Mequitazine

Base Information

• Chemical Name: Mequitazine
• CAS No.: 29216-28-2
• Molecular Formula: C20H22N2S
• Molecular Weight: 322.474
• Hs Code.: 29349990
• European Community (EC) Number: 249-521-7
• NSC Number: 303612
• UNII: Y463242LY2
• DSSTox Substance ID: DTXSID8023262
• Nikkaji Number: J342.305K
• Wikipedia: Mequitazine
• Wikidata: Q3333256
• NCI Thesaurus Code: C170162
• Metabolomics Workbench ID: 43307
• ChEMBL ID: CHEMBL73451
• Mol file: 29216-28-2.mol

Synonyms:3-methylquinuclidinyl-10-phenothiazine;LM 209;mequitazine;mequitazine hydrochloride;mequitazine tartrate, (R-(R*,R*))-isomer;Mircol;Primalan;Quitadrill

Chemical Property of Mequitazine

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 143-145 °C
• Refractive Index: 1.5800 (estimate)
• Boiling Point: 469.4 °C at 760 mmHg
• PKA: 10.43±0.33(Predicted)
• Flash Point: 237.7 °C
• PSA: 31.78000
• Density: 1.28 g/cm³
• LogP: 4.63400
• Storage Temp.: Refrigerator
• Water Solubility.: Insoluble in water
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 322.15036988
• Heavy Atom Count: 23
• Complexity: 398

Purity/Quality:

99% ^*data from raw suppliers

Mequitazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CCC1C(C2)CN3C4=CC=CC=C4SC5=CC=CC=C53
• Recent ClinicalTrials: Bronchodilator Properties and Safety in Asthma
• Recent EU Clinical Trials: Bronchodilator properties and safety of a repeated dose of V0162 inhalation powder in asthma
• Uses: It is an antihistamine
• Therapeutic Function: Antihistaminic

Technology Process of Mequitazine

There total 4 articles about Mequitazine 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: 91.0%

dehydromequitazine (151129-13-4) → mequitazine (29216-28-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 24h; under 760.051 Torr;

DOI:10.1248/cpb.57.1300

Reference yield: 85.0%

(E)-10-(1-azabicyclo[2.2.2]oct-3-ylidenemethyl)phenothiazine (151129-15-6) → mequitazine (29216-28-2)

Guidance literature:

With triethylsilane; trifluoroacetic acid; at 0 - 32 ℃; for 2.5h; Inert atmosphere; Large scale;

Reference yield:

10H-phenothiazine (92-84-2) + 3-chloromethyl-quinuclidine; hydrochloride (86014-80-4) + tartaric acid (87-69-4,138508-61-9) → mequitazine (29216-28-2)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; acetic acid methyl ester; water; ethyl acetate;

upstream raw materials:

(E)-10-(1-azabicyclo[2.2.2]oct-3-ylidenemethyl)phenothiazine

10H-phenothiazine

3-chloromethyl-quinuclidine; hydrochloride

tartaric acid

Downstream raw materials:

10-(1-azabicyclo[2.2.2]oct-3-yl-methyl)-10H-pheno-thiazine sulfoxide

Refernces

• 1、 -. "Method for industrially producing mequitazine". Paragraph 0027; 0033; 0036-0037. . Retrieved 2019/10/01.
• 2、 -. "Highly pure phenothiazine compound, production method thereof, production method of intermediate therefor, and hydrate and novel crystal as starting materials for the intermediate". . . Retrieved 2008/06/13.