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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:49 UTC
HMDB IDHMDB0014987
Secondary Accession Numbers
  • HMDB14987
Metabolite Identification
Common NameMethylphenobarbital
DescriptionMethylphenobarbital, also known as mebaral or mephobarbitone, belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups. It is the N-methylated analogue of phenobarbital and has similar indications, therapeutic value, and tolerability.1935 – Mebaral was introduced by Winthrop Pharmaceuticals.2001 – Methylphenobarbital discontinued in the UK.2003 – Mebaral was acquired by Ovation Pharmaceuticals (a specialty pharmaceutical company that acquired under-promoted branded pharmaceutical products).2009 – Ovation was acquired by Lundbeck, which now markets Mebaral.2012 – Lundbeck announced that they were abandoning the product in the US as of January 6, 2012. Methylphenobarbital is a drug which is used for the relief of anxiety, tension, and apprehension, also used as an anticonvulsant for the treatment of epilepsy. The last available tablets bore an expiration date of March 31, 2012, and the drug will no longer be available in the US when supplies are depleted. Methylphenobarbital is a very weakly acidic compound (based on its pKa). The stated reason was because "the company thoroughly evaluated all avenues for keeping Mebaral available to patients, but ultimately concluded that no matter what steps they [i.e. Lundbeck] took, patients would be forced to transition to a new therapy."The company further stated in a letter on its website that under the FDA's Unapproved Drugs Initiative, FDA is no longer willing to allow the drug to be grandfathered. Methylphenobarbital is a potentially toxic compound. A new drug application would have needed to have been submitted to gain marketing approval, which would have taken an estimated five years, during which time patients would be required to change their therapies in any case. Symptoms of overdose of mephobarbital include confusion, decrease in or loss of reflexes, somnolence, fever, irritability, hypothermia, poor judgment, shortness of breath or slow/troubled breathing, slow heartbeat, slurred speech, staggering, trouble in sleeping, unusual movements of the eyes, weakness.
Structure
Data?1582753244
Synonyms
ValueSource
1-MethylphenobarbitalChEBI
5-Ethyl-1-methyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrioneChEBI
5-Ethyl-1-methyl-5-phenyl-pyrimidine-2,4,6-trioneChEBI
5-Ethyl-1-methyl-5-phenylbarbituric acidChEBI
MebaralChEBI
MephobarbitoneChEBI
MethylphenobarbitalumChEBI
MetilfenobarbitalChEBI
N-MethylphenobarbitalChEBI
5-Ethyl-1-methyl-5-phenylbarbitateGenerator
5-Ethyl-1-methyl-5-phenylbarbitic acidGenerator
MephobarbitalHMDB
Methyl phenobarbitoneHMDB
MethylphenobarbitonumHMDB
MethylphenolbarbitalHMDB
Methylphenylbarbituric acidHMDB
MetilfenobarbitaleHMDB
N-Ethylmethylphenylbarbituric acidHMDB
N-Methylethylphenylbarbituric acidHMDB
N-MethylphenolbarbitolHMDB
MethylphenobarbitoneHMDB
Sanofi synthelabo brand OF mephobarbitalHMDB
ProminalHMDB
Sanofi brand OF mephobarbitalHMDB
MethylphenobarbitalChEBI
Chemical FormulaC13H14N2O3
Average Molecular Weight246.2619
Monoisotopic Molecular Weight246.100442324
IUPAC Name5-ethyl-1-methyl-5-phenyl-1,3-diazinane-2,4,6-trione
Traditional Namemethylphenobarbital
CAS Registry Number115-38-8
SMILES
CCC1(C(=O)NC(=O)N(C)C1=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C13H14N2O3/c1-3-13(9-7-5-4-6-8-9)10(16)14-12(18)15(2)11(13)17/h4-8H,3H2,1-2H3,(H,14,16,18)
InChI KeyALARQZQTBTVLJV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentBarbituric acid derivatives
Alternative Parents
Substituents
  • Barbiturate
  • Ureide
  • N-acyl urea
  • Monocyclic benzene moiety
  • 1,3-diazinane
  • Benzenoid
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point176 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.71 g/LNot Available
LogP1.84HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.71 g/LALOGPS
logP1.95ALOGPS
logP1.63ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)8.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.48 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.64 m³·mol⁻¹ChemAxon
Polarizability24.62 ųChemAxon
Number of Rings2ChemAxon
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]+159.28831661259
DarkChem[M-H]-154.47831661259
DeepCCS[M+H]+161.58730932474
DeepCCS[M-H]-159.22930932474
DeepCCS[M-2H]-192.11530932474
DeepCCS[M+Na]+167.68130932474
AllCCS[M+H]+155.432859911
AllCCS[M+H-H2O]+151.532859911
AllCCS[M+NH4]+159.032859911
AllCCS[M+Na]+160.132859911
AllCCS[M-H]-158.332859911
AllCCS[M+Na-2H]-158.332859911
AllCCS[M+HCOO]-158.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MethylphenobarbitalCCC1(C(=O)NC(=O)N(C)C1=O)C1=CC=CC=C13310.9Standard polar33892256
MethylphenobarbitalCCC1(C(=O)NC(=O)N(C)C1=O)C1=CC=CC=C11858.9Standard non polar33892256
MethylphenobarbitalCCC1(C(=O)NC(=O)N(C)C1=O)C1=CC=CC=C11892.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methylphenobarbital,1TMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N([Si](C)(C)C)C1=O1833.0Semi standard non polar33892256
Methylphenobarbital,1TMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N([Si](C)(C)C)C1=O2057.9Standard non polar33892256
Methylphenobarbital,1TMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N([Si](C)(C)C)C1=O2651.2Standard polar33892256
Methylphenobarbital,1TBDMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2103.4Semi standard non polar33892256
Methylphenobarbital,1TBDMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2306.4Standard non polar33892256
