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Buspirone hydrochlorideCAS NO.: 33386-08-2 CAS NO.33386-08-2
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Keywords
- Buspirone hydrochloride
- 8-[4-[4-(2-pyrimidinyl)-1-piperazin-1-iumyl]butyl]-8-azaspiro[4.5]decane-7,9-dione
- 1-cyclopentanediacetimide,n-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-h
Quick Details
- ProName: Buspirone hydrochlorideCAS NO.: 33386-...
- CasNo: 33386-08-2
- Appearance: Colorless to yellow liquid
- Application: Synthetic fragrances
- DeliveryTime: In stock
- PackAge: drum
- Port: China main port
- ProductionCapacity: 11000 Metric Ton/Month
- Purity: 99%
- Storage: Room temperature
- Transportation: By sea or by air
- LimitNum: 1 Kilogram
- first class: 1-10
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Details
| Product Name: | Buspirone hydrochloride |
| Synonyms: | 8-[4-[4-(2-pyrimidinyl)-1-piperazin-1-iumyl]butyl]-8-azaspiro[4.5]decane-7,9-dione;8-[4-[4-(2-PYRIMIDINYL)-1-PIPERAZINYL]BUTYL]-8-AZASPIRO[4,5]DECANE-7,9-DIONE HYDROCHLORIDE;BUSPIRONE HCL;1-cyclopentanediacetimide,n-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-h;8-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-8-azaspiro(4.5)decane-9-dione;axoren;bespar;buspinol |
| CAS: | 33386-08-2 |
| MF: | C21H32ClN5O2 |
| MW: | 421.96 |
| EINECS: | 251-489-4 |
| Product Categories: | Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Serotonin receptor |
| Mol File: | 33386-08-2.mol |
| Buspirone hydrochloride Chemical Properties |
| Melting point | 201.5-202.50C |
| Fp | 9℃ |
| storage temp. | 2-8°C |
| solubility | Freely soluble in water and in methanol, practically insoluble in acetone. |
| form | neat |
| Water Solubility | Soluble in methanol (50 mg/ml), water (partly), DMSO (100 mM). |
| CAS DataBase Reference | 33386-08-2(CAS DataBase Reference) |
| Safety Information |
| Hazard Codes | T,Xn,F |
| Risk Statements | 25-36/37/38-20/21/22-39/23/24/25-23/24/25-11 |
| Safety Statements | 45-36-26-36/37-16 |
| RIDADR | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | CL9915000 |
| HazardClass | 6.1 |
| HS Code | 29335995 |
| Toxicity | LD50 i.p. in rats: 136 mg/kg (Allen) |
| MSDS Information |
| Provider | Language |
|---|---|
| SigmaAldrich | English |
| Buspirone hydrochloride Usage And Synthesis |
| Description | Buspirone hydrochloride is an anxiolytic agent indicated for the management of anxiety disorders with or without accompanying depression. In contrast to the benzodiazepines, buspirone does not interact with alcohol, and lacks sedative, anticonvulsant, and muscle relaxant effects, and abuse potential. |
| Chemical Properties | White Solid |
| Originator | Mead Johnson (USA) |
| Uses | Non-benzodiazepine anxiolitic; 5-hydroxytryptamine (5-HT1) receptor agonist. |
| Uses | Non-benzodiazepine anxiolytic; 5-hydroxytryptamine (5-HT1) receptor agonist. |
| Uses | anxiolitic;serotonin receptor agonist |
| Definition | ChEBI: A hydrochloride salt resulting from the reaction of equimolar amounts of buspirone and hydrogen chloride. |
| Manufacturing Process | There is the 3 methods for preparing of 8-azaspiro(4.5)decane-7,9-dione, 8- (4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl) monohydrochloride (U.S. Patent 3,717,634). One of them is follows: a mixture of 0.1 mole of the substituted glutaric anhydride, 0.1 mole of l-(4-aminobutyl)-4-(2-pyrimidinyl)piperazine (U.S. Pat. 3,398151), and 300 ml of pyridine was refluxed until imide formation was completed. The degree of reaction was readily followed by taking an aliquot portion of the reaction mixture, removing the solvent, and obtaining the infrared absorption spectrum of the residue. When reaction is complete, the spectrum exhibited typical infrared imide bands at 1701 and 1710 cm-1 whereas if incomplete, the infrared spectrum contains amide and carboxyl absorption bands at 1680, 1760 and 3300 cm-1. 