A muscarinic acetylcholine receptor antagonist
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Oxyphenonium (bromide)

Item No. 23880

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[(2-cyclohexyl-2-hydroxy-2-phenylacetyl)oxy]-N,N-diethyl-N-methyl-ethanaminium, monobromide
CAS Number
50-10-2
Synonyms
  • (±)-Oxyphenonium
Molecular Formula
C21H34NO3 • Br
Formula Weight
428.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 33 mg/mlDMSO: 25 mg/mlEthanol: 33 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
CC[N+](CCOC(C(C1=CC=CC=C1)(O)C2CCCCC2)=O)(C)CC.[Br-]
InChi Code
InChI=1S/C21H34NO3.BrH/c1-4-22(3,5-2)16-17-25-20(23)21(24,18-12-8-6-9-13-18)19-14-10-7-11-15-19;/h6,8-9,12-13,19,24H,4-5,7,10-11,14-17H2,1-3H3;1H/q+1;/p-1
InChi Key
UKLQXHUGTKWPSR-UHFFFAOYSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $76

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    500 mg

    $321

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    Product Description

    Oxyphenonium is an antagonist of muscarinic acetylcholine receptors that binds to muscarinic receptors on isolated guinea pig atria and ileum (Kds = 0.11 and 0.17 nM, respectively).1 In vivo, oxyphenonium reverses carbaminocholine- and acetylcholine-induced decreases in blood pressure in anesthetized cats (ED50s = 0.591 and 1 μg/kg, respectively).2 It decreases rumenal ulcer formation in rats and suppresses insulin-induced gastric secretion in dogs with gastric fistulas.3 Oxyphenonium also prevents form-deprivation myopia (FDM) in a chick model of experimental myopia.4 Formulations containing oxyphenonium have been used to treat peptic ulcers.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Eglen, R.M., and Whiting, R.L. Competitive and non-competitive antagonism exhibited by “selective” antagonists at atrial and ileal muscarinic receptor subtypes. Br. J. Pharmacol. 90(4), 701-707 (1987).

    2. Wilimowski, M., Orzechowska, K., Prandota, J., et al. Comparative quantitative studies on cholinolytics. 3. The action of propanteline, methanteline, oxyphenonium and diphemanil. Arch. Immunol. Ther. Exp. (Warsz.) 18(1), 139-142 (1970).

    3. Barrett, W.E., Rutledge, R., Plummer, A.J., et al. Inhibition of ulcer formation in the Shay rat and reduction of gastric acidity in dogs by antrenyl (oxyphenonium) (BA5473) diethyl(2-hydroxyethyl)methylammonium bromide α-phenyl-cyclohexaneglycolate, an anticholinergic agent. J. Pharmacol. Exp. Ther. 108(3), 305-316 (1953).

    4. Luft, W.A., Ming, Y., and Stell, W.K. Variable effects of previously untested muscarinic receptor antagonists on experimental myopia. Invest. Ophthalmol. Vis. Sci. 44(3), 1330-1338 (2003).