Methylphenobarbital,1TBDMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2732.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methylphenobarbital EI-B (Non-derivatized)splash10-014i-7890000000-2901bd43c9c369accc5e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methylphenobarbital EI-B (Non-derivatized)splash10-014i-7890000000-2901bd43c9c369accc5e2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylphenobarbital GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1960000000-03c5912fae96e516bc082017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylphenobarbital GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylphenobarbital 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 - Methylphenobarbital 10V, Positive-QTOFsplash10-0002-0090000000-5efc4c40b94c015f15d12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylphenobarbital 20V, Positive-QTOFsplash10-00os-0930000000-00256f4ed6f9589accfb2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylphenobarbital 40V, Positive-QTOFsplash10-014l-8900000000-852f79784f92a016b5882016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylphenobarbital 10V, Negative-QTOFsplash10-0f6t-4190000000-7afe5dafc1ac46950ae92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylphenobarbital 20V, Negative-QTOFsplash10-05fr-5900000000-adbe9ddcf8d5310392d52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylphenobarbital 40V, Negative-QTOFsplash10-0006-9400000000-e18ddad976005362cdce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylphenobarbital 10V, Positive-QTOFsplash10-0002-0090000000-c3b5328faa9ccd4922742021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylphenobarbital 20V, Positive-QTOFsplash10-014i-1940000000-83b4742c95ac40de815f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylphenobarbital 40V, Positive-QTOFsplash10-00kf-9700000000-70a6a2b92d607f53d7982021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylphenobarbital 10V, Negative-QTOFsplash10-0002-0090000000-bd60669c03ea828062a52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylphenobarbital 20V, Negative-QTOFsplash10-0006-9320000000-d8726243263b97488adb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylphenobarbital 40V, Negative-QTOFsplash10-0006-9300000000-fb4279919738a6bc3b7c2021-10-11Wishart 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 DB00849 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00849 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00849
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7972
KEGG Compound IDC07829
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylphenobarbital
METLIN IDNot Available
PubChem Compound8271
PDB IDNot Available
ChEBI ID6758
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 monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. May be involved in the transmission of light information from the retina to the hypothalamus. Modulates cell surface expression of NETO2
Gene Name:
GRIK2
Uniprot ID:
Q13002
Molecular weight:
102582.5
References
  1. 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 ]
  2. 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 ]
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist
Gene Name:
GRIA2
Uniprot ID:
P42262
Molecular weight:
98820.3
References
  1. 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 ]
  2. 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 ]
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. 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 ]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
  3. 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 ]
  4. 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 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  6. 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 ]
  7. 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 ]
  8. Olsen RW, Li GD: GABA(A) receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2011 Feb;58(2):206-15. doi: 10.1007/s12630-010-9429-7. Epub 2010 Dec 31. [PubMed:21194017 ]
  9. Roden WH, Peugh LD, Jansen LA: Altered GABA(A) receptor subunit expression and pharmacology in human Angelman syndrome cortex. Neurosci Lett. 2010 Oct 15;483(3):167-72. doi: 10.1016/j.neulet.2010.08.001. Epub 2010 Aug 6. [PubMed:20692323 ]
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:
GABRA2
Uniprot ID:
P47869
Molecular weight:
51325.9
References
  1. 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 ]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
  3. Olsen RW, Li GD: GABA(A) receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2011 Feb;58(2):206-15. doi: 10.1007/s12630-010-9429-7. Epub 2010 Dec 31. [PubMed:21194017 ]
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:
GABRA3
Uniprot ID:
P34903
Molecular weight:
55164.1
References
  1. 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 ]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
  3. Olsen RW, Li GD: GABA(A) receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2011 Feb;58(2):206-15. doi: 10.1007/s12630-010-9429-7. Epub 2010 Dec 31. [PubMed:21194017 ]
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:
GABRA4
Uniprot ID:
P48169
Molecular weight:
61622.6
References
  1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
  2. Olsen RW, Li GD: GABA(A) receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2011 Feb;58(2):206-15. doi: 10.1007/s12630-010-9429-7. Epub 2010 Dec 31. [PubMed:21194017 ]
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:
GABRA5
Uniprot ID:
P31644
Molecular weight:
52145.6
References
  1. 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 ]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
  3. Olsen RW, Li GD: GABA(A) receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2011 Feb;58(2):206-15. doi: 10.1007/s12630-010-9429-7. Epub 2010 Dec 31. [PubMed:21194017 ]
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:
GABRA6
Uniprot ID:
Q16445
Molecular weight:
51023.7
References
  1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
  2. 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 ]
  3. Olsen RW, Li GD: GABA(A) receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2011 Feb;58(2):206-15. doi: 10.1007/s12630-010-9429-7. Epub 2010 Dec 31. [PubMed:21194017 ]