| Size | Price | Stock | Qty |
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| 5mg |
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| Targets |
Adrenochrome interacts with multiple biological targets and pathways, primarily through its redox activity and its ability to generate reactive oxygen species (ROS). It is known to be an inhibitor of the enzyme catechol-O-methyltransferase (COMT), which is responsible for the degradation of catecholamines like dopamine and epinephrine. By inhibiting COMT, Adrenochrome can prolong the action of these neurotransmitters, which may contribute to its psychotomimetic effects. It also affects Ca²⁺-stimulated Mg²⁺-dependent ATPase activity. Furthermore, Adrenochrome is a potent vasoconstrictor in the coronary arteries of the rat heart. Its mechanism of action in this context is complex and involves the generation of ROS and the disruption of calcium homeostasis. The compound is known to promote prostaglandin synthesis in brain tissue in vitro. Adrenochrome's cytotoxicity is mediated by its ability to undergo one-electron reduction to form a semiquinone radical, which can then react with oxygen to produce superoxide and other ROS, leading to oxidative stress and cellular damage. These diverse mechanisms make Adrenochrome a compound of interest in neurobiology and cardiovascular research, although its exact physiological roles remain to be fully elucidated.
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| ln Vitro |
Calcium uptake, microsomal calcium binding, and Ca2+-stimulated Mg2+-dependent ATPase activity are all decreased by adrenochrome. There is no correlation between pH (6.0-8.0), calcium concentration (10-200 μM), protein concentration (0.02-0.10 mg/mL), temperature (25-37 degrees C), and incubation period (2-30 minutes) and the inhibitory impact of adrenochrome on the calcium uptake activity of separation membrane microsomes [2].
In vitro studies have characterized Adrenochrome's various biological activities. It has been shown to inhibit COMT activity, which can be measured in enzyme assays using a substrate like epinephrine. It also decreases Ca²⁺-stimulated Mg²⁺-dependent ATPase activity, which is important for calcium homeostasis. One of its most well-studied in vitro activities is its role as a potent coronary constricting agent in isolated rat hearts. In these studies, Adrenochrome concentrations ranging from 1 to 1000 ng/mL induced dose- and time-dependent increases in coronary artery pressure. This effect is influenced by the concentration of CaCl2 in the perfusion medium. In addition to its cardiovascular effects, Adrenochrome is used in vitro to study oxidative stress. It can be added to cell cultures to induce the production of ROS, allowing researchers to study the cellular response to oxidative damage and the protective effects of antioxidants. It is also used to determine the activity of superoxide dismutase (SOD) in vitro. Adrenochrome is known to spontaneously oxidize, and the rate of this oxidation can be used as a measure of SOD activity, as SOD protects Adrenochrome from oxidation. These in vitro studies highlight Adrenochrome's utility as a tool for studying oxidative stress, cardiovascular function, and neurobiology. |
| ln Vivo |
Adrenochrome concentrations ranging from 1 to 1000 ng/mL induced dose- and time-dependent increases in coronary artery pressure in isolated rat hearts. Moreover, the concentration of CaCl2 in the perfusion medium determines the degree of adrenochrome contraction [1].
