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| | Trimethobenzamide hydrochloride Basic information |
| Product Name: | Trimethobenzamide hydrochloride | | Synonyms: | LABOTEST-BB LT00772325;Tribenzagan Hydrochloride;N-([2-Dimethylaminoethoxy] benzyl)-3,4,5-trimethoxybenzamide hydrochloride;TRIMETHOBENZAMIDEHYDROCHLORIDE,USP;4-(2-dimethylaminoethoxy)-n-(3,4,5-trimethoxybenzoyl)benzylaminehydrochlorid;n-(p-(2-(dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxybenzamidehydrochloride;n-(p-(2-(dimethylamino)ethoxy)-benzyl)-3,4,5-trimethoxybenzamidemonohydrochl;n-(p-(2-(dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxy-benzamidhydrochlori | | CAS: | 554-92-7 | | MF: | C21H29ClN2O5 | | MW: | 424.92 | | EINECS: | 209-075-6 | | Product Categories: | TIGAN | | Mol File: | 554-92-7.mol |  |
| | Trimethobenzamide hydrochloride Chemical Properties |
| Melting point | 187.5-190° | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | DMSO (Slightly), Methanol (Slightly), Water (Slightly) | | form | Solid | | color | White to Off-White | | Major Application | pharmaceutical (small molecule) | | InChI | 1S/C21H28N2O5.ClH/c1-23(2)10-11-28-17-8-6-15(7-9-17)14-22-21(24)16-12-18(25-3)20(27-5)19(13-16)26-4;/h6-9,12-13H,10-11,14H2,1-5H3,(H,22,24);1H | | InChIKey | WIIZEEPFHXAUND-UHFFFAOYSA-N | | SMILES | [Cl-].N(CCOc1ccc(cc1)CNC(=O)c2cc(c(c(c2)OC)OC)OC)(C)C.[H+] |
| WGK Germany | 3 | | HS Code | 2924296000 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Resp. Sens. 1
Skin Sens. 1 |
| | Trimethobenzamide hydrochloride Usage And Synthesis |
| Originator | Tigan,Beecham,US,1973 | | Uses | antiemetic | | Uses | Trimethobenzamide Hydrochloride a pharmaceutical compound used in the prevention of nausea and vomiting in patients. Also used in the treatment of Parkinson’s disease. | | Manufacturing Process | To 122 grams (1 mol) of p-hydroxybenzaldehyde in 1 liter of chlorobenzene
were added 66 grams (1.04 mols) of sodium methoxide (85%) and 108 grams
(1 mol) of 2-dimethylaminoethyl chloride. The mixture was stirred and
refluxed for 15 hours, then cooled and the precipitated sodium chloride
filtered off. The filtrate was concentrated at steam temperature under water
vacuum and the residual oil was fractionated in high vacuum, to give 4-(2-
dimethylaminoethoxy)benzaldehyde, BP2.2145°C.
Two teaspoons of Raney nickel catalyst were added to a solution of 65.6
grams (0.34 mol) of 4-(2-dimethylaminoethoxy)benzaldehyde in 300 ml of
10% ammoniacal ethanol. The mixture was hydrogenated at 80°C and a
pressure of 1,000 psi. The catalyst was filtered off, the volatiles were distilled
off and the residual oil was fractionated in high vacuum, to obtain 4-(2-
dimethylaminoethoxy)benzylamine, BP0.3120° to 123°C.
To 9.7 grams (0.05 mol) of 4-(2-dimethylaminoethoxy)benzylamine, dissolved
in 100 ml of acetonitrile, was added all at once 12 grams (0.051 mol) of
3,4,5-trimethoxybenzoyl chloride, dissolved in 75 ml of acetonitrile. The
mixture was stirred and refluxed for 8 hours, and then cooled. The crystalline
solid, which had formed, was filtered off, washed with acetonitrile and
recrystallized from acetonitrile, to give 4-(2-dimethylaminoethoxy)-N-(3,4,5-
trimethoxybenzoyl)benzylamine hydrochloride, MP 185° to 186°C. | | Brand name | Tigan (King). | | Therapeutic Function | Antinauseant |
| | Trimethobenzamide hydrochloride Preparation Products And Raw materials |
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