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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

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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)
Involvement of dopamine, but not norepinephrine, in the sex-specific regulation of juvenile socially rewarding behavior by vasopressin
Bredewold R, et al.
Neuropsychopharmacology (2018)
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)
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)
Prolonged neuroleptic effect of alpha-flupenthixol decanoate in oil.
M Nymark et al.
Acta pharmacologica et toxicologica, 33(5), 363-376 (1973-01-01)
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