CARBINOXAMINE MALEATE SALT

CARBINOXAMINE MALEATE SALT Basic information
Product Name:CARBINOXAMINE MALEATE SALT
Synonyms:2-((4-chlorophenyl)-2-pyridinylmethoxy)-n,n-dimethyl-ethanamin(z)-2-bute;2-(p-chloro-alpha-(2-(dimethylamino)ethoxy)benzyl)pyridinebimaleate;2-(p-chloro-alpha-(2-(dimethylamino)ethoxy)benzyl)pyridinemaleate;2-(p-chloro-alpha-(2-(dimethylamino)ethoxy)benzyl)-pyridinmaleate(1:1);2-[(4-chlorophenyl)-2-pyridinylmethoxy]-n,n-dimethyl-ethanamin(z)-2-butene;allergefonmaleate;ciberon;clistin
CAS:3505-38-2
MF:C20H23ClN2O5
MW:406.86
EINECS:222-498-0
Product Categories:Intermediates & Fine Chemicals;Pharmaceuticals;Alphabetic;C;CA - CGForensic and Veterinary Standards;Drugs&Metabolites;Neat Compounds;Aromatics;Heterocycles;CLISTIN
Mol File:3505-38-2.mol
CARBINOXAMINE MALEATE SALT Structure
CARBINOXAMINE MALEATE SALT Chemical Properties
Melting point 116-1180C
storage temp. Keep in dark place,Sealed in dry,Room Temperature
Water Solubility Completely soluble in water
solubility Chloroform: Slightly Soluble; Methanol: Slightly Soluble
form neat
color White to Almost white
Merck 14,1799
InChIKeyGVNWHCVWDRNXAZ-BTJKTKAUSA-N
CAS DataBase Reference3505-38-2(CAS DataBase Reference)
EPA Substance Registry SystemEthanamine, 2-[(4-chlorophenyl)-2-pyridinylmethoxy]-N,N-dimethyl-, (2Z)-2-butenedioate (1:1) (3505-38-2)
Safety Information
Hazard Codes T
Risk Statements 25-36/37/38
Safety Statements 26-36/37/39-45
RIDADR 3249
WGK Germany 3
RTECS US6350000
HazardClass 6.1(b)
PackingGroup III
HS Code 2933399090
ToxicityLD50 in mice (mg/kg): 166 i.p. (Cahen)
MSDS Information
CARBINOXAMINE MALEATE SALT Usage And Synthesis
DescriptionCarbinoxamine is a competitive histamine H1 receptor antagonist (Ki = 2.3 nM) and first generation antihistamine. It also competes with [3H]diltiazem, an L-type calcium channel blocker, for binding to the benzothiazepine site on rat cardiomyocytes (Ki = 1.08 nM). Carbinoxamine decreases negative inotropic activity in isolated guinea pig left atria by 76% (EC50 = 250 nM) and negative chronotropic activity in guinea pig spontaneously beating isolated right atria (EC50s = 250 and 480 nM, respectively) by 48% compared with control. Formulations containing carbinoxamine have been used in the treatment of allergic rhinitis.
Chemical PropertiesOff-White Solid
OriginatorClistin,McNeil,US,1953
Usesantihistaminic
UsesAnalgesic and anti-inflammatory compound
DefinitionChEBI: The maleic acid salt of carbinoxamine. An ethanolamine-type antihistamine, used for treating hay fever, as well as mild cases of Parkinson's disease.
Manufacturing ProcessAs described in US Patent 2,800,485 a solution of p-chlorophenylmagnesium bromide is prepared by adding dropwise a solution of 230 g (1.2 mols) of p-bromochlorobenzene in 900 cc of anhydrous ether to 26.7 g (1.1 g-atoms) of magnesium suspended in 100 cc of anhydrous ether containing a small crystal of iodine. To this solution, 107 g (1 mol) of 2-pyridinealdehyde are added slowly with stripping at a rate to maintain refluxing. The reaction mixture is then stirred for one hour at room temperature. The mixture is then poured onto an equal volume of crushed ice and water and acidified with concentrated hydrochloric acid. The ether layer is removed. The aqueous layer is made basic with ammonia and extracted with ether. The ether solution is evaporated and the residue dried by addition of benzene and removal by distillation to give 208 g (95%) of solid alpha-(p-chlorophenyl)-2-pyridinemethanol melting at 78° to 80°C. The p-chlorophenyl pyridinemethanol may alternatively be prepared from 4-chloroacetophenone, pyridine and granular aluminum as described in US Patent 2,606,195. In either case, the synthesis then proceeds as described in US Patent 2,800,485.
A solution of 219 g (1 mol) of α-(p-chlorophenyl)-2-pyridinemethanol in one liter of dry toluene is heated to 100°C with stirring. Twenty-three grams (1 g-atom) of sodium are then added in portions. After all the sodium has reacted, a dried solution of 2-dimethylaminoethyl chloride in benzene is added. This benzene solution is prepared by dissolving 173 g (1.2 mols) of 2- dimethylaminoethyl chloride hydrochloride in the minimum amount of water, adding 500 cc of benzene followed by 300 g of sodium carbonate decahydrate, stirring, separating the benzene layer and drying.
The mixture is refluxed with stirring for ten hours, cooled and filtered. The filtrate is extracted three times with 200 cc portions of 6 N acetic acid. The aqueous acetic acid solution is then made strongly basic with 10% sodium hydroxide solution, and extracted three times with 200 cc portions of ether. The ether extract is dried with anhydrous sodium sulfate, stirred with 5 g of activated carbon and filtered to provide 2-[p-chloro-α(2-dimethylaminoethoxy) benzyl]pyridine in solution. Addition of a solution of 116 g (1 mol) of maleic acid in 1,500 cc of ether gives 323 g (79%) of solid which, on recrystallization from ethyl acetate, gives white solid 2-[p-chloro-α(2-dimethylaminoethoxy) benzyl]pyridine maleate melting at 117° to 119°C.

Brand nameClistin (Ortho- McNeil).
Therapeutic FunctionAntihistaminic
General DescriptionCarbinoxamine is availableas a bitter bimaleate salt, (d, l)-2-[p-chloro- -[2-(dimethylamino)ethoxy]benzyl]pyridine bimaleate (Clistin), which isa white crystalline powder that is very soluble in water andfreely soluble in alcohol and in chloroform. The pH of a 1%solution is between 4.6 and 5.1.
Carbinoxamine is a potent antihistaminic and is availableas the racemic mixture. It differs structurally from chlorpheniramineonly in having an oxygen atom separate theasymmetric carbon atom from the aminoethyl side chain. Themore active levo isomer of carbinoxamine has the (S) absoluteconfiguration and can be superimposed on the moreactive dextro isomer (S configuration) of chlorpheniramine.
CARBINOXAMINE MALEATE SALT Preparation Products And Raw materials
Raw materialsMagnesium-->Sodium-->2-DIMETHYLAMINO ETHYL CHLORIDE-->4-Bromochlorobenzene-->2-Pyridinecarboxaldehyde
Lorlatinib (PF-06463922) Enalapril maleate Trimebutine maleate Flurbiprofen Fenasi Chlorphenamine maleate CARBINOXAMINE MALEATE SALT 2-(4-Chlorobenzyl)pyridine CHEMBRDG-BB 9070890 carbinoxamine 2-PYRIDINEMETHANOL HYDROCHLORIDE 1-PYRIDIN-2-YL-ETHANOL alpha-(4-chlorophenyl)pyridine-2-methanol

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