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>609.7312</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>609.296462054</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC3=CC=C(OC4=C5C(CC[N+](C)(C)[C@]5([H])CC5=CC(OC6=C(OC)C=C(CCN1C)C2=C6)=C(O)C=C5)=CC(OC)=C4O)C=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C37H41N2O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C37H40N2O6/c1-38-14-12-24-19-32(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-37-35-25(20-34(43-5)36(37)41)13-15-39(2,3)29(35)17-23-8-11-30(40)31(18-23)45-33/h6-11,18-21,28-29H,12-17H2,1-5H3,(H-,40,41)/p+1/t28-,29+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JFJZZMVDLULRGK-URLMMPGGSA-O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>187.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>66.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</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>1</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure>Injection (sting/bite) (L1256)</route_of_exposure>
  <mechanism_of_toxicity>Tubocurarine is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death.  Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.</mechanism_of_toxicity>
  <metabolism>&#13;Half Life: 1-2 hours</metabolism>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use_source>Tubocurarine is a type of curare, a plant toxin known for its use as paralyzing arrow poison by South American indigenous people. It can be extracted from a variety of plants, including Strychnos toxifera and Chondrodendron tomentosum. (L1256)</use_source>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f72263c3d50&gt;</health_effects>
  <symptoms>Curare is a muscle relaxant and thus causes paraylsis. (L1256)</symptoms>
  <treatment>If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.</treatment>
  <drugbank_id>DB01199</drugbank_id>
  <hmdb_id>HMDB15330</hmdb_id>
  <pubchem_compound_id>6000</pubchem_compound_id>
  <chembl_id>CHEMBL1687</chembl_id>
  <chemspider_id>5778</chemspider_id>
  <kegg_id>C07547</kegg_id>
  <uniprot_id/>
  <omim_id/>
  <chebi_id>9774</chebi_id>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id>Tubocurarine</stitch_id>
  <actor_id/>
  <pdb_id/>
  <wikipidia>Tubocurarine</wikipidia>
  <general_references>
    <reference>
      <pubmed_id>1889362</pubmed_id>
    </reference>
    <reference>
      <reference_text>Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare</reference_text>
    </reference>
  </general_references>
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        <reference>
          <reference_text>Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare</reference_text>
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      <references>
        <reference>
          <reference_text>Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare</reference_text>
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      <references>
        <reference>
          <reference_text>Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare</reference_text>
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    <target>
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      <constants>
        <constant>
          <constant_type>IC50</constant_type>
          <value>9.4</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 50424714</assay_source>
        </constant>
      </constants>
      <references/>
    </target>
    <target>
      <target_id>BE0004752</target_id>
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      <constants>
        <constant>
          <constant_type>IC50</constant_type>
          <value>55.5</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 50424714</assay_source>
        </constant>
      </constants>
      <references/>
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    <target>
      <target_id>BE0000411</target_id>
      <mechanism_of_action>Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors. (L1256)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare</reference_text>
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    <target>
      <target_id>BE0000738</target_id>
      <mechanism_of_action>Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors. (L1256)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare</reference_text>
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      <mechanism_of_action>Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors. (L1256)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare</reference_text>
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      <mechanism_of_action>Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors. (L1256)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare</reference_text>
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    <target>
      <target_id>BE0003586</target_id>
      <mechanism_of_action>Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors. (L1256)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare</reference_text>
        </reference>
      </references>
    </target>
    <target>
      <target_id>BE0003587</target_id>
      <mechanism_of_action>Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors. (L1256)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare</reference_text>
        </reference>
      </references>
    </target>
    <target>
      <target_id>BE0002343</target_id>
      <mechanism_of_action>Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors. (L1256)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare</reference_text>
        </reference>
      </references>
    </target>
    <target>
      <target_id>BE0000850</target_id>
      <mechanism_of_action>Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors. (L1256)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare</reference_text>
        </reference>
      </references>
    </target>
    <target>
      <target_id>BE0003588</target_id>
      <mechanism_of_action>Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors. (L1256)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare</reference_text>
        </reference>
      </references>
    </target>
    <target>
      <target_id>BE0003584</target_id>
      <mechanism_of_action>Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors. (L1256)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare</reference_text>
        </reference>
      </references>
    </target>
    <target>
      <target_id>BE0003647</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>IC50</constant_type>
          <value>78.8</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 50424714</assay_source>
        </constant>
      </constants>
      <references/>
    </target>
  </targets>
</compound>
