Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:55 UTC
HMDB IDHMDB0015285
Secondary Accession Numbers
  • HMDB15285
Metabolite Identification
Common NameThiamylal
DescriptionThiamylal is only found in individuals that have used or taken this drug. It is a barbiturate that is administered intravenously for the production of complete anesthesia of short duration, for the induction of general anesthesia, or for inducing a hypnotic state. (From Martindale, The Extra Pharmacopoeia, 30th ed, p919)Thiamylal binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Structure
Data?1582753279
Synonyms
ValueSource
5-Allyl-5-(1-methylbutyl)-2-thiobarbituric acidChEBI
5-Allyl-5-(1-methylbutyl)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedioneChEBI
5-Allyl-5-(1-methylbutyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dioneChEBI
Dihydro-5-(1-methylbutyl)-5-(2-propenyl)-2-thioxo-4,6(1H,5H)-pyrimidinedioneChEBI
ThioseconalChEBI
5-Allyl-5-(1-methylbutyl)-2-thiobarbitateGenerator
5-Allyl-5-(1-methylbutyl)-2-thiobarbitic acidGenerator
Parke davis brand OF thiamylal sodiumHMDB
ThioquinalbarbitoneHMDB
Sodium, thiamylalHMDB
SuritalHMDB
Thiamylal sodiumHMDB
Chemical FormulaC12H18N2O2S
Average Molecular Weight254.349
Monoisotopic Molecular Weight254.10889852
IUPAC Name5-(pentan-2-yl)-5-(prop-2-en-1-yl)-2-sulfanylidene-1,3-diazinane-4,6-dione
Traditional Namethiamylal
CAS Registry Number77-27-0
SMILES
CCCC(C)C1(CC=C)C(=O)NC(=S)NC1=O
InChI Identifier
InChI=1S/C12H18N2O2S/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)
InChI KeyXLOMZPUITCYLMJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiobarbituric acid derivatives. These are organic compounds containing a 2-thioxodihydropyrimidine-4,6(1H,5H)-dione skeleton.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentThiobarbituric acid derivatives
Alternative Parents
Substituents
  • Thiobarbiturate
  • 1,3-diazinane
  • Thiourea
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point132 - 133 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.051 g/LNot Available
LogP2.5Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.051 g/LALOGPS
logP3.11ALOGPS
logP2.92ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity70.64 m³·mol⁻¹ChemAxon
Polarizability26.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+158.58431661259
DarkChem[M-H]-153.41131661259
DeepCCS[M+H]+159.2730932474
DeepCCS[M-H]-156.91230932474
DeepCCS[M-2H]-190.77430932474
DeepCCS[M+Na]+166.41530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ThiamylalCCCC(C)C1(CC=C)C(=O)NC(=S)NC1=O3650.9Standard polar33892256
ThiamylalCCCC(C)C1(CC=C)C(=O)NC(=S)NC1=O1852.9Standard non polar33892256
ThiamylalCCCC(C)C1(CC=C)C(=O)NC(=S)NC1=O2020.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Thiamylal,1TMS,isomer #1C=CCC1(C(C)CCC)C(=O)NC(=S)N([Si](C)(C)C)C1=O1925.5Semi standard non polar33892256
Thiamylal,1TMS,isomer #1C=CCC1(C(C)CCC)C(=O)NC(=S)N([Si](C)(C)C)C1=O2062.7Standard non polar33892256
Thiamylal,1TMS,isomer #1C=CCC1(C(C)CCC)C(=O)NC(=S)N([Si](C)(C)C)C1=O3131.0Standard polar33892256
Thiamylal,2TMS,isomer #1C=CCC1(C(C)CCC)C(=O)N([Si](C)(C)C)C(=S)N([Si](C)(C)C)C1=O1908.0Semi standard non polar33892256
Thiamylal,2TMS,isomer #1C=CCC1(C(C)CCC)C(=O)N([Si](C)(C)C)C(=S)N([Si](C)(C)C)C1=O2089.6Standard non polar33892256
Thiamylal,2TMS,isomer #1C=CCC1(C(C)CCC)C(=O)N([Si](C)(C)C)C(=S)N([Si](C)(C)C)C1=O2618.0Standard polar33892256
Thiamylal,1TBDMS,isomer #1C=CCC1(C(C)CCC)C(=O)NC(=S)N([Si](C)(C)C(C)(C)C)C1=O2109.4Semi standard non polar33892256
Thiamylal,1TBDMS,isomer #1C=CCC1(C(C)CCC)C(=O)NC(=S)N([Si](C)(C)C(C)(C)C)C1=O2286.6Standard non polar33892256
Thiamylal,1TBDMS,isomer #1C=CCC1(C(C)CCC)C(=O)NC(=S)N([Si](C)(C)C(C)(C)C)C1=O3151.4Standard polar33892256
Thiamylal,2TBDMS,isomer #1C=CCC1(C(C)CCC)C(=O)N([Si](C)(C)C(C)(C)C)C(=S)N([Si](C)(C)C(C)(C)C)C1=O2338.5Semi standard non polar33892256
Thiamylal,2TBDMS,isomer #1C=CCC1(C(C)CCC)C(=O)N([Si](C)(C)C(C)(C)C)C(=S)N([Si](C)(C)C(C)(C)C)C1=O2510.1Standard non polar33892256
Thiamylal,2TBDMS,isomer #1C=CCC1(C(C)CCC)C(=O)N([Si](C)(C)C(C)(C)C)C(=S)N([Si](C)(C)C(C)(C)C)C1=O2723.