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2-((Aminocarbonyl)oxy)-N,N,N-trimethyl-1-propan-aminiumchlorid Produkt Beschreibung

Bethanechol Struktur
590-63-6
CAS-Nr.
590-63-6
Bezeichnung:
2-((Aminocarbonyl)oxy)-N,N,N-trimethyl-1-propan-aminiumchlorid
Englisch Name:
Bethanechol
Synonyma:
duvoid;Mictone;Uro-Carb;Mechotane;Mecothane;NSC 30783;-β-methyL;mechothane;myocholine;urecholine
CBNumber:
CB8156880
Summenformel:
C7H17ClN2O2
Molgewicht:
196.68
MOL-Datei:
590-63-6.mol

2-((Aminocarbonyl)oxy)-N,N,N-trimethyl-1-propan-aminiumchlorid Eigenschaften

Schmelzpunkt:
187-190°C
storage temp. 
Inert atmosphere,2-8°C
Löslichkeit
H2O: 1.7 g/mL stable for several days at 4°C.
Aggregatzustand
crystalline
Farbe
white
Merck 
14,1185
CAS Datenbank
590-63-6(CAS DataBase Reference)
EPA chemische Informationen
1-Propanaminium, 2-[(aminocarbonyl)oxy]-N,N,N-trimethyl-, chloride (590-63-6)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn
R-Sätze: 22
S-Sätze: 36
WGK Germany  3
RTECS-Nr. BR5425000
TSCA  Yes
HS Code  2924190002
Bildanzeige (GHS)
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitsschädlich bei Verschlucken. Akute Toxizität oral Kategorie 4 Warnung P264, P270, P301+P312, P330, P501
Sicherheit
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P330 Mund ausspülen.

2-((Aminocarbonyl)oxy)-N,N,N-trimethyl-1-propan-aminiumchlorid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R22:Gesundheitsschädlich beim Verschlucken.

S-Sätze Betriebsanweisung:

S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

Chemische Eigenschaften

White Solid

Originator

Urecholine CI,MSD,US,1949

Verwenden

Therapeutic action of Betanechol is based on this action, and it is used for treating postoperational non-obstructive retention of urine and neurogenic bladder atony. Earlier, it was used for treating gastrointestinal illnesses and Alzheimer’s disease.

Verwenden

cholinergic

Verwenden

A selective muscarinic receptor stimulant, used to treat cerebral palsy.

Definition

ChEBI: The chloride salt of bethanechol. A slowly hydrolysed muscarinic agonist with no nicotinic effects, it is used to increase smooth muscle tone, as in the gastrointestinal tract following abdominal surgery, treatment of gastro-oesophageal reflux disease, and as an alternative to catheterisation in the treatment of non-obstructive urinary retention.

Manufacturing Process

About 3 grams of β-methylcholine chloride are stirred at room temperature with an excess of phosgene dissolved in 50 grams of chloroform, for about 2 hours. Excess phosgene and hydrochloric acid are removed by distillation under vacuo. Additional chloroform is added to the syrup and the mixture is poured into excess ammonia dissolved in chloroform and cooled in solid carbon dioxide-acetone. The solid is filtered and extracted with hot absolute alcohol. The solid in the alcohol is precipitated with ether, filtered, and recrystallized from isopropanol. The carbaminoyl-β-methylcholine chloride obtained has a melting point of about 220°C.

Trademarks

Duvoid (WellSpring); Myotonachol (Glenwood); Urecholine (Odyssey).

Therapeutic Function

Cholinergic

Allgemeine Beschreibung

Bethanechol, β-methylcholinechloride carbamate, (2-hydroxypropyl)trimethylammoniumchloride carbamate, carbamylmethylcholinechloride (Urecholine), is nonspecific in its action on muscarinicreceptor subtypes but appears to be more effective ateliciting pharmacological action of M3 receptors. It haspharmacological properties similar to those of methacholine.Both are esters of β-methylcholine and have feeblenicotinic activity. Bethanechol is inactivated more slowlyby AChE in vivo than is methacholine. It is a carbamyl esterand is expected to have stability in aqueous solutions similarto that of carbachol.

Hazard

Headache, flushing, gastrointestinal distress, diarrhea, hypotension, excessive salivation, sweating, hypersensitivity.

Mechanism of action

Bentanechol is a drug, which has structurally unique qualities of both methacholine and carbachol, i.e. it contains both β-methyl and carbamate functional groups, and quite logically exhibits pharmacological properties of both the drugs. It is resistant to hydrolysis by cholinesterases and has a very minor effect on nicotinic receptors of the autonomic ganglia and neuromuscular junctions. Betanechol has more of a selective action on muscarinic receptors of the gastrointestinal tract and the bladder than do other cholinic esters.

