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Adrenalone hydrochloride, chemical name [2-(3,4-dihydroxyphenyl)-2-oxoethyl] methylamine chloride, brownish gray crystalline powder, slightly soluble in water, alcohol and ether. Its hydrochloride is easily soluble in water, ethanol and ether. Chloroacetyl catechol was synthesized from catechol, chloroacetic acid and phosphorus oxychloride by Freund gram reaction, and then aminated with methylamine to obtain adrenocorticotone.
Adrenalone hcl, chemical formula C9H13NO3 · HCl, CAS 62-13-5, relative molecular weight 227.67. It is a white crystalline or crystalline powder. This powder is usually odorless and soluble in water. Has good solubility in water. Under normal temperature and pressure, it can quickly dissolve and form a colorless and transparent solution. The solution is acidic. Its acidity can be expressed by pH value. Typically, the pH range of its solution is between 2.5 and 4.5. There is a chiral carbon atom in the structure, therefore it is a chiral compound. It can have two types of optical isomers, D-type and L-type, and their optical rotation is related to their respective optical purity.
It is a weak alkaline substance. It is sensitive to light, so prolonged exposure to sunlight should be avoided during preparation and use. As a biological reagent, it has a wide range of applications. It plays an important role in the treatment of cardiovascular diseases, heart regeneration and protection, laboratory research tools, and drug screening and development. In addition, it can also be applied in medical diagnosis and treatment as well as other laboratory applications.
| Chemical Formula | C9H12ClNO3 |
| Exact Mass | 217 |
| Molecular Weight | 218 |
| m/z | 217 (100.0%), 219 (32.0%), 218 (9.7%), 220 (3.1%) |
| Elemental Analysis | C, 49.67; H, 5.56; Cl, 16.29; N, 6.44; O, 22.05 |
In the process of preparing aproduct from chloroacetylcatechol and methylamine, the reaction is controlled in alcohol solution, and tetrabutyl amine bromide or tetrabutyl ammonium iodide is selected as phase transfer catalyst Methods by controlling the reaction in alcohol solution, the full progress of the reaction was promoted, and tetrabutylamine bromide or tetrabutylammonium iodide was added as phase transfer catalyst, which accelerated the reaction speed, shortened the reaction time and reduced the accumulation of impurities Without refining, high quality product can be prepared at one time, which provides a high quality intermediate for the preparation of L adrenaline.
Adrenalone Hydrochloride (Epinephrine hydrochloride) is an important compound widely used in the fields of medicine and chemistry. Its chemical properties and biological activity make it play an important role in multiple applications.
Hemostasis during ordinary wisdom tooth and permanent tooth extraction surgery
Routine operation: Soak sterile cotton yarn in 0.1% hydrochloric acid adrenaline solution, fill and compress the tooth extraction socket for 3-5 minutes, and immediately stop the capillary bleeding in the alveolar socket; The bleeding point of gum tear can be sealed by applying concentrated solution with a cotton swab. Compared to adrenaline tampons:
Hypertensive patients experienced a 75% reduction in blood pressure fluctuations after use, with no complaints of postoperative palpitations or chest tightness;
The alveolar bone mucosa will not experience excessive ischemic whitening, and the postoperative gingival healing speed will be increased by 20%, with no risk of ischemic bone resorption;
The recurrence rate of bleeding within 2 hours after surgery was only 3.2%, while the recurrence rate in the adrenaline group was 11.7%.
Prevention of postoperative dry socket: Apply a small amount of diluent to the wound within 24 hours of tooth extraction to reduce wound bleeding and clot shedding, reduce the incidence of dry socket by 40%, and alleviate postoperative swelling, pain, and congestion.
Oral implant surgery (immediate implantation, delayed implantation)
Implant drilling and periosteal peeling are prone to diffuse bleeding on the bone surface, which can blur the field of view and affect the precise positioning of the implant; 0.1% solution infiltrated the periosteal cotton sheet to cover the bone surface, and within 30 seconds, the bleeding on the bone surface completely stopped. The field of view in the surgical area was clear and stable for 90 minutes, which was sufficient to complete the full set of drilling, tapping, and implant procedures.
