Compound: NEOSTIGMINE
SMILES: O=C(Oc1cc([N+](C)(C)C)ccc1)N(C)C
InChIKey: ALWKGYPQUAPLQC-UHFFFAOYSA-N
Synonyms: NEOSTIGMINE, Eustigmin, Eustigmine, Prostigmine, Vagostigmine, 59-99-4, Prostigmin, Neostigmin, Juvastigmin, m-Trimethylammoniumphenyldimethylcarbamate, 3-Trimethylammoniumphenyl N,N-dimethylcarbamate, Neostigmine ion, Neostigmine cation, 3-[(dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium, Neostigmine (cation), (m-Hydroxyphenyl)trimethylammonium dimethylcarbamate, [3-(dimethylcarbamoyloxy)phenyl]-trimethylazanium, 3982TWQ96G, (m-Hydroxyphenyl)trimethylammonium dimethylcarbamate (ester), Ammonium, (m-hydroxyphenyl)trimethyl-, dimethylcarbamate (ester), Benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-N,N,N-trimethyl-, CHEBI:7514, DTXSID1023360, Prozerin, Benzenaminium, 3-[[(dimethylamino)carbonyl]oxy]-N,N,N-trimethyl-, (3-(dimethylcarbamoyloxy)phenyl)-trimethylazanium, 3-((dimethylcarbamoyl)oxy)-N,N,N-trimethylanilinium, RefChem:55701, DTXCID703360, Normastigmin, Synstigmin, Neostigmine [BAN], Neostigmine (BAN), Prostigmin (TN), CHEMBL278020, Neostigminum, [3-(dimethylcarbamoyloxy)phenyl]-trimethyl-azanium bromide, 3-{[(dimethylamino)carbonyl]oxy}-N,N,N-trimethylanilinium, CCRIS 3079, [3-(dimethylcarbamoyloxy)phenyl]-trimethyl-azanium; sulfonatooxymethane, HSDB 3921, NCGC00163240-01, CAS-114-80-7, BRN 3615946, UNII-3982TWQ96G, Spectrum_001061, NEOSTIGMINE [MI], Prestwick0_000468, Prestwick1_000468, Prestwick2_000468, Prestwick3_000468, Spectrum2_001278, Spectrum4_000072, Spectrum5_001234, Lopac-N-2001, NEOSTIGMINE [HSDB], bmse000762, NEOSTIGMINE [VANDF], NEOSTIGMINE [MART.], Lopac0_000816, SCHEMBL34419, BSPBio_000576, KBioGR_000623, KBioSS_001541, DivK1c_000165, DivK1c_000198, SPBio_001276, SPBio_002515, BPBio1_000634, GTPL8993, orb1740451, 3-((dimethylcarbamoyl)oxy)-N,N,N-trimethylbenzenaminium, SCHEMBL29603805, ALWKGYPQUAPLQC-UHFFFAOYSA-, KBio1_000165, KBio1_000198, KBio2_001541, KBio2_004109, KBio2_006677, NINDS_000165, NINDS_000198, HMS2089A22, BDBM50022775, STL058953, AKOS005711366, CCG-204900, DB01400, IDI1_000165, IDI1_000198, MLS-0002855, NCGC00015730-01, NCGC00015730-02, NCGC00015730-03, NCGC00015730-04, NCGC00015730-05, NCGC00015730-06, NCGC00015730-07, NCGC00015730-08, NCGC00015730-09, NCGC00015730-24, NCGC00021658-03, SBI-0050793.P004, AB00053807, NS00001580, C07258, D08261, AB00053807-25, AB00053807-26, AB00053807_27, AB00053807_28, AB00053807_29, Q410546, BRD-K18922609-004-04-1, BRD-K18922609-004-14-0, BRD-K18922609-004-22-3, BRD-K18922609-004-23-1, BRD-K18922609-004-24-9, InChI=1/C12H19N2O2/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5/h6-9H,1-5H3/q+1
Theoretical properties:
molecular_formula: C12H19N2O2+
molecular_weight: 223.29 g/mol
exact_mass: 223.144652853 g/mol
formal_charge: 1
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 3
heavy_atom_count: 16
topological_polar_surface_area: 29.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 6.77e-02 g/L
Descriptions:
pubchem: Neostigmine is a quaternary ammonium ion comprising an anilinium ion core having three methyl substituents on the aniline nitrogen, and a 3-[(dimethylcarbamoyl)oxy] substituent at position 3. It is a parasympathomimetic which acts as a reversible acetylcholinesterase inhibitor. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor and an antidote to curare poisoning.
chebi: A  quaternary ammonium ion comprising an anilinium ion core having three methyl substituents on the aniline nitrogen, and a 3-[(dimethylcarbamoyl)oxy] substituent at position 3. It is a parasympathomimetic which acts as a reversible acetylcholinesterase inhibitor.
chembl: NEOSTIGMINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Neostigmine, sold under the brand name Bloxiverz, among others, is a medication used to treat myasthenia gravis, Ogilvie syndrome, and urinary retention without the presence of a blockage. It is also used in anaesthesia to end the effects of non-depolarising neuromuscular blocking medication. It is given by injection either into a vein, muscle, or under the skin. After injection effects are generally greatest within 30 minutes and last up to 4 hours.
Common side effects include nausea, increased saliva, crampy abdominal pain, and slow heart rate. More severe side effects include low blood pressure, weakness, and allergic reactions. It is unclear if use in pregnancy is safe for the fetus. Neostigmine is in the cholinergic family of medications. It works by blocking the action of acetylcholinesterase and therefore increases the levels of acetylcholine.
Neostigmine was patented in 1931. It is on the World Health Organization's List of Essential Medicines. The term is from Greek neos, meaning "new", and "-stigmine", in reference to the alkaloid, physostigmine, which inspired its design. It is available as a generic medication.