A muscarinic acetylcholine receptor agonist
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Labeled Version(s)
33299Bethanechol-d6 (chloride)
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Small Molecule Modulators
Receptor Pharmacology
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Bethanechol (chloride)

Item No. 23830

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[(aminocarbonyl)oxy]-N,N,N-trimethyl-1-propanaminium, monochloride
CAS Number
590-63-6
Synonyms
  • (±)-Bethanechol
  • Carbamyl-β-methylcholine chloride
  • NSC 30783
Molecular Formula
C7H17N2O2 • Cl
Formula Weight
196.7
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 0.1 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
CC(OC(N)=O)C[N+](C)(C)C.[Cl-]
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
InChi Key
XXRMYXBSBOVVBH-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 g

    $41

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    5 g

    $103

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    10 g

    $178

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    25 g

    $349

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    Product 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.1 It inhibits M2-mediated increases in cyclic AMP induced by isoproterenol (Item No. 15592) in isolated guinea pig small intestine (IC50 = 127 µM).2 Bethanechol increases basal tone of isolated porcine intravesical ureter (EC50 = 4.27 µM).3 It also induces fluid secretion in the ileum, duodenum, and jejunum of anesthetized rats when administered at a dose of 60 µg/kg.4 Formulations containing bethanechol have been used to increase urination and improve smooth muscle tone in the gastrointestinal tract.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Richards, M.H., and van Giersbergen, P.L. Human muscarinic receptors expressed in A9L and CHO cells: Activation by full and partial agonists. Br. J. Pharmacol. 114(6), 1241-1249 (1995).

    2. Okamoto, H., Prestwich, S.A., Asai, S., et al. Muscarinic agonist potencies at three different effector systems linked to the M2 or M3 receptor in longitudinal smooth muscle of guinea-pig small intestine. Br. J. Pharmacol. 135(7), 1765-1775 (2002).

    3. Hernández, M., Símonsen, U., Prieto, D., et al. Different muscarinic receptor subtypes mediating the phasic activity and basal tone of pig isolated intravesical ureter. Br. J. Pharmacol. 110(4), 1413-1420 (1993).

    4. Young, A., and Levin, R.J. Intestinal hypersecretion of the refed starved rat: A model for alimentary diarrhoea. Gut 33(8), 1050-1056 (1992).