| Identification | More | [Name]
3-[[(Dimethylamino)carbonyl]oxy]-N,N,N-trimethylbenzenaminium methyl sulfate | [CAS]
51-60-5 | [Synonyms]
3-[[(DIMETHYLAMINO)CARBONYL]OXY]-N,N,N-TRIMETHYLBENZAMINIUM BROMIDE
3-[([DIMETHYLAMINO]CARBONYL)OXY]-N,N,N-TRIMETHYLBENZAMINIUM METHYL SULFATE
3-[[(DIMETHYLAMINO)CARBONYL]OXY]-N,N,N-TRIMETHYLBENZENAMINIUM BROMIDE
3-[[(DIMETHYLAMINO)CARBONYL]OXY]-N,N,N-TRIMETHYLBENZENAMINIUM METHYL SULFATE
(3-DIMETHYLCARBAMOYLOXYPHENYL)TRIMETHYLAMMONIUM BROMIDE
(3-DIMETHYLCARBAMOYLOXYPHENYL)TRIMETHYLAMMONIUM METHYL SULFATE
(3-HYDROXYPHENYL)TRIMETHYLAMMONIUM BROMIDE DIMETHYL CARBAMATE
(3-HYDROXYPHENYL)TRIMETHYLAMMONIUM METHYL SULFATE DIMETHYLCARBAMATE
3-[N,N-DIMETHYLCARBAMOYLOXY]-N,N,N-TRIMETHYLANILINIUM METHYL SULFATE
NEOSTIGIMINE BROMIDE
NEOSTIGMINE BROMIDE
NEOSTIGMINE METHYL SULFATE
NEOSTIGMINE METHYL SULPHATE
PROSTIGMINE
(3-(dimethylcarbamoyloxy)phenyl)trimethyl-ammoniumethylsulfate
(3-hydroxyphenyl)trimethylammoniummethylsulfatedimethylcarbamicester
(m-hydroxyphenyl)trimethylammoniummethylsulfatedimethylcarbamate
3-(((dimethylamino)carbonyl)oxy)-n,n,n-trimethyl-benzenaminiumethylsulfat
3-(dimethylcarbamoxy)phenyltrimethylammoniummethylsulfate
ammonium,(m-hydroxyphenyl)trimethyl-,methylsulfate,dimethylcarbamate | [EINECS(EC#)]
200-109-5 | [Molecular Formula]
C12H19BrN2O2 | [MDL Number]
MFCD00011795 | [Molecular Weight]
303.2 | [MOL File]
51-60-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
175-177 °C(lit.)
| [storage temp. ]
−20°C
| [solubility ]
H2O: 1 g/mL
| [form ]
powder
| [color ]
white
| [Water Solubility ]
1g/10mL | [Usage]
Cholinergic; miotic; antidote (curare) | [Merck ]
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 | [SMILES]
C1(OC(=O)N(C)C)C=CC=C([N+](C)(C)C)C=1.S([O-])(=O)(=O)OC | [CAS DataBase Reference]
51-60-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
T+ | [Risk Statements ]
R28:Very Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R42/43:May cause sensitization by inhalation and skin contact .
R26/27/28:Very Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36:Wear suitable protective clothing .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 2811 6.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
CY1225000
| [HazardClass ]
6.1(a) | [PackingGroup ]
II | [HS Code ]
29242990 | [Hazardous Substances Data]
51-60-5(Hazardous Substances Data) | [Toxicity]
LD50 in mice (mg/kg): 0.16 i.v.; 0.42 s.c.; 7.5 orally, (Randall, Lehmann) |
| Hazard Information | Back Directory | [Description]
Neostigmine is a reversible inhibitor of acetylcholinesterase (AChE; Kd = 260 μM).1 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).2 Neostigmine (5 μg, i.p.) restores muscle action potentials in mice with a thymopoietin-induced neuromuscular block.3 Formulations containing neostigmine have been used in the treatment of myasthenia gravis and Ogilvie syndrome. | [Chemical Properties]
Crystalline Solid | [Uses]
Cholinergic; miotic; antidote (curare) | [Definition]
ChEBI: Neostigmine methyl sulfate is an arylammonium sulfate salt. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor. | [Brand name]
Prostigmine (ICN). | [General Description]
Neostigmine 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 Use]
The methylsulfate salt is used postoperatively as a urinarystimulant and in the diagnosis and treatment of myastheniagravis. | [Synthesis]
Example 9 Preparation of neostigmine methyl sulfate (general procedure)
To a 250 mL four-necked round-bottomed flask was added 3-(dimethylamino)phenyldimethylcarbamate and acetone obtained in Example 1. Dimethyl sulfate (1.66 eq.) was added dropwise to the flask at room temperature. The reaction mixture was stirred overnight and then cooled to 5 °C to 10 °C and kept for 2 hours. This was followed by filtration and the filtrate was washed with isopropanol. The residue was dried under vacuum at room temperature to give the crude product neostigmine methyl sulfate. Purification was carried out by recrystallization from isopropanol.
Yield: 85%.
Properties: light yellow oil
HPLC Purity: 99.21%. | [Purification Methods]
Crystallise 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.) | [References]
[1] Patent: WO2012/131699, 2012, A1. Location in patent: Page/Page column 15
[2] Pharmazie, 2001, vol. 56, # 2, p. 181 - 182
[3] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1941, vol. 14, p. 524,526
[4] Chem.Abstr., 1942, p. 3159
[5] Patent: CH208883, 1938, |
|
|