32780-64-6

Basic information

• Product Name: Labetalol hydrochloride
• Synonyms: 5-(1-hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)salicylamidehydrochlori;5-(1-hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)-salicylamidhydroch;ah5158a;amipress;ipolab;labelol;labrocol;normadate
• CAS NO: 32780-64-6
• Molecular Formula: C₁₉H₂₄N₂O₃*ClH
• Molecular Weight: 364.87
• EINECS: 251-211-1
• Product Categories: WYAMINE
• Mol File: 32780-64-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 187-189°
• Boiling Point: 552.7 °C at 760 mmHg
• Flash Point: 288.1 °C
• Appearance: white/powder
• Vapor Pressure: 4.75E-13mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble
• CAS DataBase Reference: Labetalol hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Labetalol hydrochloride(32780-64-6)
• EPA Substance Registry System: Labetalol hydrochloride(32780-64-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: CV5376000
• Hazardous Substances Data: 32780-64-6(Hazardous Substances Data)

Usage

Chemical Properties

White or almost white powder.

Originator

Trandate,Allen and Hanburys,UK,1977

Uses

Different sources of media describe the Uses of 32780-64-6 differently. You can refer to the following data:
1. vasoconstrictor
2. tropane alkaloid, anticholinergic drug

Manufacturing Process

(a) 5-Bromoacetylsalicylamide (2.6 g), N-benzyl-N-(1-methyl-3-phenylpropyl) amine (4.8 g) and methyl ethyl ketone (50 ml) were heated at reflux for 40 minutes. The solvent was removed and the residue was treated with benzene. The secondary amine hydrobromide was filtered off and discarded, and the filtrate was evaporated to dryness. The residue was treated with an excess of ethanolic hydrogen chloride when 5-[N-benzyl-N-(1-methyl-3-phenylpropyl)- glycyl]-salicylamide hydrochloride (1.15 g) crystallized out, MP 139°C to 141°C.(b) 5-[N-benzyl-N-(1-methyl-3-phenylpropyl)glycyl]-salicylamide hydrochloride (0.75 g), 10% mixture of PdO and PtO on carbon catalyst (0.1 g) and ethanol (20 ml) were shaken at room temperature and pressure with hydrogen until uptake ceased. The catalyst was filtered off and the filtrate evaporated to dryness. The residue was crystallized from ethanol to give 5-[1- hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl]salicylamide hydrochloride as a white solid (0.40 g), MP 188°C.

Brand name

Normodyne (Schering); Trandate (Promethus).

Therapeutic Function

Alpha-adrenergic blocker, Beta-adrenergic blocker

Biological Activity

labetalol hcl is a selective antagonist for the α1-adrenergic receptor and a non-selective antagonist for the β-adrenergic receptor. labetalol hcl has been used for the treatment of high blood pressure. labetalol hcl competitively targets the α1-adrenergic receptors expressed in vascular smooth muscle, thus inhibiting adrenergic stimulation on endothelial cells and vasoconstriction in peripheral blood vessels. labetalol hcl also blocks the β-adrenergic receptors in bronchial and vascular smooth muscle to counteract adrenergic stimulation. ultimately, labetalol hcl causes decreases in resting and exercise heart rates, cardiac output, as well as in both systolic and diastolic blood pressure, exherting vasodilation, as well as negative chronotropic and inotropic cardiac effects.1. national center for biotechnology information (2021). pubchem compound summary for cid 3869, labetalol. retrieved august 21, 2021.2. dage rc, hsieh cp. direct vasodilatation by labetalol in anaesthetized dogs. british journal of pharmacology, 1980, 70(2): 287-293.

Clinical Use

#N/A

Drug interactions

Labetalol is subject to considerable first-pass metabolism. It is metabolised mainly in the liver, the metabolites being excreted in the urine with only small amounts of unchanged labetalol; its major metabolite has not been found to have significant alpha- or beta-blocking effects. Excretion also occurs in the faeces via the bile

Metabolism

Labetalol is subject to considerable first-pass metabolism. It is metabolised mainly in the liver, the metabolites being excreted in the urine with only small amounts of unchanged labetalol; its major metabolite has not been found to have significant alpha- or beta-blocking effects. Excretion also occurs in the faeces via the bile

InChI:InChI=1/C19H24N2O3.ClH/c1-13(7-8-14-5-3-2-4-6-14)21-12-18(23)15-9-10-17(22)16(11-15)19(20)24;/h2-6,9-11,13,18,21-23H,7-8,12H2,1H3,(H2,20,24);1H

Synthetic route

2-hydroxy-5-benzamide hydrochloride (32780-63-5) → labetalol hydrochloride (32780-64-6)

Conditions	Yield
With hydrogen; platinum on activated charcoal; palladium oxide on charcoal In ethanol under 760 Torr; Ambient temperature;	67%

