<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4615</id>
  <title>T3D4561</title>
  <common-name>Amobarbital</common-name>
  <description>A barbiturate with hypnotic and sedative properties (but not antianxiety). Adverse effects are mainly a consequence of dose-related CNS depression and the risk of dependence with continued use is high. (From Martindale, The Extra Pharmacopoeia, 30th ed, p565)</description>
  <cas>57-43-2</cas>
  <pubchem-id>2164</pubchem-id>
  <chemical-formula>C11H18N2O3</chemical-formula>
  <weight>226.27</weight>
  <appearance>White powder.</appearance>
  <melting-point>157 °C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>603 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>Amobarbital (like all barbiturates) works by binding to the GABAA receptor at either the alpha or the beta sub unit.  These are binding sites that are distinct from GABA itself and also distinct from the benzodiazepine binding site. Like benzodiazepines, barbiturates potentiate the effect of GABA at this receptor.  This GABAA receptor binding decreases input resistance, depresses burst and tonic firing, especially in ventrobasal and intralaminar neurons, while at the same time increasing burst duration and mean conductance at individual chloride channels; this increases both the amplitude and decay time of inhibitory postsynaptic currents.  In addition to this GABA-ergic effect, barbiturates also block the AMPA receptor, a subtype of glutamate receptor. Glutamate is the principal excitatory neurotransmitter in the mammalian CNS.  Amobarbital also appears to bind neuronal nicotinic acetylcholine receptors. </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 nil="true"/>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-30T21:04:32Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:59:43Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Amobarbital</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C07536</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>2673</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB01351</drugbank-id>
  <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>CCC1(CCC(C)C)C(=O)NC(=O)NC1=O</moldb-smiles>
  <moldb-formula>C11H18N2O3</moldb-formula>
  <moldb-inchi>InChI=1S/C11H18N2O3/c1-4-11(6-5-7(2)3)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)</moldb-inchi>
  <moldb-inchikey>VIROVYVQCGLCII-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">226.2722</moldb-average-mass>
  <moldb-mono-mass type="decimal">226.131742452</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.07</logp>
  <hmdb-id nil="true"/>
  <chembl-id>CHEMBL267894</chembl-id>
  <chemspider-id>2079</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>CHEM003521</chemdb-id>
  <dsstox-id>DTXSID9020081</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00008808</susdat-id>
  <iupac>5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione</iupac>
  <moldb-polar-surface-area>75.27</moldb-polar-surface-area>
  <moldb-refractivity>58.0029</moldb-refractivity>
  <moldb-polarizability>23.44849042106522</moldb-polarizability>
  <moldb-rotatable-bond-count>4</moldb-rotatable-bond-count>
  <moldb-acceptor-count>3</moldb-acceptor-count>
  <moldb-donor-count>2</moldb-donor-count>
  <moldb-pka-strongest-acidic>7.484748322088917</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic nil="true"/>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>1</moldb-number-of-rings>
  <moldb-alogps-logp>1.87</moldb-alogps-logp>
  <moldb-alogps-logs>-2.40</moldb-alogps-logs>
  <moldb-alogps-solubility>8.97e-01 g/l</moldb-alogps-solubility>
</compound>
