4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide

Uses

Product Name: 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide
CAS No.: 364-62-5
Chemical Name: 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide
Synonyms: Metoclopramide;DEL;Metaclopramide;Primperan;Metochlopramide;C07868;Parmid;Plasil;del1267;DEL:DEL
CBNumber: CB4506227
Molecular Formula: C14H22ClN3O2
Formula Weight: 299.8
MOL File: 364-62-5.mol

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4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Property

Melting point:: 146-148°C
Boiling point:: 418.7±45.0 °C(Predicted)
Density: 1.2432 (rough estimate)
refractive index: 1.5200 (estimate)
storage temp.: 2-8°C
solubility: Practically insoluble in water, sparingly soluble or slightly soluble in ethanol (96 per cent), slightly soluble in methylene chloride
pka: pKa 0.42± 0.03;9.71± 0.02(H2O)(Approximate)
form: Solid
color: White to Off-White
BRN: 1884366
Major Application: forensics and toxicology
pharmaceutical (small molecule)
InChI: InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)
InChIKey: TTWJBBZEZQICBI-UHFFFAOYSA-N
SMILES: C(NCCN(CC)CC)(=O)C1=CC(Cl)=C(N)C=C1OC
CAS DataBase Reference: 364-62-5(CAS DataBase Reference)
NIST Chemistry Reference: Benzamide, 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-methoxy-(364-62-5)

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Safety

Hazard Codes: Xn
Risk Statements: 22-64
Safety Statements: 36/37
WGK Germany: 3
HS Code: 2924.29.7790
Storage Class: 11 - Combustible Solids
Hazard Classifications: Acute Tox. 4 Oral
Hazardous Substances Data: 364-62-5(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: M1824990
Product name: Metoclopramide
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: 100 mg
Price: $225
Updated: 2025/07/31

Sigma-Aldrich

Product number: 32473
Product name: Metoclopramide
Purity: VETRANAL
Packaging: 100mg
Price: $143
Updated: 2025/07/31

Sigma-Aldrich

Product number: M1824990
Product name: Metoclopramide
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: m1824990
Price: $220
Updated: 2024/03/01

TCI Chemical

Product number: M2218
Product name: Metoclopramide
Purity: min. 98.0 %
Packaging: 5G
Price: $57
Updated: 2025/07/31

TCI Chemical

Product number: M2218
Product name: Metoclopramide
Purity: min. 98.0 %
Packaging: 25G
Price: $173
Updated: 2025/07/31

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4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Chemical Properties,Usage,Production

Uses

Metoclopramide is a treatment of choice of post-operative nausea and vomiting (PONV) prophylaxis.

Chemical Properties

White or almost white, fine powder.

Originator

Primperan,Delagrange,France,1964

Uses

antidiabetic

Uses

Metoclopramide is a treatment of choice of post-operative nausea and vomiting (PONV) prophylaxis.

Definition

ChEBI: A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of N,N-diethylethane-1,2-diamine.

Manufacturing Process

The N-(diethylaminoethyl)-2-methoxy-4-aminobenzamide used as the starting material may be prepared from o-toluidine. The o-toluidine is initially nitrated with nitric acid to produce 4-nitro-o-toluidine. The 4-nitro-o-toluidine is then converted to 2-hydroxy-4-nitrotoluene by heating with nitrous acid. By reacting the resulting 2-hydroxy-4-nitrotoluene with dimethyl sulfate, 2- methoxy-4-nitrotoluene is formed. The 2-methoxy-4-nitrotoluene is oxidized with potassium permanganate to produce 2-methoxy-4-nitrobenzoic acid. The latter substituted benzoic acid is treated with thionyl chloride to form 2- methoxy-4-nitrobenzoyl chloride. A methyl ethyl ketone solution of the 2- methoxy-4-nitrobenzoyl chloride is added over a period of about 1 hours to a methyl ethyl ketone solution containing an equal molecular quantity of N,Ndiethylethylene diamine while stirring and maintaining the temperature between 0°C and 5°C. The N-(diethylaminoethyl)-2-methoxy-4- nitrobenzamide hydrochloride formed precipitates. It is filtered, washed twice with methyl ethyl ketone, dissolved in alcohol, and reduced catalytically in an absolute isopropyl alcohol solution to form N-(diethylaminoethyl)-2-methoxy- 4-aminobenzamide. The base is obtained by precipitating with sodium hydroxide.
80 g (0.3mol) of N-(2-diethylaminoethyl)-2-methoxy-4-aminobenzamide are dissolved in small portions in 150 cc of acetic acid. The mixture is cooled and 45 g (0.45 mol) of acetic anhydride are added, and the solution obtained is heated for two hours on a water bath. After cooling, the solution is decanted into a round-bottomed flask with a stirrer, a thermometer and a tube for introducing the chlorine. It is stirred and the current of chlorine is passed through, the temperature being maintained between 20°C and 25°C. The stirring is continued for one hour after the completion of the absorption of the chlorine.
The mixture obtained is poured into 2 liters of water and the base is precipitated with 30% soda. The precipitated base is extracted with 400 cc of methylene chloride. After evaporation of the solvent, the N-(2- diethylaminoethyl)-2-methoxy-4-acetamino-5-chlorobenzamide formed crystallizes. The melting point is 86°C to 87°C and the yield is 95%.
To obtain the corresponding amino derivative, 109 g of base are heated under agitation in a round-bottomed flask with 300 cc of 35-36% concentrated hydrochloric acid and 600 cc of water. It is heated on a water bath until dissolution is complete, then maintained at boiling point for 90 minutes, cooled, diluted with 1 liter of water, and neutralized with about 350 cc of 30% soda. The N-(2-diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide formed crystallizes, is centrifuged and washed in water. Its melting point is 122°C and the yield is 74%.
To obtain the corresponding dihydrochloride, the base is dissolved in absolute alcohol (3 volumes) and to that solution is added 5 N alcoholic hydrochloric acid. The dihydrochloride precipitates, is centrifuged and washed with alcohol. It is a solid white material, having a melting point of 134°C to 135°C.

