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Merck
CN

V106

R(+)-Verapamil monohydrochloride hydrate

≥98% (HPLC), powder

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About This Item

Empirical Formula (Hill Notation):
C27H38N2O4 · HCl · xH2O
CAS Number:
38176-02-2
Molecular Weight:
491.06 (anhydrous basis)
NACRES:
NA.77
PubChem Substance ID:
24900706
UNSPSC Code:
12161501
EC Number:
205-800-5
MDL number:
MFCD11046028

Key Documents

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Product Name

R(+)-Verapamil monohydrochloride hydrate, ≥98% (HPLC), powder

InChI key

ICKXRKHJKXMFLR-KFSCGDPASA-N

InChI

1S/C27H38N2O4.ClH.H2O/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;1H2/t27-;;/m1../s1

SMILES string

O.Cl.COc1ccc(CCN(C)CCC[C@@](C#N)(C(C)C)c2ccc(OC)c(OC)c2)cc1OC

assay

≥98% (HPLC)

form

powder

optical activity

[α]22/D +9.6°, c = 0.5 in ethanol(lit.)

storage condition

desiccated

color

white

solubility

H2O: >30 mg/mL
ethanol: soluble

Quality Level

100

Related Categories

Application

R(+)-Verapamil monohydrochloride hydrate has been used as a P-glycoprotein (gp) inhibitor, to detect P-gp expression on the SK-OV-3 and SK-OV-3/DDP cell surface by flow cytometry. It has also been used as a calcium channel blocker, to evaluate its effect on doxorubicin (DOX) cytotoxicity.

Biochem/physiol Actions

Inhibitor of P-glycoprotein; less active enantiomer of (±)-verapamil.
Verapamil is a calcium channel blocker. Verapamil hydrochloride is a phenyl-alkyl amine derivative and is potentially used for treating hypertension, angina pectoris and arrhythmias. It is water soluble in nature.

Disclaimer

hygroscopic

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000221360
0000225380
0000221361
0000221361
0000221360

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Embryonic stem cell-derived cardiomyocytes as a model system to study cardioprotective effects of dexamethasone in doxorubicin cardiotoxicity
Farokhpour M, et al.
Toxicology in vitro, 23(7), 1422-1428 (2009)
Effect of formulation variables on verapamil hydrochloride release from hydrated HPMC matrices
Ramrez C, et al.
Journal of the Mexican Chemical Society, 48(4), 326-331 (2004)
J A Plumb et al.
Biochemical pharmacology, 39(4), 787-792 (1990-02-15)
The L-isomer of verapamil is a more potent calcium antagonist than the D-isomer. We have examined the two stereoisomers of verapamil for their ability to increase the chemosensitivity in vitro of three drug resistant cell lines (2780AD, MCF7/AdrR and H69LX10).
Formulation and evaluation of once daily sustained release matrix tablet of verapamil hydrochloride
Ray B and Gupta MM
Journal of Drug Delivery and Therapeutics, 3(1) (2013)
E G Chikhale et al.
The Journal of pharmacology and experimental therapeutics, 273(1), 298-303 (1995-04-01)
When the blood-brain barrier (BBB) transport of a series of model peptides that varied in their physicochemical properties (lipophilicity, size and hydrogen-bonding potential) was determined using an in situ rat brain perfusion technique, an unexpected increase in flux with increasing
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