An α1- and α2-adrenergic and 5-HT1 receptor agonist
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Oxymetazoline (hydrochloride)

Item No. 23826

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethyl-phenol, monohydrochloride
CAS Number
2315-02-8
Synonyms
  • SCH 9384
Molecular Formula
C16H24N2O • HCl
Formula Weight
296.8
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 25 mg/mlEthanol: 25 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
OC1=C(C)C(CC2=NCCN2)=C(C)C=C1C(C)(C)C.Cl
InChi Code
InChI=1S/C16H24N2O.ClH/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14;/h8,19H,6-7,9H2,1-5H3,(H,17,18);1H
InChi Key
BEEDODBODQVSIM-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 mg

    $69

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    1 g

    $102

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    Product Description

    Oxymetazoline is an agonist of α1- and α2-adrenergic receptors (α1- and α2-ARs; Kds = 6, 320, and 390 nM for α1A-, α1B-, and α1D-ARs, respectively, Ki = 15 nM for α2-AR).1,2 It is also an agonist of the serotonin (5-HT) receptor subtype 5-HT1 (Kds = 4.68, 25.7, and 5.01 nM for 5-HT1A, 5-HT1B, and 5-HT1D, respectively).3 Oxymetazoline increases intracellular calcium levels in CHO cells transfected with the α1A-AR (EC50 = 40.7 nM), but does not increase it measurably in cells transfected with the α1B- or α1D-AR (EC50s = 79.4 and 240 nM, respectively).1 It acts as a partial agonist of the α2-AR in isolated perfused rat heart (IC50 = 63 nM and EC50 = 13.5 nM for norepinephrine release).4,5 Oxymetazoline also acts as an agonist and antagonist of the 5-HT1C receptor in the presence of methiothepin (Kd = 110 nM; Item No. 23138) and clonidine (Kd = 257 nM; Item No. 15949), respectively.3 In functional second messenger assays, oxymetazoline inhibits forskolin-stimulated adenylate cyclase activity (EC50s = 18.6, 24.0, and 44.7 nM in tissues expressing high levels of 5-HT1A, 5-HT1B, 5-HT1D receptors, respectively) and accumulation of inositol phosphates (EC50 = 269 nM in pig choroid plexus preparations, which highly express 5-HT1C receptors). Oxymetazoline (0.2 μg/kg) decreases nasal pressure in dogs by 6.9%.6 Formulations containing oxymetazoline have been used as nasal decongestants.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Horie, K., Obika, K., Foglar, R., et al. Selectivity of the imidazoline α-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned α1-adrenoceptor subtypes. Br. J. Pharmacol. 116(1), 1611-1618 (1995).

    2. Rouot, B., Quennedey, M.C., and Schwartz, J. Characteristics of the [3H]-yohimbine binding on rat brain α2-adrenoceptors. Naunyn Schmiedebergs Arch. Pharmacol. 321(4), 253-259 (1982).

    3. Schoeffter, P., and Hoyer, D. Interaction of the α-adrenoceptor agonist oxymetazoline with serotonin 5-HT1A, 5-HT1B, 5-HT1C and 5-HT1D receptors. Eur. J. Pharmacol. 196(2), 213-216 (1991).

    4. Fuder, H., Bath, F., Wiebelt, H., et al. Autoinhibition of noradrenaline release from the rat heart as a function of the biophase concentration. Effects of exogenous α-adrenoceptor agonists, cocaine, and perfusion rate. Naunyn Schmiedebergs Arch. Pharmacol. 325(1), 25-33 (1984).

    5. Fuder, H., Braun, H.-J., and Schimkus, R. Presynaptic alpha-2 adrenoceptor activation and coupling of the receptor-presynaptic effector system in the perfused rat heart: Affinity and efficacy of phenethylamines and imidazoline derivatives. J. Pharmacol. Exp. Ther. 237(1), 237-245 (1986).

    6. Carrillo, L., Kishimoto, T., and Aviado, D.M. The nasal and bronchopulmonary effects of oxymetazoline and KB227. Ann. Otol. Rhinol. Laryngol. 78(2), 415-424 (1969).