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Chlorpromazine HCl

dopamine receptor antagonist CAS# 69-09-0

Chlorpromazine HCl

2D Structure

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Chlorpromazine HCl

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Chemical Properties of Chlorpromazine HCl

Cas No. 69-09-0 SDF Download SDF
PubChem ID 6240 Appearance Powder
Formula C17H20Cl2N2S M.Wt 355.33
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 60 mg/mL (168.86 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 3-(2-chlorophenothiazin-10-yl)-N,N-dimethylpropan-1-amine;hydrochloride
SMILES [H+].[Cl-].CN(C)CCCN1c2ccccc2Sc3ccc(Cl)cc13
Standard InChIKey FBSMERQALIEGJT-UHFFFAOYSA-N
Standard InChI InChI=1S/C17H19ClN2S.ClH/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20;/h3-4,6-9,12H,5,10-11H2,1-2H3;1H
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Chlorpromazine HCl

DescriptionDopamine receptor antagonist; reduces neurotransmitter binding. Inhibits nitric oxide synthesis in mouse brain cytosol. Also an antagonist of nAChR, histamine and 5-HT receptors. Displays growth-inhibitory effects on numerous tumor cell lines. Exhibits antipsychotic activity.

Chlorpromazine HCl Dilution Calculator

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Chlorpromazine HCl Molarity Calculator

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Preparing Stock Solutions of Chlorpromazine HCl

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8143 mL 14.0714 mL 28.1429 mL 56.2857 mL 70.3571 mL
5 mM 0.5629 mL 2.8143 mL 5.6286 mL 11.2571 mL 14.0714 mL
10 mM 0.2814 mL 1.4071 mL 2.8143 mL 5.6286 mL 7.0357 mL
50 mM 0.0563 mL 0.2814 mL 0.5629 mL 1.1257 mL 1.4071 mL
100 mM 0.0281 mL 0.1407 mL 0.2814 mL 0.5629 mL 0.7036 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Chlorpromazine HCl

Dopamine receptors are a class of G protein-coupled receptors that are prominent in the central nervous system. Dopamine receptors are implicated in many neurological processes. Thus, dopamine receptors are common neurologic drug targets. Antipsychotics are often dopamine receptor antagonists while typically psychostimulants are indirect agonists of dopamine receptors. Chlorpromazine is a dopamine antagonist.

In vitro: The antipsychotic activity of chlorpromazine has been associated with its ability to act as a dopamine-receptor antagonist. the manner in which chlorpromazine, with its phenothiazine ring structure, interacted with a receptor for dopamine. Furthermore, chlorpromazine inhibited the binding of [3H]spiperone, and the inhibition curve was consistent with a single class of binding sites [1].

In vivo: Daily administration of chlorpromazine to rats for 21 days induced catalepsy, tolerance to catalepsy and locomotor sensitization following PCP challenge. Results suggest that daily chlorpromazine treatment induced DA/NMDA-receptor sensitization to total locomotor activity following PCP challenge [2].

Clinical trial: Chlorpromazine is clinical used as a conventional antipsychotic drug that has been used for the management of psychotic disorders since its FDA approval in 1954.

Reference:
[1] Harrold MW, Chang YA, Wallace RA, Farooqui T, Wallace LJ, Uretsky N, Miller DD.  Charged analogues of chlorpromazine as dopamine antagonists. J Med Chem. 1987 Sep;30(9):1631-5.
[2] Nsimba SE.  Effects of daily chlorpromazine administration on behavioural and physiological parameters in the rat. Indian J Physiol Pharmacol. 2009 Jul-Sep;53(3):209-18.

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References on Chlorpromazine HCl

Mutually opposite effects of dopamine.HCl and chlorpromazine. HCl on the thickness of liposomal lipid bilayers.[Pubmed:20512472]

Arch Pharm Res. 2010 May;33(5):737-44.

The aim of this study was to provide a basis for examining the molecular mechanism for the pharmacological action of dopamine.HCl (DA) and chlorpromazin.HCl (CPZ). Radiationless energy transfer from the surface fluorescent probe, 1-anilinonaphthalene-8-sulfonic acid, to the hydrophobic fluorescent probe, bispyrenylpropane (Py-Py), was used to examine the effects of DA and CPZ on the thickness (D) of the liposomal lipid bilayers prepared with total lipids (SPMVTL) and phospholipids (SPMVPL) extracted from neuronal membranes. The thickness (D) of intact SPMVTL and SPMVPL (37 degrees C, pH 7.4) were 0.914 +/- 0.010 and 0.886 +/- 0.009 (arbitrary units, n = 5), respectively. DA decreased the thickness of both SPMVTL and SPMVPL in a dose-dependent manner with a significant decrease in thickness observed even at 40 x 10(-9) M and 40 x 10(-9) M, respectively. On the other hand, CPZ increased the thickness of both SPMVTL and SPMVPL in a dose-dependent manner with a significant increase in thickness observed even at 35 x 10(-5) M and 35 x 10(-5) M, respectively. The sensitivities to the decreasing and increasing effect of the membrane lipid bilayers thickness by DA and CPZ, respectively, differed according to the liposomes in descending order of SPMVPL and SPMVTL. The decreasing and increasing action of DA and CPZ, respectively, on the membrane thickness had many effects that may be responsible for the dopaminergic receptor-DA and -CPZ interaction as well as the protein-lipid interaction.

