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Depressant

Propranolol

Also called Inderal, Hemangeol, Innopran, beta-Propranolol, Betalong, Proprasylyt

Original Wikipedia articleen.wikipedia.org/wiki/Propranolol revision used (24 October 2026)

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Part of the metabolic pathway of Propranolol. See the timeline on the metabolic highway.

Enzymes that break it down: CYP1A2, CYP2D6, CYP2C19 and CYP3A4. Wikipedia’s drug infobox says: “Liver (extensive) CYP1A2, CYP2D6; minor: CYP2C19, CYP3A4; aromatic hydroxylation (mainly 4-hydroxylation), N-dealkylation, side-chain oxidation, glucuronidation” (revision 1369411043).

Common dose · Oral40–80 mg TS

Dosage

Oral

SourceThresholdLightCommonStrongHeavy
TripSit–10–30 mg TS40–80 mg TS80–140 mg. TS–

TripSit dose text

TripSit's factsheet also states its doses as text.

Oral Light: 10-30mg Common: 40-80mg Strong: 80-140mg. TS

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Duration

TripSit factsheet

Onset
10-45 minutes TS
Duration
3-7 hours TS
Aftereffects
1-8 hours TS

Mixing

For best safety practice, don't mix this drug with other depressants.

Why: respiratory depression. PsychonautWiki says:

Quotes from PsychonautWiki, CC BY-SA 4.0.

Acute combinations: what happens when these are taken close together. Entries backed by a medical journal or agency are listed first.

Backed by medical journals

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Risks and toxicity

TripSit factsheet

Avoid
All other CNS depressants. TS

Testing

Awaiting sourceReagent reactions and test kit guidance from a harm reduction testing service.

Effects

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Overview

Is a nonselective beta blocker. It is used in medication for high blood pressure, anxiety, and tremors. Also fun fact, it was the first successful beta-blocker developed. TS

Propranolol is a medication of the beta blocker class. It is used to treat high blood pressure, some types of irregular heart rate, thyrotoxicosis, capillary hemangiomas, akathisia, performance anxiety, and essential tremors, as well as to prevent migraine headaches, and to prevent further heart problems in those with angina or previous heart attacks. It can be taken orally, rectally, or by intravenous injection. The formulation that is taken orally comes in short-acting and long-acting versions. Propranolol appears in the blood after 30 minutes and has a maximum effect between 60 and 90 minutes when taken orally.[1–8] WP

Common side effects include nausea, abdominal pain, and constipation. It may worsen the symptoms of asthma. Propranolol may cause harmful effects for the fetus if taken during pregnancy; however, its use during breastfeeding is generally considered to be safe. It is a non-selective beta blocker which works by blocking β-adrenergic receptors.[3][9][10] WP

Propranolol was patented in 1962 and approved for medical use in 1964. It is on the World Health Organization's List of Essential Medicines. Propranolol is available as a generic medication. In 2023, it was the 69th most commonly prescribed medication in the United States, with more than 9 million prescriptions.[3][11–14] WP

History

History

Scottish scientist James W. Black developed propranolol in the 1960s. It was the first beta blocker effectively used in the treatment of coronary artery disease and hypertension. Black received the Nobel Prize in Physiology or Medicine in 1988 for this discovery. Propranolol is on the WHO Model list of essential medicines.[2][12][15][16][17] WP

Newer, more cardio-selective beta blockers (such as bisoprolol, nebivolol, carvedilol, or metoprolol) are used preferentially in the treatment of hypertension.[16] WP

Pharmacology

Pharmacodynamics

Propranolol is classified as a competitive non-cardioselective sympatholytic beta blocker that crosses the blood–brain barrier. It is lipid soluble and also has sodium channel-blocking effects. Propranolol is a non-selective β-adrenergic receptor antagonist, or beta blocker; that is, it blocks the action of epinephrine (adrenaline) and norepinephrine (noradrenaline) at both β₁- and β₂-adrenergic receptors. It has little intrinsic sympathomimetic activity, but has strong membrane stabilizing activity (only at high blood concentrations, e.g. overdose). Propranolol can cross the blood–brain barrier and exert effects in the central nervous system in addition to its peripheral activity.[45][46][47] WP

