Buspirone (CHEM002209)

Record Information
Version1.0
Creation Date2009-07-21 20:27:01 UTC
Update Date2026-05-14 16:40:18 UTC
Accession NumberCHEM002209
Identification
Common NameBuspirone
ClassSmall Molecule
Description
Buspirone is only found in individuals that have used or taken this drug. It is an anxiolytic agent and a serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the benzodiazepines, but it has an efficacy comparable to diazepam. 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Anti-Anxiety Agent
  • Anxiolytic
  • Drug
  • Hypnotic and Sedative
  • Metabolite
  • Organic Compound
  • Serotonin Agonist
  • Serotonin Receptor Agonist
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
8-(4-(4-(2-Pyrimidinyl)-1-piperizinyl)butyl)-8-azaspiro(4,5)decane-7,9-dioneChEBI
BuspironaChEBI
BuspironumChEBI
Gen-buspironeKegg
AnxutHMDB
BesparHMDB
BuspHMDB
Gen buspironeHMDB
Lin buspironeHMDB
Linson pharma brand OF buspirone hydrochlorideHMDB
N-(4-(4-(2-Pyrimidinyl)-1-piperazinyl)butyl)-1-cyclopentanediacetamideHMDB
Nu buspironeHMDB
Ratio-buspironeHMDB
Armstrong brand OF buspirone hydrochlorideHMDB
Bristol myers squibb brand OF buspirone hydrochlorideHMDB
Bristol-myers squibb brand OF buspirone hydrochlorideHMDB
Buspirone hydrochlorideHMDB
Hexal brand OF buspirone hydrochlorideHMDB
NeurosineHMDB
Novo buspironeHMDB
Novo-buspironeHMDB
Nu pharm brand OF buspirone hydrochlorideHMDB
Apo buspironeHMDB
Apo-buspironeHMDB
Genpharm brand OF buspironeHMDB
Novopharm brand OF buspirone hydrochlorideHMDB
Nu-pharm brand OF buspirone hydrochlorideHMDB
PMS BuspironeHMDB
Ratiopharm brand OF buspirone hydrochlorideHMDB
Apotex brand OF buspirone hydrochlorideHMDB
Bristol myers brand OF buspirone hydrochlorideHMDB
Bristol-myers brand OF buspirone hydrochlorideHMDB
BusparHMDB
Eisai brand OF buspirone hydrochlorideHMDB
Hormosan brand OF buspirone hydrochlorideHMDB
Hydrochloride, buspironeHMDB
Lin-buspironeHMDB
Nu-buspironeHMDB
PMS-BuspironeHMDB
Pharmascience brand OF buspirone hydrochlorideHMDB
UPSA brand OF buspirone hydrochlorideHMDB
Ratio buspironeHMDB
Chemical FormulaC21H31N5O2
Average Molecular Mass385.503 g/mol
Monoisotopic Mass385.248 g/mol
CAS Registry Number36505-84-7
IUPAC Name8-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione
Traditional Namebuspirone
SMILESO=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(CC1)C1=NC=CC=N1
InChI IdentifierInChI=1S/C21H31N5O2/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
InChI KeyQWCRAEMEVRGPNT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentN-arylpiperazines
Alternative Parents
Substituents
  • Azaspirodecanedione
  • N-arylpiperazine
  • Azaspirodecane
  • Piperidinedione
  • Dialkylarylamine
  • Aminopyrimidine
  • N-alkylpiperazine
  • Piperidinone
  • Delta-lactam
  • Pyrimidine
  • Piperidine
  • Carboxylic acid imide, n-substituted
  • Heteroaromatic compound
  • Carboxylic acid imide
  • Dicarboximide
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point201.5-202.5°C
Boiling PointNot Available
Solubility21.4 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.59 g/LALOGPS
logP1.95ALOGPS
logP1.78ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)7.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.64 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity108.89 m³·mol⁻¹ChemAxon
Polarizability44.12 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral. Rapidly absorbed in man. Bioavailability is low and variable (approximately 5%) due to extensive first pass metabolism.
Mechanism of ToxicityBuspirone 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.
MetabolismMetabolized 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).
Toxicity ValuesLD50: 136 mg/kg (Oral, rat)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor 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.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include dizziness, drowsiness, nausea or vomiting, severe stomach upset, and unusually small pupils.
TreatmentGeneral 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. (2)
Concentrations
Not Available
External Links
DrugBank IDDB00490
HMDB IDHMDB0014633
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBuspirone
Chemspider ID2383
ChEBI ID3223
PubChem Compound ID2477
Kegg Compound IDC06861
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

DrugSyn.org

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15876901
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20825390
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=26746121
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=8638511