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Thiamylal CI-B (Non-derivatized)splash10-0a4i-0090000000-8766fbc86b0e4f9df12c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Thiamylal CI-B (Non-derivatized)splash10-0a4i-0090000000-8766fbc86b0e4f9df12c2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thiamylal GC-MS (Non-derivatized) - 70eV, Positivesplash10-01y6-9270000000-c654329959eddd9732092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thiamylal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamylal 10V, Positive-QTOFsplash10-0a4i-1190000000-0e3bd0fbb412c080adfc2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamylal 20V, Positive-QTOFsplash10-0909-1790000000-b4f2b35dea5c7d7b95f22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamylal 40V, Positive-QTOFsplash10-008c-9200000000-b0f2760a6b889d0deb0d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamylal 10V, Negative-QTOFsplash10-0w29-2490000000-c2215a8fd83ef9a5da9c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamylal 20V, Negative-QTOFsplash10-0a4i-9010000000-a4d75b8b0d44951d26fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamylal 40V, Negative-QTOFsplash10-0a4i-9200000000-7598e665b19cdbc1f0d32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamylal 10V, Positive-QTOFsplash10-052r-0960000000-7fcdb946d222ec5772f42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamylal 20V, Positive-QTOFsplash10-0a4r-1970000000-920b6209dda20032e20c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamylal 40V, Positive-QTOFsplash10-01c9-3900000000-1d0ac0f9a99fbc9064692021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamylal 10V, Negative-QTOFsplash10-0udi-0090000000-5f9d4ba9eb406a9469e22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamylal 20V, Negative-QTOFsplash10-052f-9120000000-7d2c2f1d657b97b34a502021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamylal 40V, Negative-QTOFsplash10-0a4i-9500000000-32f064b826d15da527c12021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01154 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01154 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01154
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2297298
KEGG Compound IDC07846
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThiamylal
METLIN IDNot Available
PubChem Compound3032285
PDB IDNot Available
ChEBI ID9536
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in inward rectifier potassium channel activity
Specific function:
This receptor is controlled by G proteins. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. Can be blocked by extracellular barium
Gene Name:
KCNJ11
Uniprot ID:
Q14654
Molecular weight:
43540.4
References
  1. Kawano T, Oshita S, Takahashi A, Tsutsumi Y, Tomiyama Y, Kitahata H, Kuroda Y, Nakaya Y: Molecular mechanisms of the inhibitory effects of propofol and thiamylal on sarcolemmal adenosine triphosphate-sensitive potassium channels. Anesthesiology. 2004 Feb;100(2):338-46. [PubMed:14739809 ]
  2. Tsutsumi Y, Oshita S, Kitahata H, Kuroda Y, Kawano T, Nakaya Y: Blockade of adenosine triphosphate-sensitive potassium channels by thiamylal in rat ventricular myocytes. Anesthesiology. 2000 Apr;92(4):1154-9. [PubMed:10754636 ]
  3. Eguchi S, Kawano T, Oshita S, Nakajo N: [Effects of propofol and thiamylal on nicorandil induced ATP-sensitive potassium channel activities in cultured rat aortic smooth muscle cells]. Masui. 2005 Apr;54(4):364-9. [PubMed:15852621 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Sugimura M, Kitayama S, Morita K, Imai Y, Irifune M, Takarada T, Kawahara M, Dohi T: Effects of GABAergic agents on anesthesia induced by halothane, isoflurane, and thiamylal in mice. Pharmacol Biochem Behav. 2002 May;72(1-2):111-6. [PubMed:11900777 ]
  4. Whiting PJ: The GABAA receptor gene family: new opportunities for drug development. Curr Opin Drug Discov Devel. 2003 Sep;6(5):648-57. [PubMed:14579514 ]
  5. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
  6. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
  7. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207 ]
  8. Grasshoff C, Netzhammer N, Schweizer J, Antkowiak B, Hentschke H: Depression of spinal network activity by thiopental: shift from phasic to tonic GABA(A) receptor-mediated inhibition. Neuropharmacology. 2008 Oct;55(5):793-802. doi: 10.1016/j.neuropharm.2008.06.026. Epub 2008 Jun 21. [PubMed:18619475 ]
General function:
Involved in inward rectifier potassium channel activity
Specific function:
This potassium channel is controlled by G proteins. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. Can be blocked by external barium
Gene Name:
KCNJ8
Uniprot ID:
Q15842
Molecular weight:
47967.5
References
  1. Eguchi S, Kawano T, Oshita S, Nakajo N: [Effects of propofol and thiamylal on nicorandil induced ATP-sensitive potassium channel activities in cultured rat aortic smooth muscle cells]. Masui. 2005 Apr;54(4):364-9. [PubMed:15852621 ]
  2. Kawano T, Oshita S, Takahashi A, Tsutsumi Y, Tomiyama Y, Kitahata H, Kuroda Y, Nakaya Y: Molecular mechanisms of the inhibitory effects of propofol and thiamylal on sarcolemmal adenosine triphosphate-sensitive potassium channels. Anesthesiology. 2004 Feb;100(2):338-46. [PubMed:14739809 ]
  3. Tsutsumi Y, Oshita S, Kitahata H, Kuroda Y, Kawano T, Nakaya Y: Blockade of adenosine triphosphate-sensitive potassium channels by thiamylal in rat ventricular myocytes. Anesthesiology. 2000 Apr;92(4):1154-9. [PubMed:10754636 ]