Basic information
- CAS
51-60-5- Standard SMILES
CN(C)C(=O)Oc1cccc([N+](C)(C)C)c1.COS(=O)(=O)[O-]- InChIKey
OSZNNLWOYWAHSS-UHFFFAOYSA-M- Molecular formula
- C13H22N2O6S
- Average molar mass
- 334.39 g/mol
- Monoisotopic mass
- 334.11985742
Overview
Neostigmine methyl sulfate is an arylammonium sulfate salt. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor.
Names & identifiers
- Preferred name
- Neostigmine Methylsulfate
- IUPAC
- [3-(dimethylcarbamoyloxy)phenyl]-trimethylazanium;methyl sulfate
- English name
- Neostigmine Methyl Sulfate
- Molecular formula
- C12H19N2O2.CH3O4S
- Molecular weight
- 334.39
Names & synonyms
Neostigmine methyl sulfate51-60-5NEOSTIGMINE METHYLSULFATENeostigmine metilsulfateSyntostigminNeostigmine methylsulphateProserineIntrastigminaBloxiverz(m-Hydroxyphenyl)trimethylammonium methyl sulfate dimethylcarbamateNSC-93753Neostigmini metilsulfas
Show more names
NEOSTIGMINE METHYL SULPHATEhodostinvagostigminNEOSTIGIMINE BROMIDE3-[[(DIMETHYLAMINO)CARBONYL]OXY]-N,N,N-TRIMETHYLBENZAMINIUM BROMIDEGD-65ar-32sb-23Stiglyn
98IMH7M386Benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-N,N,N-trimethyl-, methyl sulfateCHEBI:7516DTXSID40199003PREVDUO COMPONENT NEOSTIGMINE METHYLSULFATERobinul-neostigStiglyn 1:500RefChem:55702
Database identifiers
- CAS
51-60-5- PubChem CID
- 5824
Properties
Computed structural properties
- Topological polar surface area
- 104 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 337
Experimental & physicochemical properties
Solubility>50.2 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
Breast Feeding; Lactation; Milk, Human; Cholinesterase Inhibitors; Parasympathomimetics
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal DrugsFDA approved animal drugs -> Active ingredient
Physicochemical properties
- Melting point
- 175 · 175-177 °C(lit.)
- storage temp.
- -20 °C · -20°C
- solubility
- 2 O: · H2O: 1 g/mL
- form
- powder
- color
- white
- Water Solubility
- 1 g/10mL · 1g/10mL
- Merck
- 14 · 14,6464
- InChI
- InChI=1S/C12H19N2O2.CH4O4S/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5;1-5-6(2,3)4/h6-9H,1-5H3;1H3,(H,2,3,4)/q+1;/p-1
- InChIKey
- OSZNNLWOYWAHSS-UHFFFAOYSA-M
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (43.4%): Fatal if swallowed [Danger Acute toxicity, oral]
P233, P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P342+P316, P361+P364, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 99 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 2 (43.4%)
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- CY1225000
- ridadr
- UN 2811 6.1/PG 2
- hs_code
- 29242990
- Toxicity
- LD50 in mice (mg/kg): 0.16 i.v.; 0.42 s.c.; 7.5 orally, (Randall, Lehmann)
- risk_code
- 28-36/37/38-42/43-26/27/28
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_code
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
NEOSTIGMINE METHYLSULFATE
Cholinesterase Inhibitor [EPC]; Cholinesterase Inhibitors [MoA]
MeSH Pharmacological Classification
Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system.
Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here.
Applications
DescriptionNeostigmine is a reversible inhibitor of acetylcholinesterase (AChE; Kd = 260 μM). In a rat model of knee joint inflammation, intrathecal administration of neostigmine (2-30 μg) increases endogenous acetylcholine levels and dose-dependently increases the latency of paw withdrawal in response to thermal and mechanical stimuli (ED50s = 6.6 and 3.5 μg, respectively). Neostigmine (5 μg, i.p.) restores muscle action potentials in mice with a thymopoietin-induced neuromuscular block. Formulations containing neostigmine have been used in the treatment of myasthenia gravis and Ogilvie syndrome.
UsesCholinergic; miotic; antidote (curare)
General DescriptionNeostigmine methylsulfate,(m-hydroxyphenyl)trimethylammonium methylsulfatedimethylcarbamate or the dimethylcarbamic ester of 3-hydroxyphenyltrimethylammoniummethylsulfate (Prostigminmethylsulfate), is a bitter, odorless, white, crystalline powder.It is very soluble in water and soluble in alcohol. Solutionsare stable and can be sterilized by boiling. The compound istoo hygroscopic for use in a solid form and thus is alwaysused as an injection. Aqueous solutions are neutral to litmus.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…