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Metoclopramide hydrochloride

Metoclopramide hydrochloride Structure
Metoclopramide hydrochloride
  • CAS No.7232-21-5
  • Chemical Name:Metoclopramide hydrochloride
  • CBNumber:CB4236007
  • Molecular Formula:C14H23Cl2N3O2
  • Formula Weight:336.26
  • MOL File:7232-21-5.mol
Metoclopramide hydrochloride Property
  • Melting point 171-173°C
  • storage temp. 2-8°C
  • solubility H2O: soluble
  • form solid
  • color white
  • Water Solubility H2O: soluble
  • NCI Dictionary of Cancer Terms Reglan
  • FDA UNII 7B1QZY5SWZ
  • NCI Drug Dictionary Reglan
  • UNSPSC Code 41116107
  • NACRES NA.77
Safety
  • Hazard Codes  :Xn
  • Risk Statements  :22-36/37/38
  • Safety Statements  :26-36
  • WGK Germany  :3
  • RTECS  :BZ3325000
  • HS Code  :29242990
  • NFPA 704:
    0
    2 0
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H302
  • Precautionary statements P264-P270-P301+P312-P501
Metoclopramide hydrochloride Price More Price(3)
  • Brand: Sigma-Aldrich(India)
  • Product number: M0763
  • Product name : Metoclopramide hydrochloride
  • Purity: solid
  • Packaging: 10G
  • Price: ₹6657.38
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: Sigma-Aldrich(India)
  • Product number: M0763
  • Product name : Metoclopramide hydrochloride
  • Purity: solid
  • Packaging: 25G
  • Price: ₹12935.88
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: Sigma-Aldrich(India)
  • Product number: M0763
  • Product name : Metoclopramide hydrochloride
  • Purity: solid
  • Packaging: 100G
  • Price: ₹34271.95
  • Updated: 2022/06/14
  • Buy: Buy

Metoclopramide hydrochloride 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 A D2DR inhibitor and an HTR3E inhibitor
  • Uses Antiemetic;5-HT3 antagonist
  • 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 hydrochloride Preparation Products And Raw materials
Raw materials
Preparation Products
Metoclopramide hydrochloride Suppliers
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Metoclopramide hydrochloride Spectrum
7232-21-5, Metoclopramide hydrochloride Related Search:
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