brand name

Maxolon (King); Reglan (Baxter Healthcare); Reglan (Robins); Reglan (Schwarz Pharma).

Therapeutic Function

Antiemetic

General Description

Metoclopramide is typically employed as an antiemetic drug or a gastrointestinal prokinetic drug in adults and children.

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Preparation Products And Raw materials

Raw materials

Ammonium chloride METHYL 4-AMINOSALICYLATE

Preparation Products

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4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Suppliers

Canada 1 China 312 Europe 2 Germany 2 India 11 Japan 2 Russia 1 United Kingdom 2 United States 19 Global 352

Zhengzhou Science Pharmaceutical Technology Co., Ltd

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View Lastest Price from 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide manufacturers

Guangzhou Tengyue Chemical Co., Ltd.

Product: Metoclopramide, 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide 364-62-5
Price: US $90.00/kg
Min. Order: 1kg
Purity: 99% Purity (What/sapp: +86 18145728414)
Supply Ability: 1000 Tons/Month
Release date: 2023-12-20

Wuhan Biocar Pharmacy CO.,Ltd.

Product: Metoclopramide hydrochloride 364-62-5
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 980kg
Release date: 2025-02-26

Shandong Xuhuang New material CoLTD

Product: Metoclopramide 364-62-5
Price: US $39.00/KG
Min. Order: 1KG
Purity: 99.99%
Supply Ability: 10T
Release date: 2025-02-24

364-62-5, 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamideRelated Search:

Metoclopramide monohydrochloride monohydrate 3-Hydroxytyramine tadalafi Ampicillin Sulfamethoxydiazine METARAMINOL Acetaminophen Magnesium sulfate Trimethoprim Sodium chloride Cisapride Domperidone Omeprazole Dexamethasone 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Metoclopramide hydrochloride 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide dihydrochloride 2-METHOXY-D3-BENZALDEHYDE

4-amino-5-chloro-n-(2-(diethylamino)ethyl)-n-anisamid

Methoxychloroprocainamide

Methoxychlorprocainamide

4-Amino-5-chloro-N-(2-diethylamino) ethyl-o-anisamide

Benzamide, 4-amino-5-chloro-N-2-(diethylamino)ethyl-2-methoxy-

Metoclopramide (base and/or unspecified salts)

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide

Metoclopramide

4-Amino-5-Cholo-N-[(2-diethylamino)ethyl]-2-methyloxy-

C07868

4-amino-5-chloro-n-(2-(diethylamino)ethyl)-o-anisamid

4-Amino-5-Cholo-N-[(2-diethylamino)ethyl]-2-methyloxy-benzamide

2-Methoxy-5-Chloroprocainamide

4-amino-5-chloro-n-(2-(diethylamino)ethyl)-2-methoxy-benzamid

5-Chloro-2-methoxyprocainamide

Anisamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-

DEL

DEL 1267

del1267

Metaclopramide

Metaclopromide

Methochlopramide

Methoclopramide

Metochlopramide

Metoclol

Metoclopranide

Metocobil

Metramid

Moriperan

N-(Diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide

o-Anisamide, 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-

Parmid

Plasil

Primperan

Reliveran

Metoclopramide CRS

Metoclopramide Standard

Metoclopramide&gt

4-amino-5-chloro-N - (2- (diethylamino) ethyl) -2-methoxybenzoamide

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide USP/EP/BP

5-Trimethoxyphenylacrylic acid

5-Trimethoxy-trans-cinnamic acid

Amine chloride tome

Metoclopramide, 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide

Metoclopramide B.P. /Ph.Eur

Metoclopramide, 10 mM in DMSO

DEL:DEL

364-62-5

364-65-2

PRANDIN

API

364-62-5