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SML0935

Sigma-Aldrich

Aripiprazole

≥98% (HPLC)

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

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

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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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

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
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)
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
D M Taylor
International journal of clinical practice, 57(1), 49-54 (2003-02-18)
Atypical antipsychotics generally have a lower propensity for extrapyramidal side-effects (EPSE), hyperprolactinaemia and tardive dyskinesia than that associated with typical antipsychotics but may still produce troublesome side-effects, such as weight gain, cardiac rhythm changes and impaired glucose tolerance. Aripiprazole is
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