MEQUITAZINE

MEQUITAZINE Basic information
Product Name:MEQUITAZINE
Synonyms:10-(1-Azabicyclo[2.2.2]octan-3-ylmethyl)-10H-phenothiazine;10-(Quinuclidin-3-ylmethyl)-10H-phenothiazine;MQ-A-88;10-[(1R,3R)-1-azabicyclo[2.2.2]octan-3-ylMethyl]-10H-phenothiazine;10H-Phenothiazine, 10-(1-azabicyclo[2.2.2]oct-3-ylmethyl)- (9CI);Nipolazin;NSC 303612;Phenothiazine, 10-(3-quinuclidinylmethyl)- (8CI)
CAS:29216-28-2
MF:C20H22N2S
MW:322.47
EINECS:249-521-7
Product Categories:Heterocyclic Compounds;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:29216-28-2.mol
MEQUITAZINE Structure
MEQUITAZINE Chemical Properties
Melting point 143-145°C
Boiling point 469.4±24.0 °C(Predicted)
density 1.1330 (rough estimate)
refractive index 1.5800 (estimate)
storage temp. Refrigerator
Water Solubility Insoluble in water
solubility DMSO : 16 mg/mL (49.62 mM)
form powder to crystal
pka10.43±0.33(Predicted)
color White to Almost white
Merck 14,5864
CAS DataBase Reference29216-28-2(CAS DataBase Reference)
NIST Chemistry ReferenceMequitazine(29216-28-2)
Safety Information
RIDADR UN 2811 6.1/PG III
RTECS SP5080000
HazardClass 6.1
PackingGroup III
HS Code 29349990
MSDS Information
MEQUITAZINE Usage And Synthesis
Chemical PropertiesWhite Solid
OriginatorPrimalan,Berk,UK,1976
UsesIt is an antihistamine
DefinitionChEBI: Mequitazine is a member of phenothiazines.
Manufacturing Process30 g of phenothiazine were added, all at once, to a suspension of 6 g of sodium amide in 240 ml of anhydrous xylene. The mixture was agitated and heated to reflux. When evolution of ammonia ceased (5 hours), 15 g of 3- chloromethyl-quinuclidine hydrochloride were added portionwise over a period of 50 minutes and reflux was then maintained for 22 hours. After cooling to room temperature, 250 ml of distilled water and 250 ml of ethyl acetate were added to the reaction mixture. The aqueous phase was decanted and extracted twice with a total of 250 ml of methyl acetate. The combined organic extracts were extracted three times with a total of 750 ml of a 10% aqueous solution of tartaric acid. The combined acid solutions were treated with 5 g of animal charcoal, filtered and rendered alkaline on an ice bath with 96 ml of 10 N aqueous caustic soda. The oil which separated was extracted three times with a total of 1.500 ml of ethyl acetate. The combined organic extracts were washed to neutrality by washing twice with a total of 1 liter of distilled water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure on a water bath at 45°C. 17 g of oil were obtained which was purified by chromatography on an inert alumina column. 13.3 g of crystallized product were obtained. 10-(3-Quinuclidinyl-methyl)-phenothiazine having a MP of 130°C to 131°C was obtained by recrystallization in boiling acetonitrile.
The 3-chloromethyl-quinuclidine hydrochloride used as starting material in this process can be obtained as described by Grob and coll., Helv. Chim. Acta, 37 (1954),1689.
Therapeutic FunctionAntihistaminic
MEQUITAZINE Preparation Products And Raw materials
Raw materialsPhenothiazine
Brompheniramine Clindamycin Loratadine Trimethobenzamide Mertansine Antazoline Danazol (R)-(+)-Mequitazine Trimeprazine mequitazine sulfoxide MEQUITAZINE, [2-14C]- Phenothiazine 1-(2,6-DICHLOROPHENYL)-2-INDOLINONE /MEQUITAZINE MEQUITAZINE pecazine

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