| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Targets |
Prenylamine targets multiple molecular entities. It inhibits the plasma membrane Ca2+ ATPase (PMCA) in isolated and purified pig cardiac sarcolemma. It binds to a hydrophobic site on calcium-bound calmodulin (CaM) with a Kd value of 0.5 µM. Additionally, it functions as a calcium channel blocker, inhibiting voltage-dependent calcium channels. Prenylamine also depletes myocardial catecholamine stores and acts as a beta-adrenergic antagonist, influencing heart rate and myocardial contractility.
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| ln Vitro |
In vitro, prenylamine inhibits CaM-activated cAMP phosphodiesterase (PDE) activity when used at concentrations ranging from 10 to 50 µM, an effect that is negatively associated with the concentration of calmodulin. At 30 μM, prenylamine shortens action potential duration and decreases the amplitude of peak calcium currents in single guinea pig ventricular myocytes, both in the absence and presence of propranolol and phentolamine. These effects confirm its direct action on calcium channels and calmodulin-dependent signaling.
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| ln Vivo |
In vivo, prenylamine (50 mg/kg) decreases epinephrine, serotonin, and dopamine levels in rats. It has been studied for its cardiovascular effects, including its ability to control ventricular fibrillation during induced hypothermia in cats after differential depletion of cardiac catecholamine stores. The compound's depletion of myocardial catecholamine stores contributes to its pharmacological profile as a vasodilator and antianginal agent, though its clinical use has been discontinued due to safety concerns.
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| Enzyme Assay |
Non-cellular in vitro assays for prenylamine involve calmodulin-binding studies. A typical protocol uses purified calmodulin and a fluorescent or radiolabeled probe. Varying concentrations of prenylamine are incubated with calmodulin in a buffer containing calcium. The binding affinity (Kd) is determined by measuring the displacement of the probe or by direct binding assays using techniques such as fluorescence spectroscopy or surface plasmon resonance. For PMCA inhibition, membrane preparations from cardiac sarcolemma are incubated with ATP and calcium, and the enzyme activity is measured in the presence of increasing concentrations of prenylamine.
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| Cell Assay |
Cellular assays for prenylamine are performed using primary cardiomyocytes or cell lines expressing voltage-gated calcium channels. Cells are loaded with calcium-sensitive dyes (e.g., Fura-2) and stimulated to induce calcium influx. Prenylamine is applied at various concentrations, and the changes in intracellular calcium concentration are measured using fluorescence microscopy or plate readers. Alternatively, patch-clamp electrophysiology is used to directly measure the inhibition of calcium currents in single ventricular myocytes after treatment with prenylamine at concentrations such as 30 μM.
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| Animal Protocol |
In vivo animal studies for prenylamine have been conducted in cat models of hypothermia-induced ventricular fibrillation. Cats are subjected to induced hypothermia, and prenylamine is administered to deplete cardiac catecholamine stores. The incidence and control of ventricular fibrillation are monitored. In rat models, prenylamine (50 mg/kg) is administered, and brain monoamine levels (epinephrine, serotonin, dopamine) are measured to assess its effects on neurotransmitter depletion. These studies have helped elucidate the compound's mechanism of action.
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| ADME/Pharmacokinetics |
Prenylamine has a molecular weight of 329.48 and is soluble in DMSO, chloroform, and methanol at 100 mg/mL. For in vivo studies, it can be formulated in 10% DMSO, 40% PEG300, 5% Tween-80, and 45% saline to achieve a solubility of ≥ 2.5 mg/mL. It is absorbed after oral administration and distributed to tissues, including the myocardium and brain. The compound is metabolized in the liver, and its elimination half-life is not well-documented. It is stored as a powder at -20°C for up to 3 years.
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| Toxicity/Toxicokinetics |
Prenylamine was formerly used clinically for angina pectoris but was withdrawn due to safety concerns, including cardiotoxicity and arrhythmogenic potential. Its toxicity profile includes depletion of myocardial catecholamine stores, which can lead to adverse cardiovascular effects. The oral LD50 in animal models is not well-documented, but the compound is considered hazardous. It is not approved for human use and is strictly a research chemical. Standard laboratory safety precautions should be followed when handling prenylamine.
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| References | |
| Additional Infomation |
Preniramine is a diarylmethane compound. Due to concerns about its potential to cause cardiac arrhythmias, preniramine was withdrawn from the Canadian, American, and British markets in 1988. It was previously used to treat angina, but has been superseded by less risky alternatives. Preniramine depletes cardiac catecholamine reserves and has some calcium channel blocking activity. (From Martindale Pharmacopoeia, 30th edition, p. 1406) See also: Preniramine lactate (note moved here).
Prenylamine is a calcium channel blocker and calmodulin antagonist that was previously marketed under the name Segontin for the treatment of angina pectoris. It belongs to the amphetamine chemical class and has structural similarities to other calcium channel blockers. Its clinical use was superseded by safer and more effective drugs. Today, prenylamine is primarily used as a research tool to study calcium signaling, calmodulin function, and catecholamine depletion mechanisms. It is not in clinical trials and has no current regulatory approval for therapeutic use. |
| Molecular Formula |
C24H27N
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|---|---|
| Molecular Weight |
329.487
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| Exact Mass |
329.214
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| CAS # |
390-64-7
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| PubChem CID |
9801
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| Appearance |
Light yellow to yellow ointment
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| Density |
1.023g/cm3
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| Boiling Point |
476.1ºC at 760mmHg
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| Melting Point |
36.5-37.5°
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| Flash Point |
219.4ºC
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| Index of Refraction |
1.577
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| LogP |
5.82
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
25
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| Complexity |
316
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(CC1C=CC=CC=1)NCCC(C1C=CC=CC=1)C1C=CC=CC=1
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| InChi Key |
IFFPICMESYHZPQ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C24H27N/c1-20(19-21-11-5-2-6-12-21)25-18-17-24(22-13-7-3-8-14-22)23-15-9-4-10-16-23/h2-16,20,24-25H,17-19H2,1H3
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| Chemical Name |
3,3-diphenyl-N-(1-phenylpropan-2-yl)propan-1-amine
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| Synonyms |
Prenylamine SAN-13-194 SAN 13-194
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0350 mL | 15.1750 mL | 30.3499 mL | |
| 5 mM | 0.6070 mL | 3.0350 mL | 6.0700 mL | |
| 10 mM | 0.3035 mL | 1.5175 mL | 3.0350 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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