Clinical Use

The main use of bethanechol chloride is in the relief ofurinary retention and abdominal distention after surgery.The drug is used orally and by subcutaneous injection. Itmust never be administered by intramuscular or intravenousinjection because of the danger from cholinergic overstimulationand loss of selective action. Proper administration ofthe drug is associated with low toxicity and no serious sideeffects. Bethanechol chloride should be used with caution inasthmatic patients; when used for glaucoma, it producesfrontal headaches from the constriction of the sphinctermuscle in the eye and from ciliary muscle spasms. Its durationof action is 1 hour.

Chemical Synthesis

Betanechol, 2-carbamoyloxy-1-(N,N,N-trimethyl)propyl ammonium chloride (13.1.8), is made by either the subsequent reaction of 1-(N,N,N-trimethylammonium) propan-2-ol with phosgene, followed by ammonia, or by a completely analogous synthesis of carbachol by the reaction of 1-chloro-2-propanol with phosgene followed by consequent reactions with ammonia, and then with trimethylamine, giving betanechol (13.1.8) [14,15].

Veterinary Drugs and Treatments

In veterinary medicine, bethanechol is used primarily to stimulate bladder contractions in small animals. It also can be used as an esophageal or general GI stimulant, although metoclopramide and/ or neostigmine have largely supplanted it for these uses.

2-((Aminocarbonyl)oxy)-N,N,N-trimethyl-1-propan-aminiumchlorid Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


2-((Aminocarbonyl)oxy)-N,N,N-trimethyl-1-propan-aminiumchlorid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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590-63-6(2-((Aminocarbonyl)oxy)-N,N,N-trimethyl-1-propan-aminiumchlorid)Verwandte Suche:


  • (2-hydroxypropyl)trimethylammoniumchloridecarbamate
  • 2-((aminocarbonyl)oxy)-n,n,n-trimethyl-1-propanaminiuchloride
  • 2-[(aminocarbonyl)oxy]-n,n,n-trimethyl-1-propanaminiuchloride
  • ammonium,(2-hydroxypropyl)trimethyl-,chloride,carbamate
  • beta-methylcholinechlorideurethan
  • bethainecholinechloride
  • carbaminoyl,beta-methylcholinechloride
  • carbamyl-b-methylcholinechloride*crystalline
  • carbamylmethylcholinechloride
  • duvoid
  • mechothane
  • myocholine
  • urecholine
  • urecholinechloride
  • BETHANECHOL CHLORIDE
  • CARBAMYL-BETA-METHYLCHOLINE CHLORIDE
  • Bethanechol chloride USP
  • (2-Hydroxypropyl)trimethylammonium chloride carbamate (6CI)
  • 1-Propanaminium, 2-[(aminocarbonyl)oxy]-N,N,N-trimethyl-, chloride
  • Ammonium, (2-hydroxypropyl)trimethyl-, chloride, carbamate (8CI)
  • Besacholine
  • b-Methyl carbachol chloride
  • Mechotane
  • Mecothane
  • Mictone
  • Myotonachol
  • Myotonine chloride
  • BETHANECHOL CHLORIDE, PHARMA
  • 2-(Carbamoyloxy)-N,N,N-trimethyl-1-propanaminium Chloride
  • bisaikelin
  • NSC 30783
  • Trimethyl(2-carbamoyloxypropyl)ammonium chloride
  • Uro-Carb
  • β-Methylcholine chloride urethan
  • 2-[(Aminocarbonyl)oxy]-N,N,N-trimethyl-1-propanaminium chloride
  • 2-Carbamoyloxypropyltrimethylammonium chloride
  • Bethanechol
  • CARBAMYL-B-METHYLCHOLINECHLORIDE
  • Betaine choline chloride
  • Carbamyl-β-methylcholine chloride,Bethanechol chloride
  • Bethanechol Chloride (200 mg)
  • CarbaMyl-beta-Methylcholine chlori
  • Betanechol
  • Bthanechol chloride
  • 1-PropanaMiniuM,2-[(aMinocarbonyl)oxy]-N,N,N-triMethyl-, chloride (1:1)
  • 2-[(aminocarbonyl)oxy]-N,N,N-trimethyl-1-propanaminium,chloride (1:1)
  • 2-(carbamoyloxy)-N,N,N-trimethylpropan-1-aminium chloride
  • Bethanechol Chloride >
  • -β-methyL
  • Carbamyl-β-methylcholine chloride
  • Bethanechol USP/EP/BP
  • bethanechol chloride 590-63-6
  • 590-63-6
  • 90-63-6
  • C7H18ClN2O2
  • C7H17ClN2O2
  • C7H17N2O2Cl
  • Coumarins ,Pyrans
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