Basic information
- CAS
33386-08-2- Standard SMILES
Cl.O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(c2ncccn2)CC1- InChIKey
RICLFGYGYQXUFH-UHFFFAOYSA-N- Molecular formula
- C21H32ClN5O2
- Average molar mass
- 422 g/mol
- Monoisotopic mass
- 421.224453
Names & identifiers
- Preferred name
- Buspirone Hydrochloride
- IUPAC
- 8-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-8-azaspiro[4.5]decane-7,9-dione;hydrochloride
- English name
- Buspirone hydrochloride
- Molecular formula
- C21H32ClN5O2
- Molecular weight
- 421.96
Names & synonyms
Buspirone hydrochloride33386-08-2Buspirone HCLSpamilanMJ 9022-1NSC-751138NSC-759571207LT9J9OCAPD405MJ-9022-1APD-405N-(4-(4-(2-Pyrimidinyl)-1-piperazinyl)butyl)-1,1-cyclopentanediacetamide monohydrochloride
Show more names
NarolbesparaxorentravinAnsialcensparlucelanAnsicedbuspinol
CHEBI:3224DTXSID10371938-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-8-azaspiro[4.5]decane-7,9-dione hydrochloride8-Azaspiro[4.5]decane-7,9-dione, 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-, monohydrochloride8-(4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl)-8-azaspiro(4.5)decane-7,9-dione hydrochlorideN-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl]-1,1-cyclopentanediacetamide monohydrochloride8-Azaspiro(4.5)decane-7,9-dione, 8-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-, monohydrochlorideHydrochloride, Buspirone
Database identifiers
- CAS
33386-08-2- PubChem CID
- 36431
- DTXSID
DTXSID1037193- ChEMBL
Properties
Computed structural properties
- Topological polar surface area
- 69.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 529
Experimental & physicochemical properties
Collision Cross Section197.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 201.5 · 201.5-202.50C
- Flash point
- 9 ℃ · 9℃
- storage temp.
- 2 · 2-8°C
- solubility
- Freely soluble in water and in methanol, practically insoluble in acetone.
- form
- Solid
- color
- White to off-white
- Water Solubility
- Soluble in methanol (50 mg/ml), water (partly), DMSO (100 mM).
- Major Application
- pharmaceutical
- InChI
- InChI=1S/C21H31N5O2.ClH/c27-18-16-21(6-1-2-7-21)17-19(28)26(18)11-4-3-10-24-12-14-25(15-13-24)20-22-8-5-9-23-20;/h5,8-9H,1-4,6-7,10-17H2;1H
- InChIKey
- RICLFGYGYQXUFH-UHFFFAOYSA-N
- SMILES
- C12(CCCC1)CC(N(CCCCN1CCN(C3=NC=CC=N3)CC1)C(=O)C2)=O.Cl
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 4 notifications to the ECHA C&L Inventory.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory InformationBuspirone hydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Toxicology
Treatment
General symptomatic and supportive measures should be used along with immediate gastric lavage. Respiration, pulse, and blood pressure should be monitored as in all cases of drug overdosage. No specific antidote is known to buspirone, and dialyzability of buspirone has not been determined. (L1712)
Exposure RoutesOral.
Rapidly absorbed in man. Bioavailability is low and variable (approximately 5%) due to extensive first pass metabolism.
Toxicity Summary
Buspirone binds to 5-HT type 1A serotonin receptors on presynaptic neurons in the dorsal raphe and on postsynaptic neurons in the hippocampus, thus inhibiting the firing rate of 5-HT-containing neurons in the dorsal raphe. Buspirone also binds at dopamine type 2 (DA2) receptors, blocking presynaptic dopamine receptors. Buspirone increases firing in the locus ceruleus, an area of brain where norepinephrine cell bodies are found in high concentration. The net result of buspirone actions is that serotonergic activity is suppressed while noradrenergic and dopaminergic cell firing is enhanced.
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Metabolized hepatically, primarily by oxidation by cytochrome P450 3A4 producing several hydroxylated derivatives and a pharmacologically active metabolite, 1-pyrimidinylpiperazine (1-PP) Route of Elimination: In a single-dose study using 14C-labeled buspirone, 29% to 63% of the dose was excreted in the urine within 24 hours, primarily as metabolites; fecal excretion accounted for 18% to 38% of the dose. Half Life: 2-3 hours (although the action of a single dose is much longer than the short halflife indicates).
MeSH Pharmacological Classification
Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.
Endogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS.
Uses & manufacturing
UsesFor the management of anxiety disorders or the short-term relief of the symptoms of anxiety, and also as an augmention of SSRI-treatment against depression.
Applications
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.
UsesNon-benzodiazepine anxiolitic; 5-hydroxytryptamine (5-HT1) receptor agonist.
Usesanxiolitic;serotonin receptor agonist
Non-benzodiazepine anxiolytic; 5-hydroxytryptamine (5-HT1) receptor agonist.
Related reactions
8 records
Compound notes
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