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V106

Sigma-Aldrich

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)
EC Number:
205-800-5
MDL number:
MFCD11046028
UNSPSC Code:
12161501
PubChem Substance ID:
24900706
NACRES:
NA.77

Quality Level

100

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

SMILES string

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

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

InChI key

ICKXRKHJKXMFLR-KFSCGDPASA-N

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

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.
Inhibitor of P-glycoprotein; less active enantiomer of (±)-verapamil.

Caution

hygroscopic

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311 + H331

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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)
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)
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
Assessment of the chemotherapeutic potential of a new camptothecin derivative, ZBH-1205
Wu D, et al.
Archives of Biochemistry and Biophysics, 604(1), 74-85 (2016)
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).
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