In vivo studies have primarily focused on the cardiovascular effects of Adrenochrome, particularly its role as a coronary constrictor. In isolated rat heart models, Adrenochrome has been shown to cause a dose- and time-dependent increase in coronary artery pressure, confirming its potent vasoconstrictive properties. This makes it a useful compound for studying the mechanisms of coronary vasospasm and cardiotoxicity. The degree of contraction induced by Adrenochrome has also been shown to depend on the concentration of calcium in the perfusion medium, indicating a role for calcium signaling in its mechanism. While its role in vivo in the context of the leukocyte response is suggested, the systemic effects of Adrenochrome in a whole organism are less well-defined. Its short half-life makes it a difficult molecule to study in vivo. The compound is also suggested to exhibit psychotomimetic effects, but evidence for this in vivo is largely anecdotal and has not been rigorously validated in controlled animal studies. Its primary in vivo use in research is as a tool to study acute cardiovascular events and oxidative stress. |
| Enzyme Assay |
In vitro receptor and enzyme assays for Adrenochrome are designed to measure its interaction with specific targets, such as COMT, and to quantify its effects on oxidative stress. For COMT inhibition assays, the enzyme is incubated with its substrate (e.g., epinephrine) and a methyl donor (S-adenosylmethionine) in the presence of varying concentrations of Adrenochrome. The formation of the methylated product is then measured, typically by HPLC or a radiometric assay. The IC50 for COMT inhibition can then be determined. For studying oxidative stress, Adrenochrome can be used in a superoxide dismutase (SOD) activity assay. In this assay, Adrenochrome is allowed to autoxidize in the presence of a sample containing SOD. The SOD competes with Adrenochrome for superoxide radicals, thereby inhibiting the autoxidation of Adrenochrome. The rate of Adrenochrome autoxidation is measured spectrophotometrically by monitoring the increase in absorbance at 480-490 nm. The degree of inhibition of Adrenochrome autoxidation is a measure of SOD activity. These assays provide a quantitative measure of Adrenochrome's effects on specific enzymes and its utility as a probe for oxidative stress.
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| Cell Assay |
In vitro cell-based assays for Adrenochrome are used to study its cytotoxic and oxidative effects on various cell types. A typical assay involves culturing cells (e.g., neuronal cells, cardiomyocytes, or endothelial cells) in multi-well plates and treating them with Adrenochrome at various concentrations (e.g., 1-1000 ng/mL). Cell viability is then assessed using a standard assay such as MTT, XTT, or the resazurin reduction assay, which measures the metabolic activity of living cells. To specifically measure oxidative stress, cells can be loaded with a redox-sensitive fluorescent probe, such as 2',7'-dichlorodihydrofluorescein diacetate (H2DCFDA), which becomes fluorescent upon oxidation by ROS. After treatment with Adrenochrome, the fluorescence intensity is measured using a microplate reader or flow cytometry, providing a quantitative measure of intracellular ROS production. These assays are used to establish the concentration-dependent cytotoxicity of Adrenochrome and to study the cellular mechanisms of oxidative damage and the protective effects of antioxidants. They are also used to study Adrenochrome's effects on specific signaling pathways, such as the activation of NF-κB or the expression of antioxidant genes.
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| Animal Protocol |
In vivo animal experiments involving Adrenochrome are less common, primarily due to its short half-life and potent cardiovascular effects. The most well-established in vivo model for studying Adrenochrome is the isolated, perfused rat heart (Langendorff preparation). In this model, a rat heart is excised and perfused with a physiological solution through the aorta. Adrenochrome is then administered into the perfusion system, and the coronary perfusion pressure is continuously monitored. This allows researchers to study the direct vasoconstrictive effects of Adrenochrome on the coronary arteries. The concentration of Adrenochrome (e.g., 1-1000 ng/mL) and the calcium concentration in the perfusate can be varied to study the mechanisms of this effect. Other in vivo studies would involve administering Adrenochrome systemically to an animal and monitoring physiological parameters such as blood pressure and heart rate. However, such studies are challenging due to the rapid metabolism and potential toxicity of Adrenochrome. Its primary use is as a tool in ex vivo heart models to study coronary vasospasm.
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| ADME/Pharmacokinetics |
Adrenochrome is a highly reactive and unstable molecule, which complicates its pharmacokinetic characterization. It is an endogenous compound that is rapidly produced and quickly metabolized, making it a short-lived molecule. It is formed by the oxidation of epinephrine and can be further metabolized to other compounds. Its half-life in the circulation is expected to be very short, likely on the order of minutes. For research use, Adrenochrome is typically supplied as a solid and dissolved in an appropriate solvent (e.g., DMSO or an aqueous buffer) immediately before use. Its stability in solution is limited, and it is prone to oxidation, so fresh solutions are recommended. The compound has an absorption maximum (εmax) of 3-4.5 at 485-490 nm in water, which can be used for its quantification by spectrophotometry. It is recommended to store Adrenochrome at -20°C to minimize degradation. Its physicochemical properties, such as its low molecular weight (179.17 g/mol) and its ability to undergo redox cycling, are key determinants of its biological activity and short-lived nature.
