Introduction：Basic information about DIMETHINDENE MALEATE CAS 3614-69-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
DIMETHINDENE MALEATE Basic information
| Product Name: | DIMETHINDENE MALEATE |
| Synonyms: | Einecs 222-789-2;N,N-Dimethyl-3-[1-(2-pyridinyl)ethyl]-1H-indene-2-ethanamine (2Z)-2-butenedioate;NSC 107677;2-(1-(2-(2-(dimethylamino)ethyl)inden-3-yl)ethyl)pyridinemaleate;2-(1-(2-(2-(dimethylamino)ethyl)inden-3-yl)ethyl)-pyridinmaleate(1:1);dimethindenmaleate;Dimetindine Maleate;DIMETINDENE MALEATE |
| CAS: | 3614-69-5 |
| MF: | C24H28N2O4 |
| MW: | 408.49 |
| EINECS: | 222-789-2 |
| Product Categories: | |
| Mol File: | 3614-69-5.mol |
|
DIMETHINDENE MALEATE Chemical Properties
| Melting point | 159-161℃ |
| storage temp. | -20°C Freezer, Under inert atmosphere |
| solubility | Slightly soluble in water, soluble in methanol |
| form | Solid |
| color | White to Pale Beige |
| Major Application | pharmaceutical (small molecule) |
| InChI | 1S/C20H24N2.C4H4O4/c1-15(19-10-6-7-12-21-19)20-17(11-13-22(2)3)14-16-8-4-5-9-18(16)20;5-3(6)1-2-4(7)8/h4-10,12,15H,11,13-14H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1- |
| InChIKey | SWECWXGUJQLXJF-BTJKTKAUSA-N |
| SMILES | C1(C(C)C2=NC=CC=C2)=C(CC2=CC=CC=C12)CCN(C)C.C(/C(=O)O)=C/C(=O)O |
Safety Information
| WGK Germany | WGK 3 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
| Toxicity | LD50 in rats (mg/kg): 26.8 i.v.; 618.2 orally (Barrett) |
DIMETHINDENE MALEATE Usage And Synthesis
| Chemical Properties | White or almost white, crystalline powder. |
| Originator | Fenistil,Zyma,W. Germany,1961 |
| Uses | Dimethindene Maleate is a salt of Dimethindene which is an antihistamine/anticholinergic used orally and locally as an antipruritic. Dimethindene is an H1-antagonist of high potency. |
| Uses | Antihistaminic. |
| Definition | ChEBI: Dimetindene maleate is an indene. |
| Manufacturing Process | 26 grams of 2-ethylpyridine is added dropwise with cooling to 20°C and in anatmosphere of nitrogen to a stirred solution of 650 ml of an 0.37 molarsolution of phenyl lithium in benzene. After two hours a solution of 10 gramsof 2-(2-dimethylaminoethyl)-indan-1-one in 50 ml of dry ether is added overa period of five minutes while stirring and cooling to room temperature. Afterstanding for 24 hours the organo-lithium compounds are decomposed by theaddition of 50 ml of water with external cooling. After separating the waterphase from the organic solution, the latter is washed several times with 50 mlof water, and then extracted with a mixture of 40 ml of concentratedhydrochloric acid and 100 ml of water.
The acidic solution, containing the 2-(2-dimethylaminoethyl)-1-[1-(2-pyridyl)-ethyl]-indan-1-ol is heated on the steam bath for thirty minutes to effectdehydration to the desired indene derivative. The solution is cooled, madestrongly basic with an aqueous solution of ammonia and then extracted withether. The ether phase is dried over sodium sulfate, filtered, evaporated andthe residue distilled.
At 15 mm pressure the excess of 2-ethylpyridine is removed, at 120°C/0.5mm some unreacted 2-(2-dimethylaminoethyl)-indene distills and at 165°-175°C/0.5 mm the 2-(2-dimethylaminoethyl)-3-[1-(2-pyridyl)-ethyl]-indene iscollected. It may be converted to an aqueous solution of the dihydrochlorideby dissolving it in the appropriate amount of dilute hydrochloric acid.
To a solution of 1.0 gram of 2-(2-dimethylaminoethyl)-3[1-(2-pyridyl)-ethyl]-indene in 10 ml of ethanol is added while stirring and heating 0.4 gram ofmaleic acid. On cooling the 2-(2-dimethylaminoethyl)-3-[1-(2-pyridyl)-ethyl]-indene maleate crystallizes, is filtered off, washed with a small amount ofethanol and recrystallized from ethanol, MP 158°C. |
| Brand name | Forhistal Maleate (Ciba-Geigy). |
| Therapeutic Function | Antihistaminic |
| General Description | Dimethindene maleate, (±)2-[1-[2-[2-dimethylamino)ethyl]-inden-3-yl]ethyl]pyridinebimaleate (1:1) (Forhistal Maleate), is a white to off-whitecrystalline powder that has a characteristic odor and is sparinglysoluble in water. This potent antihistaminic agent may beconsidered a derivative of the unsaturated propylamines. Theprincipal side effect is some sedation or drowsiness. The antihistaminicactivity resides mainly in the levorotatory isomer. |
DIMETHINDENE MALEATE Preparation Products And Raw materials
| Raw materials | 2-Ethylpyridine-->2-[2-(DiMethylaMino)ethyl]-1-indanone-->Phenyllithium-->Maleic acid |
