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Bethanechol

Product Name
Bethanechol
CAS No.
590-63-6
Chemical Name
Bethanechol
Synonyms
BETHANECHOL CHLORIDE;duvoid;Betanechol;Bthanechol chloride;Mictone;Uro-Carb;Mechotane;Mecothane;NSC 30783;-β-methyL
CBNumber
CB8156880
Molecular Formula
C7H17ClN2O2
Formula Weight
196.68
MOL File
590-63-6.mol
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Bethanechol Property

Melting point:
187-190°C
storage temp. 
Inert atmosphere,2-8°C
solubility 
H2O: 1.7 g/mL stable for several days at 4°C.
form 
crystalline
color 
white
Merck 
14,1185
CAS DataBase Reference
590-63-6(CAS DataBase Reference)
EPA Substance Registry System
1-Propanaminium, 2-[(aminocarbonyl)oxy]-N,N,N-trimethyl-, chloride (590-63-6)
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Safety

Hazard Codes 
Xn
Risk Statements 
22
Safety Statements 
36
WGK Germany 
3
RTECS 
BR5425000
TSCA 
Yes
HS Code 
2924190002
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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
C5259
Product name
Carbamyl-β-methylcholine chloride
Purity
≥99% (TLC), crystalline
Packaging
5g
Price
$214
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR2357
Product name
Bethanechol Chloride
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
300MG
Price
$170
Updated
2024/03/01
Sigma-Aldrich
Product number
1071009
Product name
Bethanechol chloride
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
B4828
Product name
Bethanechol Chloride
Purity
>98.0%(T)
Packaging
5g
Price
$107
Updated
2024/03/01
TCI Chemical
Product number
B4828
Product name
Bethanechol Chloride
Purity
>98.0%(T)
Packaging
25g
Price
$266
Updated
2024/03/01
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Bethanechol Chemical Properties,Usage,Production

Description

Bethanechol is an agonist of muscarinic acetylcholine receptors with IC50 values of 1,837, 25, 631, 317, and 393 μM for M1-5, respectively, in a radioligand binding assay using CHO cells expressing the human receptors. It inhibits M2-mediated increases in cyclic AMP induced by isoproterenol in isolated guinea pig small intestine (IC50 = 127 μM). Bethanechol increases basal tone of isolated porcine intravesical ureter (EC50 = 4.27 μM). It also induces fluid secretion in the ileum, duodenum, and jejunum of anesthetized rats when administered at a dose of 60 μg/kg. Formulations containing bethanechol have been used to increase urination and improve smooth muscle tone in the gastrointestinal tract.

Chemical Properties

White Solid

Originator

Urecholine CI,MSD,US,1949

Uses

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.

Uses

cholinergic

Uses

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.

brand name

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

Therapeutic Function

Cholinergic

General Description

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.

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.

Bethanechol Preparation Products And Raw materials

Raw materials

Preparation Products

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Bethanechol Suppliers

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View Lastest Price from Bethanechol manufacturers

Henan Suikang Pharmaceutical Co.,Ltd.
Product
Bethanechol 590-63-6
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99.0%
Supply Ability
1tons
Release date
2024-04-26
Hebei Weibang Biotechnology Co., Ltd
Product
Bethanechol 590-63-6
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5tons
Release date
2024-12-05
.GZ HONESTCHEM CO.,LTD
Product
bethanechol chloride 590-63-6 590-63-6
Price
US $1.00/g
Min. Order
10000000g
Purity
99.9%
Supply Ability
5000
Release date
2021-05-19

590-63-6, BethanecholRelated Search:

Acetylcholine chloride Calcium chloride Ammonium chloride Polyvinyl chloride Carbachol Acetylcholine Sulfuryl chloride Ferric chloride Choline chloride SUCCINYL CHLORIDE Sodium chloride Potassium chloride Ammonium sulfamate P-AMINOBENZAMIDE GLUTAMIC ACID ALUMINUM CLOFIBRATE Clofibrate Moclobemide BETHANECHOL

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