1-(3-Cyanopropyl)-4-(2-pyrimidinyl)-piperazine. A mixture of 1-(2- pyrimidinyl)piperazine (6.0 g, 0.04 mole), 4.6 g (0.044 mole) of 3- chloropropionitrile and sodium carbonate (4.24 g, 0.04 mole) in 50 ml of nbutanol was gently refluxed for 16 hours. The reaction mixture was concentrated in vacuo and the residual oil dissolved in about 100 ml of cyclohexane. On standing a white crystalline material separated which was crystallized from cyclohexane to provide 6.5 g (yield 70%) of the cyano intermediate, m.p. 56.6-58°C. A solution of 11.5 g (0.05 mole) of 1-(3- cyanopropyl)-4-(2-pyrimidinyl)piperazine in 150 ml of absolute ethanol was saturated with ammonia. W-6 Raney nickel catalyst was added and the mixture hydrogenated under 1200 p.s.i. When the hydrogenation was completed the mixture was filtered and the residual oil distilled under reduced pressure to provide 8.2 g (70% ) of 1-(4-aminobutyl)-4-(2- pyrimidinyl)piperazine, b.p. 143-146°C at 0.1 mm. (nD 26 = 1.5582). The azospiroalkenedione 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-8- azaspiro[4.5]decane-7,9-dione was purified as free base by stripping off the pyridine solvent and crystallizing the residue from a suitable solvent or by vacuum distillation thereof hydrochloric salt of it was prepared by treating of an ethanol solution of free base with equimolar amount of HCl. |
| Brand name | Buspar (Bristol-Myers Squibb);BESPAR. |
| Therapeutic Function | Anxiolytic |
| General Description | Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards |
| Biological Activity | Classic 5-HT 1A partial agonist with relatively high affinity (K i = 9.3 - 29.5 nM). A clinically effective anxiolytic. |
| Biochem/physiol Actions | 5-HT1A serotonin receptor agonist; anxiolytic. |
| Clinical Use | Anxiolytic |
| Veterinary Drugs and Treatments | Buspirone may be effective in treating certain behavior disorders in dogs and cats, principally those that are fear/phobia related and especially those associated with social interactions. Buspirone may also be useful for urine spraying or treatment of motion sickness in cats. |
| Drug interactions | Potentially hazardous interactions with other drugs Antibacterials: concentration increased by erythromycin - reduce dose; concentration reduced by rifampicin. Antidepressants: avoid with tranylcypromine; risk of severe hypertension with MAOIs - avoid. Antifungals: concentration increased by itraconazole - reduce dose. Antipsychotics: enhanced sedative effects; haloperidol concentration increased. Antivirals: concentration increased by ritonavir, increased risk of toxicity. Calcium-channel blockers: concentration increased by diltiazem and verapamil - reduce dose. Grapefruit juice: concentration increased by grapefruit juice - reduce dose. Methylthioninium: possible risk of CNS toxicity - avoid if possible. |
| Metabolism | Systemic bioavailability of buspirone is low because of extensive first-pass metabolism. Metabolism in the liver is extensive via the cytochrome P450 isoenzyme CYP3A4; hydroxylation yields several inactive metabolites and oxidative dealkylation produces 1-(2-pyrimidinyl)- piperazine, which is reported to be about 25% as potent as the parent drug in one model of anxiolytic activity. Buspirone is excreted mainly as metabolites in the urine, and also the faeces. |