Neostigmine Methyl Sulfate

Neostigmine Methyl Sulfate Basic information
Product Name:Neostigmine Methyl Sulfate
Synonyms:A sulfuric acid neostigmine;(3-(dimethylcarbamoyloxy)phenyl)trimethyl-ammoniumethylsulfate;(3-hydroxyphenyl)trimethylammoniummethylsulfatedimethylcarbamicester;(m-hydroxyphenyl)trimethylammoniummethylsulfatedimethylcarbamate;PROSTIGMINE;NEOSTIGMINE METHYL SULFATE;3-[N,N-DIMETHYLCARBAMOYLOXY]-N,N,N-TRIMETHYLANILINIUM METHYL SULFATE;(3-HYDROXYPHENYL)TRIMETHYLAMMONIUM BROMIDE DIMETHYL CARBAMATE
CAS:51-60-5
MF:C12H19N2O2.CH3O4S
MW:334.39
EINECS:200-109-5
Product Categories:Amines;Sulfur & Selenium Compounds;Alkaloids;Ammonium Polyhalides, etc. (Quaternary);Quaternary Ammonium Compounds;Intermediates & Fine Chemicals;Pharmaceuticals;51-60-5
Mol File:51-60-5.mol
Neostigmine Methyl Sulfate Structure
Neostigmine Methyl Sulfate Chemical Properties
Melting point 175-177 °C(lit.)
storage temp. -20°C
solubility H2O: 1 g/mL
form powder
color white
Water Solubility 1g/10mL
Merck 14,6464
CAS DataBase Reference51-60-5(CAS DataBase Reference)
Safety Information
Hazard Codes T+
Risk Statements 28-36/37/38-42/43-26/27/28
Safety Statements 36-45-36/37/39-28A
RIDADR UN 2811 6.1/PG 2
WGK Germany 3
RTECS CY1225000
HazardClass 6.1(a)
PackingGroup II
HS Code 29242990
ToxicityLD50 in mice (mg/kg): 0.16 i.v.; 0.42 s.c.; 7.5 orally, (Randall, Lehmann)
MSDS Information
Neostigmine Methyl Sulfate Usage And Synthesis
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.
Chemical PropertiesCrystalline Solid
UsesCholinergic; miotic; antidote (curare)
DefinitionChEBI: Neostigmine methyl sulfate is an arylammonium sulfate salt. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor.
Brand nameProstigmine (ICN).
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.
Clinical UseThe methylsulfate salt is used postoperatively as a urinarystimulant and in the diagnosis and treatment of myastheniagravis.
Purification MethodsCrystallise the sulfate from EtOH or Me2CO (m 143-144o). Its solubility in H2O is ~10%. [Beilstein 13 III 939.] (It is cholinergic and highly TOXIC.)
Neostigmine Methyl Sulfate Preparation Products And Raw materials
3-Dimethylaminoanisole Tetramethylammonium hydrogen sulfate Neostigmine TETRAMETHYLAMMONIUM METHYL SULFATE Ammonium bisulfite NEOSTIGIMINE BROMIDE 3-METHOXY-N-METHYLANILINE PHENYLTRIMETHYLAMMONIUM HYDROXIDE Methylcarbamic acid phenyl ester METHYLAMINE SULFATE Neostigmine Methyl Sulfate DIMETHYLAMINE SULFATE PHENYLTRIMETHYLAMMONIUM METHOSULFATE 3-AMINOPHENYL N,N-DIMETHYLCARBAMATE, 97 3-Dimethylaminophenol DIMETHYLAMMONIUM DIMETHYLCARBAMATE(DIMCARB) Phenyl carbamate 3-dimethylaminophenyl dimethylcarbamate

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