In addition to blockade of adrenergic receptors, propranolol has very weak inhibitory effects on the norepinephrine transporter and/or weakly stimulates norepinephrine release (i.e., the concentration of norepinephrine is increased in the synapse). Since propranolol blocks β-adrenoceptors, the increase in synaptic norepinephrine only results in α-adrenoceptor activation, with the α₁-adrenoceptor being particularly important for effects observed in animal models. Therefore, it can be looked upon as a weak indirect α₁-adrenoceptor agonist in addition to potent β-adrenoceptor antagonist. In addition to its effects on the adrenergic system, there is evidence that indicates that propranolol may act as a relatively weak antagonist of certain serotonin receptors, namely the 5-HT1A, 5-HT1B, and 5-HT2B receptors. The latter may be involved in the effectiveness of propranolol in the treatment of migraine at high doses. (–)-Propranolol is not a silent antagonist of the serotonin 5-HT1A receptor but is instead a very weak partial agonist of the receptor.[27][34][43][48–51] WP

Both enantiomers of propranolol have a local anesthetic (topical) effect, which is normally mediated by blockade of voltage-gated sodium channels. Studies have demonstrated propranolol's ability to block cardiac, neuronal, and skeletal voltage-gated sodium channels, accounting for its known membrane stabilizing effect and antiarrhythmic and other central nervous system effects.[52][53][54] WP

Mechanism of action

Propranolol is a non-selective beta receptor antagonist. This means that it does not have preference to β₁ or β₂ receptors. It competes with sympathomimetic neurotransmitters for binding to receptors, which inhibits sympathetic stimulation of the heart. Blockage of neurotransmitter binding to β₁ receptors on cardiac myocytes inhibits activation of adenylate cyclase, which in turn inhibits cAMP synthesis leading to reduced Protein kinase A (PKA) activation. This results in less calcium influx to cardiac myocytes through voltage-gated L-type calcium channels, meaning there is a decreased sympathetic effect on cardiac cells, resulting in antihypertensive effects including reduced heart rate and lower arterial blood pressure. Blocking neurotransmitter activity at β₂ receptors in vascular smooth muscle cells causes vasoconstriction, leading to hypertension.[45][55] WP

Absorption

Propranolol is rapidly and completely absorbed, with peak plasma levels achieved about 2 hours (range 1–3 hours) after ingestion. Its oral bioavailability is approximately 25%. Despite complete absorption, propranolol has a variable bioavailability due to extensive first-pass metabolism. Hepatic impairment therefore increases its bioavailability. Therapeutic plasma concentrations are typically between 0.02 and 0.3 mg/L. Toxicity has been reported at concentrations of 1 mg/L and above, with coma or death associated with concentrations of 4 to 10 mg/L and above. Coadministration with food appears to enhance bioavailability but does not hasten its time to peak levels. Propranolol can be absorbed along the whole intestine with the main absorption site being the colon, which means people who have lost their colon due to surgery may absorb less propranolol. Propranolol shows marked interindividual variability in pharmacokinetics, with propranolol levels varying 20-fold in different individuals.[1][2][7][56–59] WP

Distribution

The volume of distribution of propranolol is about 4 L/kg or 320 L. The plasma protein binding of propranolol is approximately 90%, with a range of 85 to 96% in different studies. Propranolol is a highly lipophilic drug achieving high concentrations in the brain. The brain-to-blood ratio of propranolol in humans ranges from 15:1 to 33:1, whereas the ratio for the peripherally selective beta blocker atenolol has been found to be 0.2:1.[2][7][60][61] WP

