ChemicalBook > CAS DataBase List > Metoclopramide hydrochloride

Metoclopramide hydrochloride

Product Name
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
Formula Weight
354.27
MOL File
54143-57-6.mol
More
Less

Metoclopramide hydrochloride Property

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)
More
Less

Safety

WGK Germany 
3
HS Code 
2924296000
More
Less

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..…

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR1132
Product name
Metoclopramide Hydrochloride
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
1g
Price
$97.5
Updated
2024/03/01
Sigma-Aldrich
Product number
M1825000
Product name
Metoclopramide hydrochloride
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
M1825000
Price
$150
Updated
2024/03/01
Sigma-Aldrich
Product number
1440808
Product name
Metoclopramide hydrochloride
Packaging
500mg
Price
$436
Updated
2024/03/01
Alfa Aesar
Product number
J61545
Product name
Metoclopramide hydrochloride
Packaging
10g
Price
$45.65
Updated
2024/03/01
Alfa Aesar
Product number
J61545
Product name
Metoclopramide hydrochloride
Packaging
25g
Price
$100.65
Updated
2024/03/01
More
Less

Metoclopramide hydrochloride Chemical Properties,Usage,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

More
Less

Metoclopramide hydrochloride Suppliers

Hubei Yilai Biotechnology Co., Ltd.
Tel
18995688786
Email
156716255@qq.com
Country
China
ProdList
308
Advantage
58
Hubei Nordina Biotechnology Co., Ltd.
Tel
18171027221; 18171027221
Fax
18162687220
Email
nuodinashengwu@163.com
Country
China
ProdList
1615
Advantage
58
Wuhan Feiyue Biotechnology Co., LTD
Tel
027-87002654 18062720658
Email
andydeng@feiyuebio.com
Country
China
ProdList
805
Advantage
58
BeiJing Hwrk Chemicals Limted
Tel
0757-86329057 18501085097
Fax
010-89508210
Email
sales3.gd@hwrkchemical.com
Country
China
ProdList
7508
Advantage
55
Beijing Ouhe Technology Co., Ltd
Tel
010-82967028 13552068683
Fax
+86-10-82967029
Email
2355560935@qq.com
Country
China
ProdList
12426
Advantage
60
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2127
Advantage
70
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696;
Email
info@hanhongsci.com
Country
China
ProdList
42982
Advantage
64
XiaoGan ShenYuan ChemPharm co,ltd
Tel
0712-0712-2580635 15527768850
Email
1791901229@qq.com
Country
China
ProdList
8850
Advantage
52
Jinan Chenghui Shuangda biological Co., LTD
Tel
0531-58897003 15550412551
Fax
0531-58897003
Email
market@jnchsd.com
Country
China
ProdList
209
Advantage
62
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9823
Advantage
79
More
Less

View Lastest Price from Metoclopramide hydrochloride manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Metoclopramide hydrochloride 54143-57-6
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-05-06
Guangzhou Tengyue Chemical Co., Ltd.
Product
Metoclopramide hydrochloride 54143-57-6
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 FORTUNA CHEMICAL CO., LTD
Product
Metoclopramide hydrochloride 54143-57-6
Price
US $0.00/Kg/Bag
Min. Order
1KG
Purity
99.0%~101.0%; EP10.0
Supply Ability
6000kg/month
Release date
2021-06-04

54143-57-6, Metoclopramide hydrochloride Related Search:


  • 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
  • MetoclopraMide HCI
  • 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
  • Metoclopramide hydrochloride CRS
  • MetocL
  • opramide hydrochL
  • Metoclopramide hydrochloride USP/EP/BP
  • Levohypropizine
  • Metoclopramide Hydrochloride (1440808)
  • Lidamidine Hydrochloride Impurity 12
  • 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide hydrochloride hydrate
  • 54143-57-6
  • C14H22ClN3O2HCl
  • C14H25Cl2N3O3
  • C14H22ClN3O2HClH2O
  • C14H22ClN3O2HClC14H23Cl2N3O2
  • C14H23Cl2N3O2
  • C14H22ClN3O2HClC14H23Cl2
  • API
  • Steroid and Hormone
  • 54143-57-6