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Merck
CN

PHR1131

(±)-Verapamil hydrochloride

Pharmaceutical Secondary Standard; Certified Reference Material

Synonym(s):

5-[N-(3,4-Dimethoxyphenylethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile hydrochloride

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About This Item

Linear Formula:
(CH3O)2C6H3CH2CH2N(CH3)(CH2)3C[C6H3(OCH3)2][CH(CH3)2]CN · HCl
CAS Number:
152-11-4
Molecular Weight:
491.06
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329823152
EC Number:
205-800-5
Beilstein/REAXYS Number:
3647093
MDL number:
MFCD00055208

Key Documents

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Product Name

(±)-Verapamil hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

InChI key

DOQPXTMNIUCOSY-UHFFFAOYSA-N

InChI

1S/C27H38N2O4.ClH/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6;/h9-12,17-18,20H,8,13-16H2,1-7H3;1H

SMILES string

Cl.COc1ccc(CCN(C)CCCC(C#N)(C(C)C)c2ccc(OC)c(OC)c2)cc1OC

grade

certified reference material
pharmaceutical secondary standard

agency

traceable to Ph. Eur. V0100000
traceable to USP 1711202

API family

verapamil

CofA

current certificate can be downloaded

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

142 °C (dec.) (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-30°C

Quality Level

300

Gene Information

human ... CACNA1C(775), CACNA1D(776), CACNA1F(778), CACNA1S(779)

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Analysis Note

These secondary standards offer multi-traceability to the USP and EP (PhEur) primary standards, where they are available.

Application

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.
Verapamil hydrochloride may be used as a pharmaceutical reference standard for the determination of the analyte in drug raw material and pharmaceutical formulations by high performance liquid chromatography and spectrophotometric method, respectively.

Biochem/physiol Actions

α1-adrenoceptor antagonist; L-type calcium channel blocker.
α1-adrenoceptor antagonist; L-type calcium channel blocker. Blocks L-type Ca2+ channels in smooth and cardiac muscle, induces apoptosis of human primary and metastatic colon adenocarcinoma cells in vitro. Drug resistance reversal agent acting on Pgp, e.g. decrease renal tubule elimination of digoxin. Increases basal ATPase activity of Pgp. Substrate of Cyp3A4 and CYP2C6.

General description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Verapamil hydrochloride is a calcium channel blocker used commonly for the management of angina, supra-ventricular tachyarrhythmia, hypertension, migraine and atrial tachyarrhythmias.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.
To see an example of a Certificate of Analysis for this material enter LRAA5980 in the slot below. This is an example certificate only and may not be the lot that you receive.

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

hcodes

H301,H411

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

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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Spectrophotometric method for the determination of verapamil hydrochloride in pharmaceutical formulations using N-bromosuccinimide as oxidant
Rahman N et al.
Il Farmaco (Societa Chimica Italiana : 1989), 59(7), 529-536 (2004)
Overdose of sustained-release verapamil
Barrow PM, et al.
British journal of anaesthesia, 72(3), 361-365 (1994)
High-performance liquid chromatographic method for the assay of verapamil hydrochloride and related compounds in raw material
Lacroix PM, et al.
Journal of Pharmaceutical and Biomedical Analysis, 9(10-12), 817-822 (1991)
Irena Roci et al.
Cell cycle (Georgetown, Tex.), 19(20), 2676-2684 (2020-10-06)
Proliferating cells must synthesize a wide variety of macromolecules while progressing through the cell cycle, but the coordination between cell cycle progression and cellular metabolism is still poorly understood. To identify metabolic processes that oscillate over the cell cycle, we
Irena Roci et al.
Cell reports, 26(7), 1691-1700 (2019-02-14)
Alterations in cell-cycle regulation and cellular metabolism are associated with cancer transformation, and enzymes active in the committed cell-cycle phase may represent vulnerabilities of cancer cells. Here, we map metabolic events in the G1 and SG2M phases by combining cell
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Protocols

LC/MS/MS Analysis of Interacting Cardiac Drugs Digoxin, Quinidine, Amiodarone and Verapamil on Titan™ C18

LC/MS/MS Analysis of Interacting Cardiac Drugs Digoxin, Quinidine, Amiodarone and Verapamil on Titan™ C18

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