Otilonium Bromide

Base Information

• Chemical Name: Otilonium Bromide
• CAS No.: 26095-59-0
• Molecular Formula: C29H43BrN2O4
• Molecular Weight: 563.575
• Hs Code.: 2923900090
• European Community (EC) Number: 247-457-4
• UNII: 21HN3N72PV
• DSSTox Substance ID: DTXSID0046357
• Wikipedia: Otilonium_bromide
• Wikidata: Q920900
• NCI Thesaurus Code: C90743
• ChEMBL ID: CHEMBL2103773
• Mol file: 26095-59-0.mol

Synonyms:N-diethylmethylammoniummethyl-p-(2-(N-octyloxy)benzoyl)aminobenzoate bromide;octylonium;octylonium bromide;octylonium iodide;otilonium bromide;Spasmomen

Chemical Property of Otilonium Bromide

Chemical Property:

• Appearance/Colour: white power
• Melting Point: 130-133 °C
• PSA: 64.63000
• LogP: 3.39840
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 17
• Exact Mass: 562.24062
• Heavy Atom Count: 36
• Complexity: 600

Purity/Quality:

99.5% ^*data from raw suppliers

Octylonium Bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCOC1=CC=CC=C1C(=O)NC2=CC=C(C=C2)C(=O)OCC[N+](C)(CC)CC.[Br-]
• Recent ClinicalTrials: FMT for Post-infectious IBS
• Recent EU Clinical Trials: A randomized controlled trial to evaluate the short-term efficacy and long-term health economic impact of a dietary intervention compared to pharmacotherapy with a musculotropic spasmolytic agent for newly diagnosed or newly treated irritable bowel syndrome in primary care.
• Uses: Treatment of gastrointestinal spasm. Inhibits platlet activating factor induced hypotension. Antispasmodic Otilonium bromide is an antimuscarinic Octylonium bromide is an antimuscarinic. Octylonium bromide is a platelet-activating factor antagonist as analgesic, anti-inflammatory, uterine contraction inhibiting, and anti-tumor agent. m bromide is used as an antispasmodic. antimuscarinic used as a spasmolytic agent
• Description: Otilonium is an inhibitor of L-type (IC50 = 2.3 μM) and T-type calcium channels (IC50s = 0.8, 1.1, and 0.4 μM for Cav3.1, Cav3.2, and Cav3.3, respectively). It is also an antagonist of muscarinic acetylcholine receptors (mAChRs; IC50s = 0.054, 0.4, 0.222, and 0.156 μM for M1, M2, M4, and M5 muscarinic receptors, respectively) and the platelet activating factor (PAF) receptor (IC50 = 0.0552 μM). Otilonium inhibits the inward calcium current in isolated rat colonic smooth muscle cells (EC50 = 885 nM), an effect that can be blocked by the L-type calcium channel inhibitor nifedipine . It inhibits contractions induced by the muscarinic acetylcholine receptor (mAChR) agonist methacholine in isolated circular muscle of the guinea pig proximal colon (IC50 = 3.7 μM). Otilonium (4 mg/kg) decreases fecal excretion and wet dog shakes and increases the tail withdrawal latency in the tail-flick test in a rat model of opioid withdrawal syndrome induced by morphine and naloxone.
• Therapeutic Function: Anticholinergic, Spasmolytic

Technology Process of Otilonium Bromide

There total 9 articles about Otilonium 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: 33.0%

methyl bromide (74-83-9) + 4-(2-Octyloxy-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester (26090-29-9) → otilonium bromide (26095-59-0)

Guidance literature:

In acetone; at 60 ℃; for 48h; Reflux; Sealed tube; Inert atmosphere;

Reference yield:

methyl salicylate (119-36-8,8024-54-2) → otilonium bromide (26095-59-0)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate / acetonitrile / 85 °C / Sealed tube; Inert atmosphere

2: sodium hydroxide / methanol; tetrahydrofuran; water / 20 - 85 °C

3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 20 °C / Inert atmosphere

4: triethylamine / dichloromethane / Inert atmosphere

5: acetone / 48 h / 60 °C / Reflux; Sealed tube; Inert atmosphere

With thionyl chloride; potassium carbonate; triethylamine; N,N-dimethyl-formamide; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile;

Reference yield:

1-bromo-octane (111-83-1) → otilonium bromide (26095-59-0)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate / acetonitrile / 85 °C / Sealed tube; Inert atmosphere

2: sodium hydroxide / methanol; tetrahydrofuran; water / 20 - 85 °C

3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 20 °C / Inert atmosphere

4: triethylamine / dichloromethane / Inert atmosphere

5: acetone / 48 h / 60 °C / Reflux; Sealed tube; Inert atmosphere

With thionyl chloride; potassium carbonate; triethylamine; N,N-dimethyl-formamide; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile;

upstream raw materials:

methyl salicylate

1-bromo-octane

2-(Diethylamino)ethanol

4-nitro-benzoyl chloride

Refernces