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| Toxicity/Toxicokinetics |
Adrenochrome is a cytotoxic and potentially toxic molecule. Its toxicity is primarily mediated through the generation of reactive oxygen species (ROS), which can cause oxidative damage to lipids, proteins, and DNA. It has been implicated in cardiotoxicity, as it is a potent coronary constricting agent that can induce vasospasm in the rat heart. This property makes it a useful tool for studying the mechanisms of cardiac ischemia and reperfusion injury. It is also thought to be neurotoxic and has been suggested to play a role in schizophrenia and other mental illnesses. However, this link is controversial and not well-established. As a short-lived molecule, its toxicity is often localized and acute. In the context of the leukocyte response, it is produced to kill bacteria, indicating that its cytotoxicity is part of the body's defense mechanism. For laboratory use, Adrenochrome should be handled with care, using appropriate personal protective equipment (PPE), including eyeshields and gloves, to avoid skin contact and inhalation, as it is a potential irritant and cytotoxic agent.
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| References |
[1]. M Karmazyn,, et al. Adrenochrome-induced coronary artery constriction in the rat heart. J Pharmacol Exp Ther. 1981 Oct;219(1):225-30.
[2]. S Takeo,et al. Effects of adrenochrome on calcium accumulating and adenosine triphosphatase activities of the rat heart microsomes. J Pharmacol Exp Ther. 1980 Sep;214(3):688-93. [3]. Koji Ueda, et al. Catecholamine oxidation-mediated transcriptional inhibition in Mn neurotoxicity. J Toxicol Sci. 2020;45(10):619-624. |
| Additional Infomation |
Adrenaline red is a type of indole compound. It is a pigment obtained by the oxidation of adrenaline.
Adrenochrome is a research compound and is not approved for any clinical or therapeutic use. It is primarily used as a tool in biochemical and pharmacological research. Its applications include: **Determination of Superoxide Dismutase (SOD) Activity**: Adrenochrome is used in a spectrophotometric assay to measure SOD activity, based on its ability to inhibit the autoxidation of Adrenochrome. **Study of Oxidative Stress**: It is used in cell culture models to induce oxidative stress, allowing researchers to study the cellular response to ROS and the protective effects of antioxidants. **Study of Cardiotoxicity**: It is used in isolated heart models to study coronary vasospasm and the mechanisms of cardiotoxicity. **Neurobiological Research**: It has been studied for its potential role in schizophrenia and other mental illnesses, although this is highly controversial. Its mechanism of action as a COMT inhibitor and a generator of ROS makes it a valuable tool for studying these pathways. However, its use is limited by its instability and potential toxicity. It is often used in conjunction with other compounds to study the complex interplay of redox biology and neurotransmission. It is a standard reagent in oxidative stress research. |
| Molecular Formula |
C9H9NO3
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|---|---|
| Molecular Weight |
179.18
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| Exact Mass |
179.058
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| Elemental Analysis |
C, 60.33; H, 5.06; N, 7.82; O, 26.79
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| CAS # |
54-06-8
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| PubChem CID |
5898
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| Appearance |
Solid powder
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| Density |
1.42g/cm3
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| Boiling Point |
375.1ºC at 760 mmHg
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| Melting Point |
115-120ºC
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| Flash Point |
180.7ºC
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| Index of Refraction |
1.63
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| LogP |
-1.3
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
13
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| Complexity |
354
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CN1CC(C2=CC(=O)C(=O)C=C21)O
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| InChi Key |
RPHLQSHHTJORHI-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3
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| Chemical Name |
3-hydroxy-1-methyl-2,3-dihydroindole-5,6-dione
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| Synonyms |
Adrenochrome Adraxone
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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) |
DMSO : ~100 mg/mL (~558.13 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (13.95 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
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 (13.95 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.5810 mL | 27.9049 mL | 55.8098 mL | |
| 5 mM | 1.1162 mL | 5.5810 mL | 11.1620 mL | |
| 10 mM | 0.5581 mL | 2.7905 mL | 5.5810 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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