Buspirone hydrochloride

Buspirone hydrochloride Basic information
Product Name:Buspirone hydrochloride
Synonyms:Buspirone hydrochloride,N-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dione hydrochloride;Buspirone Hydrochloride (200 mg);8-(4-(4-(Pyrimidin-2-yl)piperazin-1-yl)butyl)-8-azaspiro[4.5]decane-7,9-dione hydrochloride;8-Azaspiro[4.5]decane-7,9-dione,8-[4-[4-(2-pyriMidinyl)-1-piperazinyl]butyl]-, hydrochloride (1:1);Buspirone hydrochloride solution;8-[4-[4-(2-PYRIMIDINYL)-1-PIPERAZINYL]BUTYL]-8-AZASPIRO[4,5]DECANE-7,9-DIONE HYDROCHLORIDE;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
CAS:33386-08-2
MF:C21H32ClN5O2
MW:421.96
EINECS:251-489-4
Product Categories:Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Serotonin receptor;33386-08-2
Mol File:33386-08-2.mol
Buspirone hydrochloride Structure
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 Reference33386-08-2(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
ToxicityLD50 i.p. in rats: 136 mg/kg (Allen)
MSDS Information
ProviderLanguage
SigmaAldrich English
Buspirone hydrochloride Usage And Synthesis
DescriptionBuspirone 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 PropertiesWhite Solid
OriginatorMead Johnson (USA)
Usesanxiolitic;serotonin receptor agonist
UsesNon-benzodiazepine anxiolytic; 5-hydroxytryptamine (5-HT1) receptor agonist.
UsesNon-benzodiazepine anxiolitic; 5-hydroxytryptamine (5-HT1) receptor agonist.
DefinitionChEBI: A hydrochloride salt resulting from the reaction of equimolar amounts of buspirone and hydrogen chloride.
Manufacturing ProcessThere 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 nameBuspar (Bristol-Myers Squibb);BESPAR.
Therapeutic FunctionAnxiolytic
General DescriptionPharmaceutical 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 ActivityClassic 5-HT 1A partial agonist with relatively high affinity (K i = 9.3 - 29.5 nM). A clinically effective anxiolytic.
Biochem/physiol Actions5-HT1A serotonin receptor agonist; anxiolytic.
Clinical UseAnxiolytic
Veterinary Drugs and TreatmentsBuspirone 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 interactionsPotentially 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.







MetabolismSystemic 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.
storage+4°C (desiccate)
BUSPIRONE (D8) Piperacillin BUSPIRONE HYDROCHLORIDE IMP. K (EP): 8-AZASPIRO[4,5]-DECANE-7,9-DIONE Cyhalofop-butyl N-Aminoethylpiperazine 2-(1-Piperazinyl)pyrimidine Topotecan hydrochloride Methoxyammonium chloride Sibutramine hydrochloride Tramadol hydrochloride 1-(2-Pyrimidyl)piperazine hydrochloride Buprofezin N,N-Dibutylformamide 3-Ethylglutarimide 1-AdaMantanethylaMine 4,4-DIETHYLPIPERIDINE BUTYL OLEATE 3-ETHYL-3-METHYLGLUTARIMIDE Buspirone Hcl

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