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V106

R(+)-Verapamil monohydrochloride hydrate

Name: R(+)-Verapamil monohydrochloride hydrate
Brand: SIGMA

≥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

GHS06

Signal Word

Danger

Hazard Statements

H301 + H311 + H331

Precautionary Statements

P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311

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)

The activity of verapamil as a resistance modifier in vitro in drug resistant human tumour cell lines is not stereospecific.

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).

The effect of verapamil on the transport of peptides across the blood-brain barrier in rats: kinetic evidence for an apically polarized efflux mechanism.

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)

Rapid Ring-Opening Metathesis Polymerization of Monomers Obtained from Biomass-Derived Furfuryl Amines and Maleic Anhydride.

Anna Blanpain et al.

ChemSusChem, 12(11), 2393-2401 (2019-04-06)

Well-controlled and extremely rapid ring-opening metathesis polymerization of unusual oxanorbornene lactam esters by Grubbs third-generation catalyst is used to prepare a range of bio-based homo- and copolymers. Bio-derived oxanorbornene lactam monomers were prepared at room temperature from maleic anhydride and

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