590-63-6 Usage
Description
Bethanechol, also known as β-methylcholinechloride carbamate, (2-hydroxypropyl)trimethylammoniumchloride carbamate, and carbamylmethylcholinechloride (Urecholine), is a nonspecific agonist of muscarinic acetylcholine receptors. It has pharmacological properties similar to those of methacholine and is a carbamyl ester. Bethanechol is inactivated more slowly by AChE in vivo than methacholine, making it more stable in aqueous solutions.
Uses
Used in Pharmaceutical Industry:
Bethanechol is used as a selective muscarinic receptor stimulant for treating cerebral palsy and other conditions related to smooth muscle contraction.
Used in Gastrointestinal Treatment:
Bethanechol is used as a therapeutic agent for treating post-operational non-obstructive retention of urine and neurogenic bladder atony. It increases urination and improves smooth muscle tone in the gastrointestinal tract.
Used in Gastro-oesophageal Reflux Disease Treatment:
Bethanechol is used as an alternative to catheterisation in the treatment of non-obstructive urinary retention and for increasing smooth muscle tone in the gastrointestinal tract following abdominal surgery.
Used in Alzheimer's Disease Treatment:
Although not as effective as initially thought, Bethanechol was previously used for treating gastrointestinal illnesses and Alzheimer's disease.
Chemical Properties:
Bethanechol is a white solid and is available under various brand names such as Duvoid (WellSpring), Myotonachol (Glenwood), and Urecholine (Odyssey).
Originator
Urecholine CI,MSD,US,1949
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.
Therapeutic Function
Cholinergic
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.
Check Digit Verification of cas no
The CAS Registry Mumber 590-63-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 0 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 590-63:
(5*5)+(4*9)+(3*0)+(2*6)+(1*3)=76
76 % 10 = 6
So 590-63-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H16N2O2.ClH/c1-6(11-7(8)10)5-9(2,3)4;/h6H,5H2,1-4H3,(H-,8,10);1H/p+1
