Meprobamate (CED0006766)

Record Information
Version1.0
Creation Date2016-05-22 03:43:14 UTC
Update Date2026-05-14 16:36:50 UTC
Accession NumberCHEM016769
Identification
Common NameMeprobamate
ClassSmall Molecule
Description
Meprobamate is an organic compound with the formula C9H18N2O4 and an average molecular weight of 218.25 g/mol. Meprobamate belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This compound is identified in 40 recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is used as anxiolytics as well as hypnotics and sedatives. Other recorded sources include drinking water and water supply; food, food processing, and cookware, specifically processing meats, food preservation, and fermentation processes for beer; and building and construction materials such as floors, ceilings, and sunshades awnings or outside screens. It is also found in household cleaning and consumer products, including bleaching agents, ash trays, match receptacles or boxes, other smoking requisites, and non electric simulated smoking devices. Additionally, it is released from electrical and electronic equipment, including amplifiers, antennas, adjustable resistors, communication cables or conductors, and auxiliary devices, among 17 other sources. The recorded route of exposure for this compound is oral. Meprobamate interacts with 18 recorded protein targets. It acts as an inhibitor, positive allosteric modulator, or stimulator of the gamma-aminobutyric acid receptor subunit alpha-1 (GABRA1), gamma-aminobutyric acid receptor subunit alpha-2 (GABRA2), gamma-aminobutyric acid receptor subunit alpha-3 (GABRA3), and gamma-aminobutyric acid receptor subunit alpha-4 (GABRA4), in addition to 14 other proteins.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
EquanilKegg
MiltownKegg
Meprobamic acidGenerator
DEA no. 2820HMDB
ProcarbamideHMDB
Alter brand OF meprobamateHMDB
Meprobamate alter brandHMDB
Meprobamate kade brandHMDB
Wallace brand 1 OF meprobamateHMDB
DapazHMDB
Méprobamate richardHMDB
TranmepHMDB
Wallace brand 2 OF meprobamateHMDB
Meprobamate richard brandHMDB
Richard brand OF meprobamateHMDB
Meprobamate wyeth brandHMDB
Sanofi synthelabo brand OF meprobamateHMDB
Reid rowell brand OF meprobamateHMDB
Wyeth brand OF meprobamateHMDB
Kade brand OF meprobamateHMDB
Meprobamate reid-rowell brandHMDB
MeprospanHMDB
Reid-rowell brand OF meprobamateHMDB
VisanoHMDB
Chemical FormulaC9H18N2O4
Average Molecular Mass218.250 g/mol
Monoisotopic Mass218.127 g/mol
CAS Registry Number57-53-4
IUPAC Name2-[(carbamoyloxy)methyl]-2-methylpentyl carbamate
Traditional Namesowell
SMILESCCCC(C)(COC(N)=O)COC(N)=O
InChI IdentifierInChI=1S/C9H18N2O4/c1-3-4-9(2,5-14-7(10)12)6-15-8(11)13/h3-6H2,1-2H3,(H2,10,12)(H2,11,13)
InChI KeyNPPQSCRMBWNHMW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carbamate esters. Carbamate esters are compounds containing an ester of carbamic acid with the general structure R2NC(=O)OR' (R' not H). They are esters of carbamic acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCarbamate esters
Alternative Parents
Substituents
  • Carbamic acid ester
  • Carbonic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.47 g/LALOGPS
logP1.06ALOGPS
logP0.93ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)15.17ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area104.64 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity53.04 m³·mol⁻¹ChemAxon
Polarizability22.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-053u-9100000000-d890d15ca6738ce72f60Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-053u-9100000000-d890d15ca6738ce72f60Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9300000000-825aaefb8c418b2efba2Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-1900000000-8dd8e00d9af9bce5cd26Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052b-9100000000-c21398e92cac7b48f567Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-dd49a24a00b896129dbbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-c537c5c82280244f0974Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-f351c8e0d2b10b45fdc9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052b-9100000000-353e329af17fdea1fe11Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-f351c8e0d2b10b45fdc9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9100000000-06d1583af444a66f06a6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052b-9100000000-c21398e92cac7b48f567Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-1900000000-8dd8e00d9af9bce5cd26Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-dd49a24a00b896129dbbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-c537c5c82280244f0974Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