ChemicalBook > CAS DataBase List > METOCLOPRAMIDE HCL

METOCLOPRAMIDE HCL

Product Name
METOCLOPRAMIDE HCL
CAS No.
7232-21-5
Chemical Name
METOCLOPRAMIDE HCL
Synonyms
Eucil;reglan;EMperal;Maxeran;cerucal;maxolon;Gastrese;MetaMide;DraclaMid;Gastrobid
CBNumber
CB4236007
Molecular Formula
C14H23Cl2N3O2
Formula Weight
336.26
MOL File
7232-21-5.mol
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METOCLOPRAMIDE HCL Property

Melting point:
171-173°C
storage temp. 
2-8°C
solubility 
H2O: soluble
form 
solid
color 
white
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36/37/38
Safety Statements 
26-36
WGK Germany 
3
RTECS 
BZ3325000
HS Code 
29242990
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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
M0763
Product name
Metoclopramide hydrochloride
Purity
solid
Packaging
10g
Price
$69.6
Updated
2024/03/01
Sigma-Aldrich
Product number
M0763
Product name
Metoclopramide hydrochloride
Purity
solid
Packaging
25g
Price
$156
Updated
2024/03/01
Sigma-Aldrich
Product number
BP357
Product name
Metoclopramide hydrochloride
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$219
Updated
2023/06/20
Alfa Aesar
Product number
J61545
Product name
Metoclopramide hydrochloride
Packaging
10g
Price
$50.8
Updated
2023/06/20
Alfa Aesar
Product number
J61545
Product name
Metoclopramide hydrochloride
Packaging
25g
Price
$112
Updated
2023/06/20
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METOCLOPRAMIDE HCL Chemical Properties,Usage,Production

Description

Metoclopramide is an orally bioavailable serotonin (5-HT) receptor 5-HT3 antagonist with Ki and IC50 values of 995 and 308 nM, respectively, in rat cortical membranes. It is also a dopamine D2 receptor antagonist (IC50 = 483 nM in rat brain synaptic membranes). Oral administration of metoclopramide inhibits emesis induced by cisplatin and apomorphine in ferrets and dogs with ED50 values of 6.17 and 0.45 mg/kg, respectively. Metoclopramide reversibly inhibits human acetylcholinesterase (AChE) isolated from the caudate nucleus (Kis = 9.3 and 82 μM for competitive and non-competitive inhibition, respectively). Formulations containing metoclopramide have been used as anti-emetic and antipsychotic agents.

Chemical Properties

White Solid

Originator

Primperan,Delagrange,France,1964

Uses

Antiemetic;5-HT3 antagonist

Uses

A D2DR inhibitor and an HTR3E inhibitor

Uses

Dopamine D2 receptor antagonist. Antiemetic.

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.

Therapeutic Function

Antiemetic

Biochem/physiol Actions

D2 antagonist; 5-HT3 antagonist; antipsychotic; anti-emetic.

Clinical Use

Nausea and vomiting

Veterinary Drugs and Treatments

Metoclopramide has been used in veterinary species for both its GI stimulatory and antiemetic properties. It has been used clinically for gastric stasis disorders, gastroesophageal reflux, to allow intubation of the small intestine, as a general antiemetic (for parvovirus, uremic gastritis, etc.), and an antiemetic to prevent or treat chemotherapy-induced vomiting.

Drug interactions

Potentially hazardous interactions with other drugs
Ciclosporin: increased ciclosporin blood levels.

Metabolism

Metoclopramide undergoes first-pass hepatic metabolism. It is excreted in the urine, about 85% of a dose being eliminated in 72 hours, 20% as unchanged metoclopramide and the remainder as sulfate or glucuronide conjugates, or as metabolites. About 5% of a dose is excreted in faeces via the bile.

METOCLOPRAMIDE HCL Preparation Products And Raw materials

Raw materials

Preparation Products

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METOCLOPRAMIDE HCL Suppliers

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View Lastest Price from METOCLOPRAMIDE HCL manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Metoclopramide hydrochloride 7232-21-5
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-05-06
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Metoclopramide hydrochloride 7232-21-5
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%-101%
Supply Ability
1000kg
Release date
2022-11-10
Guangzhou Tengyue Chemical Co., Ltd.
Product
Metoclopramide hydrochloride 7232-21-5
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

7232-21-5, METOCLOPRAMIDE HCLRelated Search:

batanopride METOCLOPRAMIDE HCL Cloxacepride 4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDE NEMONAPRIDE Lintopride 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Metoclopramide hydrochloride 2-METHOXYBENZAMIDE pancopride Mezacopride PERALOPRIDE Benzamide, 5-chloro-N-(2-(diethylamino)ethyl)-4-((4,5-dihydro-1H-imida zol-2-yl)amino)-2-methoxy- Benzamide, 4-amino-5-chloro-N-(2-(cyclopropylethylamino)ethyl)-2-metho xy- 5-Chloro-N-(2-(diethylamino)ethyl)-4-((4,5-dihydro-2-oxazolyl)amino)-2 -methoxybenzamide Benzamide, 4-amino-5-chloro-2-methoxy-N-(2-(4-(2-pyridinyl)-1-piperazi nyl)ethyl)- METOCLOPRAMIDE HCL IMP. C (EP):4-AMINO-5-CHLORO-2-METHOXYBENZOIC ACID METOCLOPRAMIDE HCL IMP. H (EP): 4-(ACETYLAMINO)-2-HYDROXYBENZOIC ACID

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  • 7232-21-5
  • C14H22ClN3O2
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  • D2 antagonist; 5-HT3 antagonist; antipsychotic; anti-emetic
  • Amines
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