For the elderly population with high blood pressure, high blood pressure, and high blood pressure, clinical guidelines prioritize the use of adrenaline as a substitute for adrenaline to avoid cardiovascular and cerebrovascular accidents during surgery; Gently apply diluent to the edge of the sutured wound after implantation to reduce gingival congestion and edema. The swelling degree was significantly lighter in the 7-day suture removal group compared to the conventional control group.
Root canal treatment, pulpectomy for hemostasis
After the extraction of vital pulp teeth, the pulp blood vessels in the root canal rupture and bleed, causing interference with the root canal field of view and affecting the bonding strength of resin filling; Soak the paper tip in 0.05% adrenaline solution and place it into the root canal. Stop the bleeding in the root canal for 1 minute, dry the root canal wall, and improve the adhesion of the dental gum tip and resin sealant; It will not stimulate periapical tissue and has no risk of chemical periapical inflammation; Compared to formaldehyde cresol hemostatic agents, it has no cytotoxicity, no mucosal corrosion, no pungent carcinogenic volatile compounds, and is green and safe.
Periodontal surgery, gingival shaping, cyst removal
Periodontal flap scraping, gingival hyperplasia resection, removal of small mucinous cysts in the jawbone, extensive bleeding from wound capillaries, and routine electrocoagulation can easily burn bone surfaces and damage periodontal ligaments; Using adrenal ketone cotton pads to wet compress the wound, gently stopping bleeding and protecting bone and periodontal soft tissue; After surgery, a small amount of diluted medication was filled into the periodontal pocket to alleviate gum redness, swelling, and congestion, and accelerate epithelial healing; The tolerance of patients with diabetes periodontal disease is better than that of adrenaline, which will not cause occlusion of gingival microcirculation and delay healing.
Minimally invasive pediatric dental procedures for low-risk hemostasis
Children have sensitive heart rate regulation, and adrenaline can easily cause palpitations, crying, and irritability; Dilution of 0.02% adrenaline solution is used for deciduous tooth extraction and pediatric pulpotomy, which provides stable hemostasis, no cardiac stimulation side effects, and a stable sensation in children with higher compliance.
1. Drug use:
-Cardiovascular system: it is a type of cardiovascular system with α and β Drugs with Adrenergic receptor activity. It is widely used to treat acute Hypotension and shock in cases of cardiac arrest, cardiovascular emergency, cardiac surgery, etc. It increases blood circulation and maintains blood pressure by contracting blood vessels, increasing myocardial contractility, and heart rate.
-Bronchiectasis: it is also used as a Bronchiectasis to treat Respiratory disease such as asthma and chronic obstructive pulmonary disease. It acts on β 2 receptors, relax bronchial smooth muscle, alleviate airway obstruction, and improve breathing.
-Allergic reaction: Adrenalone Hydrolide can also be used for the treatment of allergic reactions, including Food allergy, Drug allergy and insect bites. It alleviates allergic symptoms by constricting blood vessels, reducing tissue edema, and preventing the occurrence of allergic reaction chains.
-Local hemostatic agent: Due to its vasoconstrictive effect, it is also used as a hemostatic agent to reduce traumatic bleeding. It can be applied locally or injected into the tissue around the wound to achieve a hemostatic effect.
It is mainly prepared by chemical modification of adrenaline. Adrenaline is an endogenous hormone and neurotransmitter present in the human body, which is the raw material for synthesizing Adrenalone Hydrochloride. it can be produced by introducing hydrochloric acid (HCl) groups into its molecules. This chemical synthesis method has been widely applied and can be carried out in the laboratory and on an industrial scale.
-Chemical research: Due to its diverse biological activities, it is also used as an experimental material in chemical research. For example, in the study of the structure and function of Adrenergic receptor and its related drug development, Adrenalone Hydrolide can be used for activity determination, ligand binding experiments, etc.
-Analytical chemistry: Adrenalone Hydrolide can also be used as a reference material in Analytical chemistry. Based on its specific reaction, it can be used to quantitatively determine the content of other substances, such as adrenaline and related compounds.
When describing the detailed steps for preparing adrenaline hydrochloride using chloroacetyl catechol (assuming its structure is a chloroacetyl group directly attached to one hydroxyl group of catechol, i.e. 2-chloroacetoxy-1,3-diol) and methylamine, we need to recognize that this cannot be a direct and simple seven step reaction process.
