CARBINOXAMINE MALEATE SALT CAS 3505-38-2
Introduction：Basic information about CARBINOXAMINE MALEATE SALT CAS 3505-38-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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 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 | Solid |
| color | White to Almost white |
| Merck | 14,1799 |
| Major Application | pharmaceutical small molecule |
| InChI | 1S/C16H19ClN2O.C4H4O4/c1-19(2)11-12-20-16(15-5-3-4-10-18-15)13-6-8-14(17)9-7-13;5-3(6)1-2-4(7)8/h3-10,16H,11-12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1- |
| InChIKey | GVNWHCVWDRNXAZ-BTJKTKAUSA-N |
| SMILES | OC(=O)\C=C/C(O)=O.CN(C)CCOC(c1ccc(Cl)cc1)c2ccccn2 |
| CAS DataBase Reference | 3505-38-2(CAS DataBase Reference) |
| EPA Substance Registry System | Ethanamine, 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 |
| TSCA | TSCA listed |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| HS Code | 2933399090 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Toxicity | LD50 in mice (mg/kg): 166 i.p. (Cahen) |
| Description | Carbinoxamine 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 Properties | Off-White Solid |
| Originator | Clistin,McNeil,US,1953 |
| Uses | Analgesic and anti-inflammatory compound |
| Uses | antihistaminic |
| Definition | ChEBI: 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 Process | As described in US Patent 2,800,485 a solution of p-chlorophenylmagnesiumbromide 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 crystalof iodine. To this solution, 107 g (1 mol) of 2-pyridinealdehyde are addedslowly with stripping at a rate to maintain refluxing. The reaction mixture isthen stirred for one hour at room temperature. The mixture is then pouredonto an equal volume of crushed ice and water and acidified with concentratedhydrochloric acid. The ether layer is removed. The aqueous layer is madebasic with ammonia and extracted with ether. The ether solution is evaporatedand the residue dried by addition of benzene and removal by distillation togive 208 g (95%) of solid alpha-(p-chlorophenyl)-2-pyridinemethanol meltingat 78° to 80°C. The p-chlorophenyl pyridinemethanol may alternatively beprepared from 4-chloroacetophenone, pyridine and granular aluminum asdescribed in US Patent 2,606,195. In either case, the synthesis then proceedsas described in US Patent 2,800,485. A solution of 219 g (1 mol) of α-(p-chlorophenyl)-2-pyridinemethanol in oneliter 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. Thisbenzene 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. Thefiltrate is extracted three times with 200 cc portions of 6 N acetic acid. Theaqueous acetic acid solution is then made strongly basic with 10% sodiumhydroxide solution, and extracted three times with 200 cc portions of ether.The ether extract is dried with anhydrous sodium sulfate, stirred with 5 g ofactivated 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 maleicacid in 1,500 cc of ether gives 323 g (79%) of solid which, on recrystallizationfrom ethyl acetate, gives white solid 2-[p-chloro-α(2-dimethylaminoethoxy)benzyl]pyridine maleate melting at 117° to 119°C. |
| Brand name | Clistin (Ortho-McNeil). |
| Therapeutic Function | Antihistaminic |
| General Description | Carbinoxamine 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. |
| References | [1] V T TRAN S H S R S Chang. Histamine H1 receptors identified in mammalian brain membranes with [3H]mepyramine.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1978, 75 12: 6290-6294. DOI: 10.1073/pnas.75.12.6290 [2] EMANUELE CAROSATI. Discovery of Novel and Cardioselective Diltiazem-like Calcium Channel Blockers via Virtual Screening[J]. Journal of Medicinal Chemistry, 2008, 51 18: 5552-5565. DOI: 10.1021/jm800151n |
CARBINOXAMINE MALEATE SALT Preparation Products And Raw materials
| Raw materials | Magnesium-->Sodium-->2-DIMETHYLAMINO ETHYL CHLORIDE-->4-Bromochlorobenzene-->2-Pyridinecarboxaldehyde |
