Mexiletine hydrochloride

Base Information

• Chemical Name: Mexiletine hydrochloride
• CAS No.: 5370-01-4
• Molecular Formula: C11H17NO^.HCl
• Molecular Weight: 215.723
• Hs Code.: 2922190900
• European Community (EC) Number: 226-362-1
• NSC Number: 758639
• UNII: 606D60IS38
• DSSTox Substance ID: DTXSID2045783
• Wikidata: Q27107357
• NCI Thesaurus Code: C652
• RXCUI: 142138
• Pharos Ligand ID: NGCHGGMTAKG5
• ChEMBL ID: CHEMBL1200606
• Mol file: 5370-01-4.mol

Synonyms:KO 1173;KO-1173;KO1173;KOE 1173;KOE-1173;KOE1173;Mexiletene;Mexiletine;Mexiletine Hydrochloride;Mexitil;Mexitil PL;Mexityl;Novo Mexiletine;Novo-Mexiletine

Chemical Property of Mexiletine hydrochloride

Chemical Property:

• Appearance/Colour: white to off-white solid
• Melting Point: 200-203 °C
• Boiling Point: 271.5 °C at 760 mmHg
• PKA: 9.0(at 25℃)
• Flash Point: 112.2 °C
• PSA: 35.25000
• Density: 0.979 g/cm3
• LogP: 3.53170
• Storage Temp.: 2-8°C
• Solubility.: ethanol: 50 mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 215.1076919
• Heavy Atom Count: 14
• Complexity: 139

Purity/Quality:

99% ^*data from raw suppliers

Mexiletine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)C)OCC(C)N.Cl
• Recent ClinicalTrials: A Phase II/III Double-Blind Study of Amitriptyline and Mexiletine for Painful Neuropathy in HIV Infection
• Recent EU Clinical Trials: An Open-label, non-Comparative Study to Evaluate the Steady-State Pharmacokinetics, Safety, and Efficacy of Mexiletine in Adolescents and Children with Myotonic Disorders
• Recent NIPH Clinical Trials: Safety and efficacy of mexiletine hydrochroride in spinal and bulbar muscular atrophy (SBMA) :a multicenter, randomised, double-blind, placebo-controlled trial
• Description: Mexiletine is a voltage-gated sodium channel blocker and class Ib antiarrhythmic agent that preferentially binds to open/inactive channels. It inhibits aconitine-induced dysrhythmias in mice with ED50 values of 57 and 107 mg/kg for intraperitoneal and oral administration, respectively. Mexiletine decreases or inhibits conduction across the Purkinje fiber-muscle junction, shortens action potential duration, and decreases the refractory period when used at concentrations less than 5 μg/ml in isolated canine Purkinje fiber and ventricular muscle preparations.
• Uses: Mexiletine hydrochloride has been used as a sodium channel blocker: expressed in chinese hamster ovary cellsin human embryonic kidney (HEK) cells for whole cell patch-clamp studieselectrophysiology studies in HEK cells expressing Nav1.7 protein Antiarrhythmic (class IB) antipsychotic
• Therapeutic Function: Antiarrhythmic
• Clinical Use: Mexiletine hydrochloride, like class I antiarrhythmicagents, blocks the fast Na channel in cardiac cells. It isespecially effective on the Purkinje fibers in the heart. Thedrug increases the threshold of excitability of myocardialcells by reducing the rate of rise and amplitude of the actionpotential and decreases automaticity.Mexiletine hydrochloride is used for long-term oral prophylaxisof ventricular tachycardia. The drug is given in200- to 400-mg doses every 8 hours.

Technology Process of Mexiletine hydrochloride

There total 5 articles about Mexiletine hydrochloride 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: 88.0%

3-{[2-(hydroxyimino)propyl]oxy}estra-1(10),2,4-trien-17-one (55304-19-3) → (rac)-mexiletine hydrochloride (5370-01-4)

Guidance literature:

3-{[2-(hydroxyimino)propyl]oxy}estra-1⁽¹⁰⁾,2,4-trien-17-one; With hydrogen; In methanol; at 60 ℃; for 4h; under 30003 Torr; Autoclave;

With hydrogenchloride; In diethyl ether; water;

DOI:10.1002/ejoc.201701266

Reference yield: 40.0%

RS-mexiletine (31828-71-4) → (rac)-mexiletine hydrochloride (5370-01-4)

Guidance literature:

With hydrogenchloride;

DOI:10.1016/j.ejmech.2016.05.046

Reference yield:

2.6-dimethylphenol (576-26-1,25134-01-4) → (rac)-mexiletine hydrochloride (5370-01-4)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C

2: ammonium acetate; sodium cyanoborohydride / methanol / 96 h / 20 °C

3: hydrogenchloride

With hydrogenchloride; ammonium acetate; sodium cyanoborohydride; potassium carbonate; In methanol; N,N-dimethyl-formamide; 1: |Williamson Ether Synthesis;

DOI:10.1016/j.ejmech.2016.05.046

upstream raw materials:

RS-mexiletine

(2,6-dimethylphenoxy)-2-propanone

2.6-dimethylphenol

3-{[2-(hydroxyimino)propyl]oxy}estra-1⁽¹⁰⁾,2,4-trien-17-one

Downstream raw materials:

N-(1-(2,6-dimethylphenoxy)propan-2-yl)acetamide

(rac)-mexiletine-N-t-butyloxycarbonyl-glycine

N-Boc-(S)-glutamine-mexiletine

N-Boc-(S)-methionine-mexiletine

Refernces

• 1、 -. "Method for synthesizing mexiletine chloride". Paragraph 0031; 0032; 0033; 0034. . Retrieved 2019/03/15.
• 2、 Naumovich, Yana A.,Golovanov, Ivan S.,Sukhorukov, Alexey Yu.,Ioffe, Sema L.. "Addition of HO-Acids to N,N-Bis(oxy)enamines: Mechanism, Scope and Application to the Synthesis of Pharmaceuticals". . p. 6209 - 6227. Retrieved 2017/11/15.