ContaminantDB: Buspirone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (10)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:01 UTC

Update Date

2016-11-09 01:08:42 UTC

Accession Number

CHEM002209

Identification

Common Name

Buspirone

Class

Small 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
8-(4-(4-(2-Pyrimidinyl)-1-piperizinyl)butyl)-8-azaspiro(4,5)decane-7,9-dione	ChEBI
Buspirona	ChEBI
Buspironum	ChEBI
Gen-buspirone	Kegg
Anxut	HMDB
Bespar	HMDB
Busp	HMDB
Gen buspirone	HMDB
Lin buspirone	HMDB
Linson pharma brand OF buspirone hydrochloride	HMDB
N-(4-(4-(2-Pyrimidinyl)-1-piperazinyl)butyl)-1-cyclopentanediacetamide	HMDB
Nu buspirone	HMDB
Ratio-buspirone	HMDB
Armstrong brand OF buspirone hydrochloride	HMDB
Bristol myers squibb brand OF buspirone hydrochloride	HMDB
Bristol-myers squibb brand OF buspirone hydrochloride	HMDB
Buspirone hydrochloride	HMDB
Hexal brand OF buspirone hydrochloride	HMDB
Neurosine	HMDB
Novo buspirone	HMDB
Novo-buspirone	HMDB
Nu pharm brand OF buspirone hydrochloride	HMDB
Apo buspirone	HMDB
Apo-buspirone	HMDB
Genpharm brand OF buspirone	HMDB
Novopharm brand OF buspirone hydrochloride	HMDB
Nu-pharm brand OF buspirone hydrochloride	HMDB
PMS Buspirone	HMDB
Ratiopharm brand OF buspirone hydrochloride	HMDB
Apotex brand OF buspirone hydrochloride	HMDB
Bristol myers brand OF buspirone hydrochloride	HMDB
Bristol-myers brand OF buspirone hydrochloride	HMDB
Buspar	HMDB
Eisai brand OF buspirone hydrochloride	HMDB
Hormosan brand OF buspirone hydrochloride	HMDB
Hydrochloride, buspirone	HMDB
Lin-buspirone	HMDB
Nu-buspirone	HMDB
PMS-Buspirone	HMDB
Pharmascience brand OF buspirone hydrochloride	HMDB
UPSA brand OF buspirone hydrochloride	HMDB
Ratio buspirone	HMDB

Chemical Formula

C₂₁H₃₁N₅O₂

Average Molecular Mass

385.503 g/mol

Monoisotopic Mass

385.248 g/mol

CAS Registry Number

36505-84-7

IUPAC Name

8-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione

Traditional Name

buspirone

SMILES

O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(CC1)C1=NC=CC=N1

InChI Identifier

InChI=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 Key

QWCRAEMEVRGPNT-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

N-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-arylpiperazine (CHEBI:3223 )
pyrimidines (CHEBI:3223 )
N-alkylpiperazine (CHEBI:3223 )
piperidones (CHEBI:3223 )
azaspiro compound (CHEBI:3223 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

EC 3.4.21.26 (prolyl oligopeptidase) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	201.5-202.5°C
Boiling Point	Not Available
Solubility	21.4 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.59 g/L	ALOGPS
logP	1.95	ALOGPS
logP	1.78	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	7.62	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	108.89 m³·mol⁻¹	ChemAxon
Polarizability	44.12 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-3930000000-f72780a741e10d32e14d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000f-0930000000-081eac0a05abab8fc5fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0009000000-429c277f63eb2ab52f57	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0009000000-170a03c9244dada2609b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0922000000-80c9aa9ae15b661116ad	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-1900000000-fafa91d49f01314afdf1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00dj-4900000000-460409b07d20201af414	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000f-0930000000-081eac0a05abab8fc5fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-00di-1900000000-1548c934ed4552c550c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00di-4900000000-3f738f9b3afda733fdbb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-0923000000-0432dbe18a87c4f8aac9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-00ea-9600000000-c19888c809dc5e1e4345	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-00ea-9600000000-306c03950ac42645d650	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00dj-4900000000-460409b07d20201af414	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00di-1900000000-cd100d009ef3ee04589b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00di-1900000000-fafa91d49f01314afdf1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-0922000000-80c9aa9ae15b661116ad	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00di-0910000000-cf8501b071281e076ac4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-000i-0009000000-f8f22927f54be6364e82	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00di-3900000000-1b0646e8d778da56bd8e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0029000000-e01810fdca67d6848abc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-5679000000-e3b3f87f2a5001651596	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-8940000000-0f2042c84fa52ff07a00	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0309000000-0cb92cbc3313c049e2b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0159-0905000000-852ca5ee117750d57ba3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-4910000000-ae14188467b44ba1ea96	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-6940000000-197b8ea9ac79cbda753b	Spectrum

Toxicity Profile

Route of Exposure

Oral. Rapidly absorbed in man. Bioavailability is low and variable (approximately 5%) due to extensive first pass metabolism.

Mechanism of Toxicity

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.

Metabolism

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).

Toxicity Values

LD50: 136 mg/kg (Oral, rat)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For 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 Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include dizziness, drowsiness, nausea or vomiting, severe stomach upset, and unusually small pupils.

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. (2)

Concentrations

Not Available

External Links

DrugBank ID

DB00490

HMDB ID

HMDB0014633

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID