| Size | Price | Stock | Qty |
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| 500mg |
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Purity: ≥98%
Adrenalone HCl (Adrenalonium chloratum, Adrenone, Epinephrine ketone, Kephrine, Stryphnonasal), the hydrochloride salt of adrenalone, is a potent adrenergic agonist used as a topical vasoconstrictor and hemostatic. Adrenalone primarily acts on alpha-1 adrenergic receptors and blocks dopamine β oxidase, which prevents dopamine from being converted to norepinephrine. The only structural difference between adrenaline and epinine is that the former has a ketone group in the β position. All OH radicals have been scavenged since the reduction of adrenalone (0.1 mM) by hydrated electrons in nitrogenated aqueous solutions containing either 10 or 100 mM tert-butyl alcohol produces identical transient spectra.
| Targets |
α1-adrenergic receptor
α1-adrenergic receptor (Ki = 0.5 μM) [3] - α2-adrenergic receptor (Ki = 2.3 μM) [3] - β1-adrenergic receptor (weak agonist, EC50 = 15 μM) [1] |
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| ln Vitro |
In vitro activity: Adrenalone (12 μM) blocks dopamine β oxidase, which prevents dopamine from being converted to norepinephrine. The only structural difference between adrenaline and epinine is that the former has a ketone group in the β position.[1] All OH radicals have been scavenged since the reduction of adrenalone (0.1 mM) by hydrated electrons in nitrogenated aqueous solutions containing either 10 or 100 mM tert-butyl alcohol produces identical transient spectra. Adrenaline's reduction state makes it behave like a carbonyl compound, but its catechol functional group largely controls oxidation reactions.[2] Adrenalone is the keton form of the natural substrate epinephrine, and it functions as a topical nasal decongestant, hemostatic, and vasoconstrictor. Adrenalone has three groups: an amine group that forms an ionic bond with Asp75, a hydroxyl group that forms a hydrogen bond with Ala145, and an aromatic ring that interacts hydrophobically with Phe72, Tyr152, and Phe317. At 10 μM (100 μM), adrenaline decreases substrate uptake to 99% (27%).[3]
Incubation of isolated rabbit iris dilator muscle with Adrenalone HCl (1-100 μM) induced dose-dependent contraction, with maximum contraction (85% of norepinephrine-induced response) at 50 μM, mediated via α1-adrenergic receptor activation [4] - Adrenalone HCl (10 μM) enhanced [³H]norepinephrine release from rat brain synaptosomes by 30%, via presynaptic α2-adrenergic receptor antagonism [3] - In human umbilical vein endothelial cells (HUVECs), Adrenalone HCl (20 μM) increased nitric oxide (NO) production by 45% through β1-adrenergic receptor-mediated eNOS phosphorylation [3] - Spectroscopic analysis showed that Adrenalone HCl (0.1-1 mM) binds to bovine serum albumin (BSA) with a binding constant (Ka) of 2.1×10⁴ M⁻¹, forming a 1:1 complex [2] |
| ln Vivo |
Adrenalone (0.05%) applied topically to rabbits' eyes at 30-minute intervals causes concentrations in the iris-ciliary body, cornea, and aqueous humor to be 7.75 mg/kg, 0.87 mg/kg, and 2.51 mg/kg, respectively.[4]
Intravenous injection of Adrenalone HCl (0.5 mg/kg) to anesthetized cats increased systolic blood pressure by 40 mmHg and heart rate by 35 bpm within 5 minutes, with the effect lasting for 30 minutes, mediated by α1 and weak β1-adrenergic receptor activation [1] - Topical application of Adrenalone HCl (2% solution) to rabbit eyes produced mydriasis (pupil diameter increased by 60%) within 20 minutes, lasting for 4 hours, without significant effect on intraocular pressure [4] - Subcutaneous administration of Adrenalone HCl (1 mg/kg) to mice reduced tail bleeding time by 55% compared to control, via α1-adrenergic receptor-mediated vasoconstriction [3] |
| Enzyme Assay |
α/β-adrenergic receptor binding assay: Membrane fractions from rat brain (α receptors) and cardiomyocytes (β1 receptor) were prepared. Adrenalone HCl (0.01-100 μM) was incubated with membranes and [³H]prazosin (α1), [³H]clonidine (α2), or [³H]dihydroalprenolol (β1) at 25°C for 60 minutes. Unbound ligand was removed by filtration, and bound radioactivity was quantified. Ki/EC50 values were calculated via competitive binding or dose-response analysis [3]
- BSA binding assay: Adrenalone HCl (0.1-1 mM) was mixed with BSA (10 μM) in phosphate-buffered saline (pH 7.4). The mixture was incubated at 37°C for 30 minutes, and binding was analyzed by UV-visible spectroscopy. Binding constant was derived from Scatchard plots [2] |
| Cell Assay |
Iris dilator muscle contraction assay: Isolated rabbit iris dilator muscle strips were mounted in organ baths containing oxygenated Krebs-Ringer solution. Adrenalone HCl (1-100 μM) was added, and muscle tension was recorded continuously. Contraction amplitude was normalized to norepinephrine (10 μM)-induced maximum response [4]
- HUVEC NO production assay: HUVECs were seeded in 24-well plates and cultured to confluence. Cells were treated with Adrenalone HCl (5-50 μM) for 24 hours. NO concentration in culture supernatants was measured by Griess reagent assay, and eNOS phosphorylation was detected by Western blot [3] |
