147780-50-5

Basic information

• Product Name: (+)-Mequitazine
• Synonyms: 10H-Phenothiazine, 10-(1-azabicyclo[2.2.2]oct-3-ylmethyl)-, (R)- (9CI);(R)-(+)-Mequitazine;(R)-10-(1-Azabicyclo[2.2.2]oct-3-ylmethyl)-10H-phenothiazine;(R)-10-(1-Azabicyclo[2.2.2]oct-3-ylMethyl);10-((1R,3S,4R)-quinuclidin-3-ylmethyl)-10H-phenothiazine(WXC05886)
• CAS NO: 147780-50-5
• Molecular Formula: C20H22N2S
• Molecular Weight: 322.47
• EINECS: 249-521-7
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Reagents, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 147780-50-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 130-131°C
• Boiling Point: 469.4°C at 760 mmHg
• Flash Point: 237.7°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 5.51E-09mmHg at 25°C
• Refractive Index: 1.707
• CAS DataBase Reference: (+)-Mequitazine(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Mequitazine(147780-50-5)
• EPA Substance Registry System: (+)-Mequitazine(147780-50-5)

Safety Data

• Hazardous Substances Data: 147780-50-5(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Solid

Uses

R-Enantiomer of Mequitazine. It is an antihistamine

InChI:InChI=1/C20H22N2S/c1-3-7-19-17(5-1)22(18-6-2-4-8-20(18)23-19)14-16-13-21-11-9-15(16)10-12-21/h1-8,15-16H,9-14H2

Upstream product

• 52346-11-9 tert-butyl 2-[(3R,4S)-3-ethenylpiperidin-4-yl]acetate 
• 1311205-55-6 (3R,4S)-4-(2-chloroethyl)-3-ethenylpiperidine 
• 1311205-56-7 (3R)-3-ethenyl-1-azabicyclo[2.2.2]octane 
• 138874-55-2 (3R)-1-azabicyclo[2.2.2]octan-3-ylmethanol 
• 92-84-2 10H-phenothiazine 
• 103027-51-6 2-[(3R,4S)-3-ethenylpiperidin-4-yl]ethan-1-ol 
• 130-95-0 quinine 
• 84-31-1 quininone 
• 1632121-46-0 C₂₀H₂₀N₂S*ClH 
• 1040270-12-9 1-aza-bicyclo[2.2.2]oct-2-en-3-ylmethyl acetate 

Relevant articles and documents

Short and straightforward enantioselective synthesis of both enantiomers of mequitazine through iridium-catalyzed asymmetric hydrogenation of a nonfunctionalized cyclic enamine

A short and straightforward asymmetric synthesis of both enantiomers of the antihistaminic drug mequitazine is reported. This atom-economical and attractive method features an iridium-catalyzed asymmetric hydrogenation of a nonfunctionalized cyclic enamine as a key step to install the C 3-stereogenic center. After a full investigation of the effects of catalyst precursors, ligands, solvents, temperature, and hydrogen pressure, mequitazine (1) is obtained in good yield (up to 80%) and with acceptable enantiomeric excesses up to 47%.Georg Thieme Verlag Stuttgart. New York.

Asymmetric synthesis of (+)-mequitazine from quinine

The first asymmetric synthesis of the antihistaminic drug mequitazine is reported. Our approach started from quinine, a Cinchona alkaloid, whose chiral information was exploited for setting up the stereogenic center of (+)-mequitazine.