PtO on carbon + 4-Phenyl-2-butanone (2550-26-7) + 5-(N,N-dibenzylamino)acetylsalicylamide (30566-92-8) → labetalol hydrochloride (32780-64-6)

Conditions	Yield
With hydrogenchloride; hydrogen; trimethyleneglycol In methanol; ethanol; acetic acid; ethyl acetate

C19H22N2O3 (85665-85-6) → labetalol hydrochloride (32780-64-6)

Conditions	Yield
Stage #1: C19H22N2O3 With water; sodium hydroxide In methanol at 1 - 20℃; for 0.5h; Stage #2: With sodium tetrahydroborate; water In methanol at 15 - 25℃; Stage #3: With hydrogenchloride In methanol; water at 20℃; for 2h; pH=2;

labetalol hydrochloride (32780-64-6) → 5-formyl-2-hydroxy-benzamide (76143-20-9)

Conditions	Yield
Stage #1: labetalol hydrochloride With sodium hydrogencarbonate In water Stage #2: With sodium periodate In water at 20℃; for 0.583333h; Stage #3: With hydrogenchloride In water for 0.0333333h;	70%

labetalol hydrochloride (32780-64-6) → (R,S)-2-hydroxy-5-<2-<(1-methyl-3-phenylpropyl)amino>ethyl>benzamide hydrochloride (32551-03-4, 83167-26-4, 83167-30-0)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium dihydroxide In ethanol under 2280 Torr; for 672h; Ambient temperature;	47%

labetalol hydrochloride (32780-64-6) → (RS)-1-methyl-3-phenylpropylamine (22374-89-6) + 5-formyl-2-hydroxy-benzamide (76143-20-9)

Conditions	Yield
With sodium periodate; sodium carbonate at 25℃; for 0.166667h;

1-methyl-2-fluoropyridinium p-toluenesulfonate (58086-67-2) + labetalol hydrochloride (32780-64-6) → C25H30N3O3(1+)*C7H7O3S(1-)

Conditions	Yield
With triethylamine In dimethyl sulfoxide; acetonitrile at 20℃; for 0.0833333h;

labetalol hydrochloride (32780-64-6) → (Z)-2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxy-phenyl)-2-phenyI-but-1-enyl]-phenoxy}-ethyl)-methyl-amino]-ethoxyimino}-methyl)-benzamide + (E)-2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxy-phenyl)-2-phenyI-but-1-enyl]-phenoxy}-ethyl)-methyl-amino]-ethoxyimino}-methyl)-benzamide

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: ethanol; water View Scheme

labetalol hydrochloride (32780-64-6) → (Z)-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxy-phenyl)-2-phenyl-but-1-enyl]-phenoxy}-ethyl)-methyl-amino]-ethoxyimino}-methyl)-benzamide]-doxorubicin + (E)-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxy-phenyl)-2-phenyl-but-1-enyl]-phenoxy}-ethyl)-methyl-amino]-ethoxyimino}-methyl)-benzamide]-doxorubicin

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: water; N,N-dimethyl-formamide / 0.75 h / 55 °C 3.1: trifluoroacetic acid / ethanol; water / 2 h / 20 °C View Scheme

labetalol hydrochloride (32780-64-6) → 5-(2-bromoethoxymethyl)-2-hydroxybenzamide (636595-41-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: 55 °C 2.2: 4 h / 20 - 55 °C View Scheme

labetalol hydrochloride (32780-64-6) → 2-hydroxy-5-(4-hydroxy-but-2-ynyloxymethyl)-benzamide (636595-52-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 60 °C View Scheme

labetalol hydrochloride (32780-64-6) → 2-hydroxy-5-[2-(2-hydroxyethoxy)ethoxymethyl]benzamide (636595-48-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 70 °C View Scheme

labetalol hydrochloride (32780-64-6) → 6-(4-bromobut-2-ynyloxymethyl)-2,2-dimethyl-2,3-dihydrobenzo[e][1,3]oxazin-4-one (636595-66-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 60 °C 3.1: toluene-4-sulfonic acid / acetone / 1.5 h / 85 °C / Heating / reflux 4.1: pyridine / tetrahydrofuran / 0.5 h / 20 °C 4.2: 1 h / 20 °C View Scheme

labetalol hydrochloride (32780-64-6) → 6-(4-hydroxybut-2-ynyloxymethyl)-2,2-dimethyl-2,3-dihydro-benzol[e][1,3]-oxazin-4-one (636595-58-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 60 °C 3.1: toluene-4-sulfonic acid / acetone / 1.5 h / 85 °C / Heating / reflux View Scheme

labetalol hydrochloride (32780-64-6) → 6-[2-(2-hydroxyethoxy)ethoxymethyl]-2,2-dimethyl-2,3-dihydro-benzo[e][1,3]oxazin-4-one (636595-54-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 70 °C 3.1: toluene-4-sulfonic acid / acetone / 1.5 h / 80 °C / Heating / reflux View Scheme

