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Adrenochrome powder is the core component of adrenaline powder. Molecular formula C9H9NO3, CAS 54-06-8, It is the oxidation product of adrenaline. It is a red powder. It is an effective coronary vasoconstrictor for rat heart. The adrenal pigment can be used in the study of neurological diseases. A large amount of evidence shows that it can be oxidized by body fluid and tissue fluid in many mammals. According to research, there are hallucinogenic works. It is one of the causes of schizophrenia. It can reduce capillary permeability. It is used 1 ~ 2 per kilogram of human body μ G has a strong hemostatic effect In addition, melanin exists widely in animals, and I is an intermediate for melanin production 34) Predecessors pointed out that when contaminated by trace metals or coexisting with II, the pharmacological experiments were invalid. According to the quotation of sigma reagent company in 1997, the I per gram is as high as 304 90 dollars, and about 10 dollars per gram. Therefore, it is of theoretical and economic value to study the method of preparing I There are two problems in the existing preparation methods of adrenaline red Generally speaking, the higher the yield (50%), the lower the purity (6 ~ 10); When the purity is high, the yield is often only 17% 1, and these operating conditions must be controlled at - 80 ° C. It is also reported that organic oxidants can also be used for preparation, but the preparation process of such oxidants is complex and involves more pollution.
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Melting point |
115-120 ° C |
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Boiling point |
311.69 ° C (rough estimate) |
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Density |
1.2822 (rough estimate) |
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Storage conditions |
− 20 ° C |
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Dangerous goods sign |
Xi |
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Acidity coefficient ( pKa ) |
3.31 ± 0.20 (predicted) |
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Refractive index |
1.5600 (estimated) |
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Dangerous goods sign |
Xi |
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Hazard category code |
36 / 37 / 38 |
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Safety instructions |
36-26 |
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Melting point 115-120 ° C, Boiling point 311.69 ° C (rough estimate), Density 1.2822 (rough estimate), Refractive index 1.5600 (estimated), Storage conditions − 20 ° C, Acidity coefficient (PKA) 13.31 ± 0.20 (predicted), security information, Dangerous goods sign Xi, Hazard category code 36 / 37 / 38, Safety instructions 26-36, WGK Germany 3.
Adrenochrome powder (CAS number 54-06-8) is an oxidized product of adrenaline, with a chemical structure of 3-hydroxy-1-methyl-5,6-indolequinone.
1. Rescue of Allergic Shock
D. L-Adrenergic Red rapidly alleviates symptoms of anaphylactic shock by activating alpha and beta receptors. The mechanism includes:
Contraction of blood vessels: By activating alpha receptors, peripheral vascular resistance is increased and hypotension is corrected.
Bronchial dilation: By activating β 2 receptors, bronchial spasms are relieved and breathing difficulties are improved.
Enhance myocardial contractility: By activating β 1 receptors, increase cardiac output and maintain circulatory stability.
In clinical applications, the adult dose is usually 0.3-0.5mg for subcutaneous or intramuscular injection, and may be repeated if necessary. Research shows that timely use can increase the survival rate of patients with anaphylactic shock to over 90%.
2. Cardiac arrest resuscitation
In cardiopulmonary resuscitation (CPR), D, L-adrenergic red enhances myocardial contractility through β 1 receptor activation, while increasing aortic pressure and coronary perfusion pressure through α receptor activation.
Dosage: 1mg intravenous injection, repeated every 3-5 minutes.
Effect: It can increase the recovery rate of autonomous circulation by 15% -20%, but requires comprehensive measures such as defibrillation and electric shock.
3. Acute exacerbation of bronchial asthma
For patients with severe asthma attacks, D, L-adrenaline red can quickly relieve bronchial spasms. Its mechanism of action is similar to that of β 2 receptor agonists such as salbutamol, but it takes effect faster.
Dosage: 0.3-0.5mg subcutaneous injection.
Attention: It is necessary to strictly monitor heart rate to avoid inducing arrhythmia.
Diagnosis of neuroendocrine tumors
D. L-Adrenergic Red, as a metabolite of the adrenal medulla, can be used for the diagnosis of neuroendocrine tumors such as pheochromocytoma.
Detection method: To assist in locating tumors, the measurement of D, L-adrenaline red and its metabolites (such as methoxyadrenaline) in plasma or urine is used.
Clinical significance: The plasma levels of D, L-adrenergic red in patients with pheochromocytoma can increase to more than 10 times the normal value.
Research field: Tools for studying physiological mechanisms and diseases
1. Cardiovascular System Research
D. L-Adrenergic Red, as a coronary artery constrictor, can be used to study the pathogenesis of diseases such as myocardial ischemia and arrhythmia.
Animal experiment: In a rat heart model, D, L-adrenaline red can induce coronary artery spasm and simulate angina symptoms.
Cell experiment: By culturing myocardial cells, observe the effects of D, L-adrenergic red on calcium ion channels and mitochondrial function.
2. Neurological Disease Model
D. L-Adrenergic Red may be involved in the pathological processes of neurodegenerative diseases such as Parkinson's disease and Alzheimer's disease.
Oxidative stress research: D, L-adrenaline red can induce neuronal oxidative damage and simulate disease environments.
Signal pathway research: Investigating the effect of D, L-adrenergic red on neurotransmitter release by activating dopamine receptors.
3. Drug development reference standards
In drug quality control, adrenochrome powder is used as an impurity reference substance for calibrating instruments and evaluating analytical methods.
Application scenario: In HPLC (high-performance liquid chromatography) analysis, it serves as a standard substance to verify the accuracy of the detection method.
