SPIPERONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H26FN3O2
Molecular Weight	395.4698
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC1=CC=C(C=C1)C(=O)CCCN2CCC3(CC2)N(CNC3=O)C4=CC=CC=C4

InChI

InChIKey=DKGZKTPJOSAWFA-UHFFFAOYSA-N

InChI=1S/C23H26FN3O2/c24-19-10-8-18(9-11-19)21(28)7-4-14-26-15-12-23(13-16-26)22(29)25-17-27(23)20-5-2-1-3-6-20/h1-3,5-6,8-11H,4,7,12-17H2,(H,25,29)

HIDE SMILES / InChI

Molecular Formula	C23H26FN3O2
Molecular Weight	395.4698
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.sciencedirect.com/science/article/pii/B9780080552323626558
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18786164 | https://www.ncbi.nlm.nih.gov/pubmed/10202608 | https://www.ncbi.nlm.nih.gov/pubmed/8866760

Spiperone (Spiroperidol; brand name: Spiropitan (JP)) is a typical antipsychotic and research chemical belonging to the butyrophenone chemical class. Spiperone is selective D2 dopamine receptor antagonist; α1B-adrenoceptor antagonist; mixed 5-HT2A/5-HT1 serotonin receptor antagonist. Additionally, spiperone was identified by compound screening to be an activator of Ca2+ activated Cl− channels (CaCCs), thus a potential target for therapy of cystic fibrosis. Spiperone is widely used as a pharmacological tool for studying neurotransmitter receptors.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 311 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26227779	Antagonist 2849	1.08 nM [Ki]
Dopamine D4 receptor 76 Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23403082	Antagonist 2849	0.2 nM [Ki]
Dopamine D3 receptor 97 Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26227779	Antagonist 2849	0.48 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10202608	Diagnostic		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
In vivo evidence for dopamine-mediated internalization of D2-receptors after amphetamine: differential findings with [3H]raclopride versus [3H]spiperone.	2003-02	12527818
Characterization of the 5-hydroxytryptamine receptors mediating contraction in the pig isolated intravesical ureter.	2003-01	12522083
Corticotropin-releasing factor as well as opioid and dopamine are involved in tail-pinch-induced food intake of rats.	2003	12559107
Nad-299 antagonises 5-HT-stimulated and spiperone-inhibited [35S]GTPgammaS binding in cloned 5-HT1A receptors.	2002-12-31	12503636
Functional cooperation between neurosteroids and D2 dopamine antagonists on KCl-evoked [3H]noradrenaline release: modulation by calcium channel blockers.	2002-12	12472876
Characterization of 5-HT receptor subtypes mediating contraction in human umbilical vein. 1. Evidence of involvement of 5-HT2A receptors using functional and radioligand binding assays.	2002-12	12444501
Inhibition of protein tyrosine/mitogen-activated protein kinase phosphatase activity is associated with D2 dopamine receptor supersensitivity in a rat model of Parkinson's disease.	2002-12	12435803
Novel (bisarylmethoxy)butylpiperidine analogues as neurotransmitter transporter inhibitors with activity at dopamine receptor sites.	2002-12	12413863
Serotonin-induced MMP-13 production is mediated via phospholipase C, protein kinase C, and ERK1/2 in rat uterine smooth muscle cells.	2002-11-08	12213812
Dopamine mediates circadian clock regulation of rod and cone input to fish retinal horizontal cells.	2002-11-01	12411525
Apomorphine induces trophic factors that support fetal rat mesencephalic dopaminergic neurons in cultures.	2002-11	12453049
Spreading depression: imaging and blockade in the rat neocortical brain slice.	2002-11	12424306
Changes in electrophysiological properties of lamprey spinal motoneurons during fictive swimming.	2002-11	12424286
In vivo serotonin 5HT(2A) receptor binding and personality traits in healthy subjects: a positron emission tomography study.	2002-11	12414286
Synthesis and structure-activity relationship of the isoindolinyl benzisoxazolpiperidines as potent, selective, and orally active human dopamine D4 receptor antagonists.	2002-10-04	12362366
Effects of rolipram on in vivo dopamine receptor binding.	2002-09	12203041
Development of an automated system for synthesizing 18F-labeled compounds using [18F]fluoroethyl bromide as a synthetic precursor.	2002-09	12201139
Antibody capture assay reveals bell-shaped concentration-response isotherms for h5-HT(1A) receptor-mediated Galpha(i3) activation: conformational selection by high-efficacy agonists, and relationship to trafficking of receptor signaling.	2002-09	12181435
Metachlorophenylpiperazine (m-CPP) induced intracavernous pressure responses in anaesthetized rats.	2002-08	12152119
The effects of dopamine synthesis inhibitors and dopamine antagonists on regeneration in the hydra Hydra attenuata.	2002-07-24	12135343
[Dopamine antibodies as neuromodulators of behavioral reactions in mice of different genotypes].	2002-07-20	12125398
Effects of intrathecal injection of diatrizoate on dopamine receptors.	2002-07	12139101
Aripiprazole, a novel antipsychotic, is a high-affinity partial agonist at human dopamine D2 receptors.	2002-07	12065741
Serotonin antagonist profiling on 5HT2A and 5HT2C receptors by nonequilibrium intracellular calcium response using an automated flow-through fluorescence analysis system, HT-PS 100.	2002-06	12097192
Functional screening of G protein-coupled receptors by measuring intracellular calcium with a fluorescence microplate reader.	2002-06	12097186
Adenosinergic modulation of the discriminative-stimulus effects of methamphetamine in rats.	2002-06	12073161
Effect of dopamine receptor agonists on sensory nerve activity: possible therapeutic targets for the treatment of asthma and COPD.	2002-06	12055141
Ketanserin and spiperone as templates for novel serotonin 5-HT(2A) antagonists.	2002-06	12052193
Design and synthesis of a piperazinylalkylisoxazole library for subtype selective dopamine receptor ligands.	2002-05-20	11992769
Hemiparkinsonism associated with a mesencephalic tumor.	2002-05-15	11997073
Contrasting effects of dopamine antagonists and frequency reduction on Fos expression induced by lateral hypothalamic stimulation.	2002-05-14	11997149
Brain neurotransmitter receptor binding and nootropic studies on Indian Hypericum perforatum Linn.	2002-05	12164263
Enhanced detection of receptor constitutive activity in the presence of regulators of G protein signaling: applications to the detection and analysis of inverse agonists and low-efficacy partial agonists.	2002-05	11961140
Physiologically identified 5-HT2-like receptors at the crayfish neuromuscular junction.	2002-04-05	11911865
Timing is everything: the effects of putative dopamine antagonists on metamorphosis vary with larval age and experimental duration in the prosobranch gastropod Crepidula fornicata.	2002-04	11971809
Positron emission tomography and ex vivo and in vitro autoradiography studies on dopamine D2-like receptor degeneration in the quinolinic acid-lesioned rat striatum: comparison of [11C]raclopride, [11C]nemonapride and [11C]N-methylspiperone.	2002-04	11929700
(+)-[76Br]A-69024: a non-benzazepine radioligand for studies of dopamine D1 receptors using PET.	2002-04	11929698
Neuropharmacological profile of a novel potential atypical antipsychotic drug Y-931 (8-fluoro-12-(4-methylpiperazin-1-yl)- 6H-[1]benzothieno[2,3-b][1,5] benzodiazepine maleate).	2002-04	11927170
Hypothalamic paraventricular 5-hydroxytryptamine: receptor-specific inhibition of NPY-stimulated eating and energy metabolism.	2002-04	11888562
The human 5-HT7 serotonin receptor splice variants: constitutive activity and inverse agonist effects.	2002-03	11906971
The atypical 5-HT2 receptor mediating tachycardia in pithed rats: pharmacological correlation with the 5-HT2A receptor subtype.	2002-03	11906967
A novel series of hybrid compounds derived by combining 2-aminotetralin and piperazine fragments: binding activity at D2 and D3 receptors.	2002-02-25	11844685
In vitro evidence that 5-hydroxytryptamine increases efflux of glial glutamate via 5-HT(2A) receptor activation.	2002-02-01	11813245
Effects of some steroids and other compounds on ovarian growth of the red swamp crayfish, Procambarus clarkii, during early vitellogenesis.	2002-01-01	11754024
Implementation and evaluation of a 3D one-step late reconstruction algorithm for 3D positron emission tomography brain studies using median root prior.	2002-01	11807602
Occurrence of dopaminergic (D(2)) receptors within the rabbit pulmonary circulation.	2002	12220945
Decreased [(3)H]spiperone binding in the anterior cingulate cortex of schizophrenia patients: an autoradiographic study.	2002	11927153
Atmospheric pressure laser desorption/chemical ionization mass spectrometry: a new ionization method based on existing themes.	2002	11921247
Modulation of [3H]quinpirole binding at striatal D2 dopamine receptors by a monoamine oxidaseA-like site: evidence from radioligand binding studies and D2 receptor- and MAO(A)-deficient mice.	2001-11-30	11787947
Patterns of cyclic AMP formation by coexpressed D1 and D2L dopamine receptors in HEK 293 cells.	2001	11918350

