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Metoclopramide hydrochloride

CAS No.
54143-57-6
Chemical Name:
Metoclopramide hydrochloride
Synonyms
MetoclopraMide HCI;Metoclopramide hydrochloride CRS;MetocL;Annavar;Gastromax;GastreseL.A;Levohypropizine;Gastrobidcontinus;opramide hydrochL;Metoclopramide hydrochloride
CBNumber:
CB1262047
Molecular Formula:
C14H25Cl2N3O3
Molecular Weight:
354.27
MDL Number:
MFCD00150634
MOL File:
54143-57-6.mol
MSDS File:
SDS
Last updated:2023-12-20 20:39:53

Metoclopramide hydrochloride Properties

Melting point 182.5-184°
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
solubility Methanol (Slightly), Water (Slightly)
color White to Off-White
Water Solubility It is very soluble in water, easily soluble in ethyl alcohol, slightly soluble in dichloromethane.
Sensitive Light Sensitive
BCS Class 3
InChIKey RVFUNJWWXKCWNS-UHFFFAOYSA-N
CAS DataBase Reference 54143-57-6(CAS DataBase Reference)
FDA UNII W1792A2RVD
NCI Drug Dictionary metoclopramide hydrochloride

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P501
WGK Germany  3
HS Code  2924296000

Metoclopramide hydrochloride price More Price(18)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHR1132 Metoclopramide Hydrochloride Pharmaceutical Secondary Standard; Certified Reference Material 54143-57-6 1g $97.5 2024-03-01 Buy
Sigma-Aldrich M1825000 Metoclopramide hydrochloride European Pharmacopoeia (EP) Reference Standard 54143-57-6 M1825000 $150 2024-03-01 Buy
Sigma-Aldrich 1440808 Metoclopramide hydrochloride 54143-57-6 500mg $436 2024-03-01 Buy
Alfa Aesar J61545 Metoclopramide hydrochloride 54143-57-6 10g $45.65 2024-03-01 Buy
Alfa Aesar J61545 Metoclopramide hydrochloride 54143-57-6 25g $100.65 2024-03-01 Buy
Product number Packaging Price Buy
PHR1132 1g $97.5 Buy
M1825000 M1825000 $150 Buy
1440808 500mg $436 Buy
J61545 10g $45.65 Buy
J61545 25g $100.65 Buy

Metoclopramide hydrochloride Chemical Properties,Uses,Production

Originator

Primperan,Delagrange,France,1964

Uses

Dopamine receptor antagonist; antiemetic.

Uses

Metoclopramide Hydrochloride may be used as a pharmaceutical reference standard for the determination of the analyte in pharmaceutical formulations and biological fluids by chromatography and chemiluminescence techniques.

Indications

Metoclopramide (Reglan) stimulates upper GI tract motility and has both central and peripheral actions. Centrally, it is a dopamine antagonist, an action that is important both for its often desirable antiemetic effect and other less desirable effects. Peripherally, it stimulates the release of intrinsic postganglionic stores of acetylcholine and sensitizes the gastric smooth muscle to muscarinic stimulation. The ability of metoclopramide to antagonize the inhibitory neurotransmitter effect of dopamine on the GI tract results in increased gastric contraction and enhanced gastric emptying and small bowel transit.

Definition

ChEBI: A hydrate that is the monohydrate form of metoclopramide monohydrochloride.

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

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Metoclopramide Hydrochloride is an antiemetic drug and is generally used for the treatment of gastrointestinal disorders. It can also exhibit sedative, extrapyrimidal, and prolactin secretion stimulation actions.

Mechanism of action

Metoclopramide is rapidly absorbed following an oral dose in a patient with intact gastric emptying. Peak plasma concentration is achieved within 40 to 120 minutes. With normal renal function, plasma half-life is about 4 hours.About 20% of an oral dose is eliminated unchanged in the urine, while 60% is eliminated as sulfate or glucuronide conjugates.

Clinical Use

Improved gastric emptying will frequently alleviate symptoms in patients with diabetic, postoperative, or idiopathic gastroparesis. Since metoclopramide also can decrease the acid reflux into the esophagus that results from slowed gastric emptying or lower esophageal sphincter pressure, the drug can be used as an adjunct in the treatment of reflux esophagitis.

Side effects

Side effects include fatigue, insomnia, and altered motor coordination. Parkinsonian side effects and acute dystonic reactions also have been reported. Metoclopramide stimulates prolactin secretion, which can cause galactorrhea and menstrual disorders. Extrapyramidal side effects seen following administration of the phenothiazines, thioxanthenes, and butyrophenones may be accentuated by metoclopramide.

Metoclopramide hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Metoclopramide hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Metoclopramide hydrochloride pictures 2023-12-20 Metoclopramide hydrochloride
54143-57-6
US $90.00 / kg 1kg 99% Purity (What/sapp: +86 18145728414) 1000 Tons/Month Guangzhou Tengyue Chemical Co., Ltd.
Metoclopramide hydrochloride pictures 2023-08-29 Metoclopramide hydrochloride
54143-57-6
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
Metoclopramide hydrochloride  pictures 2021-11-13 Metoclopramide hydrochloride
54143-57-6
US $10.00 / Kg/Bag 1Kg/Bag 99% 20 Tons Hebei Zhanyao Biotechnology Co. Ltd

Metoclopramide hydrochloride Spectrum

Annavar Benzamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxy-, monohydrochloride, monohydrate Metoclopramide monohydrochloride monohydrate Metoclopramide Hydrochloride (500 mg) METOCLOPRAMIDE HYDROCHLORIDE, MONOHYDRATE MetoclopraMide Hydrochloride, USP 4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide monohydrochloride monohydrate Metoclopramide (hydrochloride hydrate) GastreseL.A Gastrobidcontinus METOCLOPRAMIDEHYDROCHLORIDE,MONOHYDRATE,USP Gastromax 4-Amino-5-chloro-N-(2-diethylaminoethyl)-2-methoxybenzamide hydrochloride Metoclopramide hydrochloride Metoclopramide hydrochloride 54143-57-6 MetocL opramide hydrochL Metoclopramide hydrochloride USP/EP/BP Levohypropizine Metoclopramide Hydrochloride (1440808) MetoclopraMide HCI Metoclopramide hydrochloride CRS Lidamidine Hydrochloride Impurity 12 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide hydrochloride hydrate 54143-57-6 C14H22ClN3O2HCl C14H25Cl2N3O3 C14H22ClN3O2HClC14H23Cl2N3O2 C14H23Cl2N3O2 C14H22ClN3O2HClC14H23Cl2 C14H22ClN3O2HClH2O API Steroid and Hormone 54143-57-6