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V108

Sigma-Aldrich

(±)-Norverapamil hydrochloride

≥98% (HPLC)

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Synonym(s):
N-Nor-(±)-verapamil hydrochloride
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

Quality Level

100

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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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.
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
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
Marc-Etienne Castella et al.
Pharmaceutical research, 23(7), 1543-1553 (2006-06-17)
The aims of the study are to develop and evaluate an in vitro rat intestine segmental perfusion model for the prediction of the oral fraction absorbed of compounds and to assess the ability of the model to study intestinal metabolism.
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