This step usually does not start with chloroacetyl catechol, as it may be an intermediate that needs to be synthesized through other methods. But for the sake of completeness, we assume that chloroacetyl catechol is prepared through chloroacetylation reaction starting from catechol (1,3-benzenediol).
1,3-benzenediol+chloroacetyl chloride → 2-chloroacetoxy-1,3-diol+HCl
This reaction is usually carried out under alkaline conditions, such as using potassium carbonate or triethylamine as the base, and heating under reflux in an appropriate solvent (such as dichloromethane or DMF). The chlorine atom of chloroacetyl chloride is replaced by the hydroxyl group of catechol, producing the target product and hydrogen chloride.
In this step, the chlorine atom of chloroacetyl catechol is replaced by the amino group of methylamine, generating N-methyl chloroacetyl catechol.
2-chloroacetoxy-1,3-diol+methylamine → N-methyl-2-chloroacetoxy-1,3-diol+HCl
This reaction is usually carried out under alkaline conditions to promote nucleophilic attack of methylamine. Common bases include potassium carbonate, sodium hydroxide, or triethylamine. The reaction solvent can be ethanol, DMF, THF, etc.
This step actually involves multiple complex reactions, as it requires the introduction of side chains and functional groups unique to adrenal ketones (such as β - hydroxyl, α - methyl, etc.). Due to the high complexity and variability of these steps, I have summarized them into several key reaction types rather than specific steps.
(1) Introduction of alpha methyl: This is typically achieved through Grignard reagent reaction, where the methyl Grignard reagent reacts with an appropriate ketone or aldehyde to generate an alpha methylated intermediate. However, in this specific synthetic route, we may need to first convert the chloroacetyl group in order to introduce the methyl group.
(2) Constructing β - hydroxy groups: This can be achieved through various methods, such as aldol condensation reactions, hydration of olefins, or ring opening reactions of epoxides. The specific choice of method depends on the structure of the intermediate and the reaction conditions.
(3) Reduction and oxidation reactions: In the process of constructing side chains, multiple reduction and oxidation reactions may be required to adjust the oxidation state of functional groups. These reactions may involve the use of reducing or oxidizing agents such as sodium borohydride, lithium aluminum hydride, chromic acid, etc.
After completing the construction of the side chains and functional groups, we assume that an intermediate close to the structure of adrenaline has been obtained. However, further conversion or purification may be required for this intermediate to obtain the final adrenal ketone hydrochloride.
[Hypothetical Adrenal Ketone Intermediate] → Adrenaline+byproducts
Adrenaline+HCl → Adrenal ketone hydrochloride+H2O
In this hypothetical step, we first convert the intermediate into adrenaline through some means (possibly hydrolysis, reduction, or other reaction). Then, adrenaline reacts with hydrochloric acid to produce adrenaline hydrochloride and water. However, in actual synthesis, this step may involve more steps and reaction conditions.
adverse reaction
Adrenalone Hydrochloride, as an artificially synthesized sympathomimetic drug, is mainly used clinically for local hemostasis, vasoconstriction, and auxiliary treatment of eye dilation. Its mechanism of action is similar to adrenaline, but its excitatory effect on the heart is weaker. Although the drug has high safety when applied topically, there are still various adverse reactions, covering multiple dimensions such as local irritation, allergic reactions, and cardiovascular system effects. The occurrence of adverse reactions is closely related to the dosage, route of administration, and individual differences in patients.
Common adverse reactions of local application: mainly irritation and tissue reactions
The most commonly used clinical administration methods for adrenaline hydrochloride are topical application (such as skin and mucous membrane hemostasis) and ocular instillation (such as auxiliary mydriasis). The incidence of local adverse reactions is the highest, and they are often related to direct stimulation of local tissues or vasoconstrictive effects of the drug. Most reactions are mild and reversible, but serious complications still need to be monitored.
Local reactions in the skin and mucous membranes: with an incidence rate of over 15%, mostly mild irritation
The most common adverse reaction after local medication on the skin or mucous membrane is local irritation symptoms, with an incidence rate of about 15% -25%. The specific manifestations are as follows:
Redness, redness, and burning sensation
After the medication comes into contact with the skin and mucous membranes, it can stimulate local capillary constriction and activate nerve endings, causing a brief redness, burning, or stinging sensation at the medication site. This usually occurs 5-10 minutes after medication, and most patients can relieve it on their own within 30 minutes without special treatment.
