ContaminantDB: Neostigmine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:27:22 UTC

Update Date

2026-03-26 19:45:03 UTC

Accession Number

CHEM022301

Identification

Common Name

Neostigmine

Class

Small Molecule

Description

A cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike physostigmine, does not cross the blood-brain barrier.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(m-Hydroxyphenyl)trimethylammonium dimethylcarbamate	ChEBI
3-Trimethylammoniumphenyl N,N-dimethylcarbamate	ChEBI
Eustigmin	ChEBI
Eustigmine	ChEBI
m-Trimethylammoniumphenyldimethylcarbamate	ChEBI
Prostigmine	ChEBI
Vagostigmine	ChEBI
Prostigmin	Kegg
(m-Hydroxyphenyl)trimethylammonium dimethylcarbamic acid	Generator
3-Trimethylammoniumphenyl N,N-dimethylcarbamic acid	Generator
m-Trimethylammoniumphenyldimethylcarbamic acid	Generator
Proserine	HMDB
Neostigmine bromide	HMDB
Methylsulfate, neostigmine	HMDB
Polstigmine	HMDB
Syntostigmine	HMDB
Bromide, neostigmine	HMDB
Neostigmine methylsulfate	HMDB
Prozerin	HMDB
Synstigmin	HMDB

Chemical Formula

C₁₂H₁₉N₂O₂

Average Molecular Mass

223.292 g/mol

Monoisotopic Mass

223.145 g/mol

CAS Registry Number

59-99-4

IUPAC Name

3-[(dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium

Traditional Name

neostigmine

SMILES

CN(C)C(=O)OC1=CC(=CC=C1)[N+](C)(C)C

InChI Identifier

InChI=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 Key

ALWKGYPQUAPLQC-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxy compounds

Direct Parent

Phenoxy compounds

Alternative Parents

Substituents

Phenoxy compound
Aniline or substituted anilines
Quaternary ammonium salt
Carbamic acid ester
Carbonic acid derivative
Amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic salt
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic cation
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

quaternary ammonium ion (CHEBI:7514 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.068 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-2.2	ChemAxon
logS	-3.6	ALOGPS
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.28 m³·mol⁻¹	ChemAxon
Polarizability	25.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9720000000-c12a62c0ea57c3a5c3c0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-0090000000-7feec7180feed2165741	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-0090000000-33ad4a0e0807f82bab39	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0ab9-2090000000-285ee2bce4f4c2097510	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-9110000000-a2386202e9dc8c7c753f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-9100000000-b80120a3f55bb762fe51	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0a4i-0090000000-675c3ee4663579ce2125	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-3290000000-b986a6e34fcfb8d59d47	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-5920000000-f27e9d56f2a899526aed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9400000000-a34da59427598585aa1e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01400

HMDB ID

HMDB0015472

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=7200780

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=8584207

Neostigmine (CHEM022301)

Structure for CHEM022301: Neostigmine