labetalol hydrochloride (32780-64-6) → 2-hydroxy-5-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxymethyl}-benzamide (636595-50-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 70 °C View Scheme

labetalol hydrochloride (32780-64-6) → methanesulfonic acid 2-[2-(2,2-dimethyl-4-oxo-3,4-dihydro-2H-benzo[e][1,3]oxazin-6-ylmethoxy)ethoxy]ethyl ester (636595-61-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 70 °C 3.1: toluene-4-sulfonic acid / acetone / 1.5 h / 80 °C / Heating / reflux 4.1: pyridine / tetrahydrofuran / 0.5 h / 20 °C 4.2: 2 h / 20 °C View Scheme

labetalol hydrochloride (32780-64-6) → 6-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxymethyl}-2,2-dimethyl-2,3-dihydro-benzo[e][1,3]oxazin-4-one (636595-56-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 70 °C 3.1: toluene-4-sulfonic acid / acetone / 1.5 h / 80 °C / Heating / reflux View Scheme

labetalol hydrochloride (32780-64-6) → 5-{4-[3-(4-cyano-3-trifluoromethyl-phenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]-but-2-ynyloxymethyl}-2-hydroxy-benzamide (636595-81-8)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 60 °C 3.1: toluene-4-sulfonic acid / acetone / 1.5 h / 85 °C / Heating / reflux 4.1: pyridine / tetrahydrofuran / 0.5 h / 20 °C 4.2: 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C 5.2: 6 h / 20 °C 6.1: water; toluene-4-sulfonic acid / methanol / 24 h / 90 °C / Heating / reflux View Scheme

labetalol hydrochloride (32780-64-6) → 5-(2-{2-[3-(4-cyano-3-trifluoromethyl-phenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]-ethoxy}-ethoxymethyl)-2-hydroxy-benzamide

Conditions

Yield

Multi-step reaction with 6 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 70 °C 3.1: toluene-4-sulfonic acid / acetone / 1.5 h / 80 °C / Heating / reflux 4.1: pyridine / tetrahydrofuran / 0.5 h / 20 °C 4.2: 2 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C 5.2: 24 h / 60 °C 6.1: water; toluene-4-sulfonic acid / methanol / 30 h / 90 °C / Heating / reflux View Scheme

labetalol hydrochloride (32780-64-6) → 4-{3-[4-(2,2-dimethyl-4-oxo-3,4-dihydro-2H-benzo[e][1,3]oxazin-6-ylmethoxy)but-2-ynyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl}-2-trifluoromethylbenzonitrile (636595-74-9)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 60 °C 3.1: toluene-4-sulfonic acid / acetone / 1.5 h / 85 °C / Heating / reflux 4.1: pyridine / tetrahydrofuran / 0.5 h / 20 °C 4.2: 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C 5.2: 6 h / 20 °C View Scheme

labetalol hydrochloride (32780-64-6) → 4-(3-{2-[2-(2,2-dimethyl-4-oxo-3,4-dihydro-2H-benzo[e][1,3]oxazin-6-ylmethoxy)-ethoxy]-ethyl}-4,4-dimethyl-2,5-dioxo-imidazolidin-1-yl)-2-trifluoromethyl-benzonitrile (636595-68-1)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 70 °C 3.1: toluene-4-sulfonic acid / acetone / 1.5 h / 80 °C / Heating / reflux 4.1: pyridine / tetrahydrofuran / 0.5 h / 20 °C 4.2: 2 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C 5.2: 24 h / 60 °C View Scheme

labetalol hydrochloride (32780-64-6) → 5-[2-(4-{4-[3-(4-cyano-3-trifluoromethyl-phenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]-butyl}-piperazin-1-yl)-ethoxymethyl]-2-hydroxy-benzamide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: 55 °C 2.2: 4 h / 20 - 55 °C 3.1: triethylamine / tetrahydrofuran / 20 h / Heating / reflux View Scheme

labetalol hydrochloride (32780-64-6) → N-(5-{4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]but-2-ynyloxymethyl}-2-hydroxybenzamidomethyl)doxorubicin (636595-43-2)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 60 °C 3.1: toluene-4-sulfonic acid / acetone / 1.5 h / 85 °C / Heating / reflux 4.1: pyridine / tetrahydrofuran / 0.5 h / 20 °C 4.2: 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C 5.2: 6 h / 20 °C 6.1: water; toluene-4-sulfonic acid / methanol / 24 h / 90 °C / Heating / reflux 7.1: water; N,N-dimethyl-formamide / 0.25 h / 55 °C 7.2: 0.25 h / 55 °C View Scheme

labetalol hydrochloride (32780-64-6) → N-(5-{4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]but-2-ynyloxymethyl}-2-hydroxybenzamidomethyl)doxorubicin acetate

