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Chlorpromazine hydrochloride, molecular formula C17H19ClN2S · HCl, CAS 69-09-0, white or milky white crystalline powder. Melting point 179-180 ℃ (194-196 ℃) It is easily soluble in water, ethanol, and chloroform, but not in ether and benzene. It has hygroscopicity, with a pH of 5% in aqueous solution and 4-5. It's a bit smelly, very bitter. Under conventional conditions, the aqueous solution of chlrpromazine hydrochloride exhibits weak acidity (pH approximately 3-4). This product is prone to oxidation and will gradually turn reddish brown in air or sunlight. It is stored in a cool place. Shaanxi Achieve chem tech Co., Ltd. produces this product for laboratory use and is prohibited from other uses.
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Chemical Formula |
C17H20Cl2N2S |
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Exact Mass |
354 |
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Molecular Weight |
355 |
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m/z |
354 (100.0%), 356 (63.9%), 355 (18.4%), 357 (11.8%), 358 (10.2%), 356 (4.5%), 358 (2.9%), 359 (1.9%), 356 (1.6%), 358 (1.0%) |
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Elemental Analysis |
C, 57.47; H, 5.67; Cl, 19.95; N, 7.88; S, 9.02 |
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In vivo study:
Chlorpromazine (3,10,20,40 and 60 μ M) Reduce the peak current of hnav1.7 in a concentration dependent manner, with IC50 of 25.9 μ M. The Hill coefficient is 2.3. Chlorpromazine (25 μ M) It has a strong use dependent inhibition effect on hnav1.7 current. Chlorpromazine blocks the hnav1.7 channel and is independent of calmodulin. Chlorpromazine blocks the HERG potassium channel, and the IC50 value is 21.6 μ M. The Hill coefficient is 1.11. Chlorpromazine (1,10100 μ M) The HERG potassium channel expressed in Xenopus oocytes was blocked in a concentration dependent manner. Chlorpromazine blocks the HERG potassium channel in the activated state.
In vitro study:
Chlorpromazine (2 mg / kg, IP) - induced neurobehavioral abnormalities (NAS) are characterized by a significant increase in freezing behavior and prolonged spontaneous activity response time in mice. Chlorpromazine (1 or 5 mg / kg, I, P.) It can prevent ketamine (ket) from increasing δ and γ- Average spectral power of the hyperspectral band.
Synthesis of chlorpromazine hydrochloride:
1. The main ring is prepared by Ullmann reaction with o-chloroaniline as raw material, heating reflux condensation to prepare 2-carboxyl-3-diphenylamine; After decarboxylation at high temperature, it is fused with sulfur to cyclically synthesize 2-chlorophenylthiazine.
2. The side chain is prepared by heating propylene alcohol with dimethylamine in the presence of granular sodium hydroxide, and the generated 3-dimethylaminopropanol reacts with dry hydrogen chloride gas to obtain 1-chloro-3-dimethylaminopropane hydrochloride.
3. The condensation of the main ring and the side chain is carried out with sodium hydroxide as the condensation agent, and the obtained chlorpromazine is salified with hydrogen chloride gas to obtain chlorpromazin hydrochloride.
It is an antipsychotic drug. Here are the detailed steps and chemical equations of a common laboratory synthesis method:
Step 1: Preparation of dimethylaniline
1. React nitroxylene with zinc powder and concentrated hydrochloric acid.
C6H4(CH3)2(NO2)+ 6HCl + 6Zn → C6H4(CH3)2NH2 + 2H2O + 6ZnCl2
2. Filter the reaction mixture and collect the resulting dimethylaniline.
Step 2: Preparation of dimethyl aminomethyl-phenothiazine
1. React dimethylaniline with 2,3-dibromopropane.
C6H4(CH3)2NH2 + (CH2)2Br2 → C6H4(CH3)2N(CH2)2Br2
2. Distill to obtain dimethyl aminomethyl-phenothiazine.
Step 3: Preparation of product
1. React dimethyl aminomethyl-phenothiazine with chloroacetone.
C6H4 (CH3)2N (CH2)2Br2 + CH3COCH2Cl → C6H4 (CH3)2N (CH2)2CH2COCH3 + HBr
2. Add sodium hydroxide solution and filter to remove impurities from the solution.
3. The acidification product is converted into chlorpromazin hydrochloride using hydrochloric acid.
C6H4(CH3)2N(CH2)2CH2COCH3+HCl → C6H4(CH3)2N(CH2)2CH2COCH3 · HCl
Finally, chlorpromazin hydrochloride was obtained.
