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SML0935

Aripiprazole

Name: Aripiprazole
Brand: SIGMA

≥98% (HPLC), dopamine D2 and serotonin 5-HT1A receptors agonist, powder

Synonym(s):

7-[4-[4-(2,3-Dichlorophenyl)-1-piperazinyl]butoxy]-3,4-dihydro-2(1H)-quinolinone, 7-{4-[4-(2,3-Dichlorophenyl)-1-piperazinyl]butoxy}-3,4-dihydro-2(1H)-quinolinone

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About This Item

Empirical Formula (Hill Notation):

C₂₃H₂₇Cl₂N₃O₂

CAS Number:

129722-12-9

Molecular Weight:

448.39

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Product Name

Aripiprazole, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

Clc1c(cccc1N2CCN(CC2)CCCCOc3cc4c(cc3)CCC(=O)N4)Cl

InChI

1S/C23H27Cl2N3O2/c24-19-4-3-5-21(23(19)25)28-13-11-27(12-14-28)10-1-2-15-30-18-8-6-17-7-9-22(29)26-20(17)16-18/h3-6,8,16H,1-2,7,9-15H2,(H,26,29)

InChI key

CEUORZQYGODEFX-UHFFFAOYSA-N

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Bioactive Small Molecule Agonists

Bioactive Small Molecules

General description

3, 4 dihydro-2--(1H)quinolinone is the major component of aripiprazole.

Application

Aripiprazole has been used to study behavioral and neurochemical effects of aripiprazole treatment in juvenile spontaneously hypertensive rats (SHR), a model for attention deficit hyperactivity disorder (ADHD).

Aripiprazole has been used to study its effect on mammary tumorigenesis, mediated by retrovirus delivery of receptor tyrosine-protein kinase 2 or HRas proto-oncogene, GTPase or by transgenic expression of Wnt-1 (proto-oncoprotein). It has also been used to study its behavioral and neurochemical effects in juvenile spontaneously hypertensive rats.

Biochem/physiol Actions

Aripiprazole is a second generation atypical antipsychotic and anti-depressant with partial agonist activity at dopamine D2 and serotonin 5-HT1A receptors and antagonist activity at serotonin 5-HT2A receptors. Ki values are 0.34 nM, 0.8 nM, 1.7 nM, and 3.4 nM, respectively, for dopamine D2 and D3, serotonin 5-HT1A and 5-HT2A receptors. Aripiprazole is used in the treatment of schizophrenia.

Aripiprazole serves as a ‘dopaminergic stabilizer′. It is used as a potential therapeutic to treat schizophrenia patients. In addition, it is also preferably used to treat attention deficit hyperactivity disorder (ADHD) in patients with Tourette syndrome (TS).

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

0000334700

0000371654

0000434365

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Aripiprazole and Riluzole treatment alters behavior and neurometabolites in young ADHD rats: a longitudinal 1 H-NMR spectroscopy study at 11.7 T.

Rizzo F, et al.

Translational Psychiatry, 7(8), e1189-e1189 (2017)

Dual ligands targeting dopamine D2 and serotonin 5-HT1A receptors as new antipsychotical or anti-Parkinsonian agents.

Na Ye et al.

Current medicinal chemistry, 21(4), 437-457 (2013-10-30)

Psychiatric disorders like schizophrenia and neurodegenerative diseases like Parkinson's disease are associated with poly-factorial pathogenic mechanisms, with several neurotransmitter systems closely involved. In addition to the cerebral dopaminergic (DA) system, the serotoninergic (5-HT) system also plays a crucial role in

Hyperprolactinemia-inducing antipsychotics increase breast cancer risk by activating JAK-STAT5 in precancerous lesions.

Johnston A N, et al.

Breast Cancer Research, 20(1), 42-42 (2018)

Fluoxetine and aripiprazole treatment following prenatal immune activation exert longstanding effects on rat locomotor response.

Neil M Richtand et al.

Physiology & behavior, 106(2), 171-177 (2012-02-22)

Studies characterizing treatment interventions in a naturalistic setting suggest that antidepressant and antipsychotic medications may be equally effective in improving clinical outcome in individuals at high risk for first-episode psychosis. Of interest, both beneficial as well as potentially adverse effects