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Protirelin is a white or almost white powder with the molecular formula C16H22N6O4, CAS 24305-27-9, and is an important bioactive substance. It is easily soluble in methanol, ethanol, and acetone, which means that it can dissolve well in appropriate solvents, which is crucial for the preparation and storage of drugs. Meanwhile, prorelin is slightly soluble in chloroform and insoluble in water, petroleum ether, and benzene. This solubility characteristic has certain guiding significance in the preparation of drug formulations, as it determines the dispersion and solubility of drugs in different solvents. In ethanol or methanol, prorelin exhibits a square or sheet-like crystalline form. Clinically, it is mainly used to assist in the diagnosis of Graves disease and to differentiate the location of lesions with hypothyroidism.
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Customized Bottle Caps And Corks:
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Chemical Formula |
C16H22N6O4 |
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Exact Mass |
362 |
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Molecular Weight |
362 |
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m/z |
362 (100.0%), 363 (17.3%), 363 (2.2%), 364 (1.4%) |
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Elemental Analysis |
C, 53.03; H, 6.12; N, 23.19; O, 17.66 |
Protirelin is an important bioactive substance with multiple physiological and biochemical functions. In the laboratory, prorelin can be synthesized through various methods. The following is one of the commonly used synthesis methods:
Chemical equation:
(Formula 1) C4H10O2+CH2O → 4-hydroxymethyl-2-methyl-3-pentenoic acid methyl ester
(Formula 2) 4-hydroxymethyl-2-methyl-3-pentenoate methyl ester+C3H4O3+NaOH → 3-(4-hydroxymethyl-2-methylpentyl)-2-pyruvate methyl ester
(Formula 3) 3-(4-hydroxymethyl-2-methylpentyl) -2-pyruvate methyl ester+HCl → 3-(4-chloromethyl-2-methylpentyl)-2-pyruvate methyl ester
(Formula 4) 3-(4-chloromethyl-2-methylpentyl)-2-pyruvate methyl ester+NaBr+NaOH → 3-(4-bromomethyl-2-methylpentyl)-2-pyruvate methyl ester
(Formula 5) 3-(4-bromomethyl-2-methylpentyl) -2-pyruvate methyl ester+Na2S+NaOH → 3-(4-mercaptomethyl-2-methylpentyl) -2-pyruvate methyl ester
(Formula 6) 3-(4-mercaptomethyl-2-methylpentyl) -2-pyruvate methyl ester+HCl → 3-(4-hydrothiomethyl) -2-methylpentyl acetate methyl ester
(Formula 7) 3-(4-Hydrothiomethyl)-2-methylvalerate methyl ester+H2NNH2+NaOH → 3-(4-Hydrothiomethyl)-2-methylvalerate hydrazine
(Formula 8) 3-(4-Hydrothiomethyl)-2-methylvalerate hydrazine+CH3CO anhydride+ZnCl → N-(4-Hydrothiomethyl) -2,6-dimethylheptanamide
(Formula 9) N-(4-Hydrothiomethyl) -2,6-dimethylheptanamide+NH4Cl+NaOH → N-(4-Hydrothiomethyl)-N'-(2,6-dimethylheptanyl) guanidine hydrochloride
(Formula 10) N-(4-Hydrothiomethyl)-N'-(2,6-dimethylheptyl) guanidine hydrochloride+NaOH → N-(4-Hydrothiomethyl)-N'-(2,6-dimethylheptyl) guanidine
(Formula 11) N-(4-Hydrothiomethyl)-N'-(2,6-dimethylheptyl) guanidine+BrCN → C16H22N6O4
The above is a laboratory synthesis method for prorelin, through which high-purity protirelin can be obtained.
Synthesis steps
(1) Mix 1,4-butanediol with formaldehyde, add sodium hydroxide as a catalyst, stir evenly, and heat to reflux state. During this process, 1,4-butanediol undergoes a condensation reaction with formaldehyde to produce 4-hydroxymethyl-2-methyl-3-pentenoic acid methyl ester (formula 1).
(2) Mix the generated 4-hydroxymethyl-2-methyl-3-pentenoic acid methyl ester with pyruvate, add sodium hydroxide as a catalyst, and heat to reflux state. During this process, 4-hydroxymethyl-2-methyl-3-pentenoic acid methyl ester undergoes esterification reaction with pyruvate to produce 3- (4-hydroxymethyl-2-methylpentyl) -2-pyruvate methyl ester (formula 2).
(3) Mix the generated 3- (4-hydroxymethyl-2-methylpentyl) -2-pyruvate methyl ester with concentrated hydrochloric acid and heat to reflux state. During this process, 3- (4-hydroxymethyl-2-methylpentyl) -2-pyruvate methyl ester undergoes a chlorination reaction with concentrated hydrochloric acid to produce 3- (4-chloromethyl-2-methylpentyl) -2-pyruvate methyl ester (Equation 3).
