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V108

Sigma-Aldrich

(±)-Norverapamil hydrochloride

≥98% (HPLC)

Synonym(s):

N-Nor-(±)-verapamil hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C26H36N2O4 · HCl
CAS Number:
67812-42-4
Molecular Weight:
477.04
MDL number:
MFCD00078605
UNSPSC Code:
12352200
PubChem Substance ID:
24900707
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 15 mg/mL, clear

SMILES string

CC(C)C(CCCNCCC1=CC=C(OC)C(OC)=C1)(C#N)C2=CC(OC)=C(OC)C=C2.Cl

InChI

1S/C26H36N2O4.ClH/c1-19(2)26(18-27,21-9-11-23(30-4)25(17-21)32-6)13-7-14-28-15-12-20-8-10-22(29-3)24(16-20)31-5;/h8-11,16-17,19,28H,7,12-15H2,1-6H3;1H

InChI key

OEAFTRIDBHSJDC-UHFFFAOYSA-N

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Biochem/physiol Actions

Norverapamil is an N-demethylated metabolite of verapamil. It has significantly less calcium channel blocking ability and exhibit therapeutic activity.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Shan-Shan Xie et al.
The Journal of pharmacy and pharmacology, 62(4), 440-447 (2010-07-08)
The aim was to investigate the effect of Huang-Lian-Jie-Du-Decoction (HLJDD) on the pharmacokinetic behaviour of verapamil in rats. Rats orally received 3.33 g/kg of HLJDD extract for 14 days, and pharmacokinetics of verapamil was investigated after oral and intravenous verapamil.
J M Dethy et al.
Journal of chromatography. B, Biomedical applications, 654(1), 121-127 (1994-03-18)
An analytical method has been developed to determine simultaneously the verapamil and norverapamil enantiomers in human plasma using capillary electrophoresis. Among the cyclodextrins tested as chiral selector, only trimethyl-beta-cyclodextrin was suitable to resolve the four enantiomers. The analysis was achieved
Joong-Hwa Chung et al.
Biopharmaceutics & drug disposition, 30(2), 90-93 (2009-02-20)
Verapamil is known to be a P-glycoprotein (P-gp) substrate and norverapamil is formed via hepatic cytochrome P450 (CYP 3A) in the rat. Epigallocatechin gallate (EGCG), a flavonoid, was reported to be an inhibitor of both P-gp and CYP3A. Hence, it
Shuijun Li et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 847(2), 174-181 (2006-11-23)
A simple, accurate and selective LC-MS/MS method was developed and validated for simultaneous quantification of ten antiarrhythic drugs (diltiazem, amiodarone, mexiletine, propranolol, sotalol, verapamil, bisoprolol, metoprolol, atenolol, carvedilol) and a metabolite (norverapamil) in human plasma. Plasma samples were simply pretreated
Jun Shik Choi et al.
Archives of pharmacal research, 31(9), 1200-1204 (2008-09-23)
Pioglitazone, a thiazolidinedione antidiabetic drug, inhibits cytochrome P450 (CYP) 2C8 and CYP3A4 enzymes in vitro. This study investigated the effect of pioglitazone on the pharmacokinetics of verapamil and its major metabolite, norverapamil, in rats, after oral administration of verapamil (9
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