-2390000000-a65c0efdab5910621389Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05mo-7920000000-fa1a6af828f9e30ea863Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9300000000-6c3c492ff4f56df35223Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9110000000-8eddafdbe10b84364ba7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-e4ee5bd6d8f75f6b65f3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-bff1b038d3e9b7bb7e66Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fyo-5920000000-1571111c2e644492b2b0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01si-5900000000-f6410fb88e2d59529dfeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ox-9200000000-d12d6480357bf7a6b096Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052b-9810000000-801cf45e01a3599d3dc8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-9300000000-838b738f0c6ecba6d36fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01po-9000000000-238824ddc0f52f3b70fbNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
885.0Log mg/kg[500:1600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
375AnxiolyticsHealthcare, pharmaceuticals & veterinary productsNot Available
376Hypnotics and sedativesHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
501Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
502Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
523Gas Filled Discharge Tubes With Solid CathodeElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
526LoudspeakersElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
528MicrophonesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
534Still Video CamerasElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
554Ash TraysHousehold cleaning & consumer productsNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
558Match Receptables Or BoxesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
582Aircraft CarriersMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
601Lawn MowersAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
5 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)1506.15
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)2467.2
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)2023.07
Click to view 3D structureMuscarinic acetylcholine receptor M2P10980Rattus norvegicusPredicted (SEA)466.395
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)1962.35
Muscarinic acetylcholine receptor M5 structureClick to view 3D structureMuscarinic acetylcholine receptor M5P08912HumansPredicted (SEA)2777.89
Click to view 3D structureCocaine esteraseO00748HumansPredicted (SEA)222.337
Click to view 3D structureAcylcarnitine hydrolaseQ91WG0Mus musculusPredicted (SEA)20.3186
Click to view 3D structureCG8425-PA [Drosophila melanogaster]A1ZA98Drosophila melanogasterPredicted (SEA)23.0434
Farnesyl pyrophosphate synthase structureClick to view 3D structureFarnesyl pyrophosphate synthaseP14324HumansPredicted (SEA)114.516
Click to view 3D structureLiver carboxylesteraseQ29550Sus scrofaPredicted (SEA)95.0539
Click to view 3D structureJuvenile hormone esteraseQ9GPG0Manduca sextaPredicted (SEA)24.9118
Liver carboxylesterase 1 structureClick to view 3D structureLiver carboxylesterase 1P23141HumansPredicted (SEA)524.237
Click to view 3D structureFatty-acid amide hydrolase 1O00519HumansPredicted (SEA)2768.63
Click to view 3D structure1-deoxy-D-xylulose-5-phosphate synthaseB7UJP3Escherichia coli O127:H6 (strain E2348/69 / EPEC)Predicted (SEA)7.00643
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)114.75
Click to view 3D structureFarnesyl pyrophosphate synthaseQ0GKD7Leishmania donovaniPredicted (SEA)35.4992
Geranylgeranyl pyrophosphate synthase structureClick to view 3D structureGeranylgeranyl pyrophosphate synthaseO95749HumansPredicted (SEA)57.9198
Click to view 3D structureFatty-acid amide hydrolase 1P97612Rattus norvegicusPredicted (SEA)2370.04
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)2349.26
Click to view 3D structureSphingosine-1-phosphate lyase 1Q8CHN6Rattus norvegicusPredicted (SEA)16.6597
Click to view 3D structureCannabinoid receptor 1P20272Rattus norvegicusPredicted (SEA)1368.82
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)3182.48
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)4402.14
Click to view 3D structureUDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligaseQ5HMD9Staphylococcus epidermidis (strain ATCC 35984 / RP62A)Predicted (SEA)43.1285
Concentrations
Not Available
External Links
DrugBank IDDB00371
HMDB IDHMDB0014515
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMeprobamate
Chemspider ID3924
ChEBI ID199389
PubChem Compound ID4064
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References