Neostigmine (CED0002921)

Record Information
Version1.0
Creation Date2016-05-25 18:27:22 UTC
Update Date2026-08-18 19:52:09 UTC
Accession NumberCHEM022301
Identification
Common NameNeostigmine
ClassSmall Molecule
Description
Neostigmine is an organic compound with the chemical formula C12H19N2O2 and an average molecular weight of 223.29 g/mol. Neostigmine belongs to the phenoxy compounds, a subclass of benzene and substituted derivatives within the organic compounds. It is categorized under the superclass of benzenoids. In terms of biological activity, neostigmine acts as an inhibitor of the protein target acetylcholinesterase (ACHE). The compound is found in or released from seven recorded sources. These include pharmaceuticals and veterinary products, specifically miotics, antiglaucoma preparations, and parasympathomimetics. It is also associated with food, cookware, and food processing, specifically the preparation of vinegar and food preservation. Additionally, it is found in household cleaning and consumer products, such as tobacco smoke filters and non-electric simulated smoking devices, as well as in electrically stimulated smoking devices. Recorded exposure routes for neostigmine include oral, subcutaneous, intravenous, and intramuscular administration.
Contaminant TypeNot Available
Chemical Structure
SynonymsNot Available
Chemical FormulaC12H19N2O2
Average Molecular Mass223.292 g/mol
Monoisotopic Mass223.145 g/mol
CAS Registry Number59-99-4
IUPAC Name3-[(dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium
Traditional Nameneostigmine
SMILESCN(C)C(=O)OC1=CC(=CC=C1)[N+](C)(C)C
InChI IdentifierInChI=1S/C12H19N2O2/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5/h6-9H,1-5H3/q+1
InChI KeyALWKGYPQUAPLQC-UHFFFAOYSA-N
Chemical Taxonomy
ClassificationNot classified
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 Solubility0.068 g/LALOGPS
logP-1.6ALOGPS
logP-2.2ChemAxon
logS-3.6ALOGPS
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity75.28 m³·mol⁻¹ChemAxon
Polarizability25.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9720000000-c12a62c0ea57c3a5c3c0Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0090000000-7feec7180feed2165741Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0090000000-33ad4a0e0807f82bab39Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-2090000000-285ee2bce4f4c2097510Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9110000000-a2386202e9dc8c7c753fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9100000000-b80120a3f55bb762fe51Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-675c3ee4663579ce2125Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-3290000000-b986a6e34fcfb8d59d47Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dr-5920000000-f27e9d56f2a899526aedNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9400000000-a34da59427598585aa1eNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C 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
49.0Log mg/kg[30:88]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
381ParasympathomimeticsHealthcare, pharmaceuticals & veterinary productsNot Available
398Antiglaucoma preparations and mioticsHealthcare, pharmaceuticals & veterinary productsNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cholinesterase structureClick to view 3D structureCholinesteraseP06276HumansPredicted (SEA)16.8154
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)28.8042
Click to view 3D structureAcetylcholinesteraseP37136Rattus norvegicusPredicted (SEA)24.8339
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)50.602
Click to view 3D structureButyrylcholinesteraseQ9N1N9Equus caballusPredicted (SEA)15.1806
Click to view 3D structureAcetylcholinesteraseO42275Electrophorus electricusPredicted (SEA)68.1181
Click to view 3D structureAmine oxidase [flavin-containing] BP19643Rattus norvegicusPredicted (SEA)17.7496
Click to view 3D structureAmine oxidase [flavin-containing] AP21396Rattus norvegicusPredicted (SEA)18.061
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)158.657
Click to view 3D structureAcetylcholinesteraseP23795Bos taurusPredicted (SEA)20.7857
Click to view 3D structureButyrylcholinesteraseQ9JKC1Rattus norvegicusPredicted (SEA)34.0201
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)257.37
Click to view 3D structureAcetylcholinesteraseP21836Mus musculusPredicted (SEA)79.7954
LIM domain kinase 2 structureClick to view 3D structureLIM domain kinase 2P53671HumansPredicted (SEA)216.109
Click to view 3D structureAcidic phospholipase A2 CM-IP00602Naja mossambicaPredicted (SEA)21.3307
Rho-associated protein kinase 1 structureClick to view 3D structureRho-associated protein kinase 1Q13464HumansPredicted (SEA)1204.09
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)614.697
LIM domain kinase 1 structureClick to view 3D structureLIM domain kinase 1P53667HumansPredicted (SEA)1097.05
Rho-associated protein kinase 2 structureClick to view 3D structureRho-associated protein kinase 2O75116HumansPredicted (SEA)1590.54
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)2689.92
cAMP-dependent protein kinase catalytic subunit alpha structureClick to view 3D structurecAMP-dependent protein kinase catalytic subunit alphaP17612HumansPredicted (SEA)1985.0
Click to view 3D structureFatty-acid amide hydrolase 1P97612Rattus norvegicusPredicted (SEA)366.67
Dual specificity mitogen-activated protein kinase kinase 1 structureClick to view 3D structureDual specificity mitogen-activated protein kinase kinase 1Q02750HumansPredicted (SEA)1542.66
Click to view 3D structurePatatin-like phospholipase domain-containing protein 2Q8BJ56Mus musculusPredicted (SEA)47.8773
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)4717.74
Concentrations
Not Available
External Links
IdentifiersNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available