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SML0950

Sigma-Aldrich

Meclizine dihydrochloride

≥97% (HPLC)

Synonym(s):

1-(p-Chloro-α-phenylbenzyl)-4-(m-methylbenzyl)-piperazine dihydrochloride, 1-[(4-Chlorophenyl)phenylmethyl]4-[?(3-methylphenyl)methyl]piperazine dihydrochloride, NSC 28728

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About This Item

Empirical Formula (Hill Notation):
C25H27ClN2 · 2HCl
CAS Number:
1104-22-9
Molecular Weight:
463.87
EC Number:
214-164-8
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥97% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

InChI

1S/C25H27ClN2.2ClH/c1-20-6-5-7-21(18-20)19-27-14-16-28(17-15-27)25(22-8-3-2-4-9-22)23-10-12-24(26)13-11-23;;/h2-13,18,25H,14-17,19H2,1H3;2*1H

InChI key

VCTHNOIYJIXQLV-UHFFFAOYSA-N

Biochem/physiol Actions

Meclizine has the ability to increase glycolysis and decrease cellular ATP levels in media that has glucose and galactose. It guards the kidney against ischemia-reperfusion injury. Meclizine is considered as an anti-nausea and anti-dizziness drug, was identified in a ′nutrient-sensitized′ chemical screen. In human, it acts as an agonist of pregnane X receptor (PXR). It enhances the expression of CYP3A4 (cytochrome P450 3A4) mRNA and reduces CYP3A-catalyzed testosterone 6β-hydroxylation in primary cultures of human hepatocytes.
Meclizine is a potent histamine H1 receptor antagonist that is widely used as antiemetic. Recently, meclizine was identified as an inhibitor of hepstin. Also, meclizine is a potent inhibitor of mitochondrial respiration through inhibition of cytosolic CTP:phosphoethanolamine cytidylyltransferase (Pcyt2).

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

hcodes

H302,H361

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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Meclizine, a pregnane X receptor agonist, is a direct inhibitor and mechanism-based inactivator of human cytochrome P450 3A.
Foo WYB, et al.
Biochemical Pharmacology, 97(3), 320-330 (2015)
Meclizine Preconditioning Protects the Kidney Against Ischemia-Reperfusion Injury.
Kishi S, et al.
EBioMedicine, 2(9), 1090-1101 (2015)

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