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Neostigmine Methyl Sulfate

Product Name
Neostigmine Methyl Sulfate
CAS No.
51-60-5
Chemical Name
Neostigmine Methyl Sulfate
Synonyms
NEOSTIGMINE METHYL SULPHATE;neostigmine metilsulfate;hodostin;vagostigmin;NEOSTIGIMINE BROMIDE;3-[[(DIMETHYLAMINO)CARBONYL]OXY]-N,N,N-TRIMETHYLBENZAMINIUM BROMIDE;GD-65;ar-32;sb-23;Stiglyn
CBNumber
CB7853724
Molecular Formula
C12H19N2O2.CH3O4S
Formula Weight
334.39
MOL File
51-60-5.mol
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Neostigmine Methyl Sulfate Property

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
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)
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Safety

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
Toxicity
LD50 in mice (mg/kg): 0.16 i.v.; 0.42 s.c.; 7.5 orally, (Randall, Lehmann)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H300Fatal if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P284Wear respiratory protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
N2126
Product name
Neostigmine methyl sulfate
Packaging
1g
Price
$59.8
Updated
2025/07/31
Sigma-Aldrich
Product number
N0550000
Product name
Neostigmine methyl sulfate
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
50 mg
Price
$164
Updated
2025/07/31
Sigma-Aldrich
Product number
1460000
Product name
Neostigmine methyl sulfate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$392
Updated
2025/07/31
TCI Chemical
Product number
N0447
Product name
Neostigmine Methyl Sulfate
Purity
>98.0%(N)
Packaging
5g
Price
$113
Updated
2025/07/31
TCI Chemical
Product number
N0447
Product name
Neostigmine Methyl Sulfate
Purity
>98.0%(N)
Packaging
25g
Price
$410
Updated
2025/07/31
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Neostigmine Methyl Sulfate Chemical Properties,Usage,Production

Description

Neostigmine 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 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

16088-19-0

77-78-1

51-60-5

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,

Neostigmine Methyl Sulfate Preparation Products And Raw materials

Raw materials

Preparation Products

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Neostigmine Methyl Sulfate Suppliers

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View Lastest Price from Neostigmine Methyl Sulfate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Neostigmine Methyl Sulfate 51-60-5
Price
US $0.00/KG
Min. Order
10g
Purity
99%min
Supply Ability
10kg
Release date
2021-11-18
Dideu Industries Group Limited
Product
Neostigmine Methyl Sulfate 51-60-5
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons min
Release date
2021-07-27
Zhuozhou Wenxi import and Export Co., Ltd
Product
Neostigmine Methyl Sulfate 51-60-5
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10

51-60-5, Neostigmine Methyl SulfateRelated Search:

Ammonium bisulfite Tetramethylammonium hydroxide pentahydrate PHENYLTRIMETHYLAMMONIUM METHOSULFATE DIMETHYLAMMONIUM DIMETHYLCARBAMATE(DIMCARB) AMMONIUM CARBAMATE 3-METHOXY-N-METHYLANILINE Neostigmine Methyl Sulfate Ammonium sulfate Sulfuric acid Ammonium bisulfate 3-Dimethylaminophenol Tetramethylammonium hydrogen sulfate 3-dimethylaminophenyl dimethylcarbamate 3-Dimethylaminoanisole PHENYLTRIMETHYLAMMONIUM HYDROXIDE 3-AMINOPHENYL N,N-DIMETHYLCARBAMATE, 97 Phenyl carbamate Ammonium Sulfite

  • A sulfuric acid neostigmine
  • (3-(dimethylcarbamoyloxy)phenyl)trimethyl-ammoniumethylsulfate
  • (3-hydroxyphenyl)trimethylammoniummethylsulfatedimethylcarbamicester
  • (m-hydroxyphenyl)trimethylammoniummethylsulfatedimethylcarbamate
  • PROSTIGMINE
  • NEOSTIGIMINE BROMIDE
  • NEOSTIGMINE METHYL SULFATE
  • NEOSTIGMINE METHYL SULPHATE
  • 3-[N,N-DIMETHYLCARBAMOYLOXY]-N,N,N-TRIMETHYLANILINIUM METHYL SULFATE
  • (3-HYDROXYPHENYL)TRIMETHYLAMMONIUM BROMIDE DIMETHYL CARBAMATE
  • (3-HYDROXYPHENYL)TRIMETHYLAMMONIUM METHYL SULFATE DIMETHYLCARBAMATE
  • 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
  • neostigmine metilsulfate
  • Intrastigmina
  • Metastigmin
  • Stiglyn
  • NEOSTIGMINE METHYL SULPHATE(RG)
  • Ethyl N-[2-[4-(phenoxy)phenoxy]ethyl]carbamate
  • Phenoxycarb
  • GD-65
  • 3-(((dimethylamino)carbonyl)oxy)-n,n,n-trimethyl-benzenaminiumethylsulfat
  • 3-(dimethylcarbamoxy)phenyltrimethylammoniummethylsulfate
  • ammonium,(m-hydroxyphenyl)trimethyl-,methylsulfate,dimethylcarbamate
  • Ammonium,[3-(dimethylcarbamoyloxy)phenyl]trimethyl-,methylsulfate
  • ar-32
  • Benzenaminium,3-[[(dimethylamino)carbonyl]oxy]-N,N,N-trimethyl-,methylsulfate
  • carbamicacid,n,n-dimethyl-,3-(trimethylammonio)phenylester,methylsulfate
  • carbamicacid,n,n-dimethyl-,3-dimethylaminophenylester,methosulfate
  • dimethyl-carbamicaciesterwith(m-hydroxyphenyl)trimethylammoniummethy
  • dimethylcarbamicesterof3-oxyphenyltrimethylammoniummethylsulfate
  • eustigminmethylsulfate
  • hodostin
  • kirkstigminemethylsulfate
  • leostigminemethylsulfate
  • neoeserinemethylsulfate
  • neostigmeth
  • neostigminemethosulfate
  • neostigminemonomethylsulfate
  • normastigmin
  • philostigminmethylsulfate
  • polstigmine
  • proserin
  • proserinemethylsulfate
  • prostigminemethylsulfate
  • prostigminmethylsulfate
  • sb-23
  • stigmanolmethylsulfate
  • stigmosanmethylsulfate
  • synstigmine
  • syntostigmin
  • syntostigmin(injection)
  • syntostigmine
  • tl-1394