ChemicalBook > CAS DataBase List > Neostigmine Methyl Sulfate

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; K_d = 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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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