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51-60-5

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51-60-5 Usage

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

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.

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.)

Check Digit Verification of cas no

The CAS Registry Mumber 51-60-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 1 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 51-60:
(4*5)+(3*1)+(2*6)+(1*0)=35
35 % 10 = 5
So 51-60-5 is a valid CAS Registry Number.
InChI:InChI=1/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;

51-60-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Packaging
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  • Detail
  • TCI America

  • (N0447)  Neostigmine Methyl Sulfate  >98.0%(N)

  • 51-60-5

  • 5g

  • 740.00CNY

  • Detail
  • TCI America

  • (N0447)  Neostigmine Methyl Sulfate  >98.0%(N)

  • 51-60-5

  • 25g

  • 2,290.00CNY

  • Detail
  • Sigma-Aldrich

  • (N0550000)  Neostigminemethylsulfate  European Pharmacopoeia (EP) Reference Standard

  • 51-60-5

  • N0550000

  • 1,880.19CNY

  • Detail
  • USP

  • (1460000)  Neostigminemethylsulfate  United States Pharmacopeia (USP) Reference Standard

  • 51-60-5

  • 1460000-200MG

  • 4,588.74CNY

  • Detail
  • Sigma

  • (N2126)  Neostigminemethylsulfate  

  • 51-60-5

  • N2126-500MG

  • 346.32CNY

  • Detail
  • Sigma

  • (N2126)  Neostigminemethylsulfate  

  • 51-60-5

  • N2126-1G

  • 499.59CNY

  • Detail
  • Sigma

  • (N2126)  Neostigminemethylsulfate  

  • 51-60-5

  • N2126-5G

  • 1,736.28CNY

  • Detail

51-60-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-[[(Dimethylamino)carbonyl]oxy]-N,N,N-trimethylbenzenaminium methyl sulfate

1.2 Other means of identification

Product number -
Other names Benzenaminium, 3-[[(dimethylamino)carbonyl]oxy]-N,N,N-trimethyl-, methyl sulfate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:51-60-5 SDS

51-60-5Synthetic route

norneostigmine
16088-19-0

norneostigmine

dimethyl sulfate
77-78-1

dimethyl sulfate

neostigmine methyl sulfate
51-60-5

neostigmine methyl sulfate

Conditions
ConditionsYield
In acetone at 20℃; four neck round bottom flask;85%
In tetrahydrofuran at 20℃; for 8h;70%
With acetone
With acetone
Dimethylcarbaminsaeure-3-aminophenylester
19962-04-0

Dimethylcarbaminsaeure-3-aminophenylester

dimethyl sulfate
77-78-1

dimethyl sulfate

neostigmine methyl sulfate
51-60-5

neostigmine methyl sulfate

Conditions
ConditionsYield
With calcium carbonate In acetone at 25 - 30℃; Reagent/catalyst;84.6%
3-Dimethylaminophenol
99-07-0

3-Dimethylaminophenol

neostigmine methyl sulfate
51-60-5

neostigmine methyl sulfate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: acetone
View Scheme
dimethyl sulfate
77-78-1

dimethyl sulfate

3-Dimethylaminophenol
99-07-0

3-Dimethylaminophenol

N,N-Dimethylcarbamoyl chloride
79-44-7

N,N-Dimethylcarbamoyl chloride

neostigmine methyl sulfate
51-60-5

neostigmine methyl sulfate

Conditions
ConditionsYield
Stage #1: 3-Dimethylaminophenol With 18-crown-6 ether; potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 40℃; for 0.0583333h;
Stage #2: N,N-Dimethylcarbamoyl chloride In tetrahydrofuran; N,N-dimethyl-formamide at 40℃; for 0.00833333h;
Stage #3: dimethyl sulfate Further stages;
neostigmine methyl sulfate
51-60-5

neostigmine methyl sulfate

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

(3-((dimethylcarbamoyl)oxy)phenyl)boronic acid

(3-((dimethylcarbamoyl)oxy)phenyl)boronic acid

Conditions
ConditionsYield
Stage #1: neostigmine methyl sulfate; bis(pinacol)diborane With 10H-phenothiazine; caesium carbonate In acetonitrile for 18h; Irradiation; Sealed tube; Inert atmosphere;
Stage #2: With hydrogenchloride; dihydroxy-methyl-borane In acetone
Stage #3: With D-Fructose; sodium carbonate In water
74%

51-60-5Downstream Products

51-60-5Relevant articles and documents

Advanced Continuous Flow Platform for On-Demand Pharmaceutical Manufacturing

Zhang, Ping,Weeranoppanant, Nopphon,Thomas, Dale A.,Tahara, Kohei,Stelzer, Torsten,Russell, Mary Grace,O'Mahony, Marcus,Myerson, Allan S.,Lin, Hongkun,Kelly, Liam P.,Jensen, Klavs F.,Jamison, Timothy F.,Dai, Chunhui,Cui, Yuqing,Briggs, Naomi,Beingessner, Rachel L.,Adamo, Andrea

, p. 2776 - 2784 (2018/02/06)

As a demonstration of an alternative to the challenges faced with batch pharmaceutical manufacturing including the large production footprint and lengthy time-scale, we previously reported a refrigerator-sized continuous flow system for the on-demand production of essential medicines. Building on this technology, herein we report a second-generation, reconfigurable and 25 % smaller (by volume) continuous flow pharmaceutical manufacturing platform featuring advances in reaction and purification equipment. Consisting of two compact [0.7 (L)×0.5 (D)×1.3 m (H)] stand-alone units for synthesis and purification/formulation processes, the capabilities of this automated system are demonstrated with the synthesis of nicardipine hydrochloride and the production of concentrated liquid doses of ciprofloxacin hydrochloride, neostigmine methylsulfate and rufinamide that meet US Pharmacopeia standards.

PROCESS FOR PREPARATION OF HIGHLY PURE 3-DIMETHYLAMINOPHENYL DIMETHYLCARBAMATE

-

Page/Page column 15, (2012/10/18)

The invention discloses a novel process for preparation of highly pure 3-dimethylaminophenyl dimethylcarbamate via formation of aryl dimethylcarbamate which can be easily obtained from diaryl carbonate and dimethylamine.

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