<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4125</id>
  <title>T3D4071</title>
  <common-name>Gelsemine</common-name>
  <description>Gelsemine is a toxic alkaloid found in the plant Gelsemium sempervirens. It has convulsant effects with a similar mechanism of action to strychnine. Due to its complex structure, gelsemine has been the target for a number of total synthesis projects.</description>
  <cas>509-15-9</cas>
  <pubchem-id>5462429</pubchem-id>
  <chemical-formula>C20H22N2O2</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity>Gelsemine has convulsant effects with a similar mechanism of action to strychnine. Strychnine is a neurotoxin which acts as an antagonist of glycine and acetylcholine receptors. It primarily affects the motor nerves in the spinal cord which control muscle contraction. An impulse is triggered at one end of a nerve by the binding of neurotransmitters to the receptors. In the presence of a neuroinhibitor, such as glycine, a greater quantity of excitatory neurotransmitters must bind to receptors before there will be an action potential generated. Glycine acts primarily as an agonist of the glycine receptor, which is a ligand-gated chloride channel in neurons located in the spinal cord and in the brain. This chloride channel will allow the negatively charged chloride ions into the neuron, causing a hyperpolarization which pushes the membrane potential further from threshold. Strychnine is an antagonist of glycine, which means it binds to the same receptor, preventing the inhibitory effects of glycine on the postsynaptic neuron. Therefore, action potentials are triggered with lower levels of excitatory neurotransmitters. When the inhibitory signals are prevented, the motor neurons do will be more easliy activated and the victim will have spastic muscle contractions. Structure of strychnine in complex with ACh binding protein (AChBP). Strychnine is also an antagonist for acetylcholine receptors, which is known to be homologous to the glycine receptor. (Wikipedia)</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Gelsemine is a toxic alkaloid found in the plant Gelsemium sempervirens.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T05:02:45Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:26:37Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C09207</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id nil="true"/>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[H][C@]12CO[C@]3([H])CC1([H])[C@@]1(CN(C)[C@@]2([H])[C@]1([H])[C@@]31C(O)=NC2=CC=CC=C12)C=C</moldb-smiles>
  <moldb-formula>C20H22N2O2</moldb-formula>
  <moldb-inchi>InChI=1S/C20H22N2O2/c1-3-19-10-22(2)16-11-9-24-15(8-13(11)19)20(17(16)19)12-6-4-5-7-14(12)21-18(20)23/h3-7,11,13,15-17H,1,8-10H2,2H3,(H,21,23)/t11-,13?,15+,16+,17-,19-,20-/m0/s1</moldb-inchi>
  <moldb-inchikey>InChIKey=NFYYATWFXNPTRM-ICFOCEFXSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">322.4009</moldb-average-mass>
  <moldb-mono-mass type="decimal">322.168127958</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>4575404</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
