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Purity: ≥98%
Bethanechol Chloride (also known as Carbamyl-β-methylcholine chloride) is a parasympathomimetic choline carbamate and an analog of acetylcholine with a long duration of action due to improved metabolic stability. Unlike acetylcholine, bethanechol is not hydrolyzed by cholinesterase. It has been used to treat certain bladder problems such as the inability to urinate or empty the bladder completely due to certain causes. It acts as a selective muscarinic receptor agonist without any effect on nicotinic receptors. Bethanechol alleviates dry mouth and is sometimes given orally or subcutaneously to treat urinary retention resulting from general anesthetic, diabetic neuropathy of the bladder, or a side effect of antidepressants; or to treat gastrointestinal lack of muscular tone.
| Targets |
Muscarinic acetylcholine receptors (M1-M5, predominantly M3) [1]
- Muscarinic receptors (M2, M3 subtypes) and nicotinic acetylcholine receptors (minor involvement) on mouse ileal pacemaker cells [2] |
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| ln Vitro |
Ileal pacemaker potential is considerably decreased by carbachol chloride (0.3-300 μM) [2].
In isolated rabbit jejunal smooth muscle strips, Bethanechol chloride (10⁻⁷ M to 10⁻⁵ M) induced concentration-dependent contraction; the contraction amplitude increased with increasing drug concentration, and this effect was completely antagonized by atropine (a non-selective muscarinic receptor antagonist) [1] - In cultured mouse ileal tissue, Bethanechol chloride (10⁻⁶ M to 10⁻⁴ M) exerted both inhibitory and excitatory effects on ileal pacemaker activity: the excitatory effect was blocked by M3 receptor antagonists, while the inhibitory effect was reversed by M2 receptor antagonists [2] - Bethanechol chloride is resistant to hydrolysis by acetylcholinesterase, maintaining prolonged receptor activation compared to acetylcholine in in vitro assays [1] |
| ln Vivo |
In rats, dose-dependent increases in urine production and alcohol consumption are induced by methacholine (2–12 mg/kg) administered intraperitoneally [4].
In rats, intraperitoneal administration of Bethanechol chloride (0.5 mg/kg, 1 mg/kg, 2 mg/kg) induced dose-dependent water intake; the maximum effect was observed at 1 mg/kg, with a 2.8-fold increase in water consumption within 1 hour compared to the control group [3] - In a rat model of postoperative urinary retention, subcutaneous injection of Bethanechol chloride (0.1 mg/kg to 0.3 mg/kg) significantly enhanced bladder contractility, promoted urination, and reduced residual urine volume by 40-60% compared to untreated controls [1] - In mice, oral administration of Bethanechol chloride (1 mg/kg to 5 mg/kg) accelerated gastrointestinal motility, as indicated by a 30-50% reduction in gastrointestinal transit time of a non-absorbable marker [1] |
| Enzyme Assay |
Muscarinic acetylcholine receptor binding assay: Membrane fractions containing M1-M5 receptors were isolated from rabbit jejunal smooth muscle tissue. The membrane fractions were incubated with serial concentrations of Bethanechol chloride in the presence of a tritiated muscarinic receptor ligand. After incubation at 37°C for 60 minutes, unbound ligands were removed by filtration through pre-washed filters. The radioactivity of the filter-bound fraction was measured using a liquid scintillation counter to determine the binding affinity and specificity of Bethanechol chloride for muscarinic receptors [1]
- Acetylcholinesterase resistance assay: Bethanechol chloride and acetylcholine were incubated with purified acetylcholinesterase at 37°C for 30 minutes. The remaining concentration of the compounds was measured via a colorimetric assay based on the reaction with dithio-bis-nitrobenzoic acid. The assay showed minimal hydrolysis of Bethanechol chloride compared to acetylcholine [1] |
| Animal Protocol |
Animal/Disease Models: Blue Spruce Farm (SD (SD (Sprague-Dawley))) female rats (280-330 g) [4]
Doses: 2 mg/kg, 4 mg/kg, 8 mg/kg, 12 mg/kg Route of Administration: intraperitoneal (ip) injection Experimental Results: Water intake increased in a dose-dependent manner during the first hour up to the highest dose administered (12 mg/kg). Rat water intake model: Male rats were deprived of water for 18 hours before the experiment. Bethanechol chloride was dissolved in normal saline and administered via intraperitoneal injection at doses of 0.5 mg/kg, 1 mg/kg, and 2 mg/kg. Control rats received an equal volume of normal saline. Water intake was measured at 15-minute intervals for 1 hour after administration, and total water consumption was recorded [3] - Rat postoperative urinary retention model: Rats were anesthetized and subjected to a surgical procedure to induce urinary retention. Twenty-four hours after surgery, Bethanechol chloride was administered via subcutaneous injection at doses of 0.1 mg/kg, 0.2 mg/kg, and 0.3 mg/kg. Bladder pressure was monitored via a transurethral catheter, and residual urine volume was measured 2 hours after drug administration [1] - Mouse gastrointestinal motility model: Mice were fasted for 12 hours and then administered Bethanechol chloride (1 mg/kg, 3 mg/kg, 5 mg/kg) via oral gavage. Thirty minutes later, a charcoal suspension (non-absorbable marker) was administered orally. Mice were sacrificed 30 minutes after charcoal administration, and the gastrointestinal tract was excised. Gastrointestinal transit time was calculated as the distance the charcoal had traveled relative to the total length of the small intestine [1] |
| ADME/Pharmacokinetics |
Due to significant first-pass metabolism in the liver, the oral bioavailability of betanizol chloride is approximately 10-20%[1]. The steady-state volume of distribution (Vdss) is approximately 0.5 L/kg. Due to its quaternary ammonium structure, its distribution in the central nervous system is extremely limited[1]. Betanizol chloride is not easily hydrolyzed by acetylcholinesterase, and its elimination half-life is approximately 2-4 hours[1]. It is mainly excreted unchanged in the urine, with a renal clearance of approximately 10 mL/min/kg[1].
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| Toxicity/Toxicokinetics |
Common adverse reactions include gastrointestinal symptoms (nausea, vomiting, abdominal cramps, diarrhea) and cholinergic effects (salivation, sweating, lacrimation, miosis), all of which occur at therapeutic doses [1]
- High doses (≥10 mg/kg in rats) may cause severe bradycardia, hypotension, and respiratory depression due to excessive cholinergic stimulation [1] - Drug interactions: Co-administration with anticholinergic drugs (e.g., atropine) may antagonize the pharmacological effects of betanizol chloride [1] |
| References | |
| Additional Infomation |
Bethanechol chloride is the chloride of betanyl. It is a slowly hydrolyzed muscarinic receptor agonist with no nicotine-like effects, used to increase smooth muscle tone, for example, for gastrointestinal recovery after abdominal surgery, for the treatment of gastroesophageal reflux disease, and as an alternative to catheterization in the treatment of non-obstructive urinary retention. It is a muscarinic receptor agonist. It is a carbamate, quaternary ammonium salt, and chloride. It contains the betanyl molecule.
Betanyl chloride is a synthetic quaternary ammonium base derivative belonging to the parasympathomimetic class of drugs. Betanyl is a slowly hydrolyzed muscarinic receptor agonist with no nicotine-like effects. Betanyl is commonly used to increase smooth muscle tone, for the treatment of reflux esophagitis, and to promote urination after surgery, in cases of urinary tract infection, or in cases of benign prostatic hyperplasia. It may cause hypotension, heart rate changes, and bronchospasm. (NCI04) A slowly hydrolyzed muscarinic receptor agonist with no nicotine-like effects. Betanidol is commonly used to increase smooth muscle tone, such as in the gastrointestinal tract after abdominal surgery or in non-obstructive urinary retention. It may cause hypotension, heart rate changes, and bronchospasm. See also: Betanidol (containing the active ingredient). Betanyl chloride is a synthetic cholinergic agonist that selectively activates muscarinic acetylcholine receptors and has a very low affinity for nicotine receptors[1] - Its mechanism of action involves direct stimulation of M3 receptors in the gastrointestinal and urinary tracts, thereby enhancing smooth muscle contraction and glandular secretion[1][2] - Clinically, it is used to treat postoperative urinary retention, neurogenic bladder dysfunction, and gastroparesis[1] - In rats, its water-inducing effect may be achieved by stimulating gastrointestinal osmoreceptors or by directly activating the cholinergic pathway that regulates thirst in the central nervous system[3] |
| Molecular Formula |
C7H17N2O2.CL
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| Molecular Weight |
196.68
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| Exact Mass |
196.097
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| CAS # |
590-63-6
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| Related CAS # |
Bethanechol;674-38-4;Bethanechol-d6 chloride
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| PubChem CID |
11548
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| Appearance |
White to off-white solid powder
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| Melting Point |
187-190ºC
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
12
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| Complexity |
140
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
XXRMYXBSBOVVBH-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H16N2O2.ClH/c1-6(11-7(8)10)5-9(2,3)4;/h6H,5H2,1-4H3,(H-,8,10);1H
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| Chemical Name |
2-(carbamoyloxy)-N,N,N-trimethylpropan-1-aminium chloride
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 100 mg/mL (508.44 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.0844 mL | 25.4220 mL | 50.8440 mL | |
| 5 mM | 1.0169 mL | 5.0844 mL | 10.1688 mL | |
| 10 mM | 0.5084 mL | 2.5422 mL | 5.0844 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT05299008 | Recruiting | Drug: Bethanechol | Tracheobronchomalacia | Arkansas Children's Hospital Research Institute | August 11, 2022 | |
| NCT03572283 | Recruiting | Drug: Bethanechol | Pancreas Cancer | Columbia University | April 8, 2018 | Early Phase 1 |
| NCT05241249 | Recruiting | Drug: Bethanechol Drug: Gemcitabine Drug: nab-paclitaxel |
Pancreas Cancer | Susan E. Bates | February 1, 2022 | Phase 2 |
| NCT01031043 | Completed Has Results | Drug: Bethanechol | Esophageal Dysmotility | Augusta University | November 2009 | Phase 1 |
| NCT02058537 | Terminated Has Results | Drug: Bethanechol | Eosinophilic Esophagitis (EoE) | University of Iowa | February 2014 | Phase 2 |
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