Neostigmine methylsulfate

Base Information

• Chemical Name: Neostigmine methylsulfate
• CAS No.: 51-60-5
• Deprecated CAS: 59954-03-9
• Molecular Formula: C13H22N2O6S
• Molecular Weight: 334.393
• Hs Code.: 29242990
• European Community (EC) Number: 200-109-5
• NSC Number: 93753
• UNII: 98IMH7M386
• DSSTox Substance ID: DTXSID40199003
• Wikidata: Q98093892
• NCI Thesaurus Code: C76613
• RXCUI: 7316
• Pharos Ligand ID: 3Z543ANGP158
• ChEMBL ID: CHEMBL211471
• Mol file: 51-60-5.mol

Synonyms:Bromide, Neostigmine;Methylsulfate, Neostigmine;Neostigmine;Neostigmine Bromide;Neostigmine Methylsulfate;Polstigmine;Proserine;Prostigmin;Prostigmine;Prozerin;Synstigmin;Syntostigmine

Chemical Property of Neostigmine methylsulfate

Chemical Property:

• Appearance/Colour: Crystalline solid
• Melting Point: 175-177 °C(lit.)
• Boiling Point: 457oC
• PSA: 104.35000
• LogP: 2.11750
• Storage Temp.: −20°C
• Solubility.: H2O: 1 g/mL
• Water Solubility.: 1g/10mL
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 334.11985760
• Heavy Atom Count: 22
• Complexity: 337

Purity/Quality:

99% ^*data from raw suppliers

Neostigmine Methyl Sulfate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 28-36/37/38-42/43-26/27/28
• Safety Statements: 36-45-36/37/39-28A

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)C(=O)OC1=CC=CC(=C1)[N+](C)(C)C.COS(=O)(=O)[O-]
• Recent ClinicalTrials: Effect of Intrathecal Neostigmine on Post-dural Puncture Headache.
• Recent EU Clinical Trials: A Phase 4 Double-blinded, Randomized, Active Comparator-controlled Clinical Trial to Study the Efficacy, Safety, and Pharmacokinetics of Sugammadex (MK-8616) for Reversal of Neuromuscular Blockade in Pediatric Participants Aged Birth to <2 Years
• 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.
• Clinical Use: The methylsulfate salt is used postoperatively as a urinarystimulant and in the diagnosis and treatment of myastheniagravis.

Technology Process of Neostigmine methylsulfate

There total 4 articles about Neostigmine methylsulfate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

norneostigmine (16088-19-0) + dimethyl sulfate (77-78-1) → neostigmine methyl sulfate (51-60-5)

Guidance literature:

In acetone; at 20 ℃; four neck round bottom flask;

Reference yield: 84.6%

Dimethylcarbaminsaeure-3-aminophenylester (19962-04-0) + dimethyl sulfate (77-78-1) → neostigmine methyl sulfate (51-60-5)

Guidance literature:

With calcium carbonate; In acetone; at 25 - 30 ℃; Reagent/catalyst;

Reference yield:

dimethyl sulfate (77-78-1) + 3-Dimethylaminophenol (99-07-0) + N,N-Dimethylcarbamoyl chloride (79-44-7) → neostigmine methyl sulfate (51-60-5)

Guidance literature:

3-Dimethylaminophenol; With 18-crown-6 ether; potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide; at 40 ℃; for 0.0583333h;

N,N-Dimethylcarbamoyl chloride; In tetrahydrofuran; N,N-dimethyl-formamide; at 40 ℃; for 0.00833333h;

dimethyl sulfate; Further stages;

DOI:10.1002/chem.201706004

upstream raw materials:

norneostigmine

dimethyl sulfate

3-Dimethylaminophenol

Dimethylcarbaminsaeure-3-aminophenylester

Refernces

• 1、 -. "HIGHLY CHEMOSELECTIVE REACTIONS IN PRESENCE OF AROMATIC AMINO GROUPS". Page/Page column 32. . Retrieved 2017/11/06.
• 2、 Rittner,Barbarini,Hoeehr. "Synthesis of some new neostigmine methyl sulphates and related compounds". . p. 181 - 182. Retrieved 2007/10/03.