Pyridostigmine bromide

Base Information

• Chemical Name: Pyridostigmine bromide
• CAS No.: 101-26-8
• Molecular Formula: C9H13BrN2O2
• Molecular Weight: 261.118
• Hs Code.: 2933399090
• European Community (EC) Number: 202-929-9
• NSC Number: 758435,679759
• UNII: KVI301NA53
• DSSTox Substance ID: DTXSID9023540
• Wikidata: Q26840825
• NCI Thesaurus Code: C47697
• RXCUI: 9001
• Pharos Ligand ID: U2FK63XKTVJ7
• ChEMBL ID: CHEMBL812
• Mol file: 101-26-8.mol

Synonyms:Bromide, Pyridostigmine;Mestinon;Pyridostigmine;Pyridostigmine Bromide

Chemical Property of Pyridostigmine bromide

Chemical Property:

• Appearance/Colour: Pale yellow to colorless liquid
• Melting Point: 154 °C
• Boiling Point: 88 (25 torr)
• PSA: 33.42000
• Density: 0.9613 g/cm3 (20oC)
• LogP: -2.42450
• Storage Temp.: Refrigerator
• Solubility.: Very soluble in water and in ethanol (96 per cent).
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 260.01604
• Heavy Atom Count: 14
• Complexity: 183

Purity/Quality:

99% ^*data from raw suppliers

Pyridostigmine Bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/27/28-43
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[N+]1=CC=CC(=C1)OC(=O)N(C)C.[Br-]
• Recent ClinicalTrials: Pyridostigmine Efficacy and Safety for Treatment of Ileus After Colorectal Surgery
• Recent EU Clinical Trials: Improving symptomatic treatment with pyridostigmine and amifampridine: a randomized double-blinded,
• Description: Pyridostigmine is an inhibitor of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE; IC50s = 0.35 and 1 μM, respectively, for the human enzymes). Pyridostigmine (10 μM) reduces decreases in AChE activity induced by the organophosphate pesticides diisopropyl fluorophosphate, chlorpyrifos-oxon, diazinon-oxon, paraoxon, and malaoxon in isolated bovine red blood cells. It also reduces soman-induced membrane depolarization and decreases in AChE activity in isolated human muscle bundles in a concentration-dependent manner. Pyridostigmine (3 mg/kg per day for four weeks) prevents tachycardia and increases in sympathetic tone in mice following myocardial infarction induced by left coronary artery ligation. Formulations containing pyridostigmine have been used in the treatment of myasthenia gravis and as neuromuscular protective agents against organophosphate poisoning.
• Uses: Cholinergic, used in the treatment of myasthenia gravis, and is a pre-exposure antidote to chemical warfare agents.
• Clinical Use: Myasthenia gravis
• Drug interactions: Potentially hazardous interactions with other drugs Aminoglycosides, clindamycin and polymyxins antagonise effects of pyridostigmine.

Technology Process of Pyridostigmine bromide

There total 2 articles about Pyridostigmine bromide 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: 89.0%

methyl bromide (74-83-9) + 3-(N,N-Dimethylcarbamoyl)-oxipyridin (51581-32-9) → pyridostigmine bromide (101-26-8)

Guidance literature:

In acetone; for 48h; Ambient temperature;

Reference yield:

3-HYDROXYPYRIDINE (109-00-2) → pyridostigmine bromide (101-26-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 47 percent / Et₃N / toluene / 4 h / Heating

2: 89 percent / acetone / 48 h / Ambient temperature

With triethylamine; In acetone; toluene;

Reference yield:

pyridostigmine bromide (101-26-8) → 3-Hydroxy-1-methylpiperidine (3554-74-3) + 1-methyl-3-piperidone (5519-50-6) + Dimethyl-carbamic acid 1-methyl-1,2,3,6-tetrahydro-pyridin-3-yl ester + 3-<(N,N-dimethyl)-carbamoyl>-1-methyl-1,2,5,6-tetrahydropyridine + 3-dimethylcarbamoyloxy-1-methyl-piperidine (6659-30-9)

Guidance literature:

With sodium tetrahydroborate; Product distribution; different pH, temperature, time and solvents;

upstream raw materials:

methyl bromide

3-(N,N-Dimethylcarbamoyl)-oxipyridin

3-HYDROXYPYRIDINE

Downstream raw materials:

3-Hydroxy-1-methylpiperidine

1-methyl-3-piperidone

3-dimethylcarbamoyloxy-1-methyl-piperidine

Refernces