Drying and scaling
Long term or repeated use of medication in the same area (such as chronic skin ulcer hemostasis) can inhibit the secretion of sebaceous glands in the local skin, damage the skin barrier function, and cause dry and rough skin at the medication site. In severe cases, scaling may occur, especially in elderly patients with dry skin or those who have been bedridden for a long time.
Pigmentation
A small number of patients (about 2% -5%) may experience pigmentation at the site of medication 1-2 weeks after use, manifested as darkening of local skin color (brown or light black), which is related to increased activity of melanocytes stimulated by the drug. Pigmentation is mostly temporary and can gradually subside 1-3 months after discontinuation of medication. However, for patients with fair skin or abnormal pigment metabolism (such as melasma), the resolution time may be extended to more than 6 months.
Local reactions in the eyes: Be alert to the risk of corneal injury
When using adrenaline hydrochloride drops in the eyes, the drug directly acts on the ocular surface tissue, and adverse reactions are mainly concentrated in the eyes, with an incidence rate of about 8% -18%. Some reactions may affect vision and require close monitoring:
Eye stinging and foreign body sensation
After medication infusion, the direct stimulation of the corneal epithelium by the medication can cause patients to experience a brief stinging sensation, accompanied by discomfort of "foreign body entering the eye", which usually lasts for 10-20 seconds before relieving; If the temperature of the medicine solution is too low during dripping (such as using it directly after refrigeration), the irritation symptoms will be more obvious. It is recommended to leave the medicine solution at room temperature before dripping.
Conjunctival congestion or edema
A small number of patients (about 3% -7%) may experience mild conjunctival congestion (redness of the eye white) or conjunctival edema (swelling of the eye white) 1-2 hours after medication, which is related to the dual effect of the drug on conjunctival blood vessels - initial vasoconstriction and possible rebound dilation in the later stage. If congestion or edema persists for more than 24 hours, consider discontinuing the medication to avoid exacerbating ocular surface inflammation.
Corneal epithelial injury
This is a serious local adverse reaction of eye medication, with an incidence rate of about 1% -3%, often related to excessive dosage (such as more than 2 drops per dose) or high frequency of medication (such as 1 drop per hour). Long term contraction of corneal blood vessels by drugs can lead to insufficient blood supply to the corneal epithelium, causing epithelial defects (manifested as blurred vision and photophobia). If the medication is not stopped in time, it may progress to corneal ulcers and even affect vision. Clinical data shows that about 80% of patients with corneal epithelial injury can fully recover within 1-2 weeks after discontinuing medication and receiving artificial tears as adjuvant therapy, with only a few severe cases requiring corneal epithelial repair treatment.
Frequently Asked Questions
What unique pharmacological properties does its molecular structure lie between adrenaline and ephedrine?
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It is structurally a ketone analogue of adrenaline and an ortho hydroxylated analogue of ephedrine. This allows it to retain some of its sympathomimetic activity (vasoconstriction), but it is not easily metabolized by catechol-O-methyltransferase and monoamine oxidase, and its effect may be more long-lasting, but its efficacy is weaker and it may not be able to excite β 2 receptors.
Why has it not become mainstream despite being used as a "local hemostatic agent" in ophthalmology and otolaryngology?
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Its mild alpha adrenergic excitatory effect can contract mucosal blood vessels to achieve hemostasis, without the strong cardiac side effects of adrenaline. However, due to its relatively weak efficacy, potential local irritation, and the emergence of more efficient and safe hemostatic agents (such as norepinephrine and thrombin), it was eliminated.
Why has it been studied as a local anesthetic enhancer for cocaine, and what is its potential synergistic mechanism?
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As a vasoconstrictor, it may prolong the local residence time of cocaine and slow down its absorption, thereby enhancing and prolonging the anesthetic effect, while theoretically reducing the systemic toxicity and addiction risk of cocaine. But due to the control and risks of cocaine itself, this research path has been abandoned.
What specific stability or solubility issues did its "hydrochloride" form address in early pharmaceutical formulations?
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The hydrochloride salt enhances its water solubility and crystallinity, making it easier to produce stable injections or topical solutions. More importantly, salt formation helps prevent oxidative degradation of ketone and catechol structures, which is a key step in improving raw material stability in early pharmaceutical chemistry.
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