Patents

Sample Use Guides

In Vivo Use Guide

Rat: i.v. injection 12 mkCi (180 ng).

Route of Administration: Intravenous

In Vitro Use Guide

Aliquots of lymphocyte suspension containing 1 x 106- 2 x 106 cells in a final volume of 1.0 mL were incubated in duplicate for 1 hour at 37°C with varying concentrations of 3H-spiperone (0.1—4 nM) in the presence or absence of 10 5 M haloperidol. Cell viability, checked in a number of samples incubated in the absence of 3H-spiperone by their ability to exclude trypan blue, always exceeded 98%. After incubation, the samples were filtered (type GF/B) and rinsed six times with 4 ml cooled buffer B. The filters were dried and transferred to mini-vials with 5 mL hydro-luma scintillation fluid; radioactivity was counted in a liquid scintillation counter.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:10:37 GMT 2025` Edited by `admin` on `Mon Mar 31 18:10:37 GMT 2025`
Record UNII	4X6E73CJ0Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SPIROPITAN

Preferred Name

English

SPIPERONE

Official Name

English

spiperone [INN]

Common Name

English

NSC-170983

Code

English

R-5147

Code

English

SPIPERONE [MART.]

Common Name

English

Spiperone [WHO-DD]

Common Name

English

SPIPERONE [MI]

Common Name

English

SPIPERONE [USAN]

Common Name

English

SPIPERONE [JAN]

Common Name

English

R 5147

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C28197