IUPAC/Chemical Name
2-(carbamoyloxy)-N,N,N-trimethylpropan-1-aminium chloride
InChi Key
XXRMYXBSBOVVBH-UHFFFAOYSA-N
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
SMILES Code
CC(OC(N)=O)C[N+](C)(C)C.[Cl-]
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Bethanechol chloride is a mAChR agonist.
In vitro activity:
To determine whether bethanechol has a direct effect on pancreatic β cells, BrdU incorporation was investigated in the pancreatic β-cell line MIN6. BrdU incorporation increased significantly in the bethanechol-treated cells in a concentration-dependent manner (Fig. 4A,B). This increase was suppressed completely by the addition of atropine 50 µM (Fig. 4C). The Akt inhibitor perifosine (5 µM) inhibited the bethanechol (1 mM)-induced incorporation of BrdU (Fig. 4D), whereas the mitogen-activated protein kinase (MEK) inhibitor PD98059 (50 µM) did not (Fig. 4E).
Reference: Sci Rep. 2019 Nov 7;9(1):16180. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6838462/
In vivo activity:
To examine the effect of bethanechol in a mouse model of diabetes, it was administered to IRS-2−/− mice, which show insulin resistance and high glucose levels. Bethanechol (2 µg/g) was injected subcutaneously 15 min prior to oral glucose loading in wild-type mice and IRS-2−/− mice. Bethanechol increased insulin secretion and improved glucose tolerance in both types of mice (Fig. 1A). The bethanechol-induced secretion of insulin in the IRS-2−/− mice was higher than that in the wild-type mice (Fig. 1B). The results of the insulin tolerance test revealed no significant difference in glucose levels between the control and bethanechol groups of wild-type mice; however, 30 min following insulin injection, the glucose level in the bethanechol-injected IRS-2−/− mice was significantly lower than that in the control mice (Fig. 1C).
Reference: Sci Rep. 2019 Nov 7;9(1):16180. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6838462/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
16.7 |
84.96 |
|
| Ethanol |
39.0 |
198.29 |
|
| Water |
44.5 |
226.26 |
|
| PBS (pH 7.2) |
5.0 |
25.42 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
196.68
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Ito Y, Kaji M, Sakamoto E, Terauchi Y. The beneficial effects of a muscarinic agonist on pancreatic β-cells. Sci Rep. 2019 Nov 7;9(1):16180. doi: 10.1038/s41598-019-52691-8. PMID: 31700039; PMCID: PMC6838462.
In vitro protocol:
1. Ito Y, Kaji M, Sakamoto E, Terauchi Y. The beneficial effects of a muscarinic agonist on pancreatic β-cells. Sci Rep. 2019 Nov 7;9(1):16180. doi: 10.1038/s41598-019-52691-8. PMID: 31700039; PMCID: PMC6838462.
In vivo protocol:
1. Ito Y, Kaji M, Sakamoto E, Terauchi Y. The beneficial effects of a muscarinic agonist on pancreatic β-cells. Sci Rep. 2019 Nov 7;9(1):16180. doi: 10.1038/s41598-019-52691-8. PMID: 31700039; PMCID: PMC6838462.
1: Suaid HJ, Rocha JN, Martins AC, Cologna AJ, Tucci SJ. Modulation of urethral alpha-sympathetic by parasympathetic before and following bethanechol chloride injection. Int Braz J Urol. 2003 Mar-Apr;29(2):162-5. PubMed PMID: 15745502.
2: Liu L, Rittenhouse AR. Pharmacological discrimination between muscarinic receptor signal transduction cascades with bethanechol chloride. Br J Pharmacol. 2003 Apr;138(7):1259-70. PubMed PMID: 12711626; PubMed Central PMCID: PMC1573771.
3: Allen LV Jr, Erickson MA. Stability of bethanechol chloride, pyrazinamide, quinidine sulfate, rifampin, and tetracycline hydrochloride in extemporaneously compounded oral liquids. Am J Health Syst Pharm. 1998 Sep 1;55(17):1804-9. PubMed PMID: 9775343.
4: Schlatter JL, Saulnier JL. Bethanechol chloride oral solutions: stability and use in infants. Ann Pharmacother. 1997 Mar;31(3):294-6. PubMed PMID: 9066934.
5: Baranowska-Daca E, Torneli J, Popovich RP, Moncrief JW. Use of bethanechol chloride to increase available ultrafiltration in CAPD. Adv Perit Dial. 1995;11:69-72. PubMed PMID: 8534741.
6: Taillandier J, Boiteux JP, Boyer L, Guy L, Giraud B. Re: Detection of missing vesicoureteral reflux with bethanechol chloride-aided voiding cystourethrography. J Urol. 1993 Apr;149(4):867-8. PubMed PMID: 8095993.
7: Araki T, Nakano S, Sugimura Y, Tochigi H, Kawamura J, Kato T, Tajima K, Chigusa I, Saito K, Morisita H, et al. [Efficacy of combination of Ea-0643 (bunazosin hydrochloride) and bethanechol chloride in patients with neurogenic bladder]. Hinyokika Kiyo. 1990 Nov;36(11):1379-83. Japanese. PubMed PMID: 1981126.
8: Harbaugh RE, Reeder TM, Senter HJ, Knopman DS, Baskin DS, Pirozzolo F, Chui HC, Shetter AG, Bakay RA, Leblanc R, et al. Intracerebroventricular bethanechol chloride infusion in Alzheimer's disease. Results of a collaborative double-blind study. J Neurosurg. 1989 Oct;71(4):481-6. PubMed PMID: 2571689.
9: Koyanagi T, Morita H, Gotoh T, Nonomura K, Togashi M, Nantani M. Detection of missing vesicoureteral reflux with bethanechol chloride-aided voiding cystourethrography. J Urol. 1989 Mar;141(3):580-2. PubMed PMID: 2563779.
10: Zgourides GD. Bethanechol chloride as a suggested adjunct to prolonged in vivo exposure therapy in the treatment of paruresis. Percept Mot Skills. 1988 Feb;66(1):319-22. PubMed PMID: 2896331.