Formulation and stability of an extemporaneously compounded oral solution of chlorpromazine HCl.[Pubmed:25338106]

J Pain Palliat Care Pharmacother. 2014 Dec;28(4):367-70.

Chlorpromazine is a phenothiazine antipsychotic which is often used in hospice and palliative care to treat hiccups, delirium, and nausea. With the discontinuation of the commercial oral solution concentrate, there is a need to prepare this product by extemporaneous compounding. This study was initiated to identify an easy-to-prepare formulation for the compounding pharmacist. A stability study was also conducted to select the proper storage conditions and establish the beyond-use date. Chlorpromazine HCl powder and the Ora-Sweet(R) syrup vehicle were used to prepare the 100 mg/mL solution. Once the feasibility was established, a batch of the solution was prepared and packaged in amber plastic prescription bottles for a stability study. These samples were stored at refrigeration (2-8 degrees C) or room temperature (20-25 degrees C) for up to 3 months. At each monthly time point, the samples were evaluated by visual inspection, pH measurement, and high performance liquid chromatography (HPLC). A separate forced stability study was conducted to confirm that the HPLC method was stability indicating. A clear and colorless solution of 100 mg/mL Chlorpromazine HCl was obtained by dissolving the drug powder in Ora-Sweet(R) with moderate agitation. The stability study results indicated that this solution product remained unchanged in visual appearance or pH at both refrigeration and room temperature for up to 3 months. The HPLC results also confirmed that all stability samples retained 93.6-101.4% of initial drug concentration. Chlorpromazine HCl solution 100 mg/mL can be compounded extemporaneously by dissolving Chlorpromazine HCl drug powder in Ora-Sweet(R). The resulting product is stable for at least three months in amber plastic prescription bottles stored at either refrigeration or room temperature.

Effects of chlorpromazine HCl on the structural parameters of bovine brain membranes.[Pubmed:15479625]

J Biochem Mol Biol. 2004 Sep 30;37(5):603-11.

Fluorescence probes located in different membrane regions were used to evaluate the effects of chlorpromazine .HCl on structural parameters (transbilayer lateral mobility, annular lipid fluidity, protein distribution, and lipid bilayer thickness) of synaptosomal plasma membrane vesicles (SPMVs) isolated from bovine cerebral cortex. The experimental procedure was based on the selective quenching of 1,3-di(1-pyrenyl)propane (Py-3-Py) by trinitrophenyl groups, radiationless energy transfer from the tryptophan of membrane proteins to Py-3-Py, and energy transfer from Py-3-Py monomers to 1-anilinonaphthalene-8-sulfonic acid (ANS). In this study, chlorpromazine .HCl decreased the lateral mobility of Py-3-Py in a concentration dependent-manner, showed a greater ordering effect on the inner monolayer than on the outer monolayer, decreased annular lipid fluidity in a dose dependent-manner, and contracted the membrane lipid bilayer. Furthermore, the drug was found to have a clustering effect on membrane proteins.

The Effect of 4% Lignocaine gel, 5% Amiloride HCl and 10% Chlorpromazine on E.faecalis.[Pubmed:21814358]

J Conserv Dent. 2011 Apr;14(2):160-3.

INTRODUCTION: Thorough disinfection of the root canal system is essential for the success of root canal therapy. Enterococcus faecalis is the most frequently found species in persistent/secondary intracanal infection associated endodontic treatment failure. The aim of this study was to evaluate the disinfection of dentinal tubules using 10% Chlorpromazine, 4% Lignocaine gel, 5% Amiloride hydrochloride in comparison with 2% chlorhexidine gel. MATERIALS AND METHODS: The antibacterial efficacy of the four medicaments against Enterococcus faecalis was assessed in vitro using extracted human first and second mandibular premolar teeth at the depths of 200 mum and 400 mum. RESULTS: The overall percentage inhibition of bacterial growth was 100% with 2% chlorhexidine gel followed by 10% chlorpromazine (88.8%), 4% lignocaine gel (76.4%) and 5% amiloride hydrochloride (71.4%). CONCLUSION: 2% chlorhexidine gel was most effective against E. faecalis followed by the newer non- antibiotic medicament 10% chlorpromazine when compared to the other medicaments tested.

Description

Chlorpromazine Hydrochloride is an antagonist of the dopamine D2, 5HT2A, potassium channel and sodium channel. Chlorpromazine binds with D2 and 5HT2A with Kis of 363 nM and 8.3 nM, respectively.

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