Scopolamine butylbromide is an organic compound with the chemical formula C21H30BrNO4 and a molecular weight of 440.3804 g/mol. The compound is a white crystalline powder, almost insoluble in water, it can also form corresponding solutions in some organic solvents, and easily soluble in ethanol, chloroform and benzene. is an ionic compound that has a different ionization constant in water. Among them, the ionization constant of the N(CH3)3 group on the acetylcholine receptor is 9.4×10-5; and the ionization constant of the Br- ion is 7.3×10-17. It belongs to the class of acetylcholine receptor antagonists, and can relax smooth muscle and reduce the secretion of secretions by blocking the action of M1-M5 acetylcholine receptors.
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Chemical Formula |
C21H30BrNO4 |
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Exact Mass |
439 |
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Molecular Weight |
440 |
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m/z |
439 (100.0%), 441 (97.3%), 442 (22.1%), 440 (16.2%), 440 (6.5%), 441 (1.2%), 443 (1.2%), 443 (1.2%), 441 (1.1%) |
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Elemental Analysis |
C, 57.28; H, 6.87; Br, 18.14; N, 3.18; O, 14.53 |
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Scopolamine butylbromide (commonly known as Buscopan) is a drug widely used to treat gastrointestinal symptoms and belongs to a class of anticholinergic drugs. The drug mainly relaxes smooth muscle and reduces the secretion of secretions by blocking the action of acetylcholine, so as to achieve the purpose of treating and alleviating gastrointestinal problems. At present, it has been widely used in the medical field, and its use will be introduced in detail below.
It mainly acts on the smooth muscles of the digestive system, and can significantly relieve symptoms such as abdominal pain caused by spasms and contractions of the gastrointestinal tract. Therefore, it is often used to treat various diseases related to the gastrointestinal tract, such as stomach cramps, gastrointestinal ulcers, biliary ascariasis (insect bites), colitis, cholecystitis, intestinal obstruction, etc.
1.1 Stomach cramps:
Stomach cramping is a condition of pain and discomfort caused by abnormal contractions of the gastrointestinal tract. It has the effect of relaxing the smooth muscles of the gastrointestinal tract, which can effectively relieve this pain and discomfort.
1.2 Gastrointestinal ulcer:
Gastrointestinal ulcer is an injury disease of the gastrointestinal mucosa, often caused by excess gastric acid. It may play a role in the treatment of gastrointestinal ulcers by reducing the secretion of secretions to reduce irritation and symptoms of the gastrointestinal tract.
1.3 Biliary ascariasis:
Biliary ascariasis is a disease of biliary obstruction caused by roundworms parasitizing inside the bile duct. It relieves symptoms by relaxing/reducing smooth muscles in the liver, pancreas, duodenum, and gallbladder.
1.4 Colitis:
Colitis is an inflammation of the colon wall, the main symptoms of which are abdominal pain and diarrhea. it relieves these symptoms by reducing the contractions and spasms of the bowel.
1.5 Cholecystitis:
Cholecystitis is an inflammation of the gallbladder, the main symptoms of which are upper abdominal pain and fever. It reduces these symptoms by relaxing the smooth muscle of the gallbladder and reducing secretions.
1.6 Intestinal obstruction:
Intestinal obstruction is a symptom caused by a blockage in the digestive tract. Symptoms include abdominal pain, vomiting, and constipation. It can relieve these symptoms by relaxing the smooth muscles of the digestive tract.
2. Relax uterine smooth muscle:
In addition to being used to treat gastrointestinal-related diseases, it can also be used as a pre-medication for gynecological surgery to relax uterine smooth muscle. It can quickly reduce the tension and pressure of the uterus, making the operation smoother and safer.
3. Neuronal protective effect:
In addition to the above therapeutic effects, it also has certain applications in the field of neurology. Studies have shown that the drug can protect neurons by regulating neuronal membrane permeability and sodium current and other mechanisms, and relieve symptoms caused by diseases and injuries of the nervous system and muscular system.
