2,3,4,5-Tetrahydro-5-methyl-2-((5-methyl-1H-imidazol-4-yl)methyl)-1H-pyrido(4,3-b)indol-1-one
Alosetron
CAS: 122852-42-0
Molecular Formula: C17H18N4O
2,3,4,5-Tetrahydro-5-methyl-2-((5-methyl-1H-imidazol-4-yl)methyl)-1H-pyrido(4,3-b)indol-1-one - Names and Identifiers
2,3,4,5-Tetrahydro-5-methyl-2-((5-methyl-1H-imidazol-4-yl)methyl)-1H-pyrido(4,3-b)indol-1-one - Physico-chemical Properties
| Molecular Formula | C17H18N4O |
| Molar Mass | 294.35 |
| Density | 1.34±0.1 g/cm3(Predicted) |
| Melting Point | 238-240 °C |
| Boling Point | 648.1±55.0 °C(Predicted) |
| Flash Point | 345.8°C |
| Vapor Presure | 1.1E-16mmHg at 25°C |
| pKa | 14.10±0.10(Predicted) |
| Storage Condition | -20℃ |
| Refractive Index | 1.706 |
| Physical and Chemical Properties | alosetron hydrochloride, chemical name 2,3,4, 5-tetrahydro-5-methyl-2-[(5-methyl -1H-imidazol-4-yl) methyl]-1H-pyrido [4,3-b] Indole-l-one hydrochloride is a 5-HT3 receptor antagonist developed by g1axo Smith Kline, UK. |
| In vivo study | Dexamethasone and Alosetron-treated (1 mg/kg; ip; daily for 6 days) rats exhibits a significant decrease in the diarrhea index, in comparison with TNBS-control group, especially after the initial 2 days of treatment following the induction of colitis. |
2,3,4,5-Tetrahydro-5-methyl-2-((5-methyl-1H-imidazol-4-yl)methyl)-1H-pyrido(4,3-b)indol-1-one - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
2,3,4,5-Tetrahydro-5-methyl-2-((5-methyl-1H-imidazol-4-yl)methyl)-1H-pyrido(4,3-b)indol-1-one - Nature
Open Data Verified Data
an off-white or pale yellow crystal obtained from anhydrous ethanol with a melting point of 238-240 °c.
Last Update：2024-01-02 23:10:35
2,3,4,5-Tetrahydro-5-methyl-2-((5-methyl-1H-imidazol-4-yl)methyl)-1H-pyrido(4,3-b)indol-1-one - Preparation Method
Open Data Verified Data
3-methoxyformyl -2.4-dioxopiperidine sodium salt was dissolved in water, adjusted pH with concentrated hydrochloric acid, extracted with chloroform, dried, distilled under reduced pressure, most of the solvent; Cooled, filtered, the solid was dissolved in acetonitrile and reacted at reflux to give 2,4 piperidinedione after work-up. Add it to ethylene glycol monomethyl ether, then add N-Methyl Phenyl hydrazine, stir at room temperature; Add water, cool, filter, get 5,6-= hydrogen one}(2-methyl -2-Phenyl hydrazine)-2 (11-d-pyridone. The pyridone was added to sulfuric acid, and after the reaction, sodium hydroxide aqueous solution was added dropwise, filtered and recrystallized to obtain 2,3,4,5-tetrahydro-5-methyl-1h-pyrido [4,3-b] Indole -1-one. The indolinone, P-toluenesulfonic acid and 4-hydroxymethyl-5-methylimidazolium hydrochloride were dissolved in N-methylpyrrolidone, reacted at a certain temperature, and cooled to obtain alosetron. Re-dissolved in ethanol, drop into concentrated hydrochloric acid, that is, alosetron hydrochloride.
Last Update：2022-01-01 09:23:28
2,3,4,5-Tetrahydro-5-methyl-2-((5-methyl-1H-imidazol-4-yl)methyl)-1H-pyrido(4,3-b)indol-1-one - Use
Open Data Verified Data
It was developed by glaxom (Glaxo Wll-came) pharmaceutical company and was first officially listed in the United States in March 2000. A highly selective 5 HT3 receptor antagonist. Suitable for the treatment of the main symptom is Diarrhea of women with irritable bowel syndrome, but also can treat a variety of symptoms, including Abdominal Pain, urgent stool, frequent stool and constipation. But it can reduce the blood perfusion of the small intestine (ischemic enteritis), leading to severe obstruction or rupture of the intestine (rupture of the intestine is one of the complications of severe constipation).
Last Update：2022-01-01 09:23:29
2,3,4,5-Tetrahydro-5-methyl-2-((5-methyl-1H-imidazol-4-yl)methyl)-1H-pyrido(4,3-b)indol-1-one - Reference Information
| biological activity | Alosetron (GR 68755) is an efficient and highly selective 5-HT3 receptor (5-HT3 receptor) antagonist. Alosetron is used in the study of irritable bowel syndrome (IBS). Alosetron blocked 5HT3-mediated rapid depolarization of guinea pig intermuscular and submucosal neurons, IC50 was at ~ 55 nM. Alosetron reduce the visceral nociceptive effect of rectal dilatation in awake or anesthetized dogs. Has anti-inflammatory activity. |
| production method | dissolve 3-methoxyformyl -2, 4-dioxopiperidine sodium salt in water, adjust pH with concentrated hydrochloric acid, extract chloroform, dry, and evaporate most of the solvent under reduced pressure; cooling, filtering, dissolving the solid in acetonitrile, refluxing reaction, and 2, 4-piperidinedione after treatment. Add it to ethylene glycol monomethyl ether, then add N-methylphenylhydrazine, stir at room temperature; add water, cool, and filter to obtain 5, 6-dihydro-4-(2-methyl-2-phenylhydrazine)-2-(1H)-pyridone. Add the pyridone to sulfuric acid, add sodium hydroxide aqueous solution dropwise after the reaction, filter and recrystallize to obtain 2,3,4, 5-tetrahydro-5-methyl-1H-pyridino [4,3-b] indole -1-one, the indole ketone, p-toluenesulfonic acid and 4-methyl -5-methylimidazole hydrochloride are dissolved in N-methyl pyrrolidone and reacted at a certain temperature, after cooling, alosetron is obtained. Soluble in ethanol and drip in concentrated hydrochloric acid to obtain alosetron hydrochloride. |
Last Update：2024-04-09 21:01:54
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