(4) Mix the generated 3- (4-chloromethyl-2-methylpentyl) -2-pyruvate methyl ester with sodium bromide, add sodium hydroxide as a catalyst, and heat to reflux state. During this process, 3- (4-chloromethyl-2-methylpentyl) -2-pyruvate methyl ester undergoes a substitution reaction with sodium bromide to produce 3- (4-bromomethyl-2-methylpentyl) -2-pyruvate methyl ester (Equation 4).
(5) Mix the generated 3- (4-bromomethyl-2-methylpentyl) -2-pyruvate methyl ester with sodium sulfide, add sodium hydroxide as a catalyst, and heat to reflux state. During this process, 3- (4-bromomethyl-2-methylpentyl) -2-pyruvate methyl ester undergoes a substitution reaction with sodium sulfide to produce 3- (4-mercaptomethyl-2-methylpentyl) -2-pyruvate methyl ester (Equation 5).
(6) Mix the generated 3- (4-mercaptomethyl-2-methylpentyl) -2-pyruvate methyl ester with hydrogen chloride gas and heat it to reflux state. During this process, 3- (4-mercaptomethyl-2-methylpentyl) -2-pyruvate methyl ester undergoes a substitution reaction with hydrogen chloride gas to generate 3- (4-hydrothiomethyl) -2-methylpentyl ester (Equation 6).
(7) Mix the generated 3- (4-hydrothiomethyl) -2-methylvalerate methyl ester with hydrazine hydrate, add sodium hydroxide as a catalyst, and heat to reflux state. During this process, 3- (4-hydrothiomethyl) -2-methylvalerate methyl ester undergoes a reduction reaction with hydrazine hydrate to produce 3- (4-hydrothiomethyl) -2-methylvalerate hydrazine (Equation 7).
(8) Mix the generated 3- (4-hydrothiomethyl) -2-methylvalerate hydrazine with acetic anhydride, add zinc chloride as a catalyst, and heat to reflux state. During this process, 3-(4-hydrothiomethyl)-2-methylvalerate hydrazine undergoes esterification with acetic anhydride to produce N-(4-hydrothiomethyl)-2,6-dimethylheptanamide (formula 8).
(9) Mix the generated N-(4-hydrothiomethyl)-2,6-dimethylheptanamide with ammonium chloride, add sodium hydroxide as a catalyst, and heat to reflux state. During this process, N-(4-hydrothiomethyl) -2,6-dimethylheptanamide undergoes a substitution reaction with ammonium chloride to produce N-(4-hydrothiomethyl)-N'-(2,6-dimethylheptanamide) guanidine hydrochloride (Equation 9).
(10) Mix the generated N-(4-hydrothiomethyl)-N'-(2,6-dimethylheptyl) guanidine hydrochloride with sodium hydroxide and heat to reflux state. During this process, N-(4-hydrothiomethyl)-N'-(2,6-dimethylheptyl) guanidine hydrochloride reacts with sodium hydroxide to form N-(4-hydrothiomethyl)-N'-(2,6-dimethylheptyl) guanidine (Equation 10).
(11) Mix the generated N-(4-hydrothiomethyl)-N'(2,6-dimethylheptyl) guanidine with cyanide bromide and heat to reflux state. During this process, N-(4-hydrothiomethyl)-N'-(2,6-dimethylheptyl) guanidine undergoes a substitution reaction with cyanide bromide to form prorelin (Equation 11).
Protirelin is a tripeptide hormone that is one of the hormones released by the hypothalamus and has significant anti shock effects. It also effectively regulates the secretion of thyroid stimulating hormone (TSH) and prolactin (PRL) in the anterior pituitary gland.
Prorelin has the following main pharmacological properties:
1. Stimulating the secretion of thyroid stimulating hormone (TSH) and prolactin (PRL) in the anterior pituitary gland: Prolrelin stimulates the release of TSH and PRL in the anterior pituitary gland by binding to the thyrotropin releasing hormone (TRH) receptor on the pituitary cell membrane. This stimulating effect helps diagnose thyroid diseases, such as Graves disease.
2. Anti shock effect: Prorelin has a significant anti shock effect, which can improve the blood pressure and survival rate of shock patients. Its anti shock mechanism may be related to the excitation of adrenergic receptors β Receptors, inhibition of endogenous catecholamine release, excitation α Related to receptor and other functions.
3. Neuroregulatory function: Prorelin is a highly conserved neuropeptide with neuroregulatory function. It can act on the central and peripheral nervous systems, affecting the release and metabolism of neurotransmitters, thereby regulating the function of the nervous system.
4. Low toxicity and wide safety range: Prorelin has low toxicity and a wide safety range, making it a promising new type of anti shock drug.