4. Relax airway smooth muscle:
It can also relieve the symptoms caused by respiratory diseases such as asthma and bronchitis to a certain extent by relaxing the smooth muscles of the airway. The mechanism of action of the drug is still under further research and exploration.
5. Inhibit saliva secretion:
It also inhibits saliva production in the mouth and larynx, thus aiding in certain surgical and therapeutic procedures. In addition, it can relieve discomfort symptoms such as dry mouth caused by salivation.
In conclusion, it has become one of the important drugs in the medical industry, and has been widely used in many fields such as gastrointestinal tract, gynecology, neurology, and respiratory system. Although the drug has some potential risks and discomfort symptoms during the treatment process, its therapeutic effect is undoubtedly very important and necessary under proper use and monitoring.
Scopolamine butylbromide (commonly known as Buscopan) is a drug widely used to treat gastrointestinal symptoms, and its chemical structure is similar to Scopolamine hydrobromide. For manufacturers like Shaanxi Chuzhan Chemical Co., Ltd., finding an efficient and feasible synthesis method can not only greatly reduce production costs, but also ensure product quality and output.
Traditional chemical synthesis methods:
1. synthetic route one:
The synthetic route comes from a research report ("Synthesis of buscopan derivatives"), the main steps are as follows:
Step 1: Reaction of 2-bromoisopropylacetophenone with N-methyl-2-pyridinecarboxamide:
Mix 2-bromoisopropylacetophenone with N-methyl-2-pyridinecarboxamide and react at 85°C for several hours in the presence of cesium chloride to obtain the product.
Step 2: Reaction of 2-bromoisopropyl-N-methyl-2-pyridinecarboxamide with propylene oxide:
The above product is mixed with propylene oxide and stirred at room temperature in the presence of sodium hydroxide for several hours to obtain product.
The advantage of this synthetic route is that the reaction conditions are mild, and there is no need to use too many toxic and harmful solvents and reagents. However, the separation and purification steps of this method are relatively cumbersome, and the yield is not ideal.
2. Synthetic route two:
The synthetic route is derived from a patent document (US Patent 4418109 A), and the main steps are as follows:
Step 1: Reaction of cis-4-hydroxy-3-methoxyphenylacetic acid with 2,3-dibromopropionyl bromide:
cis-4-hydroxy-3-methoxyphenylacetic acid was mixed with 2,3-dibromopropionyl bromide and reacted for several hours at room temperature in the presence of ethanol to give 2-(4-hydroxy-3-methoxy phenylacetic acid)-2,3-dibromopropyl ester.
Step 2: Recrystallization of 2-(4-hydroxy-3-methoxyphenylacetic acid)-2,3-dibromopropyl ester:
The above product was recrystallized to obtain a product with higher purity.
Step 3: Reaction of 2-(4-hydroxy-3-methoxyphenylacetic acid) propionamidine with metabromic acid:
Mix 2-(4-hydroxy-3-methoxyphenylacetic acid) propionamidine with metabromide and react for several hours at room temperature in the presence of ethanol to obtain product.
The advantage of this synthetic route is that the separation and purification steps are optimized, the product has high purity, and the yield is relatively ideal. However, the reaction conditions are relatively harsh and require a certain chemical laboratory basis.
Melting point 142-1440c, Specific rotation D20 - 20.8 ° (C = 3 in water), Storage conditions 2-8 ° C, Solubility H2O: 50 mg / ml, Morphological powder, Color white, Optical activity[ α] 25/D 20.8°, c = 3 in H2O(lit.), Demonstrative warning, Hazard description H302, Precautions P301 + p312 + p330, Dangerous goods sign xn, Hazard category code 22, WGK Germany 3, RTECS No. ym350000, Toxicity LD50 in mice (mg / kg): 15.6 i.v; 74 i.p.; 570 s.c.; 3000 orally (Stockhaus, Wick)
Scopolamine butylbromide is a complex organic compound with the molecular formula C21H30BrNO4. It belongs to the dimethyloxymuscarinic class of drugs, similar to atropine, but compared with atropine, its bromide ion replaces the hydroxyl group.