Metabolism

Propranolol undergoes metabolism via aromatic hydroxylation (mainly 4-hydroxylation), N-dealkylation, side-chain oxidation, and glucuronidation. The metabolism of propranolol involves cytochrome P450 enzymes including CYP2D6, CYP1A2, and CYP2C19. CYP1A2 and CYP2D6 have a major role, while CYP2C19 and CYP3A4 have a minor role. The main metabolite 4-hydroxypropranolol, which has a longer elimination half-life than propranolol, is also pharmacologically active.[1][7][62] WP⚠ Part of this sentence could not be copied from the source. Open the source to read it in full.

Elimination

Propranolol is eliminated in urine. Approximately 91% of an oral dose of propranolol is eliminated in urine as 12 metabolites. Only about 1 to 4% of propranolol is excreted unchanged in urine or feces.[7][55] WP

The elimination half-life of propranolol ranges from 2.8 to 8 hours in different studies, with a typical half-life of around 4 hours. The duration of action of a single oral dose is longer than the half-life and may be up to 12 hours if the single dose is high enough (e.g., 80 mg).[1][7][63] WP

Pharmacogenomics

There were no significant differences in area-under-the-curve levels of propranolol in CYP2D6 poor metabolizers versus extensive metabolizers. However, area-under-the-curve propranolol levels were ~2.5-fold higher in Caucasian CYP2D6 poor metabolizers or Chinese people with a non-functional CYP2D6 gene. The contribution of CYP2D6 to the metabolism of propranolol is less than with metoprolol and is described as only "marginal".[64] WP

Receptor binding · Wikipedia

Propranolol activities

SiteKᵢ (nM)Species
5-HT1A55–272 (Kᵢ); 29 (– ((–)-propranolol)) (Kᵢ); 128 (– ((–)-propranolol)) (EC₅₀ (half-maximal effective concentration)); 15% (– ((–)-propranolol)) (Eₘₐₓ (maximal efficacy))Human; Human; Human; Human[25–29] WP
5-HT1B56–85Rat[28–31] WP
5-HT1D4,070Pig[28][29][32] WP
5-HT2A4,280Human[28][29][33] WP
5-HT2B457–513 (+ ((+)-propranolol)); 166–316 (– ((–)-propranolol))Human; Human[28][29][34] WP
5-HT2C61,700 (+ ((+)-propranolol)); 5,010 (– ((–)-propranolol)); 736–2,457Human; Human; Rodent[26][28][29][34][35] WP
5-HT₃>10,000Human[28][29][36] WP
α₁ND (No data)ND (No data)[28][29] WP
α₂1,297–2,789Rat[28][29][37] WP
β₁0.02–2.69Human[28][29][38][39] WP
β₂0.01–0.61Human[28][29][38][39] WP
β₃450Mouse[28][29][40] WP
D₁>10,000Human[26][28][29] WP
D₂>10,000Human[26][28][29] WP
H₁>10,000Human[28][29][41] WP
SERT (Serotonin transporter)3,700Rat[28][29][42] WP
NET (Norepinephrine transporter)5,000 (IC₅₀ (Half-maximal inhibitory concentration))Rat[28][29][43] WP
DAT (Dopamine transporter)29,000 (IC₅₀ (Half-maximal inhibitory concentration))Rat[28][29][43] WP
VDCC (Voltage-dependent calcium channel)>10,000Rat[28][29][44] WP

Chemistry

Formula
C16H21NO2 PC
CAS number
525-66-6 PC
Molar mass (g/mol)
259.34 PC
IUPAC name (computed by PubChem)
1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol PC
SMILES
CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O PC
InChIKey
AQHHHDLHHXJYJD-UHFFFAOYSA-N PC
PubChem CID
4946

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References

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  55. Harm reduction site Propranolol
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Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), TripSit factsheets, PubChem (public domain). Each value links to the exact revision it came from.