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F114

Sigma-Aldrich

cis-(Z)-Flupenthixol dihydrochloride

≥98% (HPLC), solid

Synonym(s):

(Z)-4-[3-[2-(Trifluoromethyl)-9H-thioxanthen-9-ylidene]propyl]-1-piperazineethanol dihydrochloride, Flupentixol dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C23H25F3N2OS · 2HCl
CAS Number:
51529-01-2
Molecular Weight:
507.44
MDL number:
MFCD00069278
UNSPSC Code:
12352202
PubChem Substance ID:
24278812
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

H2O: soluble

originator

Lundbeck

SMILES string

Cl[H].Cl[H].OCCN1CCN(CC\C=C2\c3ccccc3Sc4ccc(cc24)C(F)(F)F)CC1

InChI

1S/C23H25F3N2OS.2ClH/c24-23(25,26)17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)30-22)5-3-9-27-10-12-28(13-11-27)14-15-29;;/h1-2,4-8,16,29H,3,9-15H2;2*1H/b18-5-;;

InChI key

IOVDQEIIMOZNNA-MHKBYHAFSA-N

Gene Information

human ... DRD1(1812) , DRD2(1813) , DRD3(1814) , DRD4(1815) , DRD5(1816)

General description

cis-(Z)-Flupenthixol dihydrochloride (FLU) is a thioxanthene drug. DRD1 (dopamine receptor D1) codes for D1Rs and is located on human chromosome 5q35.2. Dopamine D1 is expressed on lung alveolar type I cells.

Application

cis-(Z)-Flupenthixol dihydrochloride has been used in drug infusions. It has been used to determine the causal involvement of extracellular LS-DA and LS-NE release patterns on social play behavior.

Biochem/physiol Actions

Antipsychotic; neuroleptic agent; dopamine receptor antagonist. cis-(Z)-Flupenthixol dihydrochloride (FLU) is used to treat schizophrenia and anxiolytic and depressive disorders Dopamine D1 plays a major role in lung fluid homeostasis. It controls the airway smooth muscle tone by producing adenylyl cyclase/cAMP, that would favor airway relaxation in asthmatics. Dopamine in the lung, serves as a neurotransmitter and noradrenaline precursor.

Features and Benefits

This compound was developed by Lundbeck. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

Sold with the permission of H. Lundbeck A/S.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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Transcriptomic context of DRD1 is associated with prefrontal activity and behavior during working memory
Fazio L, et al.
Proceedings of the National Academy of Sciences of the USA, 115(21), 5582-5587 (2018)
Effect of cis-(Z)-flupentixol on DPPC membranes in the presence and absence of cholesterol
Yonar D and Sunnetcioglu M M
Chemistry and Physics of Lipids, 198, 61-71 (2016)
The dopamine D 1 receptor is expressed and induces CREB phosphorylation and MUC5AC expression in human airway epithelium
Matsuyama N, et al.
Respiratory Research, 19(1), 53-53 (2018)
Involvement of dopamine, but not norepinephrine, in the sex-specific regulation of juvenile socially rewarding behavior by vasopressin
Bredewold R, et al.
Neuropsychopharmacology (2018)
Positive reinforcement mediated by midbrain dopamine neurons requires D1 and D2 receptor activation in the nucleus accumbens
Steinberg E E, et al.
PLoS ONE, 9(4), e94771-e94771 (2014)
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