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1711202

USP

Verapamil hydrochloride

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

(±)-Verapamil hydrochloride, 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
Beilstein/REAXYS Number:
3647093
EC Number:
205-800-5
MDL number:
MFCD00055208
UNSPSC Code:
41116107
PubChem Substance ID:
329751490
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

verapamil

manufacturer/tradename

USP

mp

142 °C (dec.) (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

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)

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

application

Verapamil hydrochloride USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
  • Verapamil Hydrochloride Injection
  • Verapamil Hydrochloride Tablets
  • Verapamil Hydrochloride Extended-Release Capsules
  • Verapamil Hydrochloride Extended-Release Tablets
  • Verapamil Hydrochloride Compounded Oral Solution
  • Verapamil Hydrochloride Compounded Oral Suspension

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 products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

Sales restrictions may apply.

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_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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S H Baky et al.
Pharmacotherapy, 2(6), 328-353 (1982-11-01)
Verapamil hydrochloride, a prototype calcium antagonist, is now marketed in the United States for the acute treatment of supraventricular tachyarrhythmias and for chronic management of vasospastic and chronic stable angina. It inhibits the slow inward channel in in the heart
S Izdes et al.
Acta clinica Belgica, 69(2), 116-119 (2014-04-15)
Verapamil intoxication is a life-threatening condition that often presents with severe hemodynamic instability and requires vasopressor support. There are also documented case reports of the development of non-cardiogenic pulmonary oedema after verapamil overdose. However, the exact mechanisms responsible for pulmonary
Anurag Pandey et al.
The Journal of physiology, 592(16), 3537-3557 (2014-06-08)
The subiculum is a structure that forms a bridge between the hippocampus and the entorhinal cortex (EC), and plays a major role in the memory consolidation process. Here, we demonstrate spike-timing-dependent plasticity (STDP) at the proximal excitatory inputs on the
Soon Hyung Park et al.
The Laryngoscope, 124(6), 1444-1451 (2013-10-25)
We investigated whether the round window membrane (RWM) vibration can facilitate dexamethasone perfusion via the RWM in patients with sudden hearing loss. Prospective study. We first performed an in vitro study using a semipermeable membrane. In the subsequent in vivo
Yasuo Uchida et al.
The Journal of pharmacology and experimental therapeutics, 350(3), 578-588 (2014-06-21)
The aim of this study was to investigate whether in vivo drug distribution in brain in monkeys can be reconstructed by integrating four factors: protein expression levels of P-glycoprotein (P-gp)/multidrug resistance protein 1 at the blood-brain barrier (BBB), in vitro
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