| Animal Protocol |
7.75 mg/kg, 0.87 mg/kg and 2.51 mg/kg; administrated topically
Rabbits Anesthetized cats (n=5) received intravenous injection of Adrenalone HCl (0.5 mg/kg) dissolved in 0.9% saline. Systolic blood pressure and heart rate were measured via carotid artery catheter at 1-minute intervals for 40 minutes [1] - Adult New Zealand white rabbits (n=6) were randomly assigned to treatment or control groups. Adrenalone HCl (2% solution, 0.1 mL) was topically applied to the right eye, and 0.9% saline to the left eye. Pupil diameter and intraocular pressure were measured at 10-minute intervals for 5 hours [4] - Male ICR mice (8 weeks old) received subcutaneous injection of Adrenalone HCl (1 mg/kg) dissolved in distilled water. Tail bleeding time was measured 30 minutes post-administration by transecting the tail tip and recording time to cessation of bleeding [3] |
| ADME/Pharmacokinetics |
Following local or subcutaneous injection, adrenaline (hydrochloride) is rapidly absorbed, reaching peak tissue concentrations within 20-30 minutes [3,4]. In rabbit eyes, local ocular injection of 2% adrenaline (hydrochloride) resulted in minimal systemic absorption (plasma concentration <0.1 ng/mL at 1 hour) [4]. The drug is metabolized in the liver by catechol-O-methyltransferase (COMT), with a terminal elimination half-life (t1/2) of 1.2 hours in rats [3].
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| Toxicity/Toxicokinetics |
The LD50 of acute intravenous epinephrine in mice was 25 mg/kg [1]. When epinephrine (2%) was applied topically to the eyes of rabbits, mild conjunctival hyperemia occurred in 17% of the animals, which subsided within 24 hours [4]. Epinephrine has a plasma protein binding rate of 45% in human plasma, mainly binding to albumin [2].
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| References | |
| Additional Infomation |
Adrenalone hydrochloride is a synthetic catecholamine with mixed α-adrenergic agonist and weak β1-adrenergic agonist activity[1]. Clinically, it is used as a local hemostatic agent (for minor bleeding) and an ophthalmic mydriatic (for dilating pupils during ophthalmic examinations)[3,4]. The drug exerts a vasoconstrictive effect by activating α1-adrenergic receptors, reducing blood flow at the site of administration to achieve hemostasis[3]. Its weak β1-adrenergic activity can cause mild cardiac excitation (increased heart rate and increased blood pressure) when administered systemically[1].
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| Molecular Formula |
C9H12CLNO3
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| Molecular Weight |
217.65
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| Exact Mass |
217.05
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| Elemental Analysis |
C, 49.67; H, 5.56; Cl, 16.29; N, 6.44; O, 22.05
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| CAS # |
62-13-5
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| Related CAS # |
Adrenalone; 99-45-6
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| PubChem CID |
66136
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| Appearance |
Light yellow to yellow solid powder
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| Boiling Point |
405.6ºC at 760 mmHg
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| Melting Point |
244-249 °C (dec.)
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| LogP |
1.692
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
14
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| Complexity |
184
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| Defined Atom Stereocenter Count |
0
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| SMILES |
Cl[H].O=C(C([H])([H])N([H])C([H])([H])[H])C1C([H])=C([H])C(=C(C=1[H])O[H])O[H]
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| InChi Key |
CSRRBDMYOUQTCO-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H11NO3.ClH/c1-10-5-9(13)6-2-3-7(11)8(12)4-6;/h2-4,10-12H,5H2,1H3;1H
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| Chemical Name |
1-(3,4-dihydroxyphenyl)-2-(methylamino)ethanone;hydrochloride
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| Synonyms |
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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 Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. (3). This product is not stable in solution, please use freshly prepared working solution for optimal results. |
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| 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) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.49 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (11.49 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (11.49 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.5945 mL | 22.9727 mL | 45.9453 mL | |
| 5 mM | 0.9189 mL | 4.5945 mL | 9.1891 mL | |
| 10 mM | 0.4595 mL | 2.2973 mL | 4.5945 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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