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Sigma-Aldrich

cis-(Z)-Flupenthixol dihydrochloride

≥98% (HPLC), solid

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Synonym(s):
(Z)-4-[3-[2-(Trifluoromethyl)-9H-thioxanthen-9-ylidene]propyl]-1-piperazineethanol dihydrochloride, Flupentixol dihydrochloride
Empirical Formula (Hill Notation):
C23H25F3N2OS · 2HCl
CAS Number:
Molecular Weight:
507.44
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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This Item
S128O5889E8284
form

solid

form

solid

form

solid

form

solid

color

white to off-white

color

light yellow

color

yellow

color

white to beige

solubility

H2O: soluble

solubility

0.1 M HCl: soluble, ethanol: soluble

solubility

H2O: ~24 mg/mL

solubility

DMSO: >10 mg/mL

originator

Lundbeck

originator

-

originator

-

originator

-

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
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)
Pharmacological properties of new antipsychotic agents: use of animal models.
A J Puech et al.
Neuropharmacology, 20(12B), 1279-1284 (1981-12-01)
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)

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