Tropisetron hydrochloride (link:https://www.bloomtechz.com/synthetic-chemical/api-researching-only/tropisetron-hydrochloride-cas-105826-92-4.html) is an organic compound. The chemical name is α-(8-phenylimidazo[1,2-α]pyridin-3-yl)-β-oxy-methacrylate hydrochloride, where α represents a chiral carbon atom. Salt is a white or off-white crystalline powder with a pungent smell and a slightly bitter taste, similar to bitter almonds. The molecular formula is C14H24ClN3O2, CAS 105826-92-4, and the relative molecular mass is about 174.2 g/mol. Soluble in many organic solvents such as alcohols, ethers and aromatic hydrocarbons. It has relatively low solubility in water. It is a phenothiazine derivative containing a pyridine ring. Its structure contains a chiral center and therefore exists as stereoisomers. It has good stability and is relatively stable to light, heat and air, and can be stored at room temperature for more than one year. The final product of this product is used to treat diseases, but it should be noted that the products produced by Shaanxi Achieve chem-tech Co.,Ltd are primary chemical products and can only be used for laboratory purposes.
Tropisetron hydrochloride Synthesis:
Indole-3-carboxylic acid is the detailed steps of raw material preparation Tropisetron hydrochloride:
Indole-3-carboxylic acid is condensed with maleic anhydride and N-methylpiperazine under reflux under heating to obtain 4-[(3-carboxy-1H-indol-2-yl)-methylamino] -N-methylpiperazine reacts with thionyl chloride to generate 4-[(3-carboxy-1H-indol-2-yl)-methylamino]-N-methylpiperazine chloride, and finally reacts with Hydrogen chloride reacts in acetonitrile to produce Tropisetron hydrochloride.
Here is the chemical equation:
1. Indole-3-carboxylic acid, maleic anhydride and N-methylpiperazine are refluxed and condensed in the presence of acetic anhydride:
HO2CCH(COOH)C5H4N + C4H4O2 → [NCH(CH2NHCH2CH2CH2CH3)C5H4N]2 + (CH3)2CO
2. The generated 4-[(3-carboxy-1H-indol-2-yl)-methylamino]-N-methylpiperazine reacts with thionyl chloride:
[NCH(CH2NHCH2CH2CH2CH3)C5H4N]2 + SOCl2 → 4-[(CH3)2NC5H4N(CH2)2NHCOCH=CH2]Cl + SO2 + HCl
Finally react with hydrogen chloride in acetonitrile to produce Tropisetron hydrochloride:
4-[(CH3)2NC5H4N(CH2)2NHCOCH=CH2]Cl + HCl → C17H21ClN2O2 + (CH3)2NC
Pharmacological Properties of Tropisetron Hydrochloride:
1. Mechanism of action: Tropisetron hydrochloride works by antagonizing 5-HT3 receptors. The 5-HT3 receptor is a receptor on the neurotransmitter serotonin that plays a signaling role in the gag reflex. Substances released by tumor cells can activate 5-HT3 receptors, triggering nausea and vomiting. Tropisetron hydrochloride can bind to 5-HT3 receptors, prevent 5-hydroxytryptamine from binding to receptors, and thus inhibit the vomiting response.
2. Pharmacokinetics: Tropisetron hydrochloride is rapidly absorbed after oral administration, and the bioavailability is about 72%. After the drug is absorbed, it is mainly distributed in the intestinal and gastric mucosal tissues, followed by the brain tissue. The volume of distribution of the drug is small, indicating that the drug is concentrated in local tissues rather than widely distributed throughout the body. The half-life of tropisetron hydrochloride is about 4 hours, and most of the drug is excreted through urine.
3. Indications: Tropisetron hydrochloride is mainly used for the prevention and treatment of nausea and vomiting caused by chemotherapy and radiotherapy. It is also effective in preventing postoperative nausea and vomiting. For mild nausea and vomiting, other medicines may be more appropriate.
Adverse reactions: The adverse reactions of tropisetron hydrochloride are mainly central nervous system reactions, such as headache and dizziness. In addition, digestive system reactions, such as nausea and vomiting, may also occur. Adverse reactions are generally mild to moderate and no special treatment is required.
4. Drug interactions: There may be interactions between tropisetron hydrochloride and other drugs. For example, when used in combination with liver drug enzyme inducers such as rifampicin and phenytoin, it may accelerate the metabolism of tropisetron hydrochloride and reduce the curative effect. When used in combination with liver drug enzyme inhibitors such as warfarin and phenytoin, it may slow down the metabolism of tropisetron hydrochloride and increase the blood drug concentration.
Tropisetron hydrochloride is a synthetic compound with a significant antiemetic effect, belonging to the indole alkaloids. Its chemical properties are mainly manifested in the following aspects:
(1) Features of the structural formula: The commanding group of tropisetron hydrochloride has a high affinity with the 5-HT3 receptor, and the length of the side chain is moderate, which is conducive to the combination of the commanding group and the receptor.
(2) Solubility: Tropisetron hydrochloride has good solubility in water, and can also be dissolved in organic solvents such as methanol and ethanol.
(3) Stability: Tropisetron hydrochloride is relatively stable under light, heat and humidity conditions, and has good storage stability.
(4) Synthetic method: The synthetic method of tropisetron hydrochloride mainly includes four steps, including synthesizing ethyl indole-2-carboxylate, tropinol, tropic acid and the final tropisetron hydrochloride.
In the Tropisetron hydrochloride molecule, there is a polycyclic aromatic compound ring, which consists of two benzene rings and a pyridine ring. A carboxymethyl group and a methylene group are connected to the ring, both of which are connected to the N atom on the pyridine ring. In addition, there is a quaternary ammonium ion in the molecule, that is, a quaternary ammonium ion formed by the H+ ion from the hydrochloride cation and a nitrogen atom in the tropisetron molecule. The molecular structure of Tropisetron is shown below:
This structure can be regarded as a polycyclic aromatic compound ring with ions, which contains structural units such as pyridine ring, benzene ring and carboxyl group. Both the N atom on the pyridine ring and the O atom of the carboxyl group have lone pairs of electrons, which can form hydrogen bonds and covalent bonds. In addition, the tropisetron hydrochloride molecule also carries a quaternary ammonium ion, which forms a covalent bond with the other two N atoms in the molecule, thereby stabilizing the structure of the entire molecule.
The molecular structure of Tropisetron hydrochloride has an important influence on its pharmacological properties and biological activity. Because the tropisetron molecule has a large number of benzene and pyridine ring structures, it can bind to 5-hydroxytryptamine receptors to exert anti-nausea and anti-emetic effects. In addition, the presence of tropisetron quaternary ammonium ions also provides additional stability to the interaction between its molecules and receptors.
In practical applications, detailed analysis and characterization of the structure of Tropisetron hydrochloride is required to understand its chemical properties and reaction characteristics. Among them, X-ray diffraction (X-ray diffraction) and nuclear magnetic resonance (Nuclear Magnetic Resonance, referred to as NMR) and other technologies are one of the important analysis methods. X-ray crystallography can be used to determine the crystal structure of a compound, thereby further understanding its molecular composition and atomic arrangement. NMR can be used to detect the molecular structure and chemical properties of compounds by analyzing parameters such as interactions between atoms in molecules and chemical shifts.