It should be noted that the above synthesis method is only a common laboratory synthesis scheme, and actual operation may vary due to experimental conditions or other factors. When conducting experiments, please strictly adhere to laboratory safety regulations and design and optimize experiments based on specific circumstances.
It as a representative of phenothiazine antipsychotic drugs, has become an indispensable medication in psychiatric and internal medicine clinical practice since its emergence in the 1950s. It exhibits a wide range of pharmacological effects by blocking dopamine receptors, serotonin receptors, M-type acetylcholine receptors, and alpha adrenergic receptors.
1. Positive symptom control of schizophrenia
It has significant therapeutic effects on positive symptoms such as excitement, restlessness, hallucinations, delusions, thinking disorders, and behavioral loss in schizophrenia. Its mechanism of action is to block dopamine D ₂ receptors in the midbrain limbic system and midbrain cortex pathways, reducing dopamine overproduction. Clinical studies have shown that in the treatment of acute phase schizophrenia, oral dosage starting from 25-50mg per day, increasing by 25-50mg every 2-3 days, until the therapeutic dose reaches 400-600mg/day, can quickly control symptoms with an effective rate of 70% -80%. For refractory patients, intramuscular or intravenous injection can achieve a faster increase in blood drug concentration. For example, after intravenous infusion of 25-50mg, patients can experience sedative effects within 30 minutes.
2. Emotional stability in manic disorder
During the manic phase of bipolar disorder, by inhibiting dopaminergic neurotransmission, the patient's excessively excited emotional state is reduced. A multicenter study involving 200 patients with bipolar disorder showed that the combination of chlorpromazine hydrochloride (300-400mg per day) and lithium salt reduced the bipolar disorder scale (BRMS) score from baseline 28 points to 12 points, significantly better than the lithium salt group alone (P<0.01). Its sedative effect can help patients restore their sleep rhythm and create conditions for subsequent psychological treatment.
3. Adjuvant treatment for other psychiatric disorders
For organic mental disorders (such as mental abnormalities after traumatic brain injury), toxic mental disorders (such as alcohol dependence withdrawal period), and childhood schizophrenia, they can be used as adjunctive drugs. For example, in patients with delirium after traumatic brain injury, low-dose chlorpromazine hcl (50-100mg per day) combined with benzodiazepines can shorten the duration of delirium by 2-3 days and reduce the risk of self injury.
Special therapeutic scenarios: diverse applications from antiemetic to artificial hibernation
The ultimate solution for stubborn vomiting
Its antiemetic effect is achieved through a dual mechanism: at low doses (12.5-25mg/day), it inhibits dopamine receptors in the medullary emetic chemosensory zone (CTZ), and at high doses (50-100mg/day), it directly inhibits the vomiting center. It has significant therapeutic effects on the following types of vomiting:
Drug induced vomiting: Acute vomiting caused by chemotherapy drugs (such as cisplatin) can be improved from 60% to 85% in complete remission when combined with 5-HT3 receptor antagonists (such as ondansetron).
Uremic vomiting: In patients with chronic renal failure, chlorpromazine hcl can reduce the frequency of vomiting from 5-8 times per day to 1-2 times per day, improving nutrient intake.
Pregnancy vomiting: For stubborn preeclampsia that is ineffective with traditional antiemetic drugs, it can reduce the risk of electrolyte imbalance in pregnant women, but strict monitoring of fetal safety is necessary.
Attention: Vomiting due to motion sickness is not effective as it involves the vestibular system.
2. Breakthrough treatment for stubborn hiccups
Hiccup lasting for more than 48 hours is defined as refractory hiccup, commonly seen in postoperative, stroke, or gastrointestinal disease patients. By blocking the hiccup center in the medulla oblongata, the hiccup cessation rate reached 80% within 30 minutes after intramuscular injection of 25-50mg.