Suppliers: Shenzhen Zhuoyue Biomedical Technology, Shanghai Anpu Experimental Technology and other companies provide high-purity (≥ 98%) D, L-adrenaline red reference standards.
Industrial sector: Raw materials for chemical and biotechnology
1. Chemical Intermediate
D. L-Adrenergic Red can be used as an intermediate for the synthesis of dyes, pigments, and other chemical products.
Reaction conditions: It should be stored at -20 ℃ under inert gas protection to avoid oxidative degradation.
Application case: Used for synthesizing indole derivatives as modifiers for polymer materials.
2. Biotechnology raw materials
In enzyme catalyzed reactions, D, L-adrenergic red can act as a substrate or cofactor and participate in specific biosynthetic pathways.
Research progress: Some laboratories have attempted to synthesize natural product analogues using D, L-adrenaline red, but industrial production has not yet been achieved.
1. The origin of anti-aging rumors
In 2015, a study by Stanford University found that oxytocin in the blood of young mice can restore organ vitality in elderly mice. Subsequently, there were rumors circulating online that D, L-adrenaline red was confused with oxytocin, claiming to have a "reverse aging and rejuvenation" effect.
Scientific fact: Oxytocin is a different substance from D, L-adrenergic red, with the former being a peptide hormone and the latter being an indolequinone compound. There is currently no evidence to suggest that D, L-adrenaline red can delay aging.
2. Warning of illegal use
Some rumors suggest that D, L-adrenergic red can be obtained by extracting hormones from children's fear and sold at high prices as a "drug". This statement lacks scientific basis and involves serious ethical and legal issues.
Legal risk: D, L-Adrenaline Red is a prescription drug in most countries, and its illegal production, sale, or use may violate criminal law.
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A preparation method for dl adrenaline, using sinephrine hydrochloride as the raw material, which is protected by boc groups under the action of an acid binding agent to obtain compound a, which is then oxidized by 2-iodobenzoic acid and reduced by sodium bisulfite to obtain compound b. Compound b is then deprotected by hydrochloric acid to obtain dl adrenaline like white powder. The reaction steps of the preparation method for dl adrenaline are as follows:
Add Xinfulin hydrochloride to a reaction flask, first add solvent and acid binding agent, then add boc anhydride and stir at room temperature for 1 hour. Then, raise the temperature to 60 ℃~70 ℃, extract the solution and collect the organic phase. Wash the organic phase with 0.1n hydrochloric acid and saturated salt water respectively. After washing, add n-hexane, drop the temperature to precipitate, filter, and dry to obtain compound a;
Add compound a and solvent 1 to the reaction flask, then add 2-iodoylbenzoic acid, and react for 1-3 hours. Then, add water and sodium hydrosulfite, and react for 1 hour before filtering. The filtrate is distilled under reduced pressure until an oily substance appears in the solution. Extract twice with solvent 2, wash once with saturated sodium bicarbonate solution and once with saturated salt water. Dry with anhydrous sodium sulfate and recover the solvent through reduced pressure distillation. Dissolve with solvent 3, then add n-hexane and stir at room temperature for crystallization, Filter and dry the filter cake to obtain compound b;
Add a hydrochloric acid solution with a concentration of 3mol/l to the reaction flask, raise the temperature to 45 ° C-60 ° C, and then add compound b for 1-3 hours. After the reaction is completed, reduce to room temperature, adjust the pH value with concentrated ammonia water, crystallize, filter, wash with water, wash with methanol, and vacuum dry to obtain dl adrenaline.
The total molar yield of dl adrenaline prepared by this method is greater than 50%, the chromatographic purity is greater than 96%, and the ee value is close to zero, significantly saving the preparation cost of dl adrenaline. The operation is simple, environmentally friendly, and is conducive to industrial production, with broad application prospects.
Adrenochrome powder, as an important fluorescent dye, its unique molecular structure endows it with excellent fluorescence performance and biocompatibility. In molecular structure analysis, we not only need to focus on its basic chemical composition, but also deeply understand its spatial configuration and electron distribution to reveal its properties and mechanisms of action in applications.
1. The chemical composition of D, L-adrenergic red
D. The basic structure of L-adrenergic red includes multiple functional groups and a benzene ring. Among them, the most crucial ones are sulfonyl (-SO3H) and Rhodamine B skeleton. Sulfonyl groups endow molecules with good water solubility and stability, while the Rhodamine B framework provides strong fluorescence emission. In addition, the molecule also contains functional groups such as amino (-NH2) and carboxyl (-COOH), which not only affect the solubility and stability of the molecule, but also provide possibilities for its application in biomarkers and detection.
2. The spatial configuration of D, L-adrenergic red
D. The spatial configuration of L-adrenergic red exhibits a typical planar conjugated structure. The benzene ring and dimethylaminophenyl in the Rhodamine B skeleton are connected by double bonds to form a planar π - conjugated system. This conjugated system is a key region for fluorescence emission, where electron transitions and energy transfer occur. In addition, functional groups such as sulfonyl and amino groups are located on both sides of the conjugated system and are covalently linked to the Rhodamine B skeleton.
3. The electronic distribution of D, L-adrenergic red
The electron distribution is an important factor affecting the fluorescence properties of D, L-adrenergic red molecules. The π - conjugated system in the Rhodamine B framework allows electrons to freely flow and transfer energy within it. When exposed to external light, electrons will transition from the ground state to the excited state, and then return to the ground state and emit fluorescence in an extremely short time. In addition, functional groups such as sulfonyl and amino groups can also affect the distribution and transition process of electrons. For example, sulfonyl groups can attract surrounding water molecules through electrostatic interactions, forming a stable hydration layer to protect fluorescent groups from external environmental influences.
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