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(±)-Verapamil hydrochloride

Pharmaceutical Secondary Standard; Certified Reference Material

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

  • CAS Number 152-11-4

  • Linear Formula (CH3O)2C6H3CH2CH2N(CH3)(CH2)3C[C6H3(OCH3)2][CH(CH3)2]CN · HCl

  • Molecular Weight 491.06

  •  Beilstein/REAXYS Number 3647093

  •  EC Number 205-800-5

  •  MDL number MFCD00055208

  •  PubChem Substance ID 329823152

  •  NACRES NA.24

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Properties

Related Categories Analytical Standards, Analytical/Chromatography, Pharmaceutical Secondary Standards, Pharmacopeia & Metrological Institutes Standards, T-Z More...
Quality Level   300
grade   certified reference material
  pharmaceutical secondary standard
application(s)   HPLC: suitable
  gas chromatography (GC): suitable
mp   142 °C (dec.) (lit.)
Featured Industry   Pharmaceutical (small molecule)
format   neat
pharmacopeia traceability   traceable to PhEur V0100000
  traceable to USP 1711202
SMILES string   Cl.COc1ccc(CCN(C)CCCC(C#N)(C(C)C)c2ccc(OC)c(OC)c2)cc1OC
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
InChI key   DOQPXTMNIUCOSY-UHFFFAOYSA-N
Gene Information   human ... CACNA1C(775), CACNA1D(776), CACNA1F(778), CACNA1S(779)

Description

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.

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. 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.

Analysis Note

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

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.

Footnote

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.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN2811 - class 6.1 - PG 3 - EHS - Toxic solids, organic, n.o.s., HI: all
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

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

From our library of Articles, Sigma-Aldrich presents LC/MS/MS Analysis of Interacting Cardiac Drugs Digoxin, Quinidine, Amiodarone and Verapamil on Titan™ C18
Keywords: Antihypertensives, Chromatography, Clinical, High performance liquid chromatography, Liquid chromatography mass spectrometry, Mass spectrometry, Precipitation, Solid phase extractions

UHPLC Analysis of Verapamil and Metabolites on Titan™ C18

From our library of Articles, Sigma-Aldrich presents UHPLC Analysis of Verapamil and Metabolites on Titan™ C18
Keywords: Chromatography, Clinical, High performance liquid chromatography, Liquid chromatography mass spectrometry, Mass spectrometry, Pharmaceutical, Solvents

Peer-Reviewed Papers
15

References

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