A study on 50 postoperative hiccup patients showed that the recurrence rate within 24 hours after a single injection was only 15%, significantly lower than that of chlorpromazine (35% recurrence rate).
3. The synergistic effect of low-temperature anesthesia and artificial hibernation
In cardiac surgery, chlorpromazine hcl (1mg/kg) combined with pethidine (1mg/kg) and promethazine (0.5mg/kg) forms an "artificial hibernation mixture" that can lower body temperature to 32-34 ℃ and reduce tissue oxygen consumption by inhibiting the hypothalamic thermoregulatory center. For example, in surgery for aortic dissection, artificial hibernation can reduce myocardial oxygen consumption by 30% and significantly improve the success rate of the surgery.
1. Synergistic effect with analgesics
Can enhance the analgesic effect of opioid drugs, especially suitable for patients with severe pain in late stage cancer. The mechanism includes:
Blocking dopamine receptors reduces the side effects of nausea and vomiting caused by opioid drugs.
Inhibit the excitability of spinal dorsal horn neurons and increase pain threshold.
Clinical practice has shown that the combination of chlorpromazine hydrochloride (25-50mg/day) and morphine (30-60mg/day) can increase the pain relief rate from 70% to 90%, while reducing morphine dosage by 30%.
3. Cautious combination with antihypertensive drugs
Its alpha adrenergic receptor blockade may lead to orthostatic hypotension, and the dosage needs to be adjusted when combined with antihypertensive drugs such as diuretics and ACE inhibitors.
For example, in patients with hypertensive crisis, if it is necessary to use it simultaneously to control psychiatric symptoms, the dose of antihypertensive drugs should be reduced by 25% -50%, and blood pressure changes should be closely monitored.
4. Interaction with anticholinergic drugs
The anticholinergic effects of chlorpromazine hcl (such as dry mouth and constipation) can be enhanced by anticholinergic drugs such as atropine, leading to serious adverse reactions. In elderly patients, the combination therapy requires evaluating the risk return ratio and monitoring changes in heart rate and bowel sounds if necessary.
The molecular structure analysis of chlorpromazine hydrochloride is a very important chemical research work. By analyzing its molecular structure, one can understand its physical and chemical properties, as well as its mechanism of action on the human body.
1. Molecular formula and molecular weight of chlorpromazin hydrochloride
The molecular formula of chlorpromazin hydrochloride is C17H19ClN2S · HCl, with a relative molecular weight of 355.33 Da. Among them, C represents carbon, H represents hydrogen, Cl represents chlorine, N represents nitrogen, S represents sulfur, and HCl represents hydrochloric acid.
2. Molecular structure of chlorpromazin hydrochloride
The molecular structure of chlorpromazin hydrochloride is composed of multiple atoms, including two benzene rings, one pyrimidine ring, and one thiophenyl methyl group. These groups are tightly arranged in their molecular structure and connected together by covalent bonds.
3. Chemical properties of chlorpromazin hydrochloride:
Chlorpromazin hydrochloride is a drug with various effects such as sedation, antipsychotic, and anti allergic effects. It has a high solubility in water and can undergo decomposition and transformation with changes in pH value in the solution. For example, under acidic conditions, chlorpromazine can be protonated to form cationic chlorpromazin hydrochloride. Under alkaline conditions, chlorpromazine is deprotonated into the form of free radicals. In addition, chlorpromazine also has certain toxicity and irritation, and it needs to be used under the guidance of medical professionals.
4. Structure and action of chlorpromazin hydrochloride:
Due to the presence of different functional groups in the molecular structure of chlorpromazin hydrochloride, it has complex chemical properties and multiple effects. It is generally believed that the antipsychotic effect of chlorpromazin hydrochloride is mainly achieved by inhibiting the activity of dopamine receptors in the central nervous system. It binds to the neurotransmitter dopamine, thereby alleviating symptoms in patients with mental disorders. Meanwhile, chlorpromazine can also affect the metabolism and release of other neurotransmitters, such as serotonin and acetylcholine.
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