<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2840</id>
  <title>T3D2798</title>
  <common-name>Metharbital</common-name>
  <description>Metharbital is only found in individuals that have used or taken this drug. It was patented in 1905 by Emil Fischer working for Merck. It was marketed as Gemonil by Abbott Laboratories. It is a barbiturate anticonvulsant, used in the treatment of epilepsy. It has similar properties to phenobarbital. Metharbital binds at a distinct binding site associated with a Cl&lt;sup&gt;-&lt;/sup&gt; ionopore at the GABA&lt;sub&gt;A&lt;/sub&gt; receptor, increasing the duration of time for which the Cl&lt;sup&gt;-&lt;/sup&gt; ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). The net result of barbiturate action is acute potentiation of inhibitory GABAergic tone. Barbiturates also act through potent (if less well characterized) and direct inhibition of excitatory AMPA-type glutamate receptors, resulting in a profound suppression of glutamatergic neurotransmission.</description>
  <cas>50-11-3</cas>
  <pubchem-id>4099</pubchem-id>
  <chemical-formula>C9H14N2O3</chemical-formula>
  <weight>198.100440</weight>
  <appearance>White powder.</appearance>
  <melting-point>150.5°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>1980 mg/L (at 25°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity>Metharbital binds at a distinct binding site associated with a Cl&lt;sup&gt;-&lt;/sup&gt; ionopore at the GABA&lt;sub&gt;A&lt;/sub&gt; receptor, increasing the duration of time for which the Cl&lt;sup&gt;-&lt;/sup&gt; ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). The net result of barbiturate action is acute potentiation of inhibitory GABAergic tone. Barbiturates also act through potent (if less well characterized) and direct inhibition of excitatory AMPA-type glutamate receptors, resulting in a profound suppression of glutamatergic neurotransmission.</mechanism-of-toxicity>
  <metabolism></metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Metharbital is used for the treatment of epilepsy.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.</health-effects>
  <symptoms>Signs of overdose include confusion (severe), decrease in or loss of reflexes, drowsiness (severe), fever, irritability (continuing), low body temperature, poor judgment, shortness of breath or slow or troubled breathing, slow heartbeat, slurred speech, staggering, trouble in sleeping, unusual movements of the eyes, weakness (severe).</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:26:57Z</created-at>
  <updated-at type="dateTime">2026-04-03T02:49:25Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Metharbital</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>102408</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Metharbital</stitch-id>
  <drugbank-id>DB00463</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CCC1(CC)C(=O)NC(=O)N(C)C1=O</moldb-smiles>
  <moldb-formula>C9H14N2O3</moldb-formula>
  <moldb-inchi>InChI=1S/C9H14N2O3/c1-4-9(5-2)6(12)10-8(14)11(3)7(9)13/h4-5H2,1-3H3,(H,10,12,14)</moldb-inchi>
  <moldb-inchikey>FWJKNZONDWOGMI-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">198.2191</moldb-average-mass>
  <moldb-mono-mass type="decimal">198.100442324</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>1.15</logp>
  <hmdb-id>HMDB14606</hmdb-id>
  <chembl-id>CHEMBL450</chembl-id>
  <chemspider-id>3957</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"/>
  <chemdb-id>CHEM002200</chemdb-id>
  <dsstox-id>DTXSID6023280</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00016843</susdat-id>
  <iupac>5,5-diethyl-1-methyl-1,3-diazinane-2,4,6-trione</iupac>
</compound>
