C8138

Sigma-Aldrich

Chlorpromazine hydrochloride

≥98% (TLC)

Synonym(s):
CPZ, 2-Chloro-10-(3-dimethylaminopropyl)phenothiazine hydrochloride, Largactil
Empirical Formula (Hill Notation):
C17H19ClN2S · HCl
CAS Number:
Molecular Weight:
355.33
Beilstein/REAXYS Number:
3779989
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (TLC)

form

powder

mp

194-196 °C

solubility

water: 50 mg/mL

originator

GlaxoSmithKline

SMILES string

Cl[H].CN(C)CCCN1c2ccccc2Sc3ccc(Cl)cc13

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

InChI key

FBSMERQALIEGJT-UHFFFAOYSA-N

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Application

Chlorpromazine hydrochloride has been used:
  • as an antagonists for calmodulin kinase
  • as a medium supplement to test its cytotoxic effects in human lung microvascular endothelial cells (HMVEC-L)
  • as an inhibitor of clathrin-mediated endocytosis in RAW 264.7 cells

Substitute for benzidine, o-dianisidine, and o-tolidine in the determination of microquantities of hemoglobin and peroxidase.

Packaging

5, 25, 100 g in glass bottle

Biochem/physiol Actions

Chlorpromazine demonstrates cytotoxic and antiproliferative activity against leukemic cells, but does not affect the viability of normal lymphocytes.
Phenothiazine antipsychotic; D2 dopamine receptor antagonist, H1 histamine receptor antagonist; inhibits calmodulin-dependent stimulation of cyclic nucleotide phosphodiesterase and nitric oxide synthase.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2811PIH 6.1 / PGI

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Enhanced uptake and siRNA-mediated knockdown of a biologically relevant gene using cyclodextrin polyrotaxane
Dandekar P, et al.
Journal of Material Chemistry B: Materials for Biology and Medicine, 3(13), 2590-2598 (2015)
Anne Y Hung et al.
Journal of neurophysiology, 97(3), 2465-2479 (2007-03-14)
The translation of prior activity into changes in excitability is essential for memory and the initiation of behavior. After brief synaptic input, the bag cell neurons of Aplysia californica undergo a nearly 30-min afterdischarge to release egg-laying hormone. The present...
Endocytic pathways used by Andes virus to enter primary human lung endothelial cells
Chiang CF, et al.
PLoS ONE, 11(10), e0164768-e0164768 (2016)
Jim Baggen et al.
Nature communications, 10(1), 3171-3171 (2019-07-20)
Enteroviruses are a major cause of human disease. Adipose-specific phospholipase A2 (PLA2G16) was recently identified as a pan-enterovirus host factor and potential drug target. In this study, we identify a possible mechanism of PLA2G16 evasion by employing a dual glycan...
Jessica M D'Amico et al.
Journal of neurophysiology, 109(6), 1473-1484 (2012-12-12)
In animals, the recovery of motoneuron excitability in the months following a complete spinal cord injury is mediated, in part, by increases in constitutive serotonin (5-HT2) and norepinephrine (α1) receptor activity, which facilitates the reactivation of calcium-mediated persistent inward currents...

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