An active metabolite of (±)-propranolol
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(±)-4-hydroxy Propranolol (hydrochloride)

Item No. 18630

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-1-naphthalenol, monohydrochloride
CAS Number
14133-90-5
Molecular Formula
C16H21NO3 • HCl
Formula Weight
311.8
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
λmax
208, 243, 319 nm
SMILES
OC1=CC=C(OCC(O)CNC(C)C)C2=C1C=CC=C2.Cl
InChi Code
InChI=1S/C16H21NO3.ClH/c1-11(2)17-9-12(18)10-20-16-8-7-15(19)13-5-3-4-6-14(13)16;/h3-8,11-12,17-19H,9-10H2,1-2H3;1H
InChi Key
ROUJENUXWIFONU-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $49

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    5 mg

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    10 mg

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    Product Description

    (±)-4-hydroxy Propranolol is an active metabolite of the β-adrenergic receptor antagonist (±)-propranolol (Item No. 23349).1 It is formed from propranolol by the cytochrome P450 (CYP) isoform CYP2D6.2 (±)-4-hydroxy Propranolol decreases tachycardia and vasodepression induced by the β1- and β2-adrenergic receptor agonist isoproterenol (Item No. 15592) in cats (EC50 = 54 µg/kg).1 It increases heart rate in rats depleted of catecholamines by the monocarboxylate transporter 1 (MCT1) and MCT2 inhibitor syrosingopine (Item No. 36402) when administered at doses of 10 and 80 µg/kg. (±)-4-hydroxy Propranolol decreases heart rate, myocardial contractility, and cardiac output in dogs in a dose-dependent manner.3 It also reduces superoxide-induced lipid peroxidation in isolated rat hepatic microsomes (IC50 = 1.1 µM) and prevents superoxide-induced depletion of glutathione (GSH) levels in bovine aortic endothelial cells (BAECs; EC50 = 1.2 µM).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fitzgerald, J.D., and O'Donnell, S.R. Pharmacology of 4-hydroxypropranolol, a metabolite of propranolol. Brit. J. Pharmacol. 43(1), 222-235 (1971).

    2. Yoshimoto, K., Echizen, H., Chiba, K., et al. Identification of human CYP isoforms involved in the metabolism of propranolol enantiomers–N-desisopropylation is mediated mainly by CYP1A2. Br. J. Clin. Pharmacol. 39(4), 421-431 (1995).

    3. Fitzgerald, J.D., and O'Donnell, S.R. A comparison of the haemodynamic effects of propranolol, 4-hydroxypropranolol and practolol in anaesthetized dogs. Brit. J. Pharmacol. 45(2), 207-217 (1972).

    4. Mak, I.T., and Weglicki, W.B. Potent antioxidant properties of 4-hydroxyl-propranolol. J. Pharmacol. Exp. Ther. 308(1), 85-90 (2004).

    Product Citations

    Negoro, R., Tasaka, M., Deguchi, S., et al. Generation of HepG2 cells with high expression of multiple drug-metabolizing enzymes for drug discovery research using a PITCh system. Cells 11(10), 1677 (2022).