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Trimethobenzamide

CAS No.
138-56-7
Chemical Name:
Trimethobenzamide
Synonyms
C07178;TRIMETHOBENZAMIDE;Ro 2-9578 free base;Trimethobenzamide USP/EP/BP;n-[(2-dimethylaminoethoxy)benzyl]-3,4,5-trimethoxybenzamide;n-(p-(2-(dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxy-benzamid;N-(4-[2-(Dimethylamino)ethoxy]benzyl)-3,4,5-trimethoxybenzamide;N-[p-[2-(Dimethylamino)ethoxy]benzyl]-3,4,5-trimethoxybenzamide;4-(2-dimethylaminoethoxy)-n-(3,4,5-trimethoxybenzoyl)benzylamine;N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxybenzamide
CBNumber:
CB5700149
Molecular Formula:
C21H28N2O5
Molecular Weight:
388.46
MDL Number:
MFCD00599601
MOL File:
138-56-7.mol
MSDS File:
SDS
Last updated:2025-04-17 18:22:24
Product description Number Pack Size Price
TRIMETHOBENZAMIDE 95.00% CHM0146945 5MG $503.21
Benzamide,N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxy- 95% AR0018I1 100mg $101
N-(4-(2-(Dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxybenzamide 138567 250mg $203.94
N-(4-(2-(Dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxybenzamide 138567 1g $388.97
Trimethobenzamide 95% CM110386 1g $464
More product size

Trimethobenzamide Properties

storage temp. 2-8°C
pka pKa 8.27±0.03(H2O) (Uncertain)
form Solid
color White to off-white
FDA UNII W2X096QY97
NIST Chemistry Reference Benzamide, n-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxy-(138-56-7)
ATC code R06AA10

SAFETY

Risk and Safety Statements

Hazardous Substances Data 138-56-7(Hazardous Substances Data)

Trimethobenzamide price

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
American Custom Chemicals Corporation CHM0146945 TRIMETHOBENZAMIDE 95.00% 138-56-7 5MG $503.21 2021-12-16 Buy
Aaron Chemicals AR0018I1 Benzamide,N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxy- 95% 138-56-7 100mg $101 2021-12-16 Buy
Alichem 138567 N-(4-(2-(Dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxybenzamide 138-56-7 250mg $203.94 2021-12-16 Buy
Alichem 138567 N-(4-(2-(Dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxybenzamide 138-56-7 1g $388.97 2021-12-16 Buy
Chemenu CM110386 Trimethobenzamide 95% 138-56-7 1g $464 2021-12-16 Buy
Product number Packaging Price Buy
CHM0146945 5MG $503.21 Buy
AR0018I1 100mg $101 Buy
138567 250mg $203.94 Buy
138567 1g $388.97 Buy
CM110386 1g $464 Buy

Trimethobenzamide Chemical Properties,Uses,Production

Originator

Tigan,Beecham,US,1973

Uses

Antiemetic.

Definition

ChEBI: The amide obtained by formal condensation of 3,4,5-trihydroxybenzoic acid with 4-[2-(N,N-dimethylamino)ethoxy]benzylamine. It is used to prevent nausea and vomitting in humans.

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

118-41-2
138-56-7
Synthesis of Trimethobenzamide from 3,4,5-Trimethoxy benzoic acid
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4-(2-dimethylaminoethoxy)-n-(3,4,5-trimethoxybenzoyl)benzylamine Benzamide, N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxy- n-((4-(2-(dimethylamino)ethoxy)phenyl)methyl)-3,4,5-trimethoxy-benzamid N-(4-[2-(Dimethylamino)ethoxy]benzyl)-3,4,5-trimethoxybenzamide n-(p-(2-(dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxy-benzamid n-[(2-dimethylaminoethoxy)benzyl]-3,4,5-trimethoxybenzamide N-[p-[2-(Dimethylamino)ethoxy]benzyl]-3,4,5-trimethoxybenzamide TRIMETHOBENZAMIDE C07178 N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxybenzamide Trimethobenzamide USP/EP/BP Ro 2-9578 free base 138-56-7 C9H1303