5. Judging the function of the hypothalamic pituitary thyroid axis and the reserve function of pituitary secretion: By measuring changes in blood TSH concentration, the functional status of the hypothalamic pituitary thyroid axis can be determined, which helps to diagnose thyroid diseases. Meanwhile, prorelin stimulates the release of TSH and PRL from the anterior pituitary gland, which can reflect the reserve function of pituitary secretion.
What are the side effects of this compound?
1. Side effects
Neurological side effects
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Some patients may experience headaches after use, which may be due to the stimulating effect of the medication on the nervous system. Headaches usually manifest as mild to moderate, but may also affect the patient's daily life and work. Dizziness is another common neurological side effect that may be related to drug-induced changes in blood pressure or neurological dysfunction. Patients may feel dizzy and disoriented after use, and may even be at risk of falling. Facial flushing is caused by vasodilation, and some patients may experience this symptom after use. Facial flushing is usually manifested as redness and fever of the facial skin, sometimes accompanied by itching or discomfort.
Cardiovascular system side effects
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Palpitation: Palpitation is one of the common cardiovascular side effects, manifested as symptoms such as increased heart rate, enhanced heartbeat, or arrhythmia. This may be due to the direct stimulating effect of the drug on the heart or causing changes in blood pressure.
Blood pressure increase or decrease: It may have a bidirectional regulatory effect on blood pressure, and some patients may experience an increase or decrease in blood pressure after use. Elevated blood pressure may increase the risk of cardiovascular events, while decreased blood pressure may lead to symptoms such as dizziness and fatigue.
Digestive system side effects
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Nausea: Nausea is one of its common digestive system side effects, which may be related to the stimulating effect of drugs on the gastrointestinal tract. Patients may experience nausea and sometimes vomiting after taking medication.
Vomiting: Vomiting is another common digestive system side effect that may be related to medication induced gastrointestinal discomfort or irritation. Vomiting may lead to serious consequences such as dehydration and electrolyte imbalance in patients.
Dysdigestion: Some patients may experience symptoms of indigestion after use, such as bloating, belching, and early satiety. These symptoms may affect the patient's appetite and nutrient intake.
Metabolic system side effects
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Elevated blood sugar: Although it mainly affects the thyroid system, it may also have an impact on the metabolic system. Some patients may experience symptoms of elevated blood sugar after using medication, which may be related to medication interfering with insulin secretion or action. High blood sugar may cause diabetes or aggravate existing diabetes.
Changes in cholesterol levels: It may also affect cholesterol levels, and some patients may experience an increase or decrease in cholesterol levels after use. Changes in cholesterol levels may increase the risk of cardiovascular disease.
Other side effects
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Oral odor: Some patients may feel an odor in their mouth after use, which may be related to drug residue or metabolism in the mouth. Bad breath may affect patients' social and self-confidence.
Allergic reactions: Although rare, some patients may experience allergic reactions to it. The symptoms of allergic reactions may include rash, itching, difficulty breathing, laryngeal edema, etc. Severe allergic reactions can lead to shock and even endanger life.
Injection site reactions: For patients who require injection administration, there may be pain, redness, swelling, and hardening at the injection site. These reactions are usually caused by the stimulating effect of drugs on local tissues.
2.Factors affecting its side effects
Individual differences
Different patients have varying levels of sensitivity and tolerance to it, which may result in different manifestations and degrees of side effects. Age, gender, genetic factors, and other factors may all affect a patient's response to medication.
Drug dosage and usage method
The dosage and usage of drugs are also important factors affecting side effects. Excessive dosage or improper use may increase the risk and severity of side effects. Therefore, when using, one should follow the doctor's guidance and administer the medication according to the prescribed dosage and usage method.
Complications and drug interactions
The possible comorbidities and interactions with other medications in patients may also affect their side effects. For example, patients with cardiovascular disease may be more prone to cardiovascular side effects when using it. Meanwhile, simultaneous use with other medications may increase the risk of side effects or generate new ones.
Neurological and Psychiatric Applications
Neuroprotective Effects
Protirelin's neuroprotective potential was highlighted in spinal cord injury (SCI) models, where it reduced neuronal apoptosis and improved locomotor recovery. Its ability to upregulate brain-derived neurotrophic factor (BDNF) and inhibit excitotoxic glutamate release suggests a role in mitigating secondary injury cascades.
Cognitive Enhancement
Protirelin improved memory and learning in rodent models of Alzheimer's disease (AD) by enhancing cholinergic transmission and reducing amyloid-β (Aβ) toxicity. In humans, a pilot study in AD patients showed trends toward improved cognitive scores after Protirelin infusion, though larger trials are needed.
Psychiatric Disorders
Protirelin's modulation of serotonin and dopamine systems has led to investigations in depression and schizophrenia. In a small trial, Protirelin (200 μg IV) reduced depressive symptoms in treatment-resistant patients, possibly by enhancing monoamine activity. However, its short half-life limits clinical utility, prompting research into longer-acting analogs.
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