The molecular structure of peoduct contains a carboxylic acid monoester structure (COOCH2CH2CH2CH3) and a benzyloxycarbonyl structure (C6H5CH2OCO) containing a bromine atom. Among them, the benzyl group and the methyl group are connected on the carbonyl to form a six-membered ring, and the six-membered ring is connected to another five-membered ring. There is a maleyl group with three hydrogen atoms, one amino group and one oxygen atom on the five-membered ring. In the imine structure, the atoms in the four different positions of the five-membered ring are connected to different groups, as shown in the figure:
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This molecular structure enables product to have an anticholinergic effect similar to that of atropine, and at the same time, the substitution of bromine atoms reduces the central effects of atropine drugs. In addition, the structure of the five-membered ring part also endows it with certain stability.
It is an anticholinergic drug, and its effect is mainly to weaken the effect of acetylcholine by competitively antagonizing the action of acetylcholine on M1-M5 receptors. In the gastrointestinal tract, it can relax smooth muscle, reduce water secretion, and have therapeutic effects on indigestion, abdominal discomfort and other diseases. In the motor system, it can relieve muscle spasm, and has a certain effect on alleviating motor system diseases such as spastic torticollis. In addition, in the respiratory system, it can also be used as a bronchodilator.
It can enter the body through the intestinal tract and the blood-brain barrier after oral administration or injection. In the gastrointestinal tract, it is absorbed relatively quickly, reaching peak blood levels in about 1-2 hours, and reaching peak blood levels in 0.5-1 hours after injection. Oral it is mainly metabolized by the liver, where it is acylated or hydroxylated to generate corresponding metabolites, which are then excreted out of the body by the kidneys or bile. Injection of product is more easily metabolized and excreted by the kidneys. In general, the metabolism and elimination of product in the body are relatively rapid, and its half-life is between 2-4 hours.
In summary, Scopolamine butylbromide is an organic compound with complex structure and strong biological activity, which has various anticholinergic effects. Its molecular structure contains benzyloxycarbonyl structure and carboxylic acid monoester structure, which is an important basis for its anticholinergic pharmacological properties. In terms of pharmacokinetics, it has good bioavailability and metabolic effects, and is widely used in clinical practice.
Frequently Asked Questions
What is scopolamine butylbromide used for?
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Uses. Scopolamine (also known as hyoscine) is used to treat cramps (spasms) of the stomach, intestines, kidney, and bladder. It helps to relieve discomfort caused by conditions such as irritable bowel syndrome, gallstones, kidney stones, and overactive/spastic bladder.
Are Buscopan and scopolamine the same?
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Hyoscine butylbromide (scopolamine butylbromide) [Buscopan/Buscapina] is an antispasmodic drug indicated for the treatment of abdominal pain associated with cramps induced by gastrointestinal (GI) spasms.
What was the twilight sedation during childbirth?
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"Twilight anesthesia," or "twilight sleep," was an early 20th-century combination of the drugs morphine and scopolamine to induce amnesia and reduce pain during childbirth, but its use has been discontinued due to significant risks. The dangers included prolonged labor, increased need for forceps, and risks to the infant, leading to its replacement by safer methods. Today, modern "twilight sedation" refers to IV sedation for various procedures, not childbirth, where patients are sedated but can still be aroused, with a focus on safety monitoring.
Is scopolamine safe for breastfeeding?
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Scopolamine is excreted in breast milk and caution is recommended for breastfeeding, especially with long-term use (like patches), as it might reduce milk supply or cause drowsiness, poor feeding, and developmental issues in infants, though single doses are less concerning. It's best to consult a doctor to weigh benefits against risks and monitor the baby for drowsiness or poor weight gain.
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