Conditions

Yield

Multi-step reaction with 8 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 60 °C 3.1: toluene-4-sulfonic acid / acetone / 1.5 h / 85 °C / Heating / reflux 4.1: pyridine / tetrahydrofuran / 0.5 h / 20 °C 4.2: 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C 5.2: 6 h / 20 °C 6.1: water; toluene-4-sulfonic acid / methanol / 24 h / 90 °C / Heating / reflux 7.1: water; N,N-dimethyl-formamide / 0.25 h / 55 °C 7.2: 0.25 h / 55 °C 8.1: chloroform View Scheme

labetalol hydrochloride (32780-64-6) → doxorubicin-5-formylsalicylamide (850256-37-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: water; N,N-dimethyl-formamide / 0.42 h / 60 °C 2.2: 0.42 h / 60 °C View Scheme

labetalol hydrochloride (32780-64-6) → doxaliform (850256-41-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: water; N,N-dimethyl-formamide / 0.75 h / 55 °C View Scheme

labetalol hydrochloride (32780-64-6) → 5-{4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxoimidazolin-1-yl]but-2-ynyloxymethyl}-2-butyryloxymethoxybenzamide

Conditions

Yield

Multi-step reaction with 7 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 60 °C 3.1: toluene-4-sulfonic acid / acetone / 1.5 h / 85 °C / Heating / reflux 4.1: pyridine / tetrahydrofuran / 0.5 h / 20 °C 4.2: 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C 5.2: 6 h / 20 °C 6.1: water; toluene-4-sulfonic acid / methanol / 24 h / 90 °C / Heating / reflux 7.1: potassium carbonate / acetone / 0.5 h / 20 °C 7.2: 4 h / Heating / reflux View Scheme

labetalol hydrochloride (32780-64-6) → N-(5-{4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]but-2-ynyloxymethyl}-2-butyryloxymethoxybenzamidomethyl)-doxorubicin

Conditions

Yield

Multi-step reaction with 8 steps 1.1: sodium hydrogencarbonate / water 1.2: 0.58 h / 20 °C 1.3: 0.03 h 2.1: decaborane / 5 h / 60 °C 3.1: toluene-4-sulfonic acid / acetone / 1.5 h / 85 °C / Heating / reflux 4.1: pyridine / tetrahydrofuran / 0.5 h / 20 °C 4.2: 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C 5.2: 6 h / 20 °C 6.1: water; toluene-4-sulfonic acid / methanol / 24 h / 90 °C / Heating / reflux 7.1: potassium carbonate / acetone / 0.5 h / 20 °C 7.2: 4 h / Heating / reflux 8.1: water; N,N-dimethyl-formamide / 0.25 h / 55 °C 8.2: 0.25 h / 55 °C View Scheme

Upstream product

• 85665-85-6 C₁₉H₂₂N₂O₃ 
• 2550-26-7 4-Phenyl-2-butanone 
• 30566-92-8 5-(N,N-dibenzylamino)acetylsalicylamide 
• 32780-63-5 2-hydroxy-5-<acetyl>benzamide hydrochloride 

Downstream Products

• 76143-20-9 5-formyl-2-hydroxy-benzamide 
• 22374-89-6 (RS)-1-methyl-3-phenylpropylamine 
• 32551-03-4 (R,S)-2-hydroxy-5-<2-<(1-methyl-3-phenylpropyl)amino>ethyl>benzamide hydrochloride 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF LABETALOL HYDROCHLORIDE

The present invention relates to process for the preparation of Labetalol Hydrochloride which gives higher yield and purity.

5-[1-HYDROXY-2-(1-METHYL-3-PHENYL-PROPYL)AMINOETHYL] SALICYLAMIDE AND PHYSIOLOGICALLY ACCEPTABLE ACID ADDITION SALTS THEROF

Compounds of the formula: STR1 and physiologically acceptable acid addition salts thereof, in which R 1 isA. AN ARYLALKYL GROUP, THE ALKYL PORTION OF WHICH CONTAINS FROM 1 TO 6 CARBON ATOMS AND THE ARYL PORTION OF WHICH MAY BE SUBSTITUTED BY ONE OR MORE ALKOXY GROUPS OR HYDROXY GROUPS; ORB. AN ARYLOXYALKYL GROUP, THE ALKYL PORTION OF WHICH CONTAINS FROM 1 TO 6 CARBON ATOMS, AND THE ARYLOXY PORTION OF WHICH IS SUBSTITUTED WITH ONE OR MORE ALKOXY OR HYDROXY GROUPS.These compounds have a blocking action on both α-and β-adrenergic receptors. Processes for the production of these